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Holmes Beach Holiday Rentals

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    Travellers to Holmes Beach are booking April dates now. Secure your holiday rental today, and have the perfect trip.
    All 654 Rentals in Holmes Beach
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    Happy Island Cottage with heated private Pool1 / 52
    (31)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Cozy Cabana West - Private Pool - Close to Beach1 / 22
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Ohana Hale North  2  Bedroom on Anna Maria1 / 17
    (23)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Absolutely Perfect - Cove at Sandy Pointe #2071 / 21
    (7)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Cable/satellite TV
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    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    Lovely apartment,clean, well appointed, like being at home, I hope it's available next year! Next to all amenities.
    Reviewed 25 November 2018
    Modern, clean, well-appointed condo. It lives up to its name - Absolutely Perfect - which is why we’ve returned for a second year. Lots of places to eat, shop and visit within...
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    About this property
    Very contemporary condo (danish style), just refurnished and remodeled, and equipped with more than everything you need for a relaxing and unforgettable vacation in Paradise. The unit is inspiring and gives you a laid back feeling immediately after entering. A huge pool with lounges and sun...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Location, location, location, this cozy quaint beach house is centrally located on Anna Maria Island and is less than a 2 minute walk from Holmes Beach. The 2 bedroom and 1 bathroom unit is not only a very short walking distance to the beach, but is also a short walking distance to shopping and...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    LARGE Key West style POOL HOME Private Tropical Paradise near beach! Anna Maria1 / 25
    (4)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Grill
    • Wi-Fi
    • Patio
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 September 2018
    Our family loves Anna Maria Island. This house is conveniently located within walking distance to beautiful beach. The house itself is fully stocked with everything we needed...
    Reviewed 20 September 2018
    Location was great, in the middle of everything the island has to offer. Beautiful private beach just a few blocks away. We enjoyed the pool and the hot tub It was nice and...
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    About this property
    Tropical Paradise on Holmes Beach and ONLY 3 blocks to the beach. Anna Maria Island, noted for its old Florida ambiance, offers this Key West styled home, where you may awaken to greet the dawn sipping coffee on the balcony or swimming in your private pool. The modern interior arrangements add to...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
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    A Pearl of a Beach Home - with luxury private heated pool and hot tub1 / 39
    (31)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Patio
    • Wi-Fi
    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 February 2019
    These folks now how to run a VRBO! It was everything and MORE....The house was immaculate and stocked with every dish imaginable. We didn't cook while we were there for the week...
    Reviewed 17 October 2018
    If you are considering this home for your vacation you will not be disappointed. This beach home is as wonderful as the pictures. The “pearl” has a lagoon feel pool and hot tub...
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    About this property
    **DISCOUNTS FOR RENTALS OF 28 NIGHTS OR MORE ANY TIME OF YEAR** *****PLEASE ASK US ABOUT SPECIAL PRICING FOR YOUR STAY***** LARGE HEATED FREE-FORM, LUXURY POOL AND SPA WITH SPACIOUS PAVED SURROUND - ADDED AUGUST 2014 TOGETHER WITH TROPICAL LANDSCAPING, AUTOMATED GARDEN LIGHTING AND LARGE GROUND...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Coconuts Beach Front 106 Ground Floor1 / 17
    (6)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Waterfront
    • Washer
    • DVD Player
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 June 2018
    This is a beautiful spot just steps from the beach and close to everything. Just be careful if you need full wheelchair accessibility for yourself or someone you are traveling...
    Reviewed 19 August 2015
    Right on the beach! Perfect view and immediate access to the warm Gulf water.Basic accomodation, nicely done recent upgrades to unit.Mentioned to office staff under bed dust...
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    About this property
    One bedroom one bath condo located on the beach. The Coconuts Beach Resort is a beach front property in Holmes Beach on Anna Maria Island. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up to 4. There are two double...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Light-filled home w/ screened balcony - one block to the beach, small dogs OK!1 / 24
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    • Washer
    • Terrace
    • Balcony
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Find cool island comfort at this two-bedroom Holmes Beach escape, a bright, spacious home with a dog-friendly interior, a screened-in balcony, free WiFi, and a perfectly walkable location close to the beach and the free island trolley. You'll find this home in the northern reaches of Holmes...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    CHARMING 2 Bed 2 Bath with Heated PRIVATE HEATED Pool SPA Sleeps 6 F1 / 26
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 October 2018
    This little bungalow was perfect for our group of four! We’ve stayed at a number of AMI rentals. Each one holds special memories for us. The pool and hot tub set this one apart...
    Reviewed 12 October 2018
    Fit all of our needs - had a great time with our family .I would recommend the area and this Villa . Lots of things to do on the island and drive done to Sarasota for shopping.
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    About this property
    Relax and unwind in this gorgeous, newly renovated 2 bedroom, 2 bath home close to everything! Salt Air West , located only a short walk to the powdery white sandy beach of the Gulf of Mexico and ½ a mile from historic Pine Avenue on Anna Maria Island. Not in the mood for the beach? No Problem!...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    On the Beach Paradise d1 / 13
    (6)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Private Garden
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Ocean Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 November 2018
    Nice location tucked into a dead end road.Your own short walkway to the beach.Perfect for my wife and I ,but could handle more .Great restaurants with a short drive to...
    Reviewed 13 August 2018
    Great time in this lower level 2 bdr unit that is about 50 yards away from the beach. Nice clean unit with just about everything that you need to make your vacation complete...
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    About this property
    This cottage is located 'on the beach' 3007 Avenue F, beautiful Holmes beach. It is the downstairs unit (1 of 2). The cottage is very comfortable and sleeps 4 comfortably with additional space for a pull-out. This quaint cottage is hidden away on a dead end street, away from it all yet close...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Recently updated two bedroom two bath condo located at Runaway Bay. Property has the largest pool on Annamarie Island. Walking distance to excellent restaurants and beach. Offers a view of the bay. Tennis court and shuffleboard on site. It is an upstairs unit. Island shuttle is out the...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Coconuts Two Bedroom 118 Upstairs Courtyard1 / 23
    (5)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Grill
    • Internet Access
    • Parking
    • DVD Player
    • Balcony
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 May 2018
    Could have been cleaner.Beds in guest bedroom need to be replaced.Every time you turned, sounded like bed would collapse. Mattress in both beds old. Needs updating
    Reviewed 10 November 2017
    Would highly recommend... the condo was perfect for our family. Master bath and kitchen had both been recently renovated- gorgeous! The pool was heated and was fun to swim in...
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    About this property
    Two bedroom two bath condo located upstairs in the courtyard. The Coconuts Beach Resort is directly on the Gulf Of Mexico Holmes Beach Anna Maria Island Florida.. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up to 6 to...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Coconuts Poolside Unit 1041 / 22
    (6)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Waterfront
    • Parking
    • Air Conditioning
    • Grill
    • Washer
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 June 2016
    Awesome, already booked this for next year! Easy to fond, easy to get to beach, great people to work with.
    Reviewed 18 January 2016
    We were there in January 2016 and we were very happy with the accommodations. The decor is a little dated but all the essentials were there. We enjoyed Holmes Beach and...
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    About this property
    One bedroom one bath condo located on the poolside. The Coconuts Beach Resort is a beach front property in Holmes Beach on Anna Maria Island. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up to 4. There are two...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Private Indoor Pool
    • DVD Player
    • Washer
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You’re sure to fall in love with island living when you book your Anna Maria Island vacation at the dog-friendly Coastal Sands. This professionally decorated home offers everything your family needs, including a private heated pool, and a location less than two blocks from the powder fine Gulf of...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Grill
    • Washer
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Make this Mediterranean-style home with a private lagoon-shaped pool, jetted tub, and easy beach access your home away from home when you come to Anna Maria Island. Come revel in luxury and local flavor! Located in the heart of Holmes Beach, yet tucked away from the hustle and bustle, this home...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Anna Maria Island (blue) Cast Away Rental1 / 14
    (4)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Balcony
    • Washer
    • Parking
    • Patio
    • Porch
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 February 2016
    beautiful apartment just a walk away from the beach! clean, well stocked, decorated in the perfect beach mode!
    Reviewed 4 July 2015
    We loved the house, very clean and tidy. The owner checked in multiple times about how things were. Loved the decor and the overall feeling of the place.
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    About this property
    Come relax and enjoy your beach vacation at The Cast Away! Located conveniently across from the Manatee Public Beach and the Gulf of Mexico. This two bedroom and one bath unit sleeps six with a queen size bed, two twin beds and a sofa bed. A full size kitchen and living room are included for your...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    HUGE PRIVATE HEATED POOL, STEPS to BEACH, ELEVATOR, Coastal Chic & Super Clean!1 / 44
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • DVD Player
    • Wi-Fi
    • Patio
    • Washer
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Planning a fun family getaway or a trip with friends? Beach Retreat is the relaxing Anna Maria Island vacation rental just for you! The backyard's heated private pool is like a tropical oasis and this home's other top-notch amenities include a Ping-Pong table in the garage, free WiFi, and an...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious condo boasts a great location as it places you a short walk away from the beach, and it even comes equipped with a shared pool. The best beaches on the island are well within reach, giving you access to beautiful stretches of sand. What's nearby: This rental's location places the...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Luxury 3 Bedrooms/3 Full Baths, Private Heated Pool with Waterfall, Beach1 / 34
    (36)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Air Conditioning
    • Grill
    • DVD Player
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 August 2018
    We have traveled to Anna Maria numerous times, and this is the best house by far! The pool is the best part of the house! Very private, outside T.V., game room, 3 bedrooms with...
    Reviewed 6 July 2018
    We really enjoyed our stay for the week. The owners contacted us in advance to ensure we would have everything needed. We were impressed by how clean and updated it was. The...
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    About this property
    http://www.villachezshell.com Villa Chez Shell is a newly renovated Mediterranean beach home that offers a luxurious getaway. The highlight of this newly renovated 3 bedroom and 3 bathroom property is its tropical private backyard complete with a lagoon shaped pool and a soothing stone waterfall....
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Patio
    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Cable/satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Slip into vacation mode at this beautiful Anna Maria Island home! Complete with panoramas of the Gulf of Mexico, a private pool and hot tub, two parking spots, and 2196 square feet of space, this luxurious home offers the ultimate Anna Maria experience. Located half-a-block from the beach and a...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Coconuts Tahitian 2051 / 14
    (1)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in Holmes Beach, on Anna Maria island. This one bedroom two bath unit is a full size apartment with full size kitchen all appliances dishwasher, stove full size refrigerator, living area, dinning area and a separate bedroom has 2 full size beds. Its just steps to the beach. Covered parking....
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Great Townhouse Very Close to the Beach, Shops, and Restaurants1 / 28
    (15)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Balcony
    • Patio
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    This was our second February stay at #59 North Beach. This great house gets better and better. In addition to what we experienced last February there were a number of updates...
    Reviewed 23 February 2018
    We've stayed at a number of places on Anna Maria Isl. and this beautiful house is one the best. You can see the new heated pool from the kids bedroom. Holmes Beach is only a 5-6...
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    About this property
    Grab your flip-flops and beach chairs! This family-friendly 3-bedroom, 2 1/2 -bath townhouse is just two quick blocks to the pristine, white sandy beaches of Anna Maria's gorgeous blue waters of the Gulf Coast. And after a relaxing day of sand and sun, come back for a refreshing dip in the heated...
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    Location Information
    Holmes Beach, Anna Maria Island 32417
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Ocean Views
    • Waterfront
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You'll be amazed by the beachfront setting of this two-bedroom Holmes Beach condo, a well-appointed island escape with a private balcony, a shared heated pool, and an ideal location within steps of the free Anna Maria Island trolley. This comfortable condo is located at the Water's Edge, a...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Surround yourself with relaxation and sun-kissed adventures when you book your trip to this sunny Holmes Beach villa. This spacious seaside home has access to a shared tropical pool with a 10-foot waterfall, parking spots for two vehicles, a shady tiki hut, and a prime beachside location. Set...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Anna Maria Island #1 Beachside Palms1 / 14
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Washer
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Housekeeping Included
    • Ocean Views
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 December 2018
    We wanted a multi condo unit near the beach for Christmas week. We found this and another unit just right for our two family vacation. Clean and comfortable with a nice deck for...
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    About this property
    Beachside Palms Anna Maria Island Resort is extremely conveniently located directly across from the famous Manatee County Public Beach on the gorgeous Gulf of Mexico. All 3 of our units were completely updated in 2016. They feature new cabinets, stainless steel appliances and granite countertops....
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Blue Bayou1 / 26
    (9)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Cable/satellite TV
    • Terrace
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 July 2018
    We rented the condo for a week for our family vacation!! This place was super clean and well maintained! The condo is stocked with everything you need like beach towels, beach...
    Reviewed 13 May 2017
    Really cute, clean condo in a great location. It was really well stocked with everything you could need, lots of dishes and kitchen things as well as tons of beach gear. It was...
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    About this property
    This well-furnished two bedroom condo is next to a quiet nature preserve and has a fine view of the bay separating Anna Maria Island from Florida's mainland as well as the Sandy Pointe heated swimming pool. The beach is just 3 small blocks away with its bright white sand and aquamarine waters. For...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    Overview Gulf Sound is a gulf side, ground level tri-plex located on Gulf Drive in the southern end of Holmes Beach. Unit A at Gulf Sound is the southern unit. It is a two bedroom, one bath that will sleep six people. The unit has been updated and is comfortably furnished. It's quiet, yet close to...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    Vacation in your own tropical sanctuary on Anna Maria Island. This 2 bedroom and 2 bathroom single family home is located on a quiet cul-de-sac and only steps away from the soft sand beaches of Anna Maria Island. Enjoy amazing sunsets at the famous picturesque Bean Point Beach only a short distance...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Anna Maria Island Private Tropical Garden Home1 / 37
    (102)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 November 2018
    We were so happy to arrive to the island again and this time almost perfected the art of doing NOTHING for a week. This home is super spacious, clean and its location is ideal...
    Reviewed 20 May 2018
    My family was celebrating Mom and Dad's 60th Anniversary and we wanted to do it up big. How lucky we were to discover this wonderful vacation home. The layout of the home was...
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    About this property
    PRIVATE ISLAND PARADISE - This unique custom home is hidden on a huge garden lot surrounded by palms, birds of paradise, tropical plants and a 6 ft fence. Few island homes offer this degree of privacy. SPACIOUS ELEGANCE - The home has 2,600 sq ft (240 sq m.) of ground level indoor living space with...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    Vacation in style with this charming cottage-style condo on Anna Maria Island. Featuring a shared pool, Gulf views from the balcony, and easy access to gorgeous beaches, this condo is perfect for a couple of friends or a romantic retreat. Located in Holmes Beach just across the street from the...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Anthony Beach Cottages Island Retreat1 / 26
    (5)Average
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 August 2015
    The house is spacious, close to the beach, convenient to numerous stores and the main road of Anna Marie Island. The Anthony beach cottage also has plenty of parking space and...
    Reviewed 8 February 2015
    First I want to thank the manager, April, for being helpful in arranging for my family and I to stay at this property at the last minute. She was really amazing to work with...
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    About this property
    Situated 3 blocks from the beach and 2 blocks from the bay with a secluded yard surrounded by mangroves, this two-story pool home includes 3 bedrooms on the first floor and a regal master suite on the second floor. Comes equipped with Wifi, cable TV in all 4 bedrooms, washer/dryer, dishwasher,...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    The Anna Maria Island Beach Retreat1 / 45
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    FAMILY/CHILD FRIENDLY CONDOMINIUM - ALL BABIES AND CHILDREN ARE WELCOME!!!! The Anna Maria Island Beach Retreat is a completely remodeled two bedroom one bathroom condo, located four houses from Anna Maria Island’s exquisite white powder sand beaches. Included with your stay is one free...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Coconuts Beach Front 109 Upstairs1 / 20
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 April 2018
    Very pleased with the condo. Stayed in unit 109 on the first floor that had a fabulous outlook. New owners have gone to town and gutted the place with all modern furnishings...
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    About this property
    One bedroom one bath condo located on the poolside. The Coconuts Beach Resort is a beach front property in Holmes Beach on Anna Maria Island. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up to 4. There are two...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Minutes away from the Gulf This 2BR/1BA Brings a Pool, Patio, and Sleeps 4!1 / 38
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Central Heating
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    Reviewed 21 May 2018
    The Sea Pirate 6 exceeded my expectations! The condo was very clean and beautifully decorated. Furniture was like new, and the beds were very comfortable. The condo really felt...
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    About this property
    Sea Pirate Condo #6, located at 3301 Gulf Drive in the heart of Holmes Beach is just a stone's throw from the tropic teal waters of the Gulf of Mexico. Situated in a much desired area, close to shopping and restaurants, this smaller complex features a large heated pool, on site coin operated...
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    Location Information
    Holmes Beach, Anna Maria Island 34218
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    90 steps to the Beach!1 / 30
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Ocean Views
    • Washer
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 June 2018
    The condo is truly only 90 steps to the beach and has a partial view of the water also. We weren’t expecting such a nice view. The condo is very comfortable and has lots of...
    Reviewed 6 March 2017
    We have stayed at this condo past 12 years. New owners have made many needed improvements and it is perfect! Great location steps to beach and a Publix nearby. Short walk to...
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    About this property
    Location! location! Spacious and light 1395 sq.ft, 2 bed, 2 bath condo on Anna Maria Island in Holmes Beach. Located on a quiet, less traveled fork of Gulf drive. No roads to cross, you can see the beach at sunset from your lanai or roof deck. Right out #3's door and up 12 steps to a huge deck with...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Smoking allowed
    About this property
    This cozy duplex with a shared pool and easy beach access is waiting for your upcoming Anna Maria Island vacation. You'll be in close proximity to dining and shopping, and you'll have space to park two cars. This rental is located two blocks from flour soft, sugar white beaches on the Gulf of...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience the joys of island living at this five-bedroom Holmes Beach escape, a palm-lined duplex with two separate living spaces, an outdoor heated pool and terrace, and a wonderful location one block from the beach. You'll find this duplex on the west side of Holmes Beach, one block from the...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy a shared, heated pool with LED lighting and a full kitchen at this newly remodeled vacation rental located just a few blocks from shops, restaurants, bars, and more right in the heart of nearby Holmes Beach. Take a short walk over to miles of soft, sandy, Gulf Coast beaches just a couple...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    For your next vacation to Anna Maria Island, how about a rental that actually feels like home? This charming condo in the desirable Palm Isle Village community offers a shared pool, Gulf views from the balcony, and exceptional comfort just minutes from a white sand beach. Located on the Gulf...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Waterfront
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    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Treat yourself to a relaxing getaway at this gulf-front Anna Maria Island vacation! This gorgeous condominium offers parking for one vehicle, a prime location close to local attractions, a shared pool, and a unique tropical feel! With the beach just a few steps away, the stunning Gulf of Mexico...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Anna Maria Island #2 Beachside Palms1 / 17
    (3)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • DVD Player
    • Ocean Views
    • Housekeeping Included
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    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 May 2018
    The Rental was very relaxing, clean and easy to find. Location to the beach was excellent. The deadbolt lock was broken, this was unfortunate as one night someone was outside...
    Reviewed 24 February 2017
    Excellent spot. Immaculate. Close to beach (3 minute walk), Publix, Walgreens and CVS. Owner (Jerry) is super nice to deal with. You can book directly from Property...
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    About this property
    Beachside Palms Anna Maria Island Resort is extremely conveniently located directly across from the famous Manatee County Public Beach on the gorgeous Gulf of Mexico. All 3 of our units were completely updated in 2016. They feature new cabinets, stainless steel appliances and granite countertops....
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax to the sound of waves crashing with views of the ocean from almost every window in this cozy cottage. This second floor cottage is only steps away from Holmes Beach and overlooks the calm waters of the Gulf of Mexico. The perfect location of this cottage also puts you less than a mile from...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy your own slice of island life with a stay at this charming, two-bedroom, waterfront condo. Located in a quiet, but vibrant neighborhood with plenty of local island flavor, there's room here for up to four guests along with the family dog for an additional nightly fee. Guests of this rental...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Wi-Fi
    • Washer
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    • Cable/satellite TV
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious condo boasts a great view of Anna Maria Island's beaches, and it even comes equipped with a shared pool. The best beaches on the island are right outside your window, giving you access to beautiful stretches of sand. What's nearby: This rental's location places the beach just a...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
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    • Cable/satellite TV
    • Hot Tub
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to this charming, dog-friendly Anna Maria Island house. With the private heated pool and hot tub, you will feel like you're miles away from your worries. There is a large, fenced-in backyard with lush landscaping, where you can soak up the warm island sun from a pool-side lounge chair....
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Porch
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One bedroom one bath condo located on the beach. The Coconuts Beach Resort is a beach front property in Holmes Beach on Anna Maria Island. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up to 4. There are two double...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Spectacular Beach House With GulfView Only Steps to a Pristine Beach1 / 13
    (5)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 July 2018
    We had a wonderful time with much time spent on the beach and eating in but as always had to visit all the ice cream shops! Our grandson even found a horse shoe crap moult.
    Reviewed 2 August 2017
    House is literally steps to the beach. Get to AMI's hot spots within minutes from this central location. Plenty of beach stuff - tents, chairs, boogie boards, floats, etc as...
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    About this property
    Spacious 3-level House with 2 large decks overlooking the beautiful Gulf of Mexico. House is fully furnished with a large flat screen TV and Bose Stereo System. Great Gulf views from living room and Master Bedroom. One Guest room also has a gulf view. Large garage is fully equipped with beach...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One bedroom one bath condo located on the beach. The Coconuts Beach Resort is a beach front property in Holmes Beach on Anna Maria Island. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up to 4. There are two double...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Island Love Nest1 / 27
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 March 2016
    The owners have provided a wonderful living space that was very clean cute and cozy. My guests were very complimentary. I can't emphasize enough the owners' responsiveness and...
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    About this property
    This property is available for rentals 7 nights or more. 99 steps from the beach! Elegantly furnished two bedroom and two bath condo with brand new Tommy Bahama style furnishings. Sit by the heated pool after a stroll on the white, sandy beach of Holmes Beach just across the street! There are 18...
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    Location Information
    Holmes Beach, Anna Maria Island 33569
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1
    Holmes Beach Holiday Rentals

    Holmes Beach is a small town on Anna Maria Island in the Gulf of Mexico just south of Tampa Bay. It boasts miles of gorgeous white, sandy beaches, emerald Gulf waters, abundant sunshine, and an eclectic selection of holiday rentals. Visitors to Holmes Beach can stay anywhere from a luxurious beachfront house to a rustic rental cottage. Friendly locals welcome everyone to relax and enjoy this “Florida old charm” paradise.

    Where to Stay in Holmes Beach

    Rental homes can provide not only flexibility but the amenities of the best resorts at a fraction of the price. If you are holidaying with the family, having extra space to spread out is also an asset. Whether you want a weekend getaway or a long trip the rental choices are endless, and you’re sure to find something that will fit your family’s needs.

    Fun things to do in Holmes Beach

    A scooter is an inexpensive and fun way of getting around the island from your holiday rental. If you want to spend a day on the water, there is excellent fishing in the waters surrounding Anna Maria Island. Take a charter boat and head out in the Gulf for an exciting day of sport fishing. The grouper, snapper, or mackerel you catch can provide the ingredients for a delicious seafood dinner at your holiday rental. Inshore or backwater fishing is also very popular.

    Enjoy a beach picnic with the locals under the Australian Pines, or find a secluded cove and enjoy some private sunbathing. Prefer an animated beach crowd? Then the all-you-can-eat pancake breakfasts at "Cafe on the Beach" is your scene.

    More beach Fun

    Join a volley ball game. There are numerous nets along the beach, and there is always an exciting game taking place. Not in for that much activity? Then lie on the beach soak up some sun while you cheer for your favorite team.

    Dining and entertainment

    Enjoy a burger and a cold beer at Dusty’s Tavern steps away from your holiday rental. The Beach House Restaurant provides beachfront dining and live music for your enjoyment. Enjoy fresh grouper and a beer close to your holiday rental. You can also rest and relax at the pool at your holiday rental and enjoy a barbeque with your family and friends. Whatever your choice, you will leave the island with unforgettable memories.

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