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Holiday Rentals and Villas in Holmes Beach, FL

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    Travellers to Holmes Beach are booking March dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 12
    4.5 of 5 stars (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    4.5 of 5 stars (8) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    4.5 of 5 stars (11) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    We installed a New pool and Spa in January 2016. Our island home just one block from the beach offers a one of a kind setting which gives you the pleasures of a spring-fed lake with a private dock being installed in Winter 2016 as well as one block walk to the beach with a peek of the gulf. The... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34218
    4 of 5 stars Reviewed 10 January 2014
    We (family with 2 adult children) stayed there over christmas 2013. The house is so comfortable and cozy, that we' ve felt us like at home. The furnishing and fittings are of a...
    5 of 5 stars Reviewed 7 January 2014
    We have now stayed twice at this vacation house and loved it both times. Ken, the owner makes it so easy to book and is a real pleasure to deal with. Booking direct with the owner...
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    1 / 11
    5 of 5 stars (3) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Terrace
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    About this property
    Fun in the Sun!~ Ground level duplex that's fun and adorable. This one bedroom, one bath unit has a private outdoor patio area. This unit has recently been renovated and is perfect for a couple with visiting guests. Decorated like a feature in Coastal Living Magazine. Pet friendly with a... View all property information
    Location Information
    Holmes Beach, Anna Maria Island
    5 of 5 stars Reviewed 19 June 2011
    The rental was very clean, had everything we needed. The neighborhood was quiet and neighbors very friendly. We enjoyed having a private back yard and being within walking...
    5 of 5 stars Reviewed 16 June 2011
    Located in a lovely neighborhood, close to the beach, 7310 Holmes Blvd. is a charming, comfortable, and welcoming spot to relax and unwind. We liked it so much that we are...
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    1 / 28
    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
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    • Ocean Views
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    • Shared Garden
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    About this property
    Direct across street from our unit at Gulf Sands. Both units use the same pristine Beach... Over 100 ft of Beach less than 100 yards away. Recently decorated lovely Pool and Barbecue Area.Spacious pool area with shaded area Bedrooms are private as well as bathrooms. rooms do not open into LV.... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 24 July 2015
    Our stay at Cayman Cay was wonderful! The condo was immaculate! Felt like we were home. Comfortable bed, great little kitchen, living room! We had our coffee every morning on the...
    5 of 5 stars Reviewed 21 July 2015
    This is a well-appointed condo in a great location on AMI. Clean, comfortable and very homey. We loved the decor! The patio right off of the pool is just beautiful. Looking...
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    1 / 32
    5 of 5 stars (13) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 21 December 2015
    Every since we booked this vacation rental we knew it would be great because of the interaction with the owners. They were on top of everything and went out of their to help us...
    5 of 5 stars Reviewed 15 October 2015
    My husband, parents and two boys decided to vacation in Florida this summer. We have always vacationed at hotels or all inclusive resorts. For this vacation we wanted to find a...
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    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    • Waterfront
    • Balcony
    • Porch
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    About this property
    Note: This property requires a 28-day minimum stay. This two-bedroom, two-bath vacation rental is the perfect size for a romantic getaway, small families or close friends. Located in the Westbay Point & Moorings condominium complex in Holmes Beach, this hidden gem is tucked away from traffic,... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    1 / 31
    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    This beautifully 2015 decorated first floor 2 bed condo is set in an idyllic, peaceful setting amongst the natural beauty of Anna Maria Island and only a short walk from the stunning white sandy beaches. This fully air conditioned condo comprises of a large lounge with a tiled floor, new leather 2... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 12 January 2015
    Always the traveler who seeks value first, I found #106-The Cove at Sandy Pointe after searching TripAdvisor's many listings on Anna Maria Island. If you are doing your research...
    5 of 5 stars Reviewed 24 April 2014
    This is a lovely spacious condo, nicely furnished, with decent wifi, aircon and all mod cons. The condos in the Sandy Point complex all share a pool and we found this to be very...
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    Located in Holmes Beach, on Anna Maria island. This two bedroom two bath unit is a full size apartment with full size kitchen all appliances dishwasher, stove full size refrigerator, living area with fireplace, dinning area and a separate bedrooms has 1 king size bed and 2 twin size beds. Its just... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Welcome to Aqua Oasis on Anna Maria Island. Built in 2015, this duplex is comprised of two stunning beach homes close to the beach in a quiet residential neighborhood that provide views of the Gulf of Mexico from the Master Suite. The Aqua Oasis side includes a private heated pool (not shared)... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    1 / 8
    5 of 5 stars (1) Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Our Sandsational family home!~ Would you care to escape to Florida with style and sophistication? Indulge friends and family while pampering yourself vacationing at this elegant residence situated on prestigious Key Royale. From the moment you enter this home, or spend quality time in the ample... View all property information
    Location Information
    Holmes Beach, Anna Maria Island
    5 of 5 stars Reviewed 16 December 2014
    We booked this though the owners directly and the photos on their website do not do the property justice. It is a stunning house with so much space and beautiful view over Bimini...
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    1 / 28
    5 of 5 stars (34) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    About this property
    From the same owners of A Lime Cottage (p277325), who've been recognized as TripAdvisor 'rated excellent' vacation rental, Flipkey 2012 and 2013 Top Vacation Rental, 2012 Top Rental Manager', we're delighted to now have Lemon Cottage. Nestled in a quiet residential boating community across from... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 1 week ago
    We recently returned from our second visit at Lemon Cottage. We had a wonderful time. The cottage is lovely, homey, comfortable, organized and has pretty well everything you'd...
    5 of 5 stars Reviewed 5 October 2015
    This is our 3rd stay at Lemon cottage, 3 consecutive years in a row, and our 4th stay at Chris & family's rentals. It is our 6th year staying on Anna Maria at the end of Sept...
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    1 / 29
    3 of 5 stars (1) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Porch
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    • Patio
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    • Waterfront
    • Air Conditioning
    • DVD Player
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    • Pet-friendly
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    About this property
    Adriel's Place in Anna Maria...located in upscale private golf club neighborhood, a stone throw from pristine beaches, restaurants and island entertainment ( less than 1 mile ). An expansive backyard dotted with majestic palms, papered terrace and pool overlooking sailboat water. Fishing and... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    3 of 5 stars Reviewed 8 October 2015
    The island is a wonderful place. The beaches are beautiful, plenty of things to do with your family: walking, biking, boating, and just enjoying the weather. I will now list the...
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    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    About this property
    Welcome to Loggerhead Beach House on Anna Maria Island. Completely remodeled in 2013, this ground level duplex is comprised of two stunning beach homes close to the beach in a quiet residential neighborhood. The Loggerhead Beach House side includes a private heated pool (not shared), hot/cold... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Brand new remodeled cottage with a beautifully landscaped private backyard, Heated pool, paver deck, full kitchen with Granite countertops and Stainless Steel appliances. Sleeps up to 6 people. 880 Sq. ft. 310B 62nd St., Holmes Beach 2 Bedroom/2 Bath Villa Rates from $800 to $1,700 per week... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Make your stay in Florida fun and easy! This 2 Bedroom, 2 Bath condo is direct beachfront with wide open views up and down the coast. The condo is on the top floor (6th) of the building and is completely furnished with a dining table that seats 6 – 8, sofa and loveseat, coffee and end tables, flat... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34218
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Patio
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    • Pet-friendly
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    About this property
    Welcome to Buddy's Beach House. A beachy chic getaway just 2 blocks to the beach. Stroll to the beach with a beverage in one hand and your beach cart in the other. After soaking up the sun all day, walk to one of the many fine restaurants, only a few blocks away. Or hop on the free trolley, which... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    1 / 12
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    The 'Flip Flop' duplex is a fantastic ground level remodeled duplex located one block from the white sandy beaches boasting professional landscaping, beautiful retro interiors, and its own private pool for each side of the duplex. Flop (the yellow side of the duplex) is a one bedroom, one bath... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 8 October 2014
    My husband and I loved Flop Cottage for many reasons. First of all, the landscaping is lush and tropical and the décor is fun and cozy - so you instantly feel like you are on...
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Elegant Beach living at it's finest! Beach front Palm Gables,3 bedroom, 2 bath condo offering state of the art kitchen, tastefully decorated with a Florida flair . Large, open and airy floor plan with sliders to the balcony where you can sip on your frozen cocktail and enjoy the balmy breezes of... View all property information
    Location Information
    Holmes Beach, Anna Maria Island
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    1 / 32
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
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    About this property
    La Plage 9 is the cream of the crop. Direct Gulf Front, high-floor views make this one of the most spectacular luxury condos on all of Anna Maria Island. What you get on the inside is no less outstanding. The deep cherry wood island style furniture is the finest around. Granite counter tops, crown... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 46
    4.5 of 5 stars (9) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Enjoy our relaxed house with brand new heated pool and its integrated jet tubes. It is just a few steps from the beach and also to best restaurants and shops on the island. This is not a duplex, this is not a condo. This is a single family house with private garden an pool. A nice dining deck with... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    3 of 5 stars Reviewed 20 September 2015
    Having been to Anna Marie several times we decided on Turtle place and booked from the end of August until the 12th September, a total of six weeks. We enjoyed our time there but...
    5 of 5 stars Reviewed 6 October 2014
    Locally known as “The Turtle Place” its in a great location halfway up the island in a quiet residential area between Gulf Drive and Marina Drive. Very easy to find. Easy key...
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    Experience Anna Maria Island at its best! This luxury beach-front home located in Holmes Beach is available for a minimum of 2 weeks and at a discounted rate monthly. An expertly decorated home that reflects the calming and relaxing atmosphere of the beach, Island Dance offers just what you are... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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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... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 24
    4 Bedrooms, 3 Bathrooms, Sleeps 11 | Quick View
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    About this property
    At 4 bedrooms and 3 full bathrooms, this is one of the most charming rentals on Anna Maria Island!! Located a few houses from the beach, it is only a two minute walk until white powdery sand is between your toes! Easy on the kids and even easier on you! Around the corner from restaurants, pubs &... View all property information
    Location Information
    Holmes Beach, Anna Maria Island
    1 / 9
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Our Holmes Beach duplex, 2 bedroom and 2 bath home is just a short walk, (500 feet), from the beach. We are west of Gulf Drive and north of the Holmes Beach public beach. The downstairs living area has a full kitchen with appliances, spacious dining and living area and a full bath. Upstairs are... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 31 December 2015
    This was the most amazing place to stay. From the condo to the location and lets not forget to mention Fran and Bob who by the way was absolutely wonderful. Bob and Fran made us...
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Steps to Beach and Free Island Trolley ***If your dates are unavailable, call us-we own the villa next door!!!*** Enjoy the best of Florida's Gulf Coast from this brand new, beautiful island vacation villa with Flat Panel TVs, Granite countertops and Stainless Steel appliances. Master Bedroom... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Enjoy Old Florida Quiet Island Living! Is a residential location near attractions important, particularly when this location comes at a reasonable price? Is an easy walk to the white-sand beaches, shopping or dining, something you would consider experiencing? Do you appreciate agreeably... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 12
    3.5 of 5 stars (2) Average
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Gulf Coast's Finest!~ Looking for the ultimate Gulf front luxury vacation? Well, look no further. You will love this ground level 2 bedroom/1 bath condo. Additional amenities include: view gulfpartial (dunes), # baths 1, distance to beach gulf front, bedroom TV yes, bed sizes king, twins, pool... View all property information
    Location Information
    Holmes Beach, Anna Maria Island
    3 of 5 stars Reviewed 10 June 2011
    Condo needs update. The location is great, close to shopping and walk to beach. We will return.
    4 of 5 stars Reviewed 9 June 2011
    We stayed 2 weeks in april and mostly enjoyed the white sandy beach and most importantly no highrisebuildings which would have taken away the beauty.This makes this place extra...
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Situated on the bay and only one block to the gulf beach, Westbay Cove is a lovely home away from home. Lush tropical landscaping surrounds expansive green lawns, 2 heated pools and tennis courts. Dining and shopping are within a short walking distance, as is access to the Island Trolley to... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 19
    4.5 of 5 stars (2) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Balcony
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    About this property
    This townhouse is beautifully decorated and completely modern with everything you need for the perfect vacation in paradise! The townhouse is convenient to everything on the island - walk to the beach, supermarket, retail shops, and restaurants. Or catch the local trolley and cruise the island to a... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    4 of 5 stars Reviewed 10 March 2015
    This was my second birthday celebration at this location. Myself and about 8 of my girlfriends gather to unwind. The location is perfect, we find that shopping at Publix and...
    5 of 5 stars Reviewed 21 October 2014
    This place met all our needs for our beach getaway. Location is close to everything but when you go on the back balconies make you feel like you are on a private getaway on the...
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    1 / 35
    5 of 5 stars (25) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Balcony
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    • Waterfront
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    • Pet-friendly
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    About this property
    TripAdvisor EXCELLENCE AWARD | Exquisite direct beachfront condo with 2 bedrooms, den, and 2 baths | Stunning views | Sleeps 4 | Open kitchen | Granite counter tops | Large storeroom near beach with beach items | Beach side screened lanai with stairway direct to beach | Ceiling fans in every room |... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 30 September 2015
    It is no wonder that this condo received the "Excellence Award", it is everything we wanted and more! The owner is so accommodating and helpful and has equipped this beautiful...
    5 of 5 stars Reviewed 18 September 2015
    The perfect place. Really not much more I can say that hasn't been said in all the other reviews. Already planning to see when we can come back. The owner is very, very...
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    1 / 8
    5 of 5 stars (2) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
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    About this property
    Welcome to Yellowfin Cottage on Anna Maria Island. Completely remodeled in 2013, this duplex is comprised of two stunning beach homes close to the beach in a quiet residential neighborhood. The Yellowfin Cottage side includes a private heated pool (not shared), hot/cold outdoor shower, lush... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 13 April 2015
    We loved this rental! From the moment we walked in, we felt welcomed and pampered. The home gleams and every little amenity was carefully and thoughtfully laid out for us. The...
    5 of 5 stars Reviewed 31 July 2014
    Anna Maria is our favorite place to escape for a beach trip, and I'm so glad we found Lizzie Lu's because their properties are top notch. The duplex we stayed in was recently...
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Patio
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    • DVD Player
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Elder access
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    About this property
    The number 3 island in the United States so says Trip Advisor. The best island beach sand so says Conde Nast Travelers. So who wouldn't want to stay right on the beach in an immaculate and roomy 2 bedroom, 2 bath condominium in the Tiffany Place Condominium located on the Gulf of Mexico in Holmes... View all property information
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    Holmes Beach, Anna Maria Island 34217
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Terrace
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    About this property
    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Have some fun entertaining friends under the covered patio next to the refreshing pool. Brand new 5 bedroom 4 bathroom vacation home in Holmes Beach, just... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 27
    5 of 5 stars (8) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
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    • Pet-friendly
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    About this property
    Perfect 2 bedroom/2 bath, with a private HEATED pool in a very lush tropical setting. Loggerhead is just a couple of blocks to the beach, and the free island Trolley! The front entry takes you right into the open great room where the entire family can hang out and talk about the great time they... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    3 of 5 stars Reviewed 3 weeks ago
    We have just returned from spending 5 weeks at Loggerhead on Holmes Beach, AMI. This property is situated in a perfect location on a quiet street, a 5 minute walk to a gorgeous...
    5 of 5 stars Reviewed 10 December 2014
    Stayed the middle of October and this property was fantastic. Spent a week and wished it was longer. The pool area was perfect, like you were in a tropical oasis. Very short...
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; The patio area and tropical palms create the perfect venue for grilling and time with friends. This beautifully decorated 3 bedroom and 2 bathroom vacation... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Relax and enjoy the tranquility of West Bay Cove with its community of waterfowl, splashing dolphins and slow moving pleasure boats while taking in the panoramic view of Tampa Bay. Your vantage point for these spectacular views is a condo located in the unique Anna Maria Island resort style... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 24
    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Waterfront
    • DVD Player
    • Balcony
    • Washer
    • Wi-Fi
    • Parking
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Elder access
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    About this property
    Grab your flip flops and get ready to head to the beach when staying in this Gulf Sands condo! With a private balcony overlooking the turquoise waters of the Gulf of Mexico, this vacation rental is a fantastic place to stay during your Anna Maria Island vacation. There is plenty of space for... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 4 January 2015
    This was our first time to Anna Maria Island, but we'll certainly come back! We left Chicago at 8:30 and were enjoying fresh fish and eggplant fries (yum!) at The Beach Cafe next...
    5 of 5 stars Reviewed 30 June 2014
    Our family consists of kids ranging from 4 yrs to 18 yrs. We have stayed at Gulf Sands multiple times and for the cost of unit 103, it was by far the best deal! The furnishings...
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    1 / 24
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Satellite TV
    • Waterfront
    • Parking
    • Air Conditioning
    • Grill
    • Outdoor Dining Area
    • DVD Player
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Elder access
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    About this property
    Once you open the door to this Gulf View, you will begin to relax. Restful and soothing beach colors throughout this two-bedroom, two-bath condo will encourage you to have a fabulous vacation on Anna Maria Island. The breathtaking view of the sparkling water through floor to ceiling windows in the... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 5 May 2014
    Gulf View was clean, comfortable and "homey". We had a great week there this april! The view is, no question, outstanding ! The condo was clean and comfortable, the beds were...
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    1 / 34
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Great location close to shopping and restaurants, yet tucked away in a small complex right across the street from the beach. This unit includes cable TV, DVD, High Speed Internet, and Washer/Dryer. Queen in the first Bedroom with TV, twins in the 2nd Bedroom with TV, and a sleeper sofa for any... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 23
    4.5 of 5 stars (3) Very good
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    • Air Conditioning
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    • DVD Player
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Elder access
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    About this property
    Part of the Spinnakers Vacation Cottages compound, Crows Nest is what some have called an adult version of a tree house, so you know kids will love it! A one bedroom, one bath vacation rental that sleeps six, Crows Nest features an awesome private deck where you'll have a great space to enjoy... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 1 week ago
    We loved 202 56th St. (Spinnakers Cottages). We stayed in the Crows Nest. The location was perfect as it was really close to the beach and easy to take the Trolley or Monkey Bus...
    4 of 5 stars Reviewed 2 August 2015
    The Crow's Nest has character and charm in spades. The open plan kitchen/living/dining area is spacious and light, bathroom is a great size and the kids loved their bedroom at...
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    1 / 34
    5 of 5 stars (3) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    This beautifully decorated 3 bedroom and 2 bathroom vacation rental offers all the comforts of home with all the benefits of paradise. Enjoy your time outside in the pool or lounging on the patio surrounded by the tropical palm tree landscaping. Grill up some burgers, steaks, or some fresh seafood... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 12 July 2013
    We stayed in this property for a week over July 4th. The house is absolutely lovely and had everything we needed. The beds were extremely comfortable and the pool is very private...
    5 of 5 stars Reviewed 30 May 2013
    Turtle Nest was in a great location, on a quiet street with easy access to the beach via White avenue. Ample towels and gear are provided for pool and beach. Kitchen well stocked...
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    1 / 23
    5 of 5 stars (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • Satellite TV
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    • DVD Player
    • Private Outdoor...
    • Patio
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Smoking allowed
    • Elder access
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    About this property
    Beautiful 3 bedroom/2 bath beach house with Florida style furnishings! Corian countertops, beautiful Ceramic tile throughout, and high ceilings with crown molding. Private backyard with Heated Pool, waterfall, tropical landscape, and covered patio. Sleeps up to 8 people. Main house 1116 Sq. ft.,... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 22 August 2013
    What an absolute beautiful place for a vacation! It had all the comforts of home, and was beautifully furnished! My kids loved the short walk to the beach, and then when we get...
    5 of 5 stars Reviewed 22 August 2013
    Great house in a perfect location. Short walk to the beach, even with kids. Also close to Publix grocery. Great, fun pool, with plenty of sun and shade. Decor inside is fun...
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Hot Tub
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Elder access
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    About this property
    200 feet to the beach-a short one minute stroll - Gulf Views Three story with elevator, private pool and spa, gourmet kitchen with granite counter tops, double refrigerators, wine cooler, dishwasher, double oven, gas cook top, built-in microwave, disposal - all stainless steel appliances, cherry... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 14
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Grill
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    About this property
    Sea Pirate 1 has been recently renovated throughout and is conveniently located close to shops and restaurants; and most of all; less than 100 feet from the beach. There are eight units total in the complex with a heated pool with easy access to the beach. Amenities Include: Full kitchen, dishes,... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 22
    5 of 5 stars (2) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • Private Outdoor...
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    Beautiful, Brand New, Ground Level 4 bedroom/3 bath home, just a short block to the beach. Beautiful back yard with Heated Pool surrounded by a large paver deck and beautiful outdoor dining and gas grill area by pool. Open Living/Family/Dining Room area for everyone to gather, and attention to... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 2 March 2014
    Our party (three couples) loved Simply Chic! It was spacious, and elegantly appointed, and had everything we needed. The heated pool was used and appreciated, as the air...
    5 of 5 stars Reviewed 18 October 2013
    Simply Chic more than lived up to it's name.Spacious,well laid out,beautifully furnished,fabulous garden, great pool,ideally located(short stroll to the beach and bus stop)quiet...
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    1 / 11
    4 of 5 stars (5) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • DVD Player
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    • Balcony
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    • Terrace
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Elder access
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    About this property
    Florida Living at it's Finest!~ Is a location near attractions important, particularly when this location comes at a reasonable price? Is an easy walk to the white-sand beaches, shopping or dining, something you would consider experiencing? Do you appreciate agreeably appointed units that work... View all property information
    Location Information
    Holmes Beach, Anna Maria Island
    5 of 5 stars Reviewed 10 August 2011
    We have stayed on anna Maria six times now, this was the first time that we have hired fountain head, and it definatly wont be our last. This property is excellent value for...
    5 of 5 stars Reviewed 12 June 2011
    We stayed at Sunset Terrace # l09 not the Fountain Head. Everything was wonderful except the sofa bed in Living Room...was like sleeping on a chain link fence, floor was used...
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    1 / 14
    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    If privacy is calling, quit stalling and come and play at 405 bay!~ 2/2 pool home in a very private tropical setting with lush landscaping. Large, open and airy floorplan. Minutes from the beach and local restaurants and shops. Additional amenities include: sofabed, # baths 2, square feet 1334,... View all property information
    Location Information
    Holmes Beach, Anna Maria Island
    5 of 5 stars Reviewed 17 April 2014
    This is the second time we stayed at the home. The home is located about a 5 min walk to the beach. The home is in a residential area so it is very quiet. The pool in the...
    5 of 5 stars Reviewed 16 June 2011
    The residence was clean and well stocked. It was close to the beach, as described. The morning after we arrived the neighbor blew grass clippings into the pool and the leasing...
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    1 / 35
    4 Bedrooms, 1 Bathroom, Sleeps 10 | Quick View
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Elder access
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    About this property
    Formerly 'Mellow Yellow'. Awesome 4 bedroom/2.5 bath home with an over-sized garage and private elevator access to all 3 levels Gorgeous tropical pool setting with large deck. Beautifully decorated furnished throughout sporting granite counter tops, stainless appliances, wood floors, and 10'... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holmes Beach Vacation 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 vacation 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 vacationing 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 vacation 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 vacation 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 vacation rental. The Beach House Restaurant provides beachfront dining and live music for your enjoyment. Enjoy fresh grouper and a beer close to your vacation rental. You can also rest and relax at the pool at your vacation rental and enjoy a barbeque with your family and friends. Whatever your choice, you will leave the island with unforgettable memories.