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Luxury Villas in Holmes Beach, FL

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    Travellers to Holmes Beach are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 24
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    ** Call +1 908 236 2966 to inquire 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... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 46
    6 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    OCEAN VIEW is a brand new construction home that features 6 bedrooms and 5.5 bathrooms and a fantastic location-just a 1 minute stroll to the White sandy beaches at the 65th st access! This lovely property offers a private heated pool with a spa, water slide and grotto. The backyard is an oasis... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 28
    4 of 5 stars (1) Very good
    8 Bedrooms, 5 Bathrooms, Sleeps 18 | Quick View
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    Welcome to the ultimate in Large Family luxury vacation Homes, with beautiful views of the Gulf of Mexico and sunsets from the Roof Top Deck. This beautiful 8 bedroom/5.5 bath home resides only one short block to the beach and features a gorgeous kitchen with Granite countertops and Stainless... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    4 of 5 stars Reviewed 8 July 2015
    We rented Poseidons Palace for our family reunion there were 18 of us in the house and we never felt like we didn't have enough space. Beds were comfy our only complaint was that...
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    1 / 35
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; The perfect condominium with direct views of the pristine Gulf of Mexico, you’ll want to vacation at “La Casa LaMar” year after year. This ground level 3... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 15
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.;   Luxury is here in this brand new direct gulf front three bedroom and three full bath Anna Maria island luxury holiday rental. Relax your cares away in the... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 39
    5 of 5 stars (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    This brand new 4 bedrooms and 4 bathrooms home has some of the best sunset views on Anna Maria Island!! Located a block from the beach, it is only a 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 & stores... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 12 November 2015
    We were a group of 6 women. Our desicion to stay was based on amenities offers in relation to proximity to the water. This was the best of everything. Beach views or walk one...
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    1 / 62
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    ** Call +1 908 236 2966 to inquire about this property You will be hard-pressed to find something more luxurious than La Casa 12. This high-end condominium is in demand year around. One step inside and you will immediately know why. This luxury property has all the touches - crown molding,... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
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    1 / 14
    3 of 5 stars (1) Average
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    The Beachcomber, located at 3306 4th Avenue in Holmes Beach is the ideal, dream vacation home. This gulf front home is newly constructed and features a brand new heated pool and spa nestled in a tropical setting. It does not get any better than this! Luxurious furnishings, an elevator, a gourmet... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    3 of 5 stars Reviewed 28 September 2014
    owners need to be honest, fix the pool and hot tub dont advertise heated pool and hot but its broke, and has been for some time according to the pool guy and beleive that its a...
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    1 / 10
    4 of 5 stars (2) Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    529 Key Royale - Private canal home 6 Bedroom / 5 Bath with private pool , maximum occupancy of 12 people. Outstanding large home perfect for a family! This beautiful Florida pool home is on a canal offering 6 bedrooms- 5 bathrooms . Luxury at its best! Sip your coffee in the morning on the... View all property information
    Location Information
    Holmes Beach, Anna Maria Island
    4 of 5 stars Reviewed 13 June 2011
    We had a large family group of all ages. We all had loads of space, the house is pretty new and had been equipped to a high standard. the pool and dock were good for relaxing and...
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    1 / 41
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    ** Call +1 908 236 2966 to inquire about this property Island Paradise is just that - the best view on Anna Maria Island. Panoramic views of the beautiful blue waters of the Gulf of Mexico and the white sand beaches. And don't forget the legendary sunsets. It simply does not get any better than... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Key Lime Cottages 202 & 204  welcomes you to this recently re-done and updated island duplex. Just steps from the Gulf of Mexico and the pure white sandy... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    6 Bedrooms, 5 Bathrooms, Sleeps 15 | Quick View
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    About this property
    SUNSET SHORES is a brand new construction home that features 6 bedrooms and 4.5 bathrooms and a fantastic location-just a 1 minute stroll to the White sandy beaches at the 65th st access! This lovely property offers a private heated pool with a spa & water slide! The backyard is an oasis with... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 9
    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    Fantastic private custom-built vacation rental home just a few houses to the white sandy beaches of Anna Maria Island and the Gulf of Mexico. Enjoy the large heated pool that boasts a cascading rock waterfall and hot tub all in a tropical paradise setting! Spend the day on the best beaches you will... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 18
    5 of 5 stars (1) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Relax in this new luxury home just a block from the beautiful beaches of Anna Maria Island. The Blue Sky Beach House is one side of a newly constructed private duplex that was completed in 2015. It is a stylish and cozy retreat with 5 bedrooms and 4 bathrooms, 5 flat screen TV's, private heated... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34218
    5 of 5 stars Reviewed 11 May 2016
    Our group of 7 friends felt right at home in this gorgeous and comfortable home. The private pool afforded our sun lovers and shade seekers equal opportunity to relax outside...
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    1 / 24
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Seabreeze Villa is a fabulous home for your vacation on Anna Maria Island. This beautiful Mediterranean designed home is located in central Holmes Beach, and is within walking distance of shopping, restaurants, and the white sand beach! This spacious home is equipped with a fantastic kitchen,... View all property information
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    Holmes Beach, Anna Maria Island
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    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 / 10
    4.5 of 5 stars (5) Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    517 Key Royal - Private canal home 5 Bedroom / 5 Bath with private pool, maximum occupancy of 10 people. Island Breezes and Magical Sunsets Await your arrival!~ 517 Key Royale - Beautiful View of Tampa Bay from upstairs Deck. Great house for large family - maximum 10 People, Handicap Friendly -... View all property information
    Location Information
    Holmes Beach, Anna Maria Island
    5 of 5 stars Reviewed 26 February 2016
    This is the 1st review I've ever written! Our party of 10 absolutely loved our stay here! We loved the island and all it had to offer. This house is fantastic, so relaxing to be...
    5 of 5 stars Reviewed 4 September 2015
    Having stayed in a less than satisfactory house on the first leg of our Florida holiday, we arrived at Key Royale Drive with feelings of trepidation. OH MY!! What a fabulous...
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    1 / 10
    5 of 5 stars (3) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    510 Bayview - Private canal home 3 Bedroom / 3 Bath with private pool , maximum occupancy of 6 people. Island Elegance for the whole family!~ Come to Anna Maria Island, bring family, friends and your boat to enjoy the simple pleasures of life: sun, sand, and surf. Relax in well-appointed rooms,... View all property information
    Location Information
    Holmes Beach, Anna Maria Island
    5 of 5 stars Reviewed 29 April 2016
    Had a fantastic week here nine adults and we did not bump into one another once 4double rooms and 1 twin all with their own bathrooms pool area great pity that the water display...
    5 of 5 stars Reviewed 29 December 2015
    I recently stayed at this beautiful house and it was the best decision I made for the holiday. First, the rental company was so easy to work with. There was no stress at all. Even...
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    1 / 31
    8 Bedrooms, 6 Bathrooms, Sleeps 22 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Enjoy this set of elevated vacation homes with two private lagoon style perfect for large family getaways. (8) Bedroom, (7) Bath, accommodates up to (23)... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 28
    6 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Luxurious custom built multi-level tropical oasis and pool paradise. (6) Bedroom, (4.5) Bath, accommodates up to (14) people: 3 Kings, 2 Queens, 1 Bunk Bed,... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 26
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Magical and stunning vacation rental with an enviable backyard that includes a wet bar and pool oasis. (5) Bedroom, (3.5) Bath, accommodates up to (12)... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    6 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Visit this marvelous private custom-built vacation rental home just a few steps from the white sandy beaches of Anna Maria Island and the Gulf of Mexico. 6... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 24
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Welcome to Sunset Glow - a Brand New vacation home in our rental program! Live the life of luxury right in the heart of Anna Maria Island. This home was... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    You’ll enjoy an amazing Anna Maria Island vacation when you visit upscale gulf front condominium L’Plage 6420 Gulf Drive in Holmes Beach! This three bedroom three bathroom home spaciously accommodates up to eight guests with beach style luxury. Everything you expect from a relaxing stay can... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 14
    5 of 5 stars (1) Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    532 70th - Private canal home 5 Bedroom / 5 Bath with private pool , maximum occupancy of 10 people. 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... View all property information
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    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 / 17
    6 Bedrooms, 4 Bathrooms, Sleeps 16 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Fantastic new private vacation rental home with outstanding Gulf Views from two of the four balconies and large heated pool equipped with a swim up Tiki hut... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    6 Bedrooms, 4 Bathrooms, Sleeps 16 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; A dream come true holiday oasis perfect for large families. (6) Bedrooms, (4.5) Bath, accommodates up to (16) people: 4 King, 1 Queen, 2 Twin, 2... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    When you arrive at Anna Maria Island vacation rental home “Mermaid Crossing” you are greeted with true island style and luxury. This three bedroom three bath room home spaciously accommodates up to six guests with one king bed, two queen beds and endless charm. Located in the central area of... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.;   Welcome to Wind Song!  This is a brand new  single family home. You are only two houses to the beautiful crystal clear waters of the Gulf Mexico!... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    5 Bedrooms, 4 Bathrooms, Sleeps 11 | Quick View
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    * SPECIAL DOES NOT INCLUDE SPRING BREAK WEEK OF APRIL 2-9TH OR MEMORIAL WEEKEND Be one of the first to enjoy this brand new 5 bedroom, 4 bathroom beach home just a one minute walk to the famous Anna Maria Island beach. The beach stretches for miles in each directions. Feel the powdery sand... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.;  Welcome to Casa Varadero a new ground level vacation rental home on Anna Maria Island in the quiet upscale neighborhood of Key Royale.This canal front home... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    4 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; (3) Bedroom, (3) Bath (Sleeps 6) – “Beachy Blue”- 129 52nd St in Holmes Beach. “Beachy Blue” is a magnificent Anna Maria Island vacation home that will... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 40
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Relax in absolute style in this immaculate 4 bedroom, 4.5 bath home. Coastal to the core with its bright, airy, sea-side inspired design and finishes. Every detail, a perfect one, to make you feel right at home and, of course, right at the beach! The front entry spills into the spacious great room... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 39
    2 of 5 stars (3) Poor
    6 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • Pet-friendly
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    • x
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    Welcome to the ultimate in Large Family luxury vacation Homes, with peeks of the Gulf of Mexico from the balconies. This Brand New, 6 bedroom/4.5 bath home with 10' ceilings, Granite countertops, and Stainless Appliances features a large privacy fenced yard, Tropical Heated Pool and Hot Tub, Swim... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    1 / 40
    5 of 5 stars (2) Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • ?
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    • x
    About this property
    Welcome to the ultimate in large family luxury vacation homes, with peeks of the Gulf of Mexico from the balconies! This 6 bedroom/4.5 bath beauty features a large, private, tropically landscaped backyard with heated pool and hot tub, gas grill, swim up tiki, and covered tiki bar area with flat... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 23 June 2015
    We travel to the beach every year with my extended family of 14 and WOW this was the most amazing place we have stayed. The pool is amazing, bar table for the adults, shallow...
    5 of 5 stars Reviewed 28 May 2015
    I found this house online and when I called to reserve it everything went smoothly with friendly service. When we arrived to check in, everything was ready and we were given...
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    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Holmes Beach vacation rental “Rest Assured” is a fun tropical inspired ground level home comfortably accommodating up to 8 vacationers. Located in beautiful... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 16
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; 3 Bedroom, 2.5 Bath (Sleeps 6) - “Palm Gables” 106 36th Street in Holmes Beach. Enjoy the gulf front Anna Maria Island vacation you deserve when you... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 24
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    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.; Spend your Anna Maria Island vacation in five star luxury when you visit “Fernweh”. This new Holmes Beach vacation rental offers both a stylish and relaxing... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 16
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Coastal and spacious vacation paradise seasonal rental  (4) Bedroom, (2.5) Baths, accommodates up to (8) people: 1 King, 1 Queen, 2 Twin, 1T with Trundle... 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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    • Pet-friendly
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    • x
    • ?
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    • x
    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
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    Holmes Beach, Anna Maria Island
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • ?
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    • x
    About this property
    At 4 bedrooms and 3 full bathrooms, this is one of the best rentals on Anna Maria Island. Straight down the road 1 block to the beach, and around the corner to restaurants, pubs & stores. Featuring a huge heated pool to relax in after your busy day, Conch Out Beach House is a luxurious and welcome... View all property information
    Location Information
    Holmes Beach, Anna Maria Island
    1 / 23
    5 of 5 stars (1) Excellent
    3 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
    other travellers have booked this property
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    • Pet-friendly
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    • x
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    • x
    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 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; If you're looking to spend your holiday in a luxurious and relaxing setting “La Casa Wendt” is the place to be! Located on direct gulf front in the “La Casa... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 28
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Terrace
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    • Shared Outdoor Pool...
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    • x
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    • x
    About this property
    541 67th - Private canal home 5 Bedroom / 4 Bath with private pool , maximum occupancy of 10 people. Beach Bound!~ If you are looking for s---5 bedroom 4 bath canal front home. Great rental for a large family---maximum 10 people. Light open kitchen with breakfast bar, home has a spacious open... View all property information
    Location Information
    Holmes Beach, Anna Maria Island
    1 / 51
    5 of 5 stars (3) Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Private Outdoor...
    • Satellite TV
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    • Air Conditioning
    • Ocean Views
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Beautiful 5 bedroom 4 bathroom vacation home in Holmes Beach, just steps from the beach with fantastic Gulf views. This home is the perfect beach getaway with everything you could want while enjoying Anna Maria Island. Just imagine waking up to the sound of the surf rolling in. Enjoy a cup of... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217
    5 of 5 stars Reviewed 3 March 2013
    We had the most wonderful four days in this house with our baby son. The house is just two blocks from the beach and comes with basic gear (towels, umbrella, chairs, wagon...
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    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
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    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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.; One of the best vacation spots on Anna Maria Island, “La Casa Marie” is an amazing  gulf front 3 bedroom 2.5 bathroom Holmes Beach vacation rental... View all property information
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    Holmes Beach, Anna Maria Island 34217
    1 / 24
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Terrace
    • Balcony
    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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.;  It’ll be hard to miss the style, taste, and indulgence waiting for you at this three story, Holmes Beach vacation home. From the moment you pull into the... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217