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54 villas

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Cozy Cabana West - Private Pool - Close to Beach

Holmes Beach villa

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 36 minutes

Travelers’ Choice award

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$188

Coconuts Two Bedroom Unit 117 Upstairs Courtyard

Holmes Beach villa

1 bedroom / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 53 minutes

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$201

3A Villa's on Anna Maria Island

Holmes Beach villa

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 51 minutes

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$138

Stunning luxury beachfront house with pool and spa

Anna Maria villa

4 bedrooms / 5 bathrooms / sleeps 8

“Fabulous beach house” After a mad week doing the theme parks in Orlando we came here for some serious relaxation - and what a great choice it was. The house is stunning and the location couldn't be bettered. Living on the beach meant we could be up for early morning shell hunts and then have evening strolls to the Sandbar for cocktails on the sand watching the glorious sunsets. We saw dolphins, manatees, rays and pelicans. The pool area got a lot of use - a nice shady retreat and good fun for our boys - but most of our time was spent outside. There are lots of lovey restaurants to walk to - the Waterfront, the Sandbar, the two pier restaurants - and you can walk there on the sand. Still picturing the crystal clear sea, sunny skies and white sand. Magical.

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$652

3B Villas on Anna Maria Island Two Bedroom

Holmes Beach villa

2 bedrooms / 1 bathroom / sleeps 6

“Vacation” Nice quiet clean and had everything we needed we had a wonderful time and the beach is only a block away

Responds fast! avg. 3 hours 13 minutes

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$184

Piece of Paradise on Beautiful Anna Maria Island VRC 20-000087

Holmes Beach villa

2 bedrooms / 1 bathroom / sleeps 4

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$159

Lemonfish, stunning and spacious 4-bed rental!

Anna Maria Island villa

4 bedrooms / 3 bathrooms / sleeps 8

“Wonderful location and property!!” We had a great vacation on aMI at Lemonfish. Terrific location for biking, kayaking and general relaxation. It was clean and decorated nicely. The only thing I would say to future renters is there is nothing in the kitchen in terms of salt and pepper, foil, or anything that is food related. In other houses we've rented there have been basic spices, ketchup, etc. Nothing here...but that is not a deal breaker for us. Again, great house and location!

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$449

1A Villas on Anna Maria Island One bedroom

Holmes Beach villa

1 bedroom / 1 bathroom / sleeps 4

“Cute cottage.” Close to the beach, unit 1a had everything we needed. It had a comfortable king bed, small kitchen and internet connection. It was a great choice for us!!! Great value for the price.

Responds fast! avg. 3 hours 13 minutes

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$144

Mintfish, beautiful views across Bimini Bay! 4-Bed

Anna Maria Island villa

4 bedrooms / 4 bathrooms / sleeps 8

“Great View!” The best thing about this home is it's location on Bimini Bay. Beautiful pool and view out over the bay. The home is decorated in a happy motif, although the beds were deemed hard as boxes by a couple of our guests. Kitchen is sufficient for cooking basics, and has nice appliances. Overall a nice stay on a quiet, north end spot of the island.

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$563

Cherryfish, a spectacular spacious 4-bed home!

Anna Maria villa

4 bedrooms / 3 bathrooms / sleeps 8

“Great home, great location!” This home was wonderful for our two families of four. Plenty of space for everyone and the pool was perfect. The only complaint we had was the cleanliness upon arrival, there was long black hair everywhere and the overly fluffy rug in living room had food and garbage stuck in it, which the crawling infants would find each day. The rug was shedding green fuzz everywhere, rug needs to go! It also seemed there must have been pets on the sectional couch at some point, all of us had allergy symptoms when sitting on the couch, even the kids. Otherwise we were very happy with the house itself and location of property and proximity to beaches!

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$492

Beach House on Anna Maria Island-Rental Openings

Holmes Beach villa

3 bedrooms / 3 bathrooms / sleeps 6

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$237

Beach Dreams " Sweet Dreams Villa"

Anna Maria Island villa

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 48 minutes

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$304

Holmes Beach villa

2 bedrooms / 3 bathrooms / sleeps 4

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$327

Beach Walk #3 Beach side Villa

Holmes Beach villa

1 bedroom / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 20 minutes

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$103

Great rentals within 20 miles that match your search

Waterfront Villa Isla Del Sol St Petersburg FL

St. Petersburg villa

2 bedrooms / 2 bathrooms / sleeps 5

“Fantastic getaway” We stayed the month of February and had a wonderful experience. Not only was Will great to work with but the location was fabulous, the views spectacular, and the entire condo was very comfortable to stay in. So much to do or just hang at the heated pool, watching dolphins swim by, and having great conversations with other snow birds from the us and Canada. Such a fun time.

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$179

Direct Beachfront on Serene Gulf of Mexico, Amazing View, Family Friendly

Longboat Key villa

2 bedrooms / 2 bathrooms / sleeps 6

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$519

Siesta Key Oceanfront on Gulf with western sunsets, 1250 sq ft Townhome

Siesta Key villa

2 bedrooms / 3 bathrooms / sleeps 4

“Absolutely Perfect---one Kodak sunset after another” This townhome was gorgeous! We totally enjoyed our 3 week stay and hated to leave. Kelley (owner) could have not been more helpful. We fished off the dock and enjoyed watching the birds fish then dry their wings. Town is a short, enjoyable jaunt. Just a few blocks further are the most gorgeous beaches with sand like flour! If you are adventureous, walk to Point of Rocks at beach access 13 for the best shelling ever (only at very low tide)!!! We would come back in a heartbeat. The views from the lanai and upstairs balcony were awesome. Townhome was beautifully maintained and fully stocked. Thanks to Kelley and her daughter for a never-to-be-forgotten vacation.

Responds fast! avg. 2 hours 13 minutes

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$148

55+ Community with pool and club house

Longboat Key villa

2 bedrooms / 2 bathrooms / sleeps 6

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$87

Bradenton villa

2 bedrooms / 2 bathrooms / sleeps 5

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$154

cozy two bedroom unit

St. Petersburg villa

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 14 minutes

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$73

Serene Sarasota Getaway near shopping and golfing.

Fruitville villa

3 bedrooms / 2 bathrooms / sleeps 6

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$124

Villa FloridaDream, Exclusive Florida Villa in Strandnähe mit Pool in Bradenton

Bradenton villa

4 bedrooms / 2 bathrooms / sleeps 8

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$175

Waterfront with a private beach

St. Petersburg villa

1 bedroom / 1 bathroom / sleeps 4

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$110

shorewalk A+ 2/2 downstair unit.5 mins IMG 10mins to beach

Bradenton villa

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 48 minutes

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$108

Beautiful 3 bedroom villa with private pool and lake view

Bradenton villa

3 bedrooms / 2 bathrooms / sleeps 6

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$173

Luxurious Lakeside Villa -Pool,Spa & Games Room

Bradenton villa

3 bedrooms / 2 bathrooms / sleeps 6

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$179

St. Pete Beach for New Year's Eve

St. Pete Beach villa

1 bedroom / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 12 minutes

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$417

Tradewinds Inland Grand Resort, St. Pete’s Beach, Florida, Sept. 24th – Sept 29t

St. Pete Beach villa

2 bedrooms / 3 bathrooms / sleeps 8

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$149

Little Palms Villa. A lakeside home with style.

Bradenton villa

3 bedrooms / 2 bathrooms / sleeps 6

“Excellent” Our stay at 4638 Runabout way was amazing. We loved that the house was very nice, spacious, and clean for my family and I. We loved swimming in the pool everyday. The service was excellent all around. We would definitely stay there again.

Responds fast! avg. 2 hours 22 minutes

Travelers’ Choice award

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Price per night from

$155

Viewing 38 of 54
villas in Anna Maria Island

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Villas Anna Maria Island

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54 villas

Viewing 38 of 54villas in Anna Maria Island

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Viewing 38 of 54
villas in Anna Maria Island