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Anna Maria Rentals with Pools

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Anna Maria Rentals with Pools

1,641 vacation rentals

Ocean View 3 bedroom, pool, North Shore Drive

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

“Amazing Oceanview Pool Home and Perfect Location On Anna Maria Island” Let me first say that Mark (the home owner) exceeded any and all expectations for our 15th wedding Anniversary! We booked last minute and when we wanted to stay an additional day M

Responds fast! avg. 49 minutes

Price per night from

$164

1 / 123

Dolphin Pointe

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 1 minutes

Price per night from

$242

1 / 39

Island Oasis - 94 North Shore Drive, Anna Maria

Anna Maria house

4 bedrooms / 5 bathrooms / sleeps 8

Price per night from

$315

1 / 26

Seabatical- 225 Willow Ave, Anna Maria

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$200

1 / 26

744 Jacaranda Rd

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 6

“Nice getaway” Nice home! Large enough for family. Decks and heated pool were great!

Price per night from

$275

1 / 32

Stay & Spoil yourself! Pool, Hot tub,Fish, Dock, Kayak* Steps to Gulfside beach!

Anna Maria house

4 bedrooms / 3 bathrooms / sleeps 8

“Terrific home” Beautiful, comfortable home with lovely pool and just a short walk to gulf. Pictures don't fully capture how nice this home is! Our family had a wonderful week and hope to return again.

Responds fast! avg. 1 hour 36 minutes

Price per night from

$356

1 / 23

Gorgeous views,spectacular home!

Anna Maria house

5 bedrooms / 3 bathrooms / sleeps 12

“Majestic Views” Our family loved our visit to Anna Maria. The house is gorgeous and spacious. My kids enjoyed the pool and eating outside. We hope to return in the near future.

Responds fast! avg. 2 hours 29 minutes

Price per night from

$374

1 / 46

Blue Heron Waterfront House Anna Maria island

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 17 minutes

Price per night from

$309

1 / 23

5 Star - Private Pool & Dock, and Steps Away from the Beach - Fall Availability

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 30 minutes

Price per night from

$348

1 / 39

Anna Maria Island "High End" Vacation Rental

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

“Excellent” Beautiful place, secluded and private. Very clean and Pet friendly. Could not ask for anything more.

Responds fast! avg. 3 hours 27 minutes

Price per night from

$225

1 / 21

Tarpon Point - 302 Tarpon Street, Anna Maria

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$286

1 / 35

Pelican Roost 505

Anna Maria house

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$464

1 / 33

Beachy Keen 408

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$275

1 / 21

Concha Marina- 235 Chilson Ave, Anna Maria

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$186

1 / 35

Crescent Wave

Anna Maria house

4 bedrooms / 3 bathrooms / sleeps 8

“Absolutely wonderful!!” This house is even better than it looks in the pictures .... everything you might want or need while on vacation is provided. It was extremely clean, and the location is perfect. The center across the street is a real bonus w

Responds fast! avg. 1 hour 29 minutes

Price per night from

$200

1 / 44

Sand Castle well appointed home steps from beaches

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 17 minutes

Price per night from

$299

1 / 25

Stunning luxury newly constructed beachfront villa

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

Price per night from

$700

1 / 22

4 bed luxury upscale executive waterfront home

Anna Maria house

4 bedrooms / 4 bathrooms / sleeps 8

“Relaxing, Fun, Fully equipped and great location.” Loved the house it has an elevator since I have really bad knees it was great. I hope to rent it again. I wish I could have used all the equipment they had like the kayaks but my knees are way to ba

Price per night from

$292

1 / 50

Gladiolus on the Water

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$239

1 / 25

The Oleander House

Anna Maria house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$343

1 / 24

Beach To Bay Getaway

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$239

1 / 23

Copacabana

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$214

1 / 21

209 Spring

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$260

1 / 57

Blue Dolphin Inn - All Units

Anna Maria house

9 bedrooms / 6 bathrooms / sleeps 26

Price per night from

$489

1 / 33

Blue Dolphin Inn - Skimmer Dow

Anna Maria house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$146

1 / 21

Egrets Perch - 208 Palmetto Ave, Anna Maria

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$172

1 / 35

Key West Condo - 1201 Gulf Drive North

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$215

1 / 29

Canalfront Anna Maria Cottage w/ Pool & Hot Tub!

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 21 minutes

Price per night from

$259

1 / 39

Blue Dolphin Inn - Ibis

Anna Maria house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$146

1 / 17

Dragonfly Pointe - a Charming Cottage Steps from the Beaches of Bean Pointe

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$325

1 / 37

Paradise Cottage

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$165

1 / 23

Haupia House

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$204

1 / 25

AMI Du Soleil

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$196

1 / 23

Las Palmas - 120 Park Avenue, Anna Maria

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$207

1 / 16

Flamingo's Nest

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$219

1 / 24

DRAGONFLY - Southern Charm in Anna Maria's Exclusive Bean Point

Anna Maria house

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$750

1 / 35

Tarpon Pointe

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$230

1 / 23

Blue Dolphin Inn - Flamingo Up

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$200

1 / 23
Viewing 38 of 1,641
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