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Anna Maria Island Rentals with Pools

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Anna Maria Island Rentals with Pools

1,601 vacation rentals

The beautiful Cove on Anna Maria Island

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Beautiful condo, close to everything!” Everything was perfect in the condo which was new and updated! The 2 new full size beds in the 2nd bedroom were too hard. The pool was a nice size and stayed sunny most of the day. Shopping was close and the c

Price per night from

$105

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Breezy Bradenton Beach Condo w/Pool & Water Views!

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 11 minutes

Price per night from

$209

1 / 24

Gulf Beach Place - Just a few steps from the beach

Holmes Beach condo

2 bedrooms / 2 bathrooms / sleeps 6

“Another Fantastic Stay” This is my second time staying at Kay’s Gulf Place Condo! Very clean, comfortable and charming! Location has it all! Sunsets from the rooftop deck are to die for! No detail missed!

Responds fast! avg. 1 hour 34 minutes

Price per night from

$111

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Holmes Beach Condo

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

“Ideal accomodation” I've been traveling from New York to anna Maria Island for nine years and anne's Holmes beach condo is tops. The perfect location.Right next to the perfect beach with great food and surrounded by fine dining and superb shopping. An

Price per night from

$126

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AMI Island Living -Walk to Beach-Ground Level Unit

Bradenton Beach apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$150

1 / 15

Club Bamboo South 223

Bradenton Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$198

1 / 17

Midnightchannel

Anna Maria Island house

7 bedrooms / 5 bathrooms / sleeps 16

Price per night from

$500

1 / 48

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

$138

1 / 123

Bermuda Bay 1467

Bradenton Beach condo

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 36 minutes

Price per night from

$142

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runaway bay 2 bedroom condo with wonderful access to restaurant, beach, shopping

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$151

1 / 18

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 26 minutes

Price per night from

$401

1 / 46

Update One Bedroom/One Bath with view and steps to beach unit 234 runaway bay

Bradenton Beach condo

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 16 minutes

Price per night from

$100

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AnnaMariaIsland a Paradise. MINUMIM RENTAL 2 WEEKS

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$151

1 / 13

Dolphin Pointe

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 1 minutes

Price per night from

$243

1 / 39

'Elegance' 100 Steps from the Beach!

Bradenton Beach house

2 bedrooms / 2 bathrooms / sleeps 5

“Amazing!” This house has it all and a perfect location makes it an even more wonderful place to vacation. We hope to be back soon!

Responds fast! avg. 2 hours 18 minutes

Price per night from

$260

1 / 25

Blue Bayou

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

“"Home from Home"” A very well appointed apartment in a great location that had everything you would wish for to enhance your vacation experience. A real home from home that is clean, well furnished and spacious. The owners have been great to deal wi

Price per night from

$126

1 / 26

Watch Sunsets, Dolphins, or Just Relax - Bermuda Bay 1453

Bradenton Beach apartment

3 bedrooms / 3 bathrooms / sleeps 7

“Great place, great location, and everything you need!” We stayed here to go to my sister's wedding at The Beach House. We loved this townhouse. It had spacious rooms, beautiful decor, and a great view of the ocean from the balcony. I was really imp

Price per night from

$179

1 / 27

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

90 steps to the Beach!

Holmes Beach condo

2 bedrooms / 2 bathrooms / sleeps 5

“Amazing” Absolutely loved our stay! Beautiful condo right next to the beach. Had everything we needed! We will definitely be back!

Responds fast! avg. 3 hours 53 minutes

Price per night from

$165

1 / 30

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

NEW! Holmes Beach Home w/ Pool - Steps to Beach!

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 29 minutes

Price per night from

$258

1 / 29

Harbor Lane 4 Harmony

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$144

1 / 34

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

Price per night from

$181

1 / 12

209 Spring

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$260

1 / 57

A Pearl of a Beach Home - with luxury private heated pool and hot tub

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 6

“out standing place to stay” I would/will stay here again when we come back down. Everything is top notch and the home has everything you need. We enjoyed the pool and hot tube, used it every night. Mike and Lesley are very easy to work with and do

Responds fast! avg. 1 hour 37 minutes

Price per night from

$229

1 / 32

Casa Playa West is a Luxury 4 bedroom home with a pool and elevator!

Bradenton Beach house

4 bedrooms / 4 bathrooms / sleeps 10

“Beautiful home and property” We spent our first family trip to Anna Maria Island at this wonderful property. Everything we could hope for came true. The pictures and reviews do not lie. This is a spacious property that will sleep it's 10 person max wi

Price per night from

$308

1 / 37

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 40 minutes

Price per night from

$359

1 / 23

Luxury 3 Bedrooms/3 Full Baths, Private Heated Pool with Waterfall, Beach

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 8

“Christmas at the Beach” It was a wonderful family vacation for two families going away for Christmas! There were 4 adults and 6 children! The pool was amazing and the house was perfect! Anna Maria Island is gorgeous and the house is in a perfect locat

Responds fast! avg. 1 hour 45 minutes

Price per night from

$206

1 / 34

Cozy Cabana West - Private Pool - Close to Beach

Holmes Beach villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$165

1 / 22

Runaway Bay - Bradenton Beach - Bay View Unit 193

Anna Maria Island condo

2 bedrooms / 2 bathrooms / sleeps 5

“Home away from home” This place is an incredible value. It's spacious and comfortable, and we felt right at home. Sarasota Bay is just steps from the back patio, and it's so lovely to sit outside and watch water--so many fish, dolphins, and birds righ

Responds fast! avg. 34 minutes

Price per night from

$114

1 / 30

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

Happy Island Cottage with heated private Pool

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 8

“Exceeded expectations!” For several years, I've wanted to spend Christmas on AMI with my family. This past Christmas, I was able to do that, and we stayed at Happy Island Cottage. This was a wonderful house to stay in, and Alex was great and very re

Responds fast! avg. 1 hour 11 minutes

Price per night from

$269

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Coconuts Beach Front 106 Ground Floor

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$200

1 / 17

Coconuts Beach Front 109 Upstairs

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$156

1 / 20

Absolute Anna Maria

Anna Maria Island apartment

2 bedrooms / 2 bathrooms / sleeps 5

“A little gem” Lovely condo, great views and ideally situated for restaurants and shopping (all within walking distance). Would definitely come back again.

Responds fast! avg. 1 hour 50 minutes

Price per night from

$130

1 / 100

Bermuda Bay Club betwn the Beach and Bay , elevator, nicely furnished

Bradenton Beach house

3 bedrooms / 3 bathrooms / sleeps 6

“Excellent condo with elevator for all the ladies” Sharkey's Bar and Grill was by far the bet prime rib around. Sandbar had the best fish platter and Skinny's the best burgers and the City Pier Restaurant had great shrimp overall excellent food all ar

Responds fast! avg. 3 hours 48 minutes

Price per night from

$158

1 / 26

Absolutely Perfect - Cove at Sandy Pointe #207

Holmes Beach condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$106

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Viewing 38 of 1,601
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