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Holmes Beach Rentals with Pools

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Holmes Beach Rentals with Pools

1,715 vacation rentals

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 30 minutes

Price per night from

$100

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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

$104

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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

$125

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Coconuts Beach Front 112 Upstairs

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 59 minutes

Price per night from

$200

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Coconuts Beach Front 109 Upstairs

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 59 minutes

Price per night from

$156

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Absolutely Perfect - Cove at Sandy Pointe #207

Holmes Beach condo

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$105

1 / 21

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

$125

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Gulf Beach Place, miles of whites sandy beach

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 48 minutes

Price per night from

$150

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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 59 minutes

Price per night from

$180

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Cozy Cabana West - Private Pool - Close to Beach

Holmes Beach villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$165

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Coconuts Two Bedroom Unit 117 Upstairs Courtyard

Holmes Beach villa

1 bedroom / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 59 minutes

Price per night from

$200

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Coconuts Courtyard 116 Ground Floor

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 59 minutes

Price per night from

$150

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Coconuts Beach Front 106 Ground Floor

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 59 minutes

Price per night from

$200

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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

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Luxury 3BR/3BA, Private Heated Pool, 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

$205

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coconuts Courtyard 114 Ground Floor

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 59 minutes

Price per night from

$150

1 / 14

Harbor Lane 4 Harmony

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$144

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LaPlayita Condo

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

“This facility was just what we expected” La Playita is very plain from the outside but the interior was very comfortable. The pool is adequate and the proximity to the beach is convenient. Everything in this condo worked which is often not the case in

Price per night from

$114

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Coconuts Two Bedroom 118 Upstairs Courtyard

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 59 minutes

Price per night from

$156

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Gulf View Townhouses 3

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$129

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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

$164

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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 59 minutes

Price per night from

$140

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Coconuts Beach Front 108 Ground floor

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

“Great” Great location! Beautiful view. The condo was was spacious enough for a small group. The beds were a little harder than I would like but the location of the condo and view were great.

Responds fast! avg. 3 hours 59 minutes

Price per night from

$200

1 / 19

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 105 Ground Floor

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 59 minutes

Price per night from

$200

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Anthony Beach Cottages Island Retreat

Holmes Beach house

4 bedrooms / 4 bathrooms / sleeps 8

“Family friendly” My family and I enjoyed our stay in Florida and we all loved being able to be under one roof again. My mothers dream was to take us 6 kids, now adults, to the ocean again. Also, she wanted her two new grand-sons to see the ocean fir t

Responds fast! avg. 2 hours 29 minutes

Price per night from

$300

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Coconuts Poolside Unit 101

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 59 minutes

Price per night from

$165

1 / 17

Island Beach Club 4

Holmes Beach apartment

2 bedrooms / 1 bathroom / sleeps 4

“What a wonderful beach and ocean” 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 special.The appartment was very comforta

Price per night from

$186

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Anna Maria The Pink Flamingo

Holmes Beach cottage

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 28 minutes

Price per night from

$199

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Coconuts Poolside Unit 104

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

“The BEST spot on the island!” 24 hours ago we got home from our vacation to Anna Maria at the Coconuts! I'm already wishing we could get a plane and head back!! We absolutely love this island.. And finally lucked out finding the perfect place to stay

Responds fast! avg. 3 hours 59 minutes

Price per night from

$165

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Island Beach Club 22

Holmes Beach apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$143

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Anna Maria Great Townhouse, Great Value!

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 6

“Famous Holiday” Everything was so perfekt ... WE CAME back next Year THE HOUSE BEAUTIFUL AND CLEAN.. THE Area perfekt

Responds fast! avg. 3 hours 13 minutes

Price per night from

$157

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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

$125

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Island Dream

Holmes Beach house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 56 minutes

Price per night from

$250

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Coconuts Beach Front 107 Ground Floor

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 59 minutes

Price per night from

$200

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AnnaMariaBeachCondo - Bright and Spacious Condo w Heated Pool!

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Significant Birthday” My "significant" birthday involved me and my closest girlfriends truly unwinding from our very busy lives. The place is extremely clean and well appointed. We prefer to prepare meals instead of going out and the kitchen has EVERY

Responds fast! avg. 3 hours 7 minutes

Price per night from

$143

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Coconuts Courtyard 119 Upstairs

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 59 minutes

Price per night from

$150

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Anthony Beach Cottages Bare Feet Retreat

Holmes Beach cottage

3 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 2 hours 29 minutes

Price per night from

$225

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