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Holmes Beach Rentals with Pools

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Holmes Beach Rentals with Pools

1,812 vacation rentals

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

$150

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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

1 / 29

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 51 minutes

Price per night from

$100

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Cozy Cabana West - Private Pool - Close to Beach

Holmes Beach villa

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 56 minutes

Price per night from

$162

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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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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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510 Bayview

Holmes Beach house

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$857

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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

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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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

$124

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Coconuts Beach Front 106 Ground Floor

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$199

1 / 17

Gulf Sound - A

Holmes Beach condo

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 40 minutes

Price per night from

$162

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Stunning 5 bedroom Pool Home just steps from the beach!

Holmes Beach house

5 bedrooms / 4 bathrooms / sleeps 10

“Absolutely Fantastic” We stayed in this property for a week over July 4th. The house is absolutely lovely and had everything we needed. The beds were extremely comfortable and the pool is very private. We would happily rent this property again.

Price per night from

$350

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

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 10 minutes

Price per night from

$256

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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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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 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

$214

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Coconuts Beach Front 109 Upstairs

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$155

1 / 20

Coconuts Two Bedroom Unit 117 Upstairs Courtyard

Holmes Beach villa

1 bedroom / 2 bathrooms / sleeps 8

Price per night from

$198

1 / 23

Coconuts Beach Front 107 Ground Floor

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$200

1 / 18

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.

Price per night from

$199

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Coconuts Two Bedroom 118 Upstairs Courtyard

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$155

1 / 23

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

Price per night from

$163

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Private Tropical Paradise in Holmes Beach! Large home with Pool and fenced yard

Holmes Beach house

4 bedrooms / 3 bathrooms / sleeps 7

Responds fast! avg. 1 hour 41 minutes

Price per night from

$200

1 / 25

3A Villa's on Anna Maria Island

Holmes Beach villa

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$139

1 / 23

Coconuts Courtyard 119 Upstairs

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$150

1 / 24

Gulf View Townhouses 3

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$129

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Sandy Pointe 110, recently remodel, pet friendly

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$145

1 / 11

Anna Maria The Pink Flamingo

Holmes Beach cottage

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 3 minutes

Price per night from

$199

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Beach Walk- 219 81st St, Holmes Beach

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$200

1 / 33

Coconuts Beach Front 105 Ground Floor

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$199

1 / 19

Coconuts Beach Front 112 Upstairs

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$200

1 / 14

Harbor Lane 4 Harmony

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$144

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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 8 minutes

Price per night from

$143

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Condo in quiet complex

Holmes Beach condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$129

1 / 18

coconuts Courtyard 114 Ground Floor

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$150

1 / 14

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

1 / 29

Gulf Beach Place, miles of whites sandy beach

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 47 minutes

Price per night from

$150

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Viewing 38 of 1,812
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