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Holmes Beach Rentals with Pools

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1,306 apartments in Holmes Beach with pools

Anna Maria Island, 2 Bed, 2 Bath Condo in quiet setting near to Beaches

Holmes Beach condo

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 city beach also was close. We would drive down the road to our favorite stretch of the beach. I would definitely stay here again, very quiet location off the beaten path, but not far from it! Love the beach chairs, towels, cooler, umbrella, pool toys, and more provided!

Match: Swimming pool

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Price per night from

$124

Gulf Beach Place - Just a few steps from the Beach

Holmes Beach condo

2 bedrooms / 2 bathrooms / sleeps 6

“Beautiful, friendly Beach Condo” Beautiful Condo right on the beach with awesome sunsets from the roof and a Dunkin Donuts within walking distance. While the teen/young adult slept in, I visited DD and walked the beach. The owner had a manual that provided lots of activities around the area and places to eat. We enjoyed our stay and would definitely visit again!

Responds fast! avg. 49 minutes

Match: Swimming pool

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Price per night from

$263

Cozy Cabana West - Private Pool - Close to Beach

Holmes Beach villa

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$207

Blue Bayou

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 4

“"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 with and nothing is too much trouble. I have already recommended this accommodation to friends who were similarly impressed and we will be staying here for the third time later this year.

Responds fast! avg. 3 hours 18 minutes

Match: Swimming pool

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Price per night from

$124

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 the first time. Her dream was made reality staying at a beautiful beach house only 1 1/2 blocks from the beach. The beach access was beyond beautiful and as close to your own private beach, for at this time of year there was no crowding. The pool at the house was great for cooling off after a day at the beach and the pool room had several toys and floating devices for the kids to use. The house was fully stocked with towels for multiple days and the washer and dryer came in handy with babies around! The living room seating was great for a big family to gather around for late night discussions and the kitchen stocked with basic appliances for cooking and cleaning.The only thing that could have made the stay better, was a little comfier mattresses in the bedrooms. However the case, this beach house was a cherry on top to my family's short fall vacation to Florida!

Match: Swimming pool

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Price per night from

$337

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!

Match: Swimming pool

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Price per night from

$195

A Pearl of a Beach Home - now with luxury Saltwater 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 anything to make things go smoothly.

Responds fast! avg. 1 hour 44 minutes

Match: Swimming pool

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Price per night from

$310

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. 1 hour 51 minutes

Match: Swimming pool

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Price per night from

$241

Anna Maria The Pink Flamingo

Holmes Beach cottage

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 36 minutes

Match: Swimming pool

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Price per night from

$203

3A Villa's on Anna Maria Island

Holmes Beach villa

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 3 minutes

Match: Swimming pool

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Price per night from

$148

PARADISIAC ENCLAVE 5* Waterfront Canal Pool Home-Dock/Kayak/Bikes/Family fun

Holmes Beach house

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$452

coconuts Courtyard 114 Ground Floor

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 51 minutes

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Price per night from

$160

Coconuts Courtyard 119 Upstairs

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 51 minutes

Match: Swimming pool

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Price per night from

$163

Island Vacation Rental

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Island Paradise” The moment we arrived, exhausted after many delays and problems, the Thomas' home became our home. The condo is well appointed, with comfortable beds, a wonderful kitchen and a fully stocked linen closet, right down to beach towels. Laine, Kevin and Howard are so responsive and saw to all of our needs. Location was prime. We walked to get groceries, eat and do other shopping. There were 7 miles of beaches to explore and the quaint villages of anna Maria and Cortez and Bridge Street kept us occupied when we weren't soaking up the sun. The lanai was my favorite place to drink my coffee and check out the action at the pool each morning . We ate the majority of our meals there, under the twinkling lights. It was a wonderful month!

Match: Swimming pool

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Price per night from

$147

Gulf Beach Place, miles of whites sandy beach

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$212

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. 1 hour 51 minutes

Match: Swimming pool

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Price per night from

$192

Coconuts Courtyard 116 Ground Floor

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 51 minutes

Match: Swimming pool

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Price per night from

$160

Anthony Beach Cottages Bare Feet Retreat

Holmes Beach cottage

3 bedrooms / 1 bathroom / sleeps 6

Match: Swimming pool

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Price per night from

$258

Coquina Sands, view beach from balcony, priv pool

Holmes Beach house

2 bedrooms / 3 bathrooms / sleeps 6

“Great place, great location, great vacation” We stay at Anna Maria for 12 days and if we could we would be there for 12 years. Awesome place and great host. Everything was ready for us. Only high marks. Thanks

Match: Swimming pool

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Price per night from

$328

Great Townhouse Very Close to the Beach, Shops, and Restaurants

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

Match: Swimming pool

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Price per night from

$258

Holmes Beach Family Home w/Private Pool & 3 Decks!

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 48 minutes

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Price per night from

$295

Lifestyle on the island

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 4

Match: Swimming pool

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Price per night from

$125

Anna Maria Island Beach Paradise 6

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 27 minutes

Match: Swimming pool

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Price per night from

$180

Castnetter Beach Resort 5

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 21 minutes

Match: Swimming pool

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Price per night from

$281

Direct Beachfront 2 BR Condo on Florida’S Beautiful Gulf Coast!

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 4

“A trip to paradise.” From the breathtaking views of both the Gulf and the Bay to the wonderful, eclectic furnishings, this condo is everything one could hope for. It has great amenities for entertaining friends and every convenience you will need. The heated pool overlooks the Gulf and allows direct access to the beach and the elevator provides ease in getting up to the condo. This vacation was the most enjoyable I've ever experienced.

Responds fast! avg. 3 hours 20 minutes

Match: Swimming pool

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Price per night from

$378

Contemporary Beach House, Very Private Yard & Pool - 1.5 Blocks to Beach

Holmes Beach house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 32 minutes

Match: Swimming pool

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Price per night from

$197

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. 2 hours 14 minutes

Match: Swimming pool

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Price per night from

$148

Coconuts Poolside Unit 101

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 38 minutes

Match: Swimming pool

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Price per night from

$174

Beach View 7 - a 2 Bed/ 2 Bath 2nd floor condo w/pool and close to the beach

Holmes Beach condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 15 minutes

Match: Swimming pool

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Price per night from

$100

Sunkissed

Holmes Beach townhouse

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$294

3003 AVE F - WEST

Holmes Beach house

2 bedrooms / 1 bathroom / sleeps 6

Match: Swimming pool

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Price per night from

$343

129 51ST STREET

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 10

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Price per night from

$432

Palm Villa - a 3 bedroom, 3 bath home with heated pool

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 15 minutes

Match: Swimming pool

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Price per night from

$277

104 30TH ST

Holmes Beach house

3 bedrooms / 2 bathrooms / sleeps 10

Match: Swimming pool

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Price per night from

$628

Sapphire Beach House

Holmes Beach villa

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$294

Gertie's East - a great 1/1, just steps to the beach. With Relaxing Pool!

Holmes Beach cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 15 minutes

Match: Swimming pool

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Price per night from

$110

Moorings - pool view from this 2 bedroom/ 2 bath condo on Anna Maria Island!!

Holmes Beach condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 15 minutes

Match: Swimming pool

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Price per night from

$140

3004 AVE E

Holmes Beach house

3 bedrooms / 2 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$362

Viewing 38 of 1,306
rentals in Holmes Beach

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