Holmes Beach Rentals with Pools

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799 apartments in Holmes Beach with pools

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 14 minutes

Match: Swimming pool

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Price per night from

$123

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

$344

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.

Match: Swimming pool

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Price per night from

$475

Anna Maria The Pink Flamingo

Holmes Beach cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$263

Anna Maria 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!

Responds fast! avg. 1 hour 11 minutes

Match: Swimming pool

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Price per night from

$166

Gulf Beach Place, miles of whites sandy beach

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$286

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

$315

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

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$344

Lifestyle on the island

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 57 minutes

Match: Swimming pool

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Price per night from

$213

Anna Maria Island Beach Paradise 6

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$218

Castnetter Beach Resort 5

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$315

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.

Match: Swimming pool

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Price per night from

$429

Sunkissed

Holmes Beach townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 47 minutes

Match: Swimming pool

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Price per night from

$337

129 51ST STREET

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 47 minutes

Match: Swimming pool

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Price per night from

$472

Sapphire Beach House

Holmes Beach villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 47 minutes

Match: Swimming pool

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Price per night from

$337

1 Step Closer

Holmes Beach villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 48 minutes

Match: Swimming pool

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Price per night from

$274

7 Doors Down

Holmes Beach villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 48 minutes

Match: Swimming pool

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Price per night from

$337

Blue Coconut Bungalow

Holmes Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 3 minutes

Match: Swimming pool

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Price per night from

$337

Walk to the beach, from this remodeled condo! Pool, WIFI, restaurants, shopping

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Swimming pool

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Price per night from

$229

Ebb Tide

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 13 minutes

Match: Swimming pool

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Price per night from

$337

Castnetter Beach Resort 6

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$315

SeaStar Villa

Holmes Beach house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 48 minutes

Match: Swimming pool

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Price per night from

$337

Anna Maria Island Beach Paradise 5

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$244

BEACHVIEW CONDO

Holmes Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 47 minutes

Match: Swimming pool

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Price per night from

$250

PALM CAY 9

Holmes Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 47 minutes

Match: Swimming pool

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Price per night from

$339

The Villas 2A

Holmes Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 3 minutes

Match: Swimming pool

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Price per night from

$164

The Villas 2B

Holmes Beach house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 13 minutes

Match: Swimming pool

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Price per night from

$254

Playa Encantada 214

Holmes Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 13 minutes

Match: Swimming pool

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Price per night from

$254

SANDY POINTE 203

Holmes Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 47 minutes

Match: Swimming pool

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Price per night from

$197

Anna Maria Island Beach Paradise 10

Holmes Beach studio

  • Studio
  • 1 bathroom
  • sleeps 2

Match: Swimming pool

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Price per night from

$227

THE BEACH 3

Holmes Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 47 minutes

Match: Swimming pool

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Price per night from

$215

West Bay Point Moorings 214

Holmes Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 47 minutes

Match: Swimming pool

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Price per night from

$228

West Bay Point Moorings 274

Holmes Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 47 minutes

Match: Swimming pool

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Price per night from

$182

West Bay Point Moorings 26

Holmes Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 47 minutes

Match: Swimming pool

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Price per night from

$182

Coconut Breeze

Holmes Beach log cabin

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 13 minutes

Match: Swimming pool

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Price per night from

$300

Port Royal

Holmes Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 47 minutes

Match: Swimming pool

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Price per night from

$255

SUNSET BEACH 202

Holmes Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 47 minutes

Match: Swimming pool

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Price per night from

$287

Viewing 38 of 799
rentals in Holmes Beach

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