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Vacation Rentals & Beach Rentals in Anna Maria Island

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369 beach rentals

Holmes Beach Home w/Pool & Hot Tub, Walk to Beach!

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 29 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$305

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: Private outdoor pool (unheated)

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Price per night from

$343

Longboat Key Waterfront Home with Private Enclosed Pool & Spa | Near Beach

Bradenton Beach house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (unheated)

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Price per night from

$348

Anthony Beach Cottages Bare Feet Retreat

Holmes Beach cottage

3 bedrooms / 1 bathroom / sleeps 6

Match: Private outdoor pool (unheated)

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Price per night from

$259

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

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 29 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$268

Canalfront Anna Maria Cottage w/ Pool & Hot Tub!

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 29 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$355

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. 46 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$125

Coconut Bayou - a gem with heated pool on a fantastic location in Anna Maria

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 46 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$300

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

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 46 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$277

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. 46 minutes

Match: Private outdoor pool (unheated)

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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. 46 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$100

Aquaville A - 2/1 beauty with private pool in the heart of Anna Maria. Pets!

Anna Maria apartment

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 46 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$180

Seashell - Less than 1 minute to the beach - PRIVATE POOL and PET friendly!

Anna Maria condo

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 46 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$229

It's my Dream - private heated pool, 2 minute walk to the beach! Pet friendly

Holmes Beach apartment

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 46 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$242

Marbella - GULF FRONT CONDO WITH BEAUTIFUL VIEW - Sleeps 4!

Bradenton Beach condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 46 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$143

Coral Breeze (A) Perfect 2 bedroom/2 bathroom with private pool! Pet friendly

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 46 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$190

Sunflower condo with two pools - one is directly on the beach! Elevator

Bradenton Beach condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 46 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$143

Home w/ Dock, Pool, Kayaks: Walk to Palma Sola Bay

Bradenton Beach house

4 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 2 hours 29 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$213

Canal Front Bradenton Home - 2 Miles to Beach

Bradenton Beach house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 29 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$253

Coral Breeze (B) 2BR / 2BA Duplex with private pool! Pet friendly!

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 46 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$190

Sandcastle - Spacious home with amazing private pool - only minutes to beach!

Holmes Beach townhouse

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 46 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$172

NEW! Pet-Friendly Waterfront Retreat in Bradenton!

Bradenton Beach house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 29 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$213

Egret's Landing - A private pool home, only minutes to the beach!

Holmes Beach apartment

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 46 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$220

Coastal Cottage - NORTH END 3 bedroom, 2 bath pet friendly pool home!

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 46 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$220

Sea Pearl - on the Canal in Anna Maria with heated pool. Pet friendly!

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 46 minutes

Match: Private outdoor pool (unheated)

All filters match

Price per night from

$300

Sunrise Serenity - Spacious 3/2.5 town home with community heated pool

Holmes Beach apartment

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 46 minutes

Match: Private outdoor pool (unheated)

All filters match

Price per night from

$180

Jacaranda Beach House - one minute walk to the beach! Private Pool

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 46 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$279

MYKONOS - A 3/2 heated pool home just steps to the beach. PET FRIENDLY!

Holmes Beach apartment

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 46 minutes

Match: Private outdoor pool (unheated)

All filters match

Price per night from

$220

Isle Haven A - steps to the beach and many other conveniences - pet friendly!

Holmes Beach apartment

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 46 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$218

Anna Maria Island Beach Sands 101

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (unheated)

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Price per night from

$203

Canalfront Bradenton Home w/ Dock & Pool!

Bradenton Beach house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 29 minutes

Match: Private outdoor pool (unheated)

All filters match

Price per night from

$272

A SHORE THING WATERFRONT HOME

Holmes Beach house

3 bedrooms / 2 bathrooms / sleeps 8

Match: Private outdoor pool (unheated)

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Price per night from

$257

Aquaville B - a 3/1 beauty with pool in the heart of Anna Maria, pet friendly

Anna Maria apartment

3 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 46 minutes

Match: Private outdoor pool (unheated)

All filters match

Price per night from

$200

Canalfront ‘Caribbean Retreat’ w/Pool & Boat Dock

Bradenton Beach house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 29 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$240

Sunbreeze - charming 3/2.5 home, great pool, steps to the beach!

Holmes Beach house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 46 minutes

Match: Private outdoor pool (unheated)

All filters match

Price per night from

$220

Anna Maria Island Beach Palms 6B

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (unheated)

All filters match

Price per night from

$150

Anna Maria Island Beach Sands 203

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 5

Match: Private outdoor pool (unheated)

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Price per night from

$155

Viewing 37 of 369
rentals in Anna Maria Island

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