Vacation Rentals & Beach Rentals in Anna Maria Island

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419 beach rentals

Upscale tropical getaway with private pool & spa, elevator, and more!

Holmes Beach house

3 bedrooms / 4 bathrooms / sleeps 6

Match: Private outdoor pool (unheated)

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Price per night from

$277

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

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 39 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 3BR w/ 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

$359

Charming cottage w/ island views, entertainment & nearby beach access!

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Match: Private outdoor pool (unheated)

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Price per night from

$225

The Anna Maria Island Beach Palms 5B

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 31 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$149

Anna Maria Island Beach Sands

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Paradise” We loved this place, felt right at home the minute we walked in the door. Had a view minor problems and the service to deal with them was awesome. Thanks Terry for a great experience, being our first time here on anna Maria Island. If we didn't need the extra bedroom, we would have booked for next yr. Location~~!! wow, close to great restaurants Love the view...can't say enough of the sunsets and of course the dolphins, got chills every time I seen them, almost daily...first class...thanks...

Responds fast! avg. 2 hours 31 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$148

The Anna Maria Island Beach Palms 7A

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 31 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$126

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

$258

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

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 4 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$295

The Anna Maria Island Beach Sands 201

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 31 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$150

Canalfront Anna Maria Cottage w/ Pool & Hot Tub!

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 48 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$318

The Anna Maria Island Beach Castle

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 31 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$172

The Anna Maria Island Beach Paradise 6

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 31 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$306

The Anna Maria Island Beach View 207

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 31 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$125

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

Holmes Beach townhouse

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 6 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$172

Peace 'n Paradise

Holmes Beach townhouse

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 51 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$201

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

Holmes Beach house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 6 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$200

Absolutely Perfect

Holmes Beach house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 51 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$936

Coco Cabana

Holmes Beach house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 51 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$295

The Anna Maria Island Beach Paradise 5

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 31 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$287

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. 6 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$110

Great 2 bed/2 bath Condo with Amazing Pool within Steps of the Beach

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$165

The Anna Maria Island Beach View 208

Bradenton Beach condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 31 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$149

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

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 6 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$185

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

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 6 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$172

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. 6 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$208

A Wright Place

Holmes Beach house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 51 minutes

Match: Private outdoor pool (unheated)

All filters match

Price per night from

$137

BEACH WALK #1 BEACH SIDE VILLA

Holmes Beach villa

2 bedrooms / 2 bathrooms / sleeps 8

Match: Private outdoor pool (unheated)

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Price per night from

$117

Island Delight - a brand new sparkling private heated pool and hot tub

Holmes Beach apartment

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 6 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$143

The Anna Maria Island Beach View 209

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 31 minutes

Match: Private outdoor pool (unheated)

All filters match

Price per night from

$149

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. 6 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$172

NEW! Canalfront Retreat w/Dock, Pool, BBQ & Kayaks

Bradenton Beach house

4 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 39 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$181

Spacious home moments away from the beach, gorgeous views & near plenty to do!

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 39 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$676

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. 6 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$236

Bridge Port Beach Resort

Bradenton Beach condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 31 minutes

Match: Private outdoor pool (unheated)

All filters match

Price per night from

$99

BEACH WALK #3 BEACH SIDE VILLA

Holmes Beach villa

1 bedroom / 1 bathroom / sleeps 6

Match: Private outdoor pool (unheated)

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Price per night from

$97

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. 6 minutes

Match: Private outdoor pool (unheated)

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Price per night from

$143

Viewing 38 of 419
rentals in Anna Maria Island

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