Condos Anna Maria Island

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1,072 condos

Chinaberry 922 at Midnight Cove Siesta Key, FL.

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$171

Firethorn 612 at Midnight Cove Siesta Key, FL.

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$142

Luxury Water Front Condo - Intercoastal Waterway

Treasure Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$206

Kima 503 Madeira Beach Front 2bd/2bath Condo Top Floor WHITE SANDY BEACHES!

Madeira Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Wonderful !!!” I never know from the pictures posted when they were taken and the true condition of the home. With this property we were not disappointed. We took beach chairs, towels and all of that was provided at the house. The house was clean and just as pictured. The only thing that I can suggest is knife's for the kitchen. There are towels and lines galore. and the location was good. Close to all we wanted to do but quiet as we wanted it to be. The house has an apartment upstairs that we rented for our son and it worked out great. Plenty of room. No fighting for bathroom time to shower. There was 7 of us and we have already voted on this property for our next years trip to the beach...

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$222

Responds fast! avg. 4 minutes

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$103

These homes match some but not all of your filters. Clear all filters

Beach house for rent in siesta key beach.

Siesta Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

Responds fast! avg. 2 hours 0 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

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Price per night from

$1,004

Beautiful house for rent at siesta key beach with pool, theater and game room

Siesta Key house

  • 7 bedrooms
  • 3 bathrooms
  • sleeps 15

Responds fast! avg. 2 hours 0 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

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Price per night from

$2,856

Tropical Paradise

Bradenton house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

1 of 2 match: Rental types, Private outdoor pool (unheated)

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Price per night from

$1,004

Serene Retreat Pool House

St. Petersburg house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Rental types, Private outdoor pool (unheated)

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Price per night from

$345

Updated 4/2 pool home, 5 Mins to Siesta Key

Siesta Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

Responds fast! avg. 1 hour 26 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

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Price per night from

$327

Zen Bungalow

Sarasota house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Rental types, Private outdoor pool (unheated)

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Price per night from

$258

Hibiscus Hideaway B - Top Floor Unit

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 39 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

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Price per night from

$283

The Salty Dog on North Shore

Anna Maria house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 39 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

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Price per night from

$389

Casa Sea Esta Executive Studio / Condo at Sara Cay

Tallevast studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 39 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

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Price per night from

$92

Blue Heron Studio / Condo 2 miles from Airport!

Tallevast studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 39 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$119

Copacabana Boaters Dream Home in Anna Maria

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 39 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

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Price per night from

$416

Spectacular views! By LoveRentals

Holmes Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 39 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

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Price per night from

$363

Beautiful home- Private getaway-Heated Pool/HotTub IMG 5 Close to Beaches

Palma Sola house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 22

1 of 2 match: Rental types, Private outdoor pool (unheated)

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Price per night from

$830

Hibiscus Hideaway Condo Walk to Historic Bridge St

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 1 hour 39 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

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Price per night from

$298

Luxury waterfront home with a heated pool and spa!

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 1 hour 39 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$537

#1 EXCLUSIVE Siesta Key Beach House /3 payments

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$259

Beautiful Location On Bay Side, Water View, Pool

Sarasota villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$229

Anna Maria Island Beach Sands 203

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$214

Anna Maria Island Beach Sands 101

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$274

Anna Maria Island Beach Palms 6B

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$189

Responds fast! avg. 3 hours 41 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$212

Responds fast! avg. 3 hours 41 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

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Price per night from

$243

Beachfront mansion w/pool. Exceptional Location and accommodations.

St. Pete Beach house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 3 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$848

Responds fast! avg. 3 hours 41 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$218

Responds fast! avg. 3 hours 41 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$161

Responds fast! avg. 3 hours 41 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$192

Responds fast! avg. 3 hours 41 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$184

Responds fast! avg. 3 hours 41 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$149

Responds fast! avg. 3 hours 41 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$133

Responds fast! avg. 3 hours 41 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$196

Minutes to Anna Maria Island Beaches, Bring the Boat/Jet Ski, Private Pool

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 41 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$162

Responds fast! avg. 3 hours 41 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$181

Responds fast! avg. 3 hours 41 minutes

1 of 2 match: Rental types, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$201

Viewing 38 of 1,072
rentals in Anna Maria Island

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