Cottages Anna Maria Island

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209 cottages

Luxury Beach Cotttage

Sarasota cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Beautiful little cottage” We stayed at this lovely little cottage on Siesta Key mid-April. The cottage is very nice, with all the amenities, even a washer/dryer for extended stays. It's cozy, with high ceilings, a nice bathroom and kitchen/living room. The bed seemed a little small (only a double), but it was very comfortable. The wireless internet was not working when we were there, which was a little frustrating. There is a beautiful pool and nice garden areas. The private beach was also very nice. All of the staff and the owner were extremely pleasant and welcoming. We enjoyed our time there.

Match: Rental types Private outdoor pool (unheated)

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Price per night from

$532

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Beach house for rent in siesta key beach.

Siesta Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

Responds fast! avg. 1 hour 59 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. 1 hour 59 minutes

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

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Price per night from

$2,854

Tropical Paradise

Bradenton house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

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

1 of 2 filters match

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

$344

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

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

Copacabana Boaters Dream Home in Anna Maria

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 40 minutes

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

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Price per night from

$416

The Salty Dog on North Shore

Anna Maria house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 40 minutes

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

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Price per night from

$389

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

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

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

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)

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Price per night from

$119

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...

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

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Price per night from

$222

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

$832

Hibiscus Hideaway Condo Walk to Historic Bridge St

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 1 hour 40 minutes

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

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Price per night from

$283

Luxury waterfront home with a heated pool and spa!

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 1 hour 40 minutes

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

1 of 2 filters match

Price per night from

$424

#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

$258

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

$213

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

$186

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

$285

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

$196

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

$186

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

Private Saltwater Pool, 5 minutes to Bradenton Beach, Superb location near Walki

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

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

$163

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

$201

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

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

$202

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

$173

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

Private Pool Oasis Home - Near Beaches- Great Neighborhood

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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

$168

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

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

$130

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

$227

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

$198

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

Viewing 38 of 209
rentals in Anna Maria Island

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