Heritage Harbor Rentals

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541 Houses

River Strand Golf and Country Club Resort

Bradenton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Private pool

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Price per night from

$230

Great rentals within 20 miles that match your search

Beautiful Sunkst Cottage Bradenton Beach - AMI-Tropical Setting - Heated Pool

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Private pool

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Price per night from

$517

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

Match: Private pool

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Price per night from

$1,001

Little Palms Villa. A lakeside home with style.

Bradenton villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Excellent” Our stay at 4638 Runabout way was amazing. We loved that the house was very nice, spacious, and clean for my family and I. We loved swimming in the pool everyday. The service was excellent all around. We would definitely stay there again.

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Price per night from

$195

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.

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Price per night from

$533

AnnaMariaIsland a Paradise. MINUMIM RENTAL 2 WEEKS

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 3 hours 22 minutes

Match: Private pool

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Price per night from

$197

Gorgeous views,spectacular home!

Anna Maria house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

“Majestic Views” Our family loved our visit to Anna Maria. The house is gorgeous and spacious. My kids enjoyed the pool and eating outside. We hope to return in the near future.

Match: Private pool

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Price per night from

$631

A Siesta Tropical Retreat - Island Pool Oasis in Village & 2 blocks to Beach

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

“Your best choice for location!” We stayed for 10 lovely days in this home and I have to say It was an even better location than I expected. Everything you could want to do is in walking distance or you can walk to the village (maybe a 3 minute walk)and hop in a free taxi . The house is well appointed and beds are very comfortable. We traveled with a 10 yr.old, 11yr. old , and 15 yr. old my 15 yr. old niece slept in the trundle bed and commented on how comfortable the bed was. In the kitchen you will find a drawer full of menus for the many nearby restaurants and information for water activities. I highly recommend parasailing while your there ! Considering how close everything is the street is very quiet and the owners were great to deal with. Thanks Kathi and Grant!

Match: Private pool

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Price per night from

$501

4 Bedroom with Gulf View Siesta Key FL Beach Fun

Siesta Key apartment

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

“Fantastic Location and Beautiful Accomodations” Our daughters and their families stayed here in February. The condo was everything we expected and more. It has a breathtaking view of the Gulf from the screened in lani which runs the width of the unit. The four bedrooms were perfect for our group of nine and the kitchen / dining area was well stocked with appliances , pots & pans , dishes , glassware , etc. Condo has easy access to heated pool and ample parking. Owner made the rental process smooth as silk , and we all felt right at home as soon as we had checked in. Right across street from world famous Siesta Beach. Would highly recommend.

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Price per night from

$515

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Price per night from

$230

Anna Maria Island Beach Paradise 10

Holmes Beach studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 20 minutes

Match: Private pool

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Price per night from

$228

Lovely 3 BR Home with Office & Heated Pool at Tara

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Private pool

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Price per night from

$167

Luxury Sarasota Golf Home

Sarasota house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Private pool

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Price per night from

$369

NW Bradenton Exectitive Home

Bradenton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Private pool

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Price per night from

$493

Stunning 2,550 Sq.ft House, FL

Bradenton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Private pool

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Price per night from

$286

Captiva Paradise Home close to IMG Academy & Siesta Key Beach

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Responds fast! avg. 9 minutes

Match: Private pool

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Price per night from

$373

Vacation Waterfront Cottage

Myakka City cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Private pool

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Price per night from

$158

Oceanfront home w/sunset views of Sarasota Bay

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Private pool

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Price per night from

$630

Lakefront Oasis 3 Bdrm House with Heated Pool minutes from village and beach

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Private pool

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Price per night from

$689

Family Reunion Villa on Anna Maria Island, Florida

Bradenton Beach villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Private pool

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Price per night from

$574

Another Day in Paradise

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 1 minutes

Match: Private pool

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Price per night from

$545

NEAR IMG ACADEMY AND SIESTA KEY BEACH PARADISE

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 9 minutes

Match: Private pool

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Price per night from

$431

#1 EXCLUSIVE Siesta Key Beach House /3 payments

Siesta Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Private pool

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Price per night from

$259

Beach house for rent in siesta key beach.

Siesta Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

Responds fast! avg. 2 hours 0 minutes

Match: Private pool

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Price per night from

$1,004

Anna Maria Islands best location Heated pool Best prices!

Anna Maria Island house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Private pool

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Price per night from

$861

Siesta Key Beach Cottages on Crescent

Siesta Key cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Private pool

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Price per night from

$224

Condo wOcean view on Siesta

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 39 minutes

Match: Private pool

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Price per night from

$402

University Park Country Club Property

Lakewood Ranch house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Private pool

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Price per night from

$482

BeautifulHome with Pool - 3 miles from Siesta Key Beach

Gulf Gate Estates house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 38 minutes

Match: Private pool

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Price per night from

$241

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

Match: Private pool

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Price per night from

$2,856

Oceanfront home

Gulf Gate Estates house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Private pool

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Price per night from

$688

Casa Del Mar in Apollo Beach

Apollo Beach house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 11

Match: Private pool

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Price per night from

$1,033

Match: Private pool

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Price per night from

$574

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Price per night from

$275

Anna Maria Island Martinique On The Beach

Holmes Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 20 minutes

Match: Private pool

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Price per night from

$780

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Price per night from

$310

Gorgeous Pool Home. 12 min from the beaches of Anna Maria, IMG

Bradenton villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Private pool

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Price per night from

$281

Match: Private pool

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Price per night from

$287

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