Heritage Harbor Rentals

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1,200 Houses

River Strand Luxury Condo-Tennis & Golf Community

Bradenton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$86

River Strand Golf and Country Club Resort

Bradenton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$229

Great rentals within 20 miles that match your search

University Park Country Club Property

Lakewood Ranch house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$482

Piece of Paradise

Sarasota townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 7

Price per night from

$109

Beach condo

Longboat Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$517

Great location, quiet, peaceful, and comfortable

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$46

*** SUPER SPECIAL RATES at Harbor Towers ***

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 56 minutes

Price per night from

$114

Sarasota Stoneybrook Golf Condo, overlooking #3 Hole, near Siesta Key

Osprey condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$161

Lakeside Point 2 bedrooms condo with golf and lake view

Lakewood Ranch apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 36 minutes

Price per night from

$138

Serenity Shore

Lakewood Ranch apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 36 minutes

Price per night from

$299

Sunny Daze

Lakewood Ranch apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 36 minutes

Price per night from

$253

Dream Weavers

Lakewood Ranch apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 36 minutes

Price per night from

$287

Endless Summer

Lakewood Ranch apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 36 minutes

Price per night from

$253

Lakeview Oasis

Lakewood Ranch condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 36 minutes

Price per night from

$253

Golf Haven

Lakewood Ranch apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 36 minutes

Price per night from

$253

Skyline Resort

Lakewood Ranch apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 36 minutes

Price per night from

$253

Eagles Nest

Lakewood Ranch apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 36 minutes

Price per night from

$253

March 23-March 30, 2024 Springbreak 3bdr on the beach Longboat key

Longboat Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$746

Paradise Found

Lakewood Ranch apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 36 minutes

Price per night from

$253

"Lido Lookout" Beach Paradise Private Home on Lido Key

Lido Key house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$2,983

Island Hideaway! Bermuda-esque Guest House! Steps to the Sand!

Longboat Key guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$121

Island Village Hideaway! Steps to Sand

Longboat Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$193

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

Price per night from

$241

The Suite Retreat Room at The Breathing Space Wellness House

Sarasota house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$345

Newly remodeled condo on the Bradenton Riverwalk

Bradenton condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Price per night from

$109

NEW! Luxurious Coastal Condo 5 minutes to Anna Maria Island

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$402

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

Price per night from

$2,856

Luxury Waterfront Views/Pool/1400sf/2 min to Beach

Siesta Key condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 32 minutes

Price per night from

$340

Siesta Key vaca rental

Siesta Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$230

Hidden gem close to everything

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 14 minutes

Price per night from

$217

Oceanfront home

Gulf Gate Estates house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$688

Beach to Bay Tropical Oasis! 2Bed/2Bath Longboat Key Condo

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$153

Anna Maria Island Beach Haven

Cortez house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 20 minutes

Price per night from

$1,503

New York Avenue Rancher

Gulf Gate Estates house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$446

Paradise Palms Resort at Lakewood National

Lakewood Ranch apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 36 minutes

Price per night from

$253

Casa Del Mar in Apollo Beach

Apollo Beach house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 11

Price per night from

$1,033

Newly renovated beach house near AMI free trolley stop with Private pool

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$563

The Meadows golf course view villa

North Sarasota villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$122

Viewing 38 of 1,200
rentals in Heritage Harbor

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