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158 Houses

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LUX VILLAs close to sparkling Siesta Key Beach.

Osprey villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$161

Coral Reef Cutie 2Bedroom Bungalow - 4 Miles to Siesta Key

Osprey cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 14 minutes

Match: Garden

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Price per night from

$132

CKBH (Casey Key Beach House)

Osprey house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$654

Great rentals within 20 miles that match your search

Cozy Home Near Mineral Springs

Warm Mineral Springs house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

Match: Garden

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Price per night from

$229

Private Retreat on Siesta Dr

Sarasota house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 49 minutes

Match: Garden

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Price per night from

$515

5 min away from the beach

Gulf Gate Estates house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Garden

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Price per night from

$229

Home in Palm Aire Golfing community

North Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Garden

All filters match

Price per night from

$293

Sarasota Vacation • 15 Minutes to Beach • Sleeps 6

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$194

Live like a Millionaire

Fruitville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Garden

All filters match

Price per night from

$229

PRIME Location! 60 Steps to PRIVATE BEACH Dogs OK!

Manasota Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Match: Garden

All filters match

Price per night from

$434

The Hideaway: 4/2 W Heated Pool and Outdoor Spaces, 10 mins to Sarasota Beach

Gulf Gate Estates house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Garden

All filters match

Price per night from

$372

St Armand's Private Home on Jackson Drive

Lido Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Garden

All filters match

Price per night from

$381

Coastal Cottage

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$172

Flamingo Cottage

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$172

Sea Shell Cottage

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Garden

All filters match

Price per night from

$172

Tropical Breeze Triple Cottages, Sleeps 16

Sarasota house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 16

Match: Garden

All filters match

Price per night from

$681

Sea Glass Dual Cottages, Sleeps 12, Heated Pool

Sarasota house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Garden

All filters match

Price per night from

$401

Captains Quarters

Casey Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Garden

All filters match

Price per night from

$155

Dream beach, pool/spa retreat!

Siesta Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

Match: Garden

All filters match

Price per night from

$344

Just another day in paradise! Sunrise condominiums!

Bee Ridge condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Garden

All filters match

Price per night from

$115

Sarasota San Jose Retreat

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Garden

All filters match

Price per night from

$164

Match: Garden

All filters match

Price per night from

$138

3 bedroom tropical Family home with private pool.

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Garden

All filters match

Price per night from

$285

Ahhh! Getaway Retreat - Private and convenient

Sarasota studio

  • Studio
  • 1 bathroom
  • sleeps 2

Match: Garden

All filters match

Price per night from

$201

Match: Garden

All filters match

Price per night from

$143

CLOSE TO THE BEACHES WITH A POOL

South Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$258

Modern Home close to Beach & Downtown

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$229

Bow-Tie Suite

Englewood house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Garden

All filters match

Price per night from

$229

Remodeled 4BR Pool Home / Golf View/Near Beaches

South Bradenton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 14

Match: Garden

All filters match

Price per night from

$515

Lady Palm Apt: 1/1 with 2 beds, garden vibes and outdoor spaces! Pet friendly

Bradenton apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Garden

All filters match

Price per night from

$143

Match: Garden

All filters match

Price per night from

$172

"Fountain of Youth” 2bedroom, 2 bath, bikes, BBQ

Warm Mineral Springs house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Garden

All filters match

Price per night from

$179

Sandy Oasis 4-bedroom with Pool Sarasota/Bradenton

Braden River house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 33 minutes

Match: Garden

All filters match

Price per night from

$303

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

Match: Garden

All filters match

Price per night from

$326

SIestaKeyBNB

Gulf Gate Estates house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

Match: Garden

All filters match

Price per night from

$240

New Coastal Pool + Game Room home - sleeps 10

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Garden

All filters match

Price per night from

$566

Siesta Key Villa

Siesta Key villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$332

Match: Garden

All filters match

Price per night from

$971

Viewing 38 of 158
rentals in Osprey

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