Osprey Rentals

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864 Houses

Dunmore

Osprey house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$218

LUX VILLAs close to sparkling Siesta Key Beach.

Osprey villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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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

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Price per night from

$133

CKBH (Casey Key Beach House)

Osprey house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$657

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

Osprey condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$161

Great rentals within 20 miles that match your search

2 bedroom Condo Bay Oaks Siesta Key

Sarasota condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

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Price per night from

$575

Beautiful Crescent Beach on Siesta Key One of the

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$302

Lovely Brandnew Pool Villa w/ Private Beach, WiFi

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$213

Amazing Beachfront Condo, Siesta Key,

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$345

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

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Price per night from

$1,003

Monthly Rental, 2 bed, 2 bath, Ocean view.

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$115

Vacation Home on Coral Sands Ct. Spring Special !

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$156

Shorewalk Condo ED near the Beaches Anna Maria Island, Longboat Key, IMG, Shops

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$403

3BR/4BA TOWNHOUSE - POOL VIEW PARADISE - PRIVATE BEACH ACCESS

Siesta Key townhouse

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 38 minutes

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Price per night from

$432

Manasota Beach Vacation Rental

Englewood house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$271

ZILLI VILLA

Longboat Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$489

Beach front condo in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$432

Quiet pool home with lake view, close to beaches

Venice house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$230

Tara Golf & Country Club Condo

Bradenton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Wonderful, peaceful location and beautiful condo.” This condo is wonderful and has everything anyone would want or need for a wonderful stay. We loved the property and the owners. It is located in a private championship golf course community and is just across the street from all the amenities. The amenities include tennis, pool, workout room, and of course golf at its best. There is a wonderful grill room and beautiful dining room facing the driving range. Very close to a hugh shopping area and enclosed mall. Very convenient to travel anywhere from here. Very nice rental in a wonderful area.

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Price per night from

$144

Brand new villa with heated pool for swimmers

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$190

“Clean comfortable Siesta Key Condo with all the comforts of home...Perfect!” The condo is walking distance to shops, restaurants and quaint local tiki bar! The beach is a short walk across the street and through the beach-front section of the complex with lounge chairs and umbrellas available, very nice! I didn't mention the 2 pools (one beachside) and nice gym facilities also just downstairs of the unit. The covered parking space was an added plus! The condo was clean and very comfortable with all of the amenities of home which is greatly appreciated! You can even enjoy the view of the bayside inlet and beautiful landscaping from the kitchen through the entire wall of glass doors in the living/dining room! We had a wonderful week! The property owner Vic supplied more than enough information on the condo, local businesses and area maps! He was such a pleasure to work with! Thanks again Vic! We are already planning our next trip to Siesta Key in May!!

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Price per night from

$144

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Price per night from

$144

Serene Sarasota Getaway near shopping and golfing.

Fruitville villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$128

Ideal Retreat next to USA's #1 Beach—Siesta Key

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$161

Quiet and Comfortable Condo Near Turtle Beach

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Siesta sweet spot” Great value for location. Nice pool, visits with the manitees. Close to everything. This time of year ocean water was amazing

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$127

All Inclusive Executive Rental

Sarasota apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 46 minutes

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Price per night from

$167

Luxury Sarasota Golf Home

Sarasota house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$369

Light and Airy and Private, Great Location

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$230

Siesta Vacation Home - 3 miles to beach

Venice house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$212

****Walk to Beach-5min! Waterfront Canal! Private Pool~spa~Kayaks, Bikes!

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$456

Lido Sunshine M

Lido Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$183

Downtown Sarasota five star home

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$196

Jamaica Royale #104! Completely renovated, Gulf side, beautiful 2b/2b Condo!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$338

Ground Level 2 Bedroom Beach Themed Condo

Venice condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$230

~ Cozy Apartment Close to Siesta Key with own washer and dryer ~

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 56 minutes

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Price per night from

$68

Convenient + Cozy + Quite + Comfortable :-)

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 55 minutes

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Price per night from

$317

Newly Remodeled Spacious Loft in Sarasota!

Sarasota apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$296

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Price per night from

$334

Viewing 38 of 864
rentals in Osprey

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