Osprey Rentals

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158 Houses

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

$656

Great rentals within 20 miles that match your search

Vacation Home on Coral Sands Ct. Spring Special !

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Garden

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Price per night from

$155

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: Garden

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Price per night from

$533

Sunset Point Siesta Key FL AWESOME RENTAL !!

Siesta Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Beautiful inside and out. Perfect location” My family and I stayed in this beautiful rental during February 2015. We could not have asked for a more perfect spot. The rental is just steps away from the beach and has a wonderful view of the beautiful sunsets. Siesta Key Village is an easy walk away and has great restaurants and shops. We are hoping to go back as soon as we can!

Responds fast! avg. 3 hours 50 minutes

Match: Garden

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Price per night from

$804

Vacation Home on Alligator Drive . Winter 2025 Special !

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Garden

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Price per night from

$150

Sandy Toes Town Home

Siesta Key townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Time in Paradise” We recently had the luck to spend two months in paradise. This condo was comfortably appointed, well stock to meet all our needs, and most importantly in the perfect location. The beach was a short walk to the left and stores and restaurants were just a short walk to the right. We had a great time and enjoyed everything Sarasota, Siesta Key, and this Sandy Toes Condo had to offer. Thanks Mark!

Match: Garden

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Price per night from

$273

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: Garden

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Price per night from

$502

Siesta Key private beach access

Siesta Key villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Siesta Key Townhouse” This was a wonderful place to stay! The house was very clean and spacious and had everything we needed for a week at the beach.

Match: Garden

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Price per night from

$510

Clean comfort in Sarasota-book now for comfort

Sarasota caravan/mobile home

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Match: Garden

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Price per night from

$135

A Wonderful Pool House on a lake full of wildlife.

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Location location” Great house convincent , clean , close to everything

Match: Garden

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Price per night from

$122

LEMON BAY COTTAGE

Englewood house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Perfect family cottage in Lemon Bay” Such a great little house and surprisingly bigger than pictures reveal. Perfect for a family with kids. 3rd toilet tucked away in laundry shed for easy access from pool. Great location as well, close to beaches, parks and many restaurants within walking distance. Definitely will rent there again. House was fresh, clean and inviting.

Responds fast! avg. 3 hours 39 minutes

Match: Garden

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Price per night from

$104

Lovely 3 BR Home with Office & Heated Pool at Tara

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$167

Luxury Venice Florida 4 Bedroom home with Pool

Venice villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Garden

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Price per night from

$287

Charming Lido Key Beach House 5 min Walk to Beach!

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Garden

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Price per night from

$410

Manasota Beach Vacation Rental

Englewood house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$270

Beachfront Getaway in Siesta Key

Siesta Key townhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Very comfortable, nice amenities and well run.” Loved the beach and the nearby restaurants. The free trolly ride was easy to use and a great way to go into the village.

Match: Garden

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Price per night from

$224

Lido Sunshine L

Lido Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Garden

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Price per night from

$171

Manasota Beachy Cottage

Manasota Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

“Our 2017 vacation” This was our first time ever renting a house. Peter was the best. This house had everything we need or wanted. It was super clean and beautiful. The screened porch was perfect to drink coffee in the morning. Didn't have to worry about the bugs or anything. Beach was a short walk around the corner over a bridge. The town was great and hardly no traffic. Safe for younger kids to play in the yard. Can't wait to rent again next year. Thank you!!

Match: Garden

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Price per night from

$155

Quiet pool home with lake view, close to beaches

Venice house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Garden

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Price per night from

$230

All Inclusive Executive Rental

Sarasota apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 46 minutes

Match: Garden

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Price per night from

$167

Luxury Sarasota Golf Home

Sarasota house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Garden

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Price per night from

$369

Siesta Vacation Home - 3 miles to beach

Venice house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$212

Match: Garden

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Price per night from

$150

Lido Sunshine M

Lido Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Garden

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Price per night from

$183

Charming Artist's Cottage In Laurel Park

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Garden

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Price per night from

$144

Convenient + Cozy + Quite + Comfortable :-)

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 55 minutes

Match: Garden

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Price per night from

$316

Stunning 2,550 Sq.ft House, FL

Bradenton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Garden

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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: Garden

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Price per night from

$373

Addy's Villas: 2BR

Nokomis villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Garden

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Price per night from

$194

Match: Garden

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Price per night from

$132

Vacation Sarasota in great location to all venues....

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$229

GUEST HOUSE

Fruitville guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 29 minutes

Match: Garden

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Price per night from

$107

Venice Immaculate RemodeledHome-2 Bdr/2 Bath-Pool-WIFl&CABLE-2 Miles to Beach

South Venice house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$173

Beautiful and completely remodeled cottage retreat minutes from the beach!!

Englewood apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Garden

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Price per night from

$144

Tiny House Siesta - Red Lifeguard Stand

Siesta Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Garden

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Price per night from

$443

Seasonal Rental

Venice house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$293

Viewing 38 of 158
rentals in Osprey

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