Houses Osprey

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433 houses

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$112

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Price per night from

$236

Dunmore

Osprey house

3 bedrooms / 2 bathrooms / sleeps 6

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$163

CKBH (Casey Key Beach House)

Osprey house

3 bedrooms / 3 bathrooms / sleeps 6

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$581

BEACH NEAR, EXCLUSIVE VILLA, PRIVATE POOL, QUIET SEA VIEW

Osprey house

3 bedrooms / 2 bathrooms / sleeps 6

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$173

BEACH NEAR, EXCLUSIVE VILLA, PRIVATE POOL, QUIET SEA VIEW

Osprey house

3 bedrooms / 2 bathrooms / sleeps 6

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$193

Great rentals within 20 miles that match your search

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

6 bedrooms / 5 bathrooms / sleeps 14

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$1,027

Sandy Toes Siesta Key Florida (6798)

Siesta Key house

2 bedrooms / 2 bathrooms / sleeps 6

“Very good” It's was great stay ,close to the beach (3-5)min walk,private,quite for vacation location. Car was parked in the garage and we loved it !!! Also you have everything you possibly need in a kitchen !! And condo has everything you need to go to the beach too !!(beach chairs,umbrellas,towels ....Will stay again Thank you Kathey and Joe

Responds fast! avg. 1 hour 2 minutes

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$354

Bright 2 bedroom home 10 minutes to Siesta Key - Lots of restaurants nearby

Gulf Gate Branch house

2 bedrooms / 2 bathrooms / sleeps 4

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$96

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$203

Casita Blanca- 2BR, Private Beach Access, Communal Heated Pool [Sleeps 4]

Sarasota house

2 bedrooms / 1 bathroom / sleeps 4

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$309

The MacGregor House is 1925 Old Florida elegance

Sarasota house

4 bedrooms / 3 bathrooms / sleeps 7

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$324

Venice Home w/Fire Pit & Grill - 10 Mins to Beach!

Venice house

2 bedrooms / 1 bathroom / sleeps 8

Responds fast! avg. 57 minutes

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$77

Nice holiday home with pool and lake view at a short distance to the beach

Gulf Gate Estates house

3 bedrooms / 2 bathrooms / sleeps 6

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$177

Siesta Key Canal + Pool Home- 3 Bedroom

Siesta Key house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 1 minutes

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$530

Quiet Family Lido Beach Condo (Lido Key)

Sarasota house

2 bedrooms / 2 bathrooms / sleeps 5

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$84

Beautiful Spot In Paradise

Englewood house

2 bedrooms / 2 bathrooms / sleeps 6

“Peaceful Get-Away” We really enjoyed our stay. The home was very comfortable and the pool and spa tub is where we spent most of our time. We especially like the location and made use of the wonderful walking trails and Lemon Bay Park. I only have a couple of minor suggestions - A cutting board for the kitchen and a lounge chair for the pool area. Other than that the home provided everything that we needed. We would defiantly make a return stay if possible. Thank you Dennis!

Responds fast! avg. 3 hours 19 minutes

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$89

Long Term 4 Bd. Rental Home

South Venice house

4 bedrooms / 2 bathrooms / sleeps 8

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$63

Water Lover's Delight! 3/2 fully renovated home with boat ramp & davits.

Manasota Key house

3 bedrooms / 2 bathrooms / sleeps 6

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$169

6 Bedroom 4 Bathroom house New pool Siesta Key Florida Walk to the Beach

Siesta Key house

6 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 3 hours 41 minutes

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Price per night from

$1,413

Sarasota House Near Arlington Park and Siesta Key Beach!

Sarasota house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 21 minutes

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$218

Spacious house on creek, steps to the beach

Venice house

3 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 2 hours 7 minutes

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$177

Vacation Home with Private Beach !

Venice house

3 bedrooms / 2 bathrooms / sleeps 5

“Pleasantly surprised!” We stayed at this property in March, 2014 for five nights. The house was very well maintained and clean and appears to have been renovated recently. The furniture throughout the house and the appliances all looked new. The kitchen was very well equipped and the bathrooms were very neat and spotless. We enjoyed staying at this house and recommend it to everyone without any hesitation.

Responds fast! avg. 2 hours 52 minutes

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$106

Modern Tranquil River House

Bradenton house

1 bedroom / 1 bathroom / sleeps 3

“Beautiful House and View, Great Choice!” This house was not only, brand new but beautifully decorated. The space was so well panned and all the amenties were new and modern. The house is super clean and right on the water. There are bikes and a kayak. This is by the best house rental I have ever stayed at and I have stayed at many. I felt we got more then what we paid for and got what we needed from ur trip.

Responds fast! avg. 2 hours 1 minutes

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$118

Beautiful gated community near Siesta Key beach and downtown Sarasota

Sarasota house

2 bedrooms / 2 bathrooms / sleeps 4

“Great location and community” We loved our stay here. The location suited us. The community is clean and quiet. The people are friendly. Everything worked out for us, our first time renting. We would stay here again. Thank you.

Responds fast! avg. 26 minutes

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$117

Park Model with lanai, large deck, block from pool

Venice house

1 bedroom / 1 bathroom / sleeps 3

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$124

Tropical Pool Home Near Siesta Key, Pet Friendly! Private POOL

Sarasota house

2 bedrooms / 2 bathrooms / sleeps 4

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$89

Siesta Get Away

Siesta Key house

3 bedrooms / 2 bathrooms / sleeps 8

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$206

Sandy Toes Siesta Key Florida (6796)

Siesta Key house

2 bedrooms / 2 bathrooms / sleeps 6

“Fantastic!!!” Loved it!!! This place was very clean, close enough to beach, very spacious, tastefully decorated with upgrades, decent pool, a manager on site, and more beach gear than you could ask for. ...Chairs, games, rafts, umbrellas, bikes, towels, coolers, etc. we absolutely loved it!!! We had a family of 6....Parents and 4 teenagers. We also liked that across the street was convenience stores, grocery, and restaurants. The Toasted Mango and The Fish Market have great, great food. Also, our flight was canceled to fly in, and they were out of rental cars at newly appointed airport. How relieving it was to finally show up to such a nice place and relax The owner was also so very kind to accommodate us if needed.

Responds fast! avg. 1 hour 2 minutes

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$354

Stunning 2,550 Sq.ft House, FL

Bradenton house

4 bedrooms / 2 bathrooms / sleeps 8

“Awesome stay” We had a great stay at this property. We were there for my wife graduation our family and us loved it and will rent this property again.

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$174

Gorgeous Furnished Pool Home in Desirable Venetia!

South Venice house

3 bedrooms / 2 bathrooms / sleeps 6

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$110

Charming White Cottage

Sarasota house

1 bedroom / 1 bathroom / sleeps 5

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$165

Sea Turtle Beach House

Sarasota house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 46 minutes

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$248

New Rental: Dawson House "A kitchen that is truly warm at heart"

Sarasota house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 1 minutes

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$271

Brand new villa with heated pool for swimmers

Venice house

3 bedrooms / 2 bathrooms / sleeps 6

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$144

3 Bedroom 3 Bath, Heated Pool, St. Armands Circle

Sarasota house

3 bedrooms / 3 bathrooms / sleeps 10

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$412

Pool ⭐Home with Hot Tub - Close to Siesta Key, Shopping, Restaurants

Gulf Gate Estates house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 40 minutes

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$260

Warm Mineral Spring Vacation Home

Warm Mineral Springs house

3 bedrooms / 3 bathrooms / sleeps 6

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$87

Viewing 38 of 433
houses in Osprey

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