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Osprey Rentals
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$10 - $500
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Osprey Rentals
1,840 Houses
Price per night from
$170
Responds fast! avg. 10 minutes
Price per night from
$110
Sarasota Condo w/Deck - 1/2 mile to Turtle Beach!
Osprey apartment
2 bedrooms / 1 bathroom / sleeps 4
Responds fast! avg. 2 hours 48 minutes
Price per night from
$141
Price per night from
$99
Spacious Sarasota Waterfront Pool Home with Dock - Amazing Sunsets Included
Osprey condo
3 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$280
Sunny 3BR Oasis w/ New Appliances & Furnishings—Near Coast, Dining
Osprey house
3 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$97
Pet friendly paradise with heated pool close to Sarasota-Osprey-Nokomis-Venice
Osprey house
3 bedrooms / 2 bathrooms / sleeps 5
Price per night from
$175
Responds fast! avg. 1 hour 58 minutes
Price per night from
$143
Condo with 2 pools, WiFi, Tennis/Pickleball Courts, Kayak Storage, Legacy Trail,
Osprey condo
2 bedrooms / 2 bathrooms / sleeps 4
Responds fast! avg. 8 minutes
Price per night from
$64
Beautiful South Sarasota Bay Home in Harbor Front Community
Osprey house
3 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$75
2 BR / 2 BA Condo in Stoneybrook Golf & County Club - Sarasota & Siesta Key
Osprey condo
2 bedrooms / 2 bathrooms / sleeps 4
Price per night from
$60
Price per night from
$31
Price per night from
$68
Price per night from
$501
Great rentals within 20 miles that match your search
Jamaica Royale #92 on the #1 Beach in the USA!
Siesta Key apartment
2 bedrooms / 2 bathrooms / sleeps 6
Responds fast! avg. 1 hour 50 minutes
Price per night from
$248
Luxury Venice Home with (heated) Private Pool and Lake View
Venice house
4 bedrooms / 3 bathrooms / sleeps 8
“I wish I was there right now :) !!!” My family and I had a wonderful time while at this beautiful, brand new, and completely furnished home. This was our first vacation since our daughter was born, and this place was the perfect retreat for the entir
Price per night from
$193
The Top Location on Siesta Key - Gertrude's Village House
Siesta Key house
3 bedrooms / 2 bathrooms / sleeps 10
“Location, location, location!” This little gem is the perfect get-a-way for a family or group of friends. I went with my daughter and her friends for her bachelorette weekend, and the fact that we were walking distance to ALL restaurants and shops was
Responds fast! avg. 50 minutes
Price per night from
$227
“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 t
Responds fast! avg. 56 minutes
Price per night from
$240
Honeymoon Suite - Gulf views - next to Siesta Key Beach
Siesta Key apartment
1 bedroom / 2 bathrooms / sleeps 4
Responds fast! avg. 1 hour 16 minutes
Price per night from
$197
“Absolutely Perfect---one Kodak sunset after another” This townhome was gorgeous! We totally enjoyed our 3 week stay and hated to leave. Kelley (owner) could have not been more helpful. We fished off the dock and enjoyed watching the birds fish then
Price per night from
$158
“Florida Trip” We rented this lovely home through Flipkey. This was a great rental for two couples and had everything you could possibly want at your fingertips. Just like home. Location was great and is located in a nice quiet neighborhood. Monica, th
Responds fast! avg. 44 minutes
Price per night from
$183
Beachfront Ground Level Suite - Remodeled - 2 king bedrooms
Siesta Key condo
3 bedrooms / 2 bathrooms / sleeps 6
Responds fast! avg. 1 hour 58 minutes
Price per night from
$154
Island Oasis - steps to the Gulf & Bay, heated swimming pool
Manasota Key house
3 bedrooms / 2 bathrooms / sleeps 10
Price per night from
$204
Top in Siesta Village at Best Beaches, Food & Entertainment! - Casa Van Lopik(J)
Siesta Key house
3 bedrooms / 2 bathrooms / sleeps 10
“Location, Location, Location!” Great house. Just as pictured and described. Dan and Jon are super-easy hosts. I like the little things - that the house is set up and fully ready. Abundance of supplies and towels, even beach chairs await! This having
Responds fast! avg. 50 minutes
Price per night from
$207
2 BR plus Den Condo. Golf Course & Water View
Sarasota apartment
3 bedrooms / 2 bathrooms / sleeps 6
“Wonderful” Fantastic place and owner Robin C very accomadating and very helpful everything here is all we need, so relaxed. This condo is near any kind of shopping, restaurants you could possibly be interested in! We don’t want our time to end!
Price per night from
$67
4 Bedroom with Gulf View Siesta Key FL Beach Fun
Siesta Key apartment
4 bedrooms / 4 bathrooms / sleeps 10
“Fantastic Location and Beautiful Accomodations” Our daughters and their families stayed here in February. The condo was everything we expected and more. It has a breathtaking view of the Gulf from the screened in lani which runs the width of the uni
Price per night from
$353
“Great vacation home, Strongly recommend to fellow travlers” We Had a great time at this vacation Rental home. The pool was clean and very well maintained. The House was very clean and very well equiept with everything you would need. The Beds are eve
Responds fast! avg. 2 hours 21 minutes
Price per night from
$193
Price per night from
$108
Price per night from
$126
Responds fast! avg. 2 hours 57 minutes
Price per night from
$142
Responds fast! avg. 1 hour 59 minutes
Price per night from
$126
Lovely 3 BR Home with Office & Heated Pool at Tara
Bradenton house
3 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$124
Siesta Key Beach with gorgeous sunsets in Siesta Key
Sarasota condo
2 bedrooms / 2 bathrooms / sleeps 4
Price per night from
$104
