House holiday rentals in Osprey
Find and book unique houses on Airbnb
Top-rated house rentals in Osprey
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Osprey
House rentals with a pool
Home in Nokomis
4.89 out of 5 average rating, 149 reviews4/2.5 Oak Bahay, Heated Pool! 5min to Beach,4Acres
Home in Sarasota
4.98 out of 5 average rating, 161 reviewsThe Palms-Heated Private Pool Hot Tub-5mi to beach
Home in Englewood
4.95 out of 5 average rating, 103 reviewsCoastal Home Away From Home with Pool
Home in Sarasota
4.9 out of 5 average rating, 128 reviewsCottage On Bay (private backyard, near beaches)
Home in Sarasota
4.81 out of 5 average rating, 108 reviews1 House 1400sq. ft. 12 min from Siesta Key!
Home in Sarasota
4.97 out of 5 average rating, 209 reviewsYour private retreat near Siesta Key Beach.
Home in Siesta Key
5.0 out of 5 average rating, 127 reviewsOne-of-a-kind*Beach, Village, Dock & Private Pool!
Home in Sarasota
4.97 out of 5 average rating, 112 reviewsGorgeous Home / Heated Pool and Spa
Weekly house rentals
Home in Sarasota
4.88 out of 5 average rating, 208 reviewsThe Pineapple Suite.Teal tropical home in Sarasota
Home in Osprey
4.92 out of 5 average rating, 36 reviewsSand Dollar Cottage - 15m to Siesta / Casey Key
Home in Osprey
4.92 out of 5 average rating, 39 reviewsPrivate house with loft
Home in Nokomis
4.9 out of 5 average rating, 42 reviewsCheerful, sparkling 2 bedroom cottage, 1.8 miles from beach
Home in Sarasota
5.0 out of 5 average rating, 6 reviewsCute 2 bedroom home close to it all.
Home in Osprey
4.96 out of 5 average rating, 23 reviewsCharming Florida Cottage - Kayaks Included
Home in Osprey
4.97 out of 5 average rating, 33 reviewsSarasota vacation Home!
Home in Nokomis
5.0 out of 5 average rating, 10 reviewsUpdated house close to the Beach
Private house rentals
Home in Sarasota
5.0 out of 5 average rating, 31 reviewsSiesta Key Fully-Renovated Unit 5 min to the beach
Home in Nokomis
4.99 out of 5 average rating, 74 reviewsPeaceful Getaway just minutes from the beach
Home in Venice
5.0 out of 5 average rating, 19 reviewsEndless Summer 3br/2ba
Home in Venice
4.97 out of 5 average rating, 68 reviewsVenice Getaway 3 bedrooms, private heated pool
Home in Nokomis
4.95 out of 5 average rating, 19 reviewsThe Pineapple Escape
Home in Nokomis
5.0 out of 5 average rating, 50 reviewsCharming vacation home, short walk to the beach
Home in Nokomis
4.98 out of 5 average rating, 58 reviewsTiki Oasis 3bed on .6 acre paradise 5 min to Beach
Home in Nokomis
5.0 out of 5 average rating, 34 reviewsDiscount for 30+ day stays, fast wifi-work desk!
Quick stats about house rentals in Osprey
Total rentals
40 properties
Rentals with a pool
20 properties have a pool
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
540 reviews
Nightly prices starting at
€ 74 before taxes and fees
Destinations to explore
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