Osprey vacation rentals
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Osprey
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Osprey vacation rentals
Other great vacation rentals in Osprey
Guest suite in Sarasota
4.98 out of 5 average rating, 103 reviewsMid-Century Modern Beach Getaway
Sep 6 – 13
Guest suite in Sarasota
4.97 out of 5 average rating, 350 reviewsAdorable studio close to Siesta beach!
Sep 10 – 17
Guesthouse in Sarasota
4.86 out of 5 average rating, 369 reviewsThe Cottage, very close to Siesta Beach!
Aug 20 – 27
Home in Sarasota
4.9 out of 5 average rating, 131 reviewsThe lovely place getaway-SRQ
May 1 – 6
Guesthouse in Sarasota
4.93 out of 5 average rating, 454 reviewsLa Casetta: "the little house" near to the beaches
Aug 12 – 19
Cottage in Osprey
4.95 out of 5 average rating, 22 reviewsMattie’s Cottage by the Bay
Jun 12 – 19
Home in Osprey
4.92 out of 5 average rating, 38 reviewsPrivate house with loft
Sep 8 – 15
Condo in Nokomis
5.0 out of 5 average rating, 16 reviewsPrivate Studio (entire space)
Apr 7 – 14
Other great vacation rentals in Osprey
Home in Osprey
4.91 out of 5 average rating, 33 reviewsSand Dollar Cottage - 15m to Siesta / Casey Key
Dec 12 – 19
Guest suite in Venice
4.98 out of 5 average rating, 53 reviewsVenice Beach Studio
Dec 22 – 29
Bungalow in Nokomis
5.0 out of 5 average rating, 24 reviewsNokomis Beach Cottage. 2 Blocks to Beach. 2BD/1BA
Aug 16 – 23
Cottage in Nokomis
4.92 out of 5 average rating, 84 reviewsThe "Turtle Cottage" - a charming beachy retreat.
Dec 11 – 18
Home in Nokomis
5.0 out of 5 average rating, 9 reviewsUpdated house close to the Beach
Aug 11 – 18
Condo in Sarasota
4.98 out of 5 average rating, 56 reviewsLovely 2-Bedroom Condo, 7 min from Siesta Beach
Sep 18 – 25
Condo in Venice
4.95 out of 5 average rating, 41 reviewsLovely large one+ in the heart of downtown Venice
Jul 7 – 14
Apartment in Sarasota
4.98 out of 5 average rating, 43 reviewsStudio Minutes to Siesta key, Lido Key, and SMH!
Jun 6 – 13
Quick stats about vacation rentals in Osprey
Total rentals
80 properties
Rentals with a pool
60 properties have a pool
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
60 properties are a good fit for families
Total number of reviews
1.6K reviews
Nightly prices starting at
R1,151 ZAR before taxes and fees
Frequently Asked Questions
Are there vacation rentals with a dedicated workspace in Osprey?
Yes! Work meets play with ease at over 50 vacation rentals in Osprey featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Osprey?
Four-legged friends are welcome in Osprey. Choose from more than 30 vacation rentals for guests traveling with pets.
Are there Osprey vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 60 vacation homes with pools in Osprey, available on Airbnb. Make a splash and soak up the sun in style!
Do condo rentals in Osprey have a gym?
Absolutely! We offer over 10 condo rentals with a gym in Osprey. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Osprey?
Osprey has more than 30 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Osprey?
Experience the best of Osprey with our house rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Osprey have wifi?
Absolutely! We offer over 40 house rentals with wifi in Osprey. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Osprey have air conditioning?
Absolutely! We offer over 40 house rentals with air conditioning in Osprey. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Osprey have a bbq area?
Absolutely! We offer over 10 house rentals with a bbq area in Osprey. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Osprey?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a bbq area, over 40 homes with wifi, over 40 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
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