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
4.91 out of 5 average rating, 277 reviewsSiesta Keys stylish and affordable Airbnb.
Guest suite in Sarasota
4.88 out of 5 average rating, 346 reviewsPrivate, cozy, studio 2 miles from Siesta Key!
Apartment in Sarasota
4.99 out of 5 average rating, 102 reviews*Cozy Private Oasis centrally located* 1
Guest suite in Sarasota
4.94 out of 5 average rating, 483 reviewsStudio Apartment. Priv Yard. 5 min to Siesta Key!
Cottage in Sarasota
4.92 out of 5 average rating, 154 reviewsCasa El Sueño - 8 min to Siesta Key - Intracoastal
Guest suite in Sarasota
4.96 out of 5 average rating, 353 reviewsAdorable studio close to Siesta beach!
Tiny home in Sarasota
4.9 out of 5 average rating, 178 reviews@Tiffanythetinyhome| island | netflix|bike|hammock
Home in Sarasota
4.96 out of 5 average rating, 248 reviewsLovely guest house
Other great vacation rentals in Osprey
Home in Nokomis
4.91 out of 5 average rating, 43 reviewsCheerful, sparkling 2 bedroom cottage, 1.8 miles from beach
Apartment in Nokomis
4.99 out of 5 average rating, 68 reviewsCharming 1 bedroom apartment for 2 with pool.
Cottage in Nokomis
4.92 out of 5 average rating, 85 reviewsThe "Turtle Cottage" - a charming beachy retreat.
Apartment in Nokomis
4.93 out of 5 average rating, 14 reviewsThe Hub
Condo in Nokomis
5.0 out of 5 average rating, 17 reviewsPrivate Studio (entire space)
Home in Osprey
4.78 out of 5 average rating, 51 reviewsLIME ON GREEN Osprey, Florida 34229
Vacation home in Nokomis
4.96 out of 5 average rating, 55 reviews"Dolphin" Shore Beach Houses Resort
Condo in Sarasota
4.98 out of 5 average rating, 63 reviewsLovely 2-Bedroom Condo, 7 min from Siesta Beach
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
$60 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 condo rentals in Osprey?
Osprey has more than 10 family-friendly condo 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 condo rentals in Osprey have wifi?
Absolutely! We offer over 10 condo rentals with wifi in Osprey. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Osprey have air conditioning?
Absolutely! We offer over 10 apartment 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 Apartment Rentals in Osprey?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
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