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
4.97 out of 5 average rating, 351 reviewsAdorable studio close to Siesta beach!
Home in Sarasota
4.99 out of 5 average rating, 131 reviewsAdorable Bungalow Fire pit/outdoor shower 2/1 Cute
Guest suite in Sarasota
4.97 out of 5 average rating, 117 reviewsPrivate & Luxurious studio. “The Beach house”
Condo in Venice
4.87 out of 5 average rating, 142 reviewsThe Studio at the Beach 56
Home in Venice
4.9 out of 5 average rating, 162 reviewsVenice Pool Villa with Bikes Kayaks Great Beaches!
Guesthouse in Sarasota
4.86 out of 5 average rating, 373 reviewsThe Cottage, very close to Siesta Beach!
Cottage in Osprey
4.92 out of 5 average rating, 25 reviewsMattie’s Cottage by the Bay
Home in Osprey
4.92 out of 5 average rating, 38 reviewsPrivate house with loft
Other great vacation rentals in Osprey
Vacation home in Nokomis
4.96 out of 5 average rating, 54 reviews"Dolphin" Shore Beach Houses Resort
Cottage in Nokomis
4.92 out of 5 average rating, 84 reviewsThe "Turtle Cottage" - a charming beachy retreat.
Guest suite in Venice
4.98 out of 5 average rating, 55 reviewsVenice Beach Studio
Condo in Sarasota
4.98 out of 5 average rating, 60 reviewsLovely 2-Bedroom Condo, 7 min from Siesta Beach
Home in Nokomis
5.0 out of 5 average rating, 10 reviewsUpdated house close to the Beach
Condo in Venice
4.97 out of 5 average rating, 58 reviewsShort walk to beach 4, King bed, Dog Friendly
Apartment in Nokomis
4.92 out of 5 average rating, 13 reviewsThe Hub
Home in Osprey
5.0 out of 5 average rating, 23 reviewsHeated Pool | 3 Beds | Near Beaches and parks
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 condo rentals in Osprey?
Experience the best of Osprey with our condo rentals, starting at about $60 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 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 Apartment Rentals in Osprey?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
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