House vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Osprey house rentals
House rentals with a pool
Home in Sarasota
4.94 out of 5 average rating, 296 reviews☀Coastal Gem☀Heated pool & amazing location!☀
Aug 2 – 9
Home in Sarasota
4.97 out of 5 average rating, 206 reviewsYour private retreat near Siesta Key Beach.
May 15 – 22
Home in Sarasota
4.93 out of 5 average rating, 106 reviewsLake Front House with a Pool
Oct 13 – 20
Home in Sarasota
4.95 out of 5 average rating, 181 reviews2bed/2bath with POOL house, close by SIESTA KEY!!!
Aug 29 – Sep 5
Home in Sarasota
4.81 out of 5 average rating, 107 reviews1 House 1400sq. ft. 12 min from Siesta Key!
Dec 12 – 19
Home in Nokomis
4.88 out of 5 average rating, 147 reviews4/2.5 Oak Bahay, Heated Pool! 5min to Beach,4Acres
Dec 23 – 30
Home in Osprey
5.0 out of 5 average rating, 23 reviewsHeated Pool | 3 Beds | Near Beaches and parks
Jun 3 – 10
Home in Nokomis
4.96 out of 5 average rating, 27 reviewsTropical Pool Paradise - Minutes from the Beach!
Sep 20 – 27
Weekly house rentals
Home in Sarasota
4.9 out of 5 average rating, 144 reviewsSunshine Suite, Minutes to Beach,Tropical Paradise
Dec 25 – Jan 1
Home in Osprey
4.92 out of 5 average rating, 38 reviewsPrivate house with loft
Sep 25 – Oct 2
Home in Osprey
4.91 out of 5 average rating, 33 reviewsSand Dollar Cottage - 15m to Siesta / Casey Key
Oct 3 – 10
Home in Osprey
4.96 out of 5 average rating, 23 reviewsCharming Florida Cottage - Kayaks Included
Aug 20 – 27
Home in Nokomis
4.9 out of 5 average rating, 40 reviewsCheerful, sparkling 2 bedroom cottage, 1.8 miles from beach
Sep 5 – 12
Home in Nokomis
5.0 out of 5 average rating, 9 reviewsUpdated house close to the Beach
Sep 14 – 21
Home in Sarasota
5.0 out of 5 average rating, 4 reviewsCute 2 bedroom home close to it all.
Aug 31 – Sep 7
Home in Osprey
4.97 out of 5 average rating, 33 reviewsSarasota vacation Home!
Sep 1 – 8
Private house rentals
Home in Sarasota
5.0 out of 5 average rating, 29 reviewsSiesta Key Fully-Renovated Unit 5 min to the beach
Sep 26 – Oct 3
Home in Sarasota
5.0 out of 5 average rating, 9 reviewsCozy Getaway Home near Siesta Key Beach
May 18 – 25
Home in Nokomis
4.92 out of 5 average rating, 24 reviewsCheerful 3-bedroom
Jul 16 – 23
Home in Nokomis
5.0 out of 5 average rating, 42 reviewsMinutes to Nokomis Beach Updated and Spacious
May 14 – 21
Home in Nokomis
5.0 out of 5 average rating, 20 reviewsSea Turtle Cottage
Aug 5 – 12
Home in Sarasota
4.92 out of 5 average rating, 53 reviews1 Bed 1 bath 7 mins to the beach
Sep 20 – 27
Home in Venice
4.92 out of 5 average rating, 24 reviewsPalmetto Cottage Retreat
Jun 16 – 23
Home in Nokomis
4.98 out of 5 average rating, 56 reviewsTiki Oasis 3bed on .6 acre paradise 5 min to Beach
Sep 17 – 24
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
R1,504 ZAR before taxes and fees
Destinations to explore
- Sarasota Vacation rentals
- Anna Maria Island Vacation rentals
- Tampa Vacation rentals
- Naples Vacation rentals
- Kissimmee Vacation rentals
- Orlando Vacation rentals
- West Palm Beach Vacation rentals
- Boca Raton Vacation rentals
- Fort Lauderdale Vacation rentals
- Miami Vacation rentals
- Miami Beach Vacation rentals
- Key West Vacation rentals
- Lighthouse rentals United States
- Guesthouse rentals United States
- House rentals United States
- Earth house rentals United States
- Townhouse rentals United States
- Guesthouse rentals Florida
- Townhouse rentals Florida
- Tiny house rentals Florida
- House rentals Florida
- Beach house rentals Florida
- Lakehouse rentals Florida
- Guesthouse rentals Florida
- Townhouse rentals Florida
- Tiny house rentals Florida
- House rentals Florida
- Beach house rentals Florida
- Lakehouse rentals Florida
- Beach house rentals Tampa
- Tiny house rentals Tampa
- Guesthouse rentals Tampa
- House rentals Tampa
- Townhouse rentals Tampa
- Townhouse rentals Naples
- House rentals Naples
- Beach house rentals Naples
- Tiny house rentals Sarasota County
- House rentals Sarasota County
- Townhouse rentals Sarasota County
- Guesthouse rentals Sarasota County
- Rentals with a patio Osprey
- Fitness-friendly rentals Osprey
- Family-friendly rentals Osprey
- Pet-friendly rentals Osprey
- Rentals with pools Osprey
- Rentals with outdoor seating Osprey
- Rentals with a hot tub Osprey
- Rentals with a fire pit Osprey
- Rentals with a washer and dryer Osprey
- Monthly Rentals Osprey
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom