House
10.0(17 Reviews)
2 Bedrooms
5 Guests
Parking
Kitchen
Air Conditioner
Internet
AU $221/Night
7 Nights - AU $1,549
Osprey Villa Rentals
We compare villas and rental homes from owners across Booking.com, Vrbo and Expedia.
- Up-front pricing
- No markup
- Trusted partners
Compare Villas, Resorts, & Rentals in Osprey
10.0
House
10.0(1 Review)
2 Bedrooms
6 Guests
Oceanfront- Parking
Ocean View
Balcony/Terrace
AU $330/Night
7 Nights - AU $2,308
House
8.0(2 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
AU $326/Night
7 Nights - AU $2,279
House
10.0(6 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
AU $233/Night
7 Nights - AU $1,631
Apartment
9.0(1 Review)
1 Bedroom
4 Guests
- Oceanfront
Breakfast- Parking
Pool
AU $310/Night
7 Nights - AU $2,167
House
10.0(5 Reviews)
2 Bedrooms
5 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
AU $437/Night
7 Nights - AU $3,060
House
10.0(5 Reviews)
1 Bedroom
6 Guests
- Oceanfront
Hot Tub- Parking
- Ocean View
AU $289/Night
7 Nights - AU $2,025
Condo
10.0(4 Reviews)
2 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Kitchen
AU $303/Night
7 Nights - AU $2,121
Condo
10.0(4 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
AU $289/Night
7 Nights - AU $2,023
Luxury Places to Stay in Osprey
Over 118+ Luxury Places to Stay in or Near Osprey
House
10.0(27 Reviews)
5 Bedrooms
8 Guests
Private Pool- Oceanfront
- Parking
- Pool
AU $5,143/Night
7 Nights - AU $36,003
House
5 Bedrooms
10 Guests
Pet Friendly
Child Friendly
Security/Safety
AU $2,903/Night
7 Nights - AU $20,324
House
9.6(39 Reviews)
3 Bedrooms
6 Guests
- Hot Tub
- Parking
- Balcony/Terrace
View
AU $1,106/Night
7 Nights - AU $7,739
New
House
5 Bedrooms
12 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
AU $1,051/Night
7 Nights - AU $7,356
Condo
8.6(17 Reviews)
3 Bedrooms
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
AU $950/Night
7 Nights - AU $6,651
Cottage
9.8(10 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $584/Night
7 Nights - AU $4,089
House
3 Bedrooms
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $547/Night
7 Nights - AU $3,829
House
4 Bedrooms
10 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
AU $531/Night
7 Nights - AU $3,715
RV Rental
1 Bedroom
6 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
AU $525/Night
7 Nights - AU $3,674
Top-Rated Villas with a Pool in Osprey
Over 67+ Top-Rated Private Villas with a Pool in or Near Osprey
Condo
10.0(8 Reviews)
3 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- View
AU $348/Night
7 Nights - AU $2,435
Condo
10.0(4 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
AU $224/Night
7 Nights - AU $1,571
Condo
10.0(2 Reviews)
1 Bedroom
3 Guests
- Oceanfront
- Parking
- Pool
Spa
AU $202/Night
7 Nights - AU $1,415
AU $418/Night
7 Nights - AU $2,926
Condo
10.0(1 Review)
1 Bedroom
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
AU $292/Night
7 Nights - AU $2,045
House
9.8(62 Reviews)
3 Bedrooms
5 Guests
- Private Pool
- Parking
- Pool
- Ocean View
AU $431/Night
7 Nights - AU $3,016
House
9.8(20 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
AU $393/Night
7 Nights - AU $2,751
House
9.8(6 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
AU $328/Night
7 Nights - AU $2,295
Condo
9.4(3 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
AU $293/Night
7 Nights - AU $2,050
Pet-Friendly Villas in Osprey
Over 39+ Pet-Friendly Private Villas in or Near Osprey
House
10.0(2 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
AU $443/Night
7 Nights - AU $3,099
AU $163/Night
7 Nights - AU $1,140
House
6.8(3 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
AU $335/Night
7 Nights - AU $2,344
RV Rental
10.0(1 Review)
1 Bedroom
6 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
AU $525/Night
7 Nights - AU $3,674
RV Rental
1 Bedroom
6 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
AU $525/Night
7 Nights - AU $3,674
House
2 Bedrooms
5 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
AU $419/Night
7 Nights - AU $2,933
Condo
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
AU $187/Night
7 Nights - AU $1,309
House
10.0(4 Reviews)
3 Bedrooms
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $325/Night
7 Nights - AU $2,272
House
9.6(4 Reviews)
4 Bedrooms
12 Guests
- Air Conditioner
- Pet Friendly
- Child Friendly
Laundry
AU $153/Night
7 Nights - AU $1,071
Large Private Villas in Osprey
Over 10+ Large Villas in or Near Osprey for Groups and Families
House
7.4(3 Reviews)
4 Bedrooms
12 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
AU $328/Night
7 Nights - AU $2,299
AU $361/Night
7 Nights - AU $2,529
AU $359/Night
7 Nights - AU $2,516
House
2 Bedrooms
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $448/Night
7 Nights - AU $3,132
Villa
3 Bedrooms
6 Guests
- Air Conditioner
- Pet Friendly
- Child Friendly
- Laundry
AU $272/Night
7 Nights - AU $1,906
Villa
9.0(22 Reviews)
5 Bedrooms
12 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
AU $941/Night
7 Nights - AU $6,585
House
9.0(15 Reviews)
4 Bedrooms
13 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
AU $841/Night
7 Nights - AU $5,886
House
4 Bedrooms
12 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
AU $607/Night
7 Nights - AU $4,250
House
4 Bedrooms
12 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
AU $587/Night
7 Nights - AU $4,111
Wheelchair Accessible Holiday Homes in Osprey
Over 10+ Wheelchair Accessible Villas and Holiday Homes in or Near Osprey
Condo
9.2(5 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
AU $345/Night
7 Nights - AU $2,414
Condo
9.2(5 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
AU $343/Night
7 Nights - AU $2,400
Condo
8.8(3 Reviews)
1 Bedroom
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
AU $347/Night
7 Nights - AU $2,430
Condo
1 Bedroom
4 Guests
- Balcony/Terrace
- Kitchen
- Child Friendly
Wheelchair Accessible
AU $426/Night
7 Nights - AU $2,984
Condo
1 Bedroom
2 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
AU $294/Night
7 Nights - AU $2,055
AU $489/Night
7 Nights - AU $3,420
Apartment
1 Bedroom
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
AU $201/Night
7 Nights - AU $1,405
Condo
3 Bedrooms
8 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
AU $370/Night
7 Nights - AU $2,592
AU $313/Night
7 Nights - AU $2,192
Osprey Villas, Airbnb and Holiday Homes Under $200
Over 35+ Osprey Private Villas, Airbnb and Holiday Homes Under $200
Apartment
9.8(36 Reviews)
2 Bedrooms
5 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
AU $223/Night
7 Nights - AU $1,558
Apartment
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
AU $262/Night
7 Nights - AU $1,832
House
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
AU $255/Night
7 Nights - AU $1,786
Apartment
1 Bedroom
4 Guests
- Parking
- Pool
- Air Conditioner
- Internet
AU $252/Night
7 Nights - AU $1,766
AU $171/Night
7 Nights - AU $1,198
AU $148/Night
7 Nights - AU $1,038
Apartment
10.0(3 Reviews)
1 Bedroom
4 Guests
- Hot Tub
- Parking
- Pool
- Spa
AU $215/Night
7 Nights - AU $1,505
Condo
10.0(3 Reviews)
3 Bedrooms
3 Guests
- Oceanfront
- Parking
- Pool
- Spa
AU $191/Night
7 Nights - AU $1,334
Apartment
10.0(1 Review)
1 Bedroom
2 Guests
- Private Pool
- Parking
- Pool
- Ocean View
AU $219/Night
7 Nights - AU $1,529
Instantly Bookable Villa Rentals in Osprey
Over 28+ Instantly Bookable Private Villas in or Near Osprey
House
10.0(2 Reviews)
2 Bedrooms
7 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
AU $409/Night
7 Nights - AU $2,862
RV Rental
1 Bedroom
6 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
AU $525/Night
7 Nights - AU $3,674
House
10.0(1 Review)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
AU $631/Night
7 Nights - AU $4,415
House
9.4(73 Reviews)
1 Bedroom
2 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
AU $143/Night
7 Nights - AU $1,003
Condo
9.0(2 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
AU $219/Night
7 Nights - AU $1,532
House
8.6(3 Reviews)
4 Bedrooms
8 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
AU $805/Night
7 Nights - AU $5,632
House
8.0(2 Reviews)
2 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $354/Night
7 Nights - AU $2,477
House
6.8(3 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
AU $324/Night
7 Nights - AU $2,268
House
5.0(3 Reviews)
3 Bedrooms
8 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
AU $704/Night
7 Nights - AU $4,927
Book a Last Minute Place to Stay in Osprey
About Osprey Vacation Rentals
There are more than 127 incredible getaway rentals that are available in Osprey. These choices include villas, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Relax with BedroomVillas and uncover great stays in Osprey.
BedroomVillas features numerous last-minute deals on villas, hotels, and rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With BedroomVillas in Osprey, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the BedroomVillas vacation rentals, resorts, and Airbnb-style properties in Osprey. Places to stay near Osprey are 821.7 ft² on average, with prices averaging AU $430 a night.
BedroomVillas helps you find the ideal holiday rental to create lifetime travel memories in Osprey. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect place to stay today.
Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods Osprey, FL
There are 1 hotels in Osprey and 84 rentals
- Prices for a holiday home in Osprey start at AU $153
- Top rated vacation home in Osprey is Rare private beachfront estate on the Gulf.
- Most popular short term in Osprey is Casey Key Resorts - Mainland
- Cheapest place to stay in Osprey is 4-bedroom heated pool house 5 minutes to the beach
- Most expensive holiday rental in Osprey is Rare private beachfront estate on the Gulf.
Recently Booked Hotels, Resorts, or Rentals in Osprey
Frequently Asked Questions About Osprey?
What are the top hotels or resorts in Osprey?
We provide an array of great vacation destinations in Osprey. If you are looking to stay in or around the Osprey area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Osprey:
- Rare private beachfront estate on the Gulf.
- 2-bedroom Spacious townhome in Osprey
- Sarasota Vacation paradise!
- Furnished and meticulous! Near Nokomis, Venice and Siesta Beaches.
- Sunny Coastal Escape
- Welcome to Lime on Green! I also have a rental CAR listed/available on TURO.COM
- Private guest house with king bed & loft. Deck with hot tub and putting green
- Renovated Tranquil 3-Bdrm- w/yard, workspace, great kitchen in Osprey dogs ok
- 2 Bedroom Ground Floor Condo in Osprey - lots of light & beautiful water view!
- Windsor Lodge Unit #10 studio
How many vacation rentals have private pools in Osprey?
We have 10 luxury villas and vacation rentals featuriung a private pool in and near Osprey. Some of the best destinations to stay that feature or have access to a swimming pool are:
Which hotel or resort in Osprey is best for families?
Searching for a family-friendly getaway in Osprey? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.
How many hotels, resorts, or rentals are available in Osprey?
BedroomVillas offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by BedroomVillas in 2026 is over 127 in the Osprey area, and that number rises every day. By combining listings from multiple websites and travel providers, BedroomVillas can provide you with a diverse amount of choices of the best luxury stays in Osprey.
Nearby Neighborhood (5)
| Neighborhood | Property Count |
|---|---|
| Vamo Rental Villas and Private Getaways in Sarasota, Florida | 49 |
| Palmer Ranch Rental Villas and Private Getaways in Sarasota, Florida | 35 |
| Sorrento Shores Rental Villas and Private Getaways in Sarasota, Florida | 593 |
| Bay Acres Rental Villas and Private Getaways in Sarasota, Florida | 739 |
| Rivendell Rental Villas and Private Getaways in Sarasota, Florida | 395 |
