We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation rentals in Osprey, Florida and nearby

Use a credit card to book with our Peace of Mind Protection.
Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
More filters
Find more rentals you can book on TripAdvisor!   We're showing you properties you can book on TripAdvisor first.
All 431 Rentals in the Osprey Area
loading...

The following rentals are within 15 kilometres of Osprey, Florida.

Show Prices
Siesta Key
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
15 photos Details
Reviews (7) Make Enquiry
Show Prices
Siesta Key
1 Bedroom, 1 Bathroom, Sleeps 3
15 photos Details
Reviews (1) Make Enquiry
Show Prices
Venice
3 Bedrooms, 2 Bathrooms, Sleeps 12
18 photos Details
Reviews (8) Make Enquiry
Also consider
Siesta Key Beach Villa - #1 rated Beach in America
2 Bedrooms, sleeps 6
$151 - $204 / night
Harbour Towers Yacht Club
2 Bedrooms, sleeps 4
$877 - $1,042 / week
Kid friendly Luxury home on Siesta Key
4 Bedrooms, sleeps 10
$263 / night
WATER FRONT PARADISE IN OSPREY FLORIDA
2 Bedrooms, sleeps 6
$767 - $1,316 / week
Show Prices
Venice
2 Bedrooms, 2 Bathrooms, Sleeps 6
15 photos Details
Reviews (2) Make Enquiry
Show Prices
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
11 photos Details
Reviews (1) Make Enquiry
Show Prices
Siesta Key
2 Bedrooms, 1 Bathroom, Sleeps 6
20 photos Details
Reviews (30) Make Enquiry
Show Prices
Venice
4 Bedrooms, 3 Bathrooms, Sleeps 14
39 photos Details
Reviews (33) Make Enquiry
Show Prices
Siesta Key
9 Bedrooms, 9 Bathrooms, Sleeps 24
20 photos Details
Reviews (40) Make Enquiry
Get the List
Show Prices
Siesta Key
4 Bedrooms, 4 Bathrooms, Sleeps 10
14 photos Details
Reviews (8) Make Enquiry
Show Prices
Siesta Key
5 Bedrooms, 4 Bathrooms, Sleeps 10
15 photos Details
Reviews (2) Make Enquiry
Show Prices
Venice
2 Bedrooms, 2 Bathrooms, Sleeps 6
36 photos Details
Reviews (4) Make Enquiry
Show Prices
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 4
30 photos Details
Reviews (6) Make Enquiry
Show Prices
Venice
4 Bedrooms, 2 Bathrooms, Sleeps 10
28 photos Details
Reviews (31) Make Enquiry
Show Prices
Siesta Key
3 Bedrooms, 3 Bathrooms, Sleeps 8
38 photos Details
Reviews (14) Make Enquiry
Show Prices
Siesta Key
3 Bedrooms, 2 Bathrooms, Sleeps 4
8 photos Details
Reviews (1) Make Enquiry
Show Prices
Siesta Key
3 Bedrooms, 3 Bathrooms, Sleeps 6
36 photos Details
Reviews (15) Make Enquiry
Show Prices
Venice
1 Bedroom, 1 Bathroom, Sleeps 4
27 photos Details
Reviews (5) Make Enquiry
Show Prices
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
36 photos Details
Reviews (15) Make Enquiry
Show Prices
Siesta Key
2 Bedrooms, 3 Bathrooms, Sleeps 4
16 photos Details
Reviews (4) Make Enquiry
Show Prices
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
23 photos Details
Reviews (7) Make Enquiry
Show Prices
Siesta Key
3 Bedrooms, 2 Bathrooms, Sleeps 6
26 photos Details
Reviews (3) Make Enquiry
Show Prices
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
22 photos Details
Reviews (7) Make Enquiry
Show Prices
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
17 photos Details
Reviews (36) Make Enquiry
Show Prices
Siesta Key
3 Bedrooms, 2 Bathrooms, Sleeps 8
29 photos Details
Reviews (24) Make Enquiry
Show Prices
Venice
2 Bedrooms, 2 Bathrooms, Sleeps 6
21 photos Details
Reviews (2) Make Enquiry
Show Prices
Siesta Key
3 Bedrooms, 3 Bathrooms, Sleeps 8
23 photos Details
Reviews (28) Make Enquiry
Show Prices
Venice
1 Bedroom, 1 Bathroom, Sleeps 6
-77 photos Details
Reviews (20) Make Enquiry
Show Prices
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
15 photos Details
Reviews (11) Make Enquiry
Show Prices
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 4
30 photos Details
Reviews (18) Make Enquiry
Show Prices
Siesta Key
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
28 photos Details
Reviews (4) Make Enquiry
Show Prices
Siesta Key
3 Bedrooms, 2 Bathrooms, Sleeps 6
28 photos Details
Reviews (16) Make Enquiry
Show Prices
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
27 photos Details
Reviews (16) Make Enquiry
Show Prices
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
25 photos Details
Reviews (18) Make Enquiry
Show Prices
Siesta Key
2 Bedrooms, 1 Bathroom, Sleeps 4
32 photos Details
Reviews (8) Make Enquiry
Show Prices
Siesta Key
Studio, 1 Bathroom, Sleeps 2
17 photos Details
Reviews (8) Make Enquiry
Show Prices
Siesta Key
3 Bedrooms, 2 Bathrooms, Sleeps 10
23 photos Details
Reviews (11) Make Enquiry
Show Prices
Siesta Key
3 Bedrooms, 2 Bathrooms, Sleeps 10
15 photos Details
Reviews (12) Make Enquiry
Show Prices
Siesta Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
20 photos Details
Reviews (4) Make Enquiry
Show Prices
Siesta Key
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
9 photos Details
Reviews (8) Make Enquiry
Show Prices
Siesta Key
1 Bedroom, 1 Bathroom, Sleeps 4
51 photos Details
Reviews (33) Make Enquiry
Go to map view
Book Online(197)
Use filters to find the best results!

Suitability

  • Wheelchair access (70)
  • Elder access (179)
  • Suitable for children (225)
  • Pet friendly (89)
  • Smoking allowed (7)

Amenities

  • Air Conditioning (352)
  • Internet (335)
  • Other outdoor space (294)
  • All pools (281)
  • Grill (226)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List
Nearby cities