A marina with docked boats, a wooden bridge, and a building with a red roof.

Osprey Vacation Rentals

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Our top choices for Osprey vacation rentals

1. Charming Osprey Home

Charming Osprey Home
Bay Acres
10.0 out of 10, Exceptional, (2 reviews)
"We had a positive experience staying at Linda’s duplex in Osprey. Linda was a lovely host and even furnished us with beach chairs and a cabana . The place was spotless & location was convenient for us as we explored most of the Sarasota, Venice & Naples area. Highly recommended staying at this lovely duplex. "
United States
Diane S.
The price is CA $220
CA $541 total
includes taxes & fees
Aug 23 - Aug 24
Charming Osprey Home

2. Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida

Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida
Sarasota
The price is CA $382
CA $485 total
includes taxes & fees
Aug 24 - Aug 25
Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida

3. Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida

Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida
Sarasota
The price is CA $382
CA $485 total
includes taxes & fees
Aug 24 - Aug 25
Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida

4. Fantastic Tented Cabin with Fire Pit in Sarasota, Florida

Fantastic Tented Cabin with Fire Pit in Sarasota, Florida
Sarasota
10.0 out of 10, Exceptional, (1 review)
The price is CA $382
CA $485 total
includes taxes & fees
Aug 24 - Aug 25
Fantastic Tented Cabin with Fire Pit in Sarasota, Florida

5. Charming Secluded Tented Cabin in Sarasota, Florida

Charming Secluded Tented Cabin in Sarasota, Florida
Sarasota
The price is CA $382
CA $485 total
includes taxes & fees
Aug 24 - Aug 25
Charming Secluded Tented Cabin in Sarasota, Florida

6. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (384 reviews)
"Great place"
United States
Mario
The price is CA $116
CA $318 total
includes taxes & fees
Sep 13 - Sep 14
Tiny House Siesta

7. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,780 reviews)
"Great place to visit!"
United States
Margaret Lai Ling
The price is CA $175
CA $234 total
includes taxes & fees
Aug 23 - Aug 24
Tropical Beach Resorts

8. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,418 reviews)
"We stayed for 2 nights, the location was perfect for our needs! The beds were very comfortable and the kitchen was a added bonus!"
United States
Justine
The price is CA $153
CA $173 total
includes taxes & fees
Sep 16 - Sep 17
Hibiscus Suites - Gateway to Siesta Key

9. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,300 reviews)
"The proximity to the beach and the ambient of the place"
United States
natalia
The price is CA $207
CA $257 total
includes taxes & fees
Sep 9 - Sep 10
Captiva Beach Resort

10. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (668 reviews)
"Lovely place on a family beach."
United States
Robert
The price is CA $254
CA $287 total
includes taxes & fees
Aug 27 - Aug 28
A Beach Retreat

11. Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (80 reviews)
"Great location, very clean and spacious."
United States
Jason
The price is CA $152
CA $461 total
includes taxes & fees
Aug 25 - Aug 26
Siesta Key Island Rentals

12. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (173 reviews)
"Beautiful hotel comfortable bed nice and friendly staff!!!!"
United States
Isabel
The price is CA $256
CA $289 total
includes taxes & fees
Sep 2 - Sep 3
SeaSpray Resort

13. Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
South Village
9.6 out of 10, Exceptional, (49 reviews)
"We enjoyed our stay alot of stores n restaurants nearby, don’t need to use the car. "
United States
maureen p.
The price is CA $192
CA $424 total
includes taxes & fees
Aug 23 - Aug 24
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

14. Siesta Key Village-Suite #3: A Block to the Beach!

Siesta Key Village-Suite #3: A Block to the Beach!
Siesta Key Village
9.2 out of 10, Wonderful, (77 reviews)
"Great stay"
United States
Allison H.
The price is CA $195
CA $520 total
includes taxes & fees
Aug 23 - Aug 24
Siesta Key Village-Suite #3: A Block to the Beach!

15. Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.

Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.
South Village
9.8 out of 10, Exceptional, (34 reviews)
"Great stay."
United States
James J.
The price is CA $147
CA $313 total
includes taxes & fees
Sep 13 - Sep 14
Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.

16. [lounge like locals] walk to siesta beach +bikes

[lounge like locals] walk to siesta beach +bikes
Siesta Key
9.8 out of 10, Exceptional, (37 reviews)
"Thanks for a great stay, Jayme! Perfect location and extremely accurate Vrbo listing! Beds super comfy!"
United States
Sue H.
The price is CA $128
CA $429 total
includes taxes & fees
Aug 24 - Aug 25
[lounge like locals] walk to siesta beach +bikes

17. Jetties Pointe Cottage #5 - 408 “Casey Key”

Jetties Pointe Cottage #5 - 408 “Casey Key”
Casey Key
9.6 out of 10, Exceptional, (33 reviews)
"Amazing view and beach access, really great stay."
United States
Evan T.
The price is CA $213
CA $530 total
includes taxes & fees
Aug 30 - Aug 31
Jetties Pointe Cottage #5 - 408 “Casey Key”

18. Bright & Beachy–Beach Club Siesta Key 100A by RVA

Bright & Beachy–Beach Club Siesta Key 100A by RVA
South Village
9.0 out of 10, Wonderful, (119 reviews)
"The pool and proximity to the beach are great "
United States
Evan C.
The price is CA $219
CA $471 total
includes taxes & fees
Aug 24 - Aug 25
Bright & Beachy–Beach Club Siesta Key 100A by RVA

19. Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach

Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach
South Village
8.8 out of 10, Excellent, (90 reviews)
"It was a great experience, definitely would come back."
United States
Alicia
The price is CA $238
CA $498 total
includes taxes & fees
Aug 24 - Aug 25
Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach

20. Siesta Key Village-Suite #1: A block to the Beach!

Siesta Key Village-Suite #1: A block to the Beach!
Siesta Key Village
9.8 out of 10, Exceptional, (47 reviews)
"Great place to stay"
United States
Brad S.
The price is CA $195
CA $520 total
includes taxes & fees
Aug 23 - Aug 24
Siesta Key Village-Suite #1: A block to the Beach!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Osprey Hotel Reviews

Find out more about Osprey

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Osprey. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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Frequently asked questions

Can I find vacation rentals in Osprey?

Yes, we have vacation rentals in Osprey near Jim Neville Marine Preserve, or you can go with a more secluded option if you're looking for extra privacy while you relax. Visitors to Osprey speak positively about the popular beaches and top-notch restaurants in this destination. While you're in the area, you can also enjoy the lively bars and shops.

What are some of the best vacation rentals in Osprey?

Siesta Key Island Rentals: This vacation home rental near Osprey comes with WiFi so you can feel at home during your trip. This vacation rental also comes with free parking to give you added peace of mind.

How many vacation rentals are there in Osprey?

With 13 Expedia vacation rentals, you're sure to find just the right place for your Osprey stay.

What’s there to see and do in Osprey?

Family-friendly attractions include Jim Neville Marine Preserve and Nancy's Consignments, whereas Turtle Beach and Nokomis Beach are a couple of great spots to enjoy the outdoors. While in the area, you can also visit popular places like Siesta Key Beach and Venice Beach.

What’s a vacation rental in Osprey like?

Vacation rentals are private properties you can stay in for a long or short time in Osprey. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for families.