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 $224
CA $554 total
includes taxes & fees
Oct 28 - Oct 29
Charming Osprey Home

2. Sunny Coastal Escape

Sunny Coastal Escape
Bay Acres
10.0 out of 10, Exceptional, (6 reviews)
"We were centerally located and had an easy drive to the beach and park. "
United States
Jennifer A.
The price is CA $343
CA $654 total
includes taxes & fees
Nov 8 - Nov 9
Sunny Coastal Escape

3. 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 $403
CA $493 total
includes taxes & fees
Oct 29 - Oct 30
Fantastic Tented Cabin with Fire Pit in Sarasota, Florida

4. 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 $403
CA $498 total
includes taxes & fees
Nov 4 - Nov 5
Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida

5. Charming Secluded Tented Cabin in Sarasota, Florida

Charming Secluded Tented Cabin in Sarasota, Florida
Sarasota
The price is CA $403
CA $493 total
includes taxes & fees
Oct 29 - Oct 30
Charming Secluded Tented Cabin in Sarasota, Florida

6. 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 $403
CA $493 total
includes taxes & fees
Oct 29 - Oct 30
Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida

7. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (6,018 reviews)
"Loved our stay"
United States
Julie anne
The price is CA $186
CA $247 total
includes taxes & fees
Oct 28 - Oct 29
Tropical Beach Resorts

8. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,326 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
The price is CA $219
CA $271 total
includes taxes & fees
Oct 28 - Oct 29
Captiva Beach Resort

9. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,475 reviews)
"This place was perfect!"
United States
Kat
The price is CA $164
CA $185 total
includes taxes & fees
Oct 28 - Oct 29
Hibiscus Suites - Gateway to Siesta Key

10. Oceanfront home

Oceanfront home
Vamo
9.8 out of 10, Exceptional, (94 reviews)
"It looks just like the pictures and the sunset daily is absolutely gorgeous. The neighborhood is nice and the people are kind. We loved being short car rides away from stores, beaches and the legacy trail. The owners had great communication. Would definitely stay again."
United States
Ashley H.
The price is CA $357
CA $865 total
includes taxes & fees
Oct 28 - Oct 29
Oceanfront home

11. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (695 reviews)
"Enjoyed our stay"
United States
Robin
The price is CA $258
CA $292 total
includes taxes & fees
Nov 4 - Nov 5
A Beach Retreat

12. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (202 reviews)
"The room was clean and the staff were very kind."
United States
Geraldine
The price is CA $292
CA $330 total
includes taxes & fees
Nov 2 - Nov 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 $150
CA $372 total
includes taxes & fees
Oct 29 - Oct 30
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

14. Siesta Key, Sea Horse Villa, Pool. Daily rentals

Siesta Key, Sea Horse Villa, Pool. Daily rentals
South Village
9.4 out of 10, Exceptional, (55 reviews)
"Perfect weekend getaway stay for my husband and I! The cottage had everything we needed, was thoroughly cleaned and location was perfect for restaurant hopping and beach going. Would definitely stay again!"
United States
Allie A.
The price is CA $150
CA $372 total
includes taxes & fees
Oct 29 - Oct 30
Siesta Key, Sea Horse Villa, Pool. Daily rentals

15. Couple’s Escape-Beach Club at Siesta Key 106C by RVA

Couple’s Escape-Beach Club at Siesta Key 106C by RVA
South Village
9.4 out of 10, Exceptional, (105 reviews)
"Great birthday weekend. Awesome location to the beach and nightlife. Highly recommend."
United States
Cindy F.
The price is CA $214
CA $470 total
includes taxes & fees
Oct 29 - Oct 30
Couple’s Escape-Beach Club at Siesta Key 106C by RVA

16. Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
South Village
9.8 out of 10, Exceptional, (91 reviews)
"Would definitely stay here again. Great location and great house! Owner was quick and helpful with communication."
United States
Clarissa S.
The price is CA $139
CA $425 total
includes taxes & fees
Nov 3 - Nov 4
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

17. Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (135 reviews)
"Cute little cottage right on the beach. Doesn’t get any better than that."
United States
kelly h.
The price is CA $277
CA $674 total
includes taxes & fees
Nov 11 - Nov 12
Casey Key Beachfront Escape: Charming 1BR Cottage

18. Romantic Getaway Beach Club Siesta 202B by RVA

Romantic Getaway Beach Club Siesta 202B by RVA
South Village
8.8 out of 10, Excellent, (57 reviews)
"Peaceful getaway. Throughly enjoyed the stay. "
United States
Anonymous traveller
The price is CA $239
CA $505 total
includes taxes & fees
Oct 29 - Oct 30
Romantic Getaway Beach Club Siesta 202B by RVA

19. 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 $224
CA $484 total
includes taxes & fees
Oct 29 - Oct 30
Bright & Beachy–Beach Club Siesta Key 100A by RVA

20. Dolphin Villa | Pool | Steps to Siesta Key Village

Dolphin Villa | Pool | Steps to Siesta Key Village
Siesta Key Village
9.4 out of 10, Exceptional, (17 reviews)
"The place was clean and location was perfect! 2 blocks to the beach and 2 blocks to the village. It’s really great and helpful that they provided beach wagon, chairs and umbrella. "
United States
Amy
The price is CA $161
CA $527 total
includes taxes & fees
Oct 31 - Nov 1
Dolphin Villa | Pool | Steps to Siesta Key Village
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?

Tropical Villas of Venice Beach: This vacation home rental near Osprey is located near the beach and has an outdoor pool, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a microwave, and kitchenware. Make the most of the garden in this rental home to help you unwind.

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?

Turtle Beach and Nokomis Beach are a couple of scenic spots to enjoy the outdoors, whereas Historic Spanish Point is one of the cultural attractions. While in the area, you can also visit popular places like Siesta Key Beach and Lido 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.