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

Osprey Vacation Rentals

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Osprey vacation rentals

A modern kitchen with a white countertop, a black kettle, a sink with a black faucet, and a hanging light fixture.

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.
$325 nightly
The price is $365
Nov 8 - Nov 9
Total with taxes and fees
Charming Osprey Home
A modern kitchen with a central island, bar stools, and a clock on the wall.

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.
$362 nightly
The price is $406
Nov 8 - Nov 9
Total with taxes and fees
Sunny Coastal Escape
A tented accommodation with a bed, pillows, a desk, and chairs.

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)
$329 nightly
The price is $357
Nov 16 - Nov 17
Total with taxes and fees
Fantastic Tented Cabin with Fire Pit in Sarasota, Florida
A tented accommodation with a central bed, bedside tables, a hanging light fixture, and a patterned floor.

4. Charming Secluded Tented Cabin in Sarasota, Florida

Charming Secluded Tented Cabin in Sarasota, Florida
Sarasota
$329 nightly
The price is $357
Nov 9 - Nov 10
Total with taxes and fees
Charming Secluded Tented Cabin in Sarasota, Florida
A tented accommodation with a bed, pillows, a desk, and chairs.

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

Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida
Sarasota
$327 nightly
The price is $355
Nov 9 - Nov 10
Total with taxes and fees
Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida
A tent with two chairs and a checkered mat in a forest.

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

Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida
Sarasota
$329 nightly
The price is $357
Nov 9 - Nov 10
Total with taxes and fees
Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida
A pool area with a waterfall feature, lounge chairs, and palm trees.

7. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (6,042 reviews)
"Great resort and location!"
United States
Christine
$175 nightly
The price is $198
Nov 9 - Nov 10
Total with taxes and fees
Tropical Beach Resorts
An outdoor patio with a grill, white chairs, and a red umbrella.

8. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,479 reviews)
"This place was perfect!"
United States
Kat
$152 nightly
The price is $172
Nov 24 - Nov 25
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key
A compact living space with a sofa, a television, a ceiling fan, and a door.

9. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (391 reviews)
"It's a very cute tiny house in a great location. Walking distance to Siesta Keys beach and numerous restaurants. I loved the decor in the sea turtle house. I would definitely stay here again next time I'm in Florida."
United States
Staci
$179 nightly
The price is $202
Dec 1 - Dec 2
Total with taxes and fees
Tiny House Siesta
A modern living room with a sofa, a dining area, and a kitchen area.

10. Casey Key Resort

Casey Key Resort
3.0 star property
Casey Key
8.4 out of 10, Very good, (286 reviews)
"My boyfriend and I had a wonderful time. Easy late check in. Nice clean room. Property beautiful. Private beach beautiful. We definitely plan to come back and have family join."
United States
Jamie
$215 nightly
The price is $240
Dec 2 - Dec 3
Total with taxes and fees
Casey Key Resort
A modern kitchen with a stainless steel sink, a dining area with a table and chairs, and a living room with a sofa and a TV.

11. 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.
$567 nightly
The price is $637
Nov 15 - Nov 16
Total with taxes and fees
Oceanfront home
An outdoor dining area with clear plastic chairs and tables, surrounded by greenery and a building in the background.

12. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,332 reviews)
"We liked the clean room, friendly staff, close to the beach and outdoor amenities."
United States
Andriy
$188 nightly
The price is $210
Nov 17 - Nov 18
Total with taxes and fees
Captiva Beach Resort
A bedroom with a view of a swimming pool and outdoor seating.

13. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (206 reviews)
"The room was clean and the staff were very kind."
United States
Geraldine
$206 nightly
The price is $233
Nov 9 - Nov 10
Total with taxes and fees
SeaSpray Resort
A living room with a view of the ocean, a ceiling fan, and a wooden coffee table.

14. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (700 reviews)
"Enjoyed our stay"
United States
Robin
$205 nightly
The price is $231
Dec 6 - Dec 7
Total with taxes and fees
A Beach Retreat
A swimming pool with a hot tub area, surrounded by a glass enclosure, and palm trees in the background.

15. The Dolphin

The Dolphin
Nokomis
9.8 out of 10, Exceptional, (21 reviews)
"The cottage was comfortable and the pool was relaxing. "
United States
daniel
$198 nightly
The price is $223
Nov 8 - Nov 9
Total with taxes and fees
The Dolphin
A house with a gravel driveway, two blue chairs facing the front, and a porch with a green chair and a red umbrella.

16. 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.
$244 nightly
The price is $274
Nov 8 - Nov 9
Total with taxes and fees
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
Two blue chairs facing a house with a porch, surrounded by palm trees and a gravel driveway.

17. 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.
$244 nightly
The price is $274
Nov 8 - Nov 9
Total with taxes and fees
Siesta Key, Sea Horse Villa, Pool. Daily rentals
A patio with lounge chairs and a table, a wooden fence, and a view of the beach and ocean.

18. 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.
$418 nightly
The price is $467
Nov 9 - Nov 10
Total with taxes and fees
Casey Key Beachfront Escape: Charming 1BR Cottage
A pool area with palm trees, a small pool, and a wooden fence.

19. 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 traveler
$267 nightly
The price is $300
Nov 8 - Nov 9
Total with taxes and fees
Romantic Getaway Beach Club Siesta 202B by RVA
Two blue chairs facing a house with a porch, surrounded by palm trees and a gravel driveway.

20. 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.
$191 nightly
The price is $214
Nov 10 - Nov 11
Total with taxes and fees
Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to 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

Hyatt Place Sarasota/Bradenton Airport

Hyatt Place Sarasota/Bradenton Airport

10/10 Excellent
"The staff Ricky and manager Olivia was the best. They help and answered all questions. They was attentive and professional"
Israel 3-night trip
Posted 2 hours ago
Hyatt Place Sarasota/Bradenton Airport

Find out more about Osprey

Everything you need to know about Osprey vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Osprey vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Osprey vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Osprey vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Osprey. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Osprey in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $172 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Osprey rentals

At Expedia, we put the best Osprey vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Osprey rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Osprey vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Osprey. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.