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
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Osprey vacation rentals

An aerial view of a beach with a large number of people, a clear blue sky, and a calm sea. There are buildings and palm trees visible in the foreground.

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.
$350 nightly
The price is $390
Sep 8 - Sep 9
Total with taxes and fees
Charming Osprey Home
A room with two beds, each with a black metal frame, white bedding, and striped pillows. There is a small table with a plant, a sign that says 'HAPPY CAMPING,' and a wooden floor.

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

Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida
Sarasota
$318 nightly
The price is $354
Sep 7 - Sep 8
Total with taxes and fees
Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida
A tent-style room with bunk beds, a central table, and a colorful rug.

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

Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida
Sarasota
$318 nightly
The price is $354
Sep 7 - Sep 8
Total with taxes and fees
Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida
A cozy room with a bed, a small table with a welcome sign, a refrigerator, and a coffee maker.

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)
$318 nightly
The price is $354
Sep 7 - Sep 8
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.

5. Charming Secluded Tented Cabin in Sarasota, Florida

Charming Secluded Tented Cabin in Sarasota, Florida
Sarasota
$318 nightly
The price is $354
Sep 7 - Sep 8
Total with taxes and fees
Charming Secluded Tented Cabin in Sarasota, Florida
A pool area with a waterfall feature, lounge chairs, and palm trees.

6. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,841 reviews)
"This place is awesome, super clean close to the beach and the pool small But completely renovated and great"
United States
Diana
$158 nightly
The price is $179
Sep 7 - Sep 8
Total with taxes and fees
Tropical Beach Resorts
A compact living space with a kitchen, a dining area, and a sofa with cushions.

7. 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
$203 nightly
The price is $229
Sep 25 - Sep 26
Total with taxes and fees
Tiny House Siesta
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
8.6 out of 10, Excellent, (2,437 reviews)
"This place was perfect!"
United States
Kat
$116 nightly
The price is $131
Sep 8 - Sep 9
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key
A large orange armchair against a white wall with a 'Captiva' sign. There are two potted plants beside the chair.

9. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,303 reviews)
"The proximity to the beach and the ambient of the place"
United States
natalia
$165 nightly
The price is $184
Sep 8 - Sep 9
Total with taxes and fees
Captiva Beach Resort
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

10. 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
$286 nightly
The price is $323
Sep 7 - Sep 8
Total with taxes and fees
Siesta Key Island Rentals
A living room with a view of the ocean, a ceiling fan, and a wooden coffee table.

11. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (672 reviews)
"Lovely place on a family beach."
United States
Robert
$205 nightly
The price is $231
Sep 7 - Sep 8
Total with taxes and fees
A Beach Retreat
A modern living room with a flat-screen TV on a wooden cabinet, a grey sofa with patterned cushions, and a large window with sheer curtains.

12. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (176 reviews)
"Beautiful hotel comfortable bed nice and friendly staff!!!!"
United States
Isabel
$204 nightly
The price is $231
Oct 7 - Oct 8
Total with taxes and fees
SeaSpray Resort
A garden with various plants and a utility pole.

13. Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (131 reviews)
"A beautiful location and super comfortable!"
United States
K B.
$431 nightly
The price is $480
Sep 7 - Sep 8
Total with taxes and fees
Casey Key Beachfront Escape: Charming 1BR Cottage
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

14. 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.
$299 nightly
The price is $333
Sep 7 - Sep 8
Total with taxes and fees
Couple’s Escape-Beach Club at Siesta Key 106C by RVA
A wooden deck with blue lounge chairs, orange chairs, and a barbecue area.

15. 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)
"Great location to downtown, beach. Kitchen and furnishing updated and in great condition. Negatives would be the lock on the backdoor, air conditioning from the ceiling that could not be controlled from our apartment. The pool was great and had plenty of seating. Only issue with the Dolphin apartment is the many windows, which kind of made it feel like living in a fish bowl. That might not be an issues for others. "
United States
Sandra C.
$332 nightly
The price is $345
Sep 7 - Sep 8
Total with taxes and fees
Dolphin Villa - Pool - Steps to Siesta Key Village
A beach with clear blue water, gentle waves, and a distant sailboat.

16. 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.
$357 nightly
The price is $386
Sep 8 - Sep 9
Total with taxes and fees
Siesta Key Village-Suite #1: A block to the Beach!
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

17. Siesta Key 1-Bedroom Condo w Private Patio | The Beach Club Vacation Rental

Siesta Key 1-Bedroom Condo w Private Patio | The Beach Club Vacation Rental
South Village
8.8 out of 10, Excellent, (89 reviews)
"Great location and easy access to the beach."
United States
Erica B.
$319 nightly
The price is $355
Sep 7 - Sep 8
Total with taxes and fees
Siesta Key 1-Bedroom Condo w Private Patio | The Beach Club Vacation Rental
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

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.
$307 nightly
The price is $342
Sep 7 - Sep 8
Total with taxes and fees
Bright & Beachy–Beach Club Siesta Key 100A by RVA
A beach with tall grasses and a sunset.

19. Beachside Studio Located Across from Main Beach and Half Mile to Village

Beachside Studio Located Across from Main Beach and Half Mile to Village
Sarasota
8.8 out of 10, Excellent, (170 reviews)
"The rental had everything promised. The bed and couch were very comfortable. Everything was clean. Beach access was great. The chairs, cooler, and canopy were were just what was needed to maximize our enjoyment on a great beach."
United States
Karen G.
$236 nightly
The price is $263
Sep 8 - Sep 9
Total with taxes and fees
Beachside Studio Located Across from Main Beach and Half Mile to Village
A modern bedroom with a bed, a bedside table, a round dining table with chairs, and a large window with curtains.

20. [escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (33 reviews)
"Easy process in and out. Would definitely do business with them again. A"
United States
Derek J.
$259 nightly
The price is $263
Sep 7 - Sep 8
Total with taxes and fees
[escape to paradise] siesta key beach getaway
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Osprey Hotel Reviews

Tropical Beach Resorts

Tropical Beach Resorts

10/10 Excellent
"We had a wonderful time here!! Close to a beautiful beach with amazing sunsets!! Their new pool was AMAZING with waterfalls and plenty of comfortable lounges and umbrellas! The front desk person learned it was our 30th wedding anniversary and changed our room to a better location. We also arrived really early and were prepared to be turned away, but we were welcomed and allowed early check in! It is walking distance to and amazing seafood restaurant, awesome pizza, a breakfast restaurant, ice cream and more!! Highly recommend and hope to make stays here a yearly thing!!"
Mark 4-night trip
Posted 4 hours ago
Tropical Beach Resorts

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 $131 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?

Siesta Key Island Rentals: This vacation home rental near Osprey comes with free 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 14 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?

Jim Neville Marine Preserve and Turtle 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.