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

Osprey Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Osprey vacation rentals

A spacious living room with a leather sofa, a glass coffee table, and a wooden dining table. Large windows provide ample natural light and a view of the outdoors.

1. Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very good, (45 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is ₩126,882
₩415,733 total
includes taxes & fees
Sep 30 - Oct 1
Siesta Heron Suites & Villas
A pool area with a waterfall feature, lounge chairs, and palm trees.

2. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,924 reviews)
"Amazing resort,"
United States
kurt
The price is ₩183,002
₩241,985 total
includes taxes & fees
Sep 29 - Sep 30
Tropical Beach Resorts
A large orange armchair against a white wall with a 'Captiva' sign. There are two potted plants beside the chair.

3. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,311 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
The price is ₩223,259
₩275,234 total
includes taxes & fees
Sep 29 - Sep 30
Captiva Beach Resort
An outdoor patio with a grill, white chairs, and a red umbrella.

4. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,454 reviews)
"This place was perfect!"
United States
Kat
The price is ₩165,831
₩187,389 total
includes taxes & fees
Sep 29 - Sep 30
Hibiscus Suites - Gateway to Siesta Key
A compact living space with a kitchen, a dining area, and a sofa with cushions.

5. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (386 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
The price is ₩85,252
₩279,047 total
includes taxes & fees
Oct 8 - Oct 9
Tiny House Siesta
A modern kitchen with stainless steel appliances, granite countertops, and wooden cabinets.

6. Explore Sarasota: Condo w/ Pool Access, Near Dtwn

Explore Sarasota: Condo w/ Pool Access, Near Dtwn
3.5 star property
Sarasota
The price is ₩102,909
₩359,614 total
includes taxes & fees
Sep 29 - Sep 30
Explore Sarasota: Condo w/ Pool Access, Near Dtwn
A living room with a view of the ocean, a ceiling fan, and a wooden coffee table.

7. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (685 reviews)
"Great stay!!"
United States
Genghis
The price is ₩255,919
₩289,188 total
includes taxes & fees
Sep 29 - Sep 30
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.

8. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (185 reviews)
"Property and room were beautiful!! Right across the street from the beach ⛱️"
United States
Michelle Suzanne
The price is ₩303,447
₩342,896 total
includes taxes & fees
Sep 29 - Sep 30
SeaSpray Resort
A wooden structure with a thatched roof overlooking a beach.

9. Casey Key Resort

Casey Key Resort
3.0 star property
Casey Key
8.4 out of 10, Very good, (284 reviews)
"Nice little property,very well kept.Host was very nice and helpful.Will be back again."
United States
Greg
The price is ₩252,697
₩310,827 total
includes taxes & fees
Sep 30 - Oct 1
Casey Key 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
9.4 out of 10, Exceptional, (81 reviews)
"The property was clean and had great decor! They provide everything you need for the beach and the pool is a great added bonus. Perfect location with being so close the restaurants and the beach. We are already planning our next stay!"
United States
Meghan
The price is ₩134,094
₩434,521 total
includes taxes & fees
Sep 30 - Oct 1
Siesta Key Island Rentals
A living room with a sofa, armchair, coffee table, and a potted plant.

11. Siesta Vibe Pool Walk To Crescent Beach

Siesta Vibe Pool Walk To Crescent Beach
2.0 star property
South Village
The price is ₩161,771
₩528,090 total
includes taxes & fees
Sep 29 - Sep 30
Siesta Vibe Pool Walk To Crescent Beach
A beach with tall grasses and a sunset sky.

12. Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
The price is ₩530,795
₩957,071 total
includes taxes & fees
Oct 6 - Oct 7
Siesta Heron 6 / Sunset
An aerial view of a coastal city with a long sandy beach, numerous hotels, and clear blue waters.

13. Lulu's Crescent Cottage #2

Lulu's Crescent Cottage #2
2.5 star property
Siesta Key
Lulu's Crescent Cottage #2
A modern living room with a sofa, coffee table, and artwork on the walls.

14. Pineapple Paradise 1 13 min to Beach Fire Pit

Pineapple Paradise 1 13 min to Beach Fire Pit
2.0 star property
Central Sarasota
The price is ₩161,226
₩536,065 total
includes taxes & fees
Sep 29 - Sep 30
Pineapple Paradise 1 13 min to Beach Fire Pit
A wooden-paneled room with a round table and four chairs, a flat-screen TV mounted on the wall, and a refrigerator in the background.

15. Sun Outdoors Sarasota

Sun Outdoors Sarasota
2.5 star property
Fordville
The price is ₩609,332
₩688,546 total
includes taxes & fees
Sep 29 - Sep 30
Sun Outdoors Sarasota
A residential backyard with a lawn, a wooden deck, and a white house with a grey roof.

16. 4 Mi to Dtwn! Studio w/ Screened Porch in Sarasota

4 Mi to Dtwn! Studio w/ Screened Porch in Sarasota
3.0 star property
Ridge Wood Heights
The price is ₩162,488
₩342,715 total
includes taxes & fees
Sep 29 - Sep 30
4 Mi to Dtwn! Studio w/ Screened Porch in Sarasota
A water slide in a pool area with a rocky backdrop and a small waterfall.

17. Cedar Run Resort - Roam Hospitality

Cedar Run Resort - Roam Hospitality
3.5 star property
South Bradenton
9.4 out of 10, Exceptional, (9 reviews)
"I would stay again, very accommodating"
United States
Deliondra
The price is ₩203,111
₩616,632 total
includes taxes & fees
Sep 29 - Sep 30
Cedar Run Resort - Roam Hospitality
An aerial view of a coastal town with beachfront properties, a marina, and clear blue waters.

18. Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
8.8 out of 10, Excellent, (30 reviews)
"Without a doubt, the best place—very spacious and in an excellent location. You have the beach right out front, and Gasparilla Beach—which is very beautiful—is just 25 minutes away. Communication with the owner was excellent, the sunsets were fantastic, and the terrace overlooking the bay—with the breeze blowing—was a delight. We will definitely be back!"
United States
Niovys
The price is ₩217,653
₩853,104 total
includes taxes & fees
Sep 29 - Sep 30
Chadwick Cove Resort & Marina
A covered outdoor area with white furniture, including chairs and a table, overlooking a beach.

19. Gulf View Condominiums

Gulf View Condominiums
3.5 star property
Manasota Key
The price is ₩575,818
₩1,389,656 total
includes taxes & fees
Sep 29 - Sep 30
Gulf View Condominiums
An aerial view of a coastal city with a long sandy beach, numerous hotels, and clear blue waters.

20. Lulu's Key House Leatherback 2/2 Downstairs

Lulu's Key House Leatherback 2/2 Downstairs
4.0 star property
Siesta Key Village
The price is ₩389,904
₩934,868 total
includes taxes & fees
Oct 10 - Oct 11
Lulu's Key House Leatherback 2/2 Downstairs
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

Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway

10/10 Excellent
"1"
Daniel 2-night trip
Posted less than an hour ago
Spark by Hilton Sarasota Siesta Key Gateway

Find out more about Osprey

Search for Vacation rentals in Osprey on Expedia.co.uk! You can easily find your home rentals, villas, Vacation apartments in Osprey using one of the methods below:

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Look no further and take a look at our great range of rental properties in Osprey!

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 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?

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.