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
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Osprey vacation rentals

Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, sun loungers

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,366 reviews)
"Excellent location, great place to stay! "
United States
Lynn
The price is P8,290
P9,367 total
includes taxes & fees
Aug 3 - Aug 4
Hibiscus Suites - Gateway to Siesta Key
Premium bedding, pillowtop beds, individually decorated

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (647 reviews)
"Nice place ,clean and good location,quiet and relaxing."
United States
yohana
The price is P10,176
P11,498 total
includes taxes & fees
Aug 3 - Aug 4
A Beach Retreat
Front of property

Home < 1-mi Walk to Warm Mineral Springs Park!

Home < 1-mi Walk to Warm Mineral Springs Park!
3.0 star property
North Port
The price is P9,230
P27,442 total
includes taxes & fees
Jul 12 - Jul 13
Home < 1-mi Walk to Warm Mineral Springs Park!
Property grounds

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,647 reviews)
"perfect stay and location for a family!"
United States
Jessica
The price is P9,362
P12,179 total
includes taxes & fees
Aug 9 - Aug 10
Tropical Beach Resorts
Outdoor wedding area

Casey Key Resort - Gulf Shores

Casey Key Resort - Gulf Shores
3.0 star property
Casey Key
8.4 out of 10, Very Good, (277 reviews)
"Is was a great place to stay, everything was perfect!"
United States
Tracie Costello
The price is P9,893
P12,297 total
includes taxes & fees
Aug 9 - Aug 10
Casey Key Resort - Gulf Shores
In-room safe, iron/ironing board, free WiFi

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (148 reviews)
"Very nice room and easy access to an amazing beach."
United States
Michael
The price is P16,559
P18,712 total
includes taxes & fees
Jul 19 - Jul 20
SeaSpray Resort
Living area

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very Good, (374 reviews)
"The house was clean and simple. Perfect for a couple to stay for a few nights. Not too far from the beach. Very quiet and safe area."
United States
bruno
The price is P4,133
P12,147 total
includes taxes & fees
Jul 16 - Jul 17
Tiny House Siesta
Exterior

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
9.4 out of 10, Exceptional, (22 reviews)
"Nic place to stay and enjoy the area"
United States
isabel
The price is P7,476
P36,063 total
includes taxes & fees
Jul 17 - Jul 18
Chadwick Cove Resort & Marina
Balcony

Gulf View Condominiums

Gulf View Condominiums
3.5 star property
Manasota Key
The price is P20,934
P57,289 total
includes taxes & fees
Aug 6 - Aug 7
Gulf View Condominiums
Living area

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.6 out of 10, Excellent, (44 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is P7,292
P20,617 total
includes taxes & fees
Jul 12 - Jul 13
Siesta Heron Suites & Villas
Outdoor pool, pool umbrellas, sun loungers

Cedar Run Resort - Roam Hospitality

Cedar Run Resort - Roam Hospitality
3.5 star property
South Bradenton
9.2 out of 10, Wonderful, (7 reviews)
"The room was very clean and well maintained/new. Staff was friendly and helpful. The air conditioner was great. The room we stayed at had lots of accessories for the beach like chairs and kid’s toys for the beach along with an umbrella. The surroundings are peaceful and beautiful. It was a great experience overall."
United States
Jose Luis Alberti
The price is P8,492
P38,509 total
includes taxes & fees
Jul 12 - Jul 13
Cedar Run Resort - Roam Hospitality
Front of property - evening/night

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,282 reviews)
"Very helpful staff and excellent beach!"
United States
Vania
The price is P10,146
P12,507 total
includes taxes & fees
Aug 2 - Aug 3
Captiva Beach Resort
Interior

Waterfront Luxury Remodeled Studio! Pool Tiki Bar

Waterfront Luxury Remodeled Studio! Pool Tiki Bar
3.0 star property
Whitfield Estates
The price is P7,692
P13,455 total
includes taxes & fees
Jul 14 - Jul 15
Waterfront Luxury Remodeled Studio! Pool Tiki Bar
Front of property

The Ringling Beach House

The Ringling Beach House
3.5 star property
Siesta Key
9.0 out of 10, Wonderful, (371 reviews)
"Having everything within reach is the key to a great vacation.."
United States
Vakeshia
The price is P11,304
P19,727 total
includes taxes & fees
Jul 12 - Jul 13
The Ringling Beach House
Beach nearby, white sand, beach umbrellas, beach towels

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (199 reviews)
"The room was clean and spacious with all the amenities. The location was perfect. I would highly recommend!"
United States
Amanda
The price is P17,246
P22,896 total
includes taxes & fees
Jul 12 - Jul 13
The Inn On Siesta Key
Exterior

Lulu's Crescent Cottage #2

Lulu's Crescent Cottage #2
2.5 star property
Siesta Key
The price is P17,638
P40,654 total
includes taxes & fees
Jul 27 - Jul 28
Lulu's Crescent Cottage #2
Terrace/patio

Palm Haven at Cape Leyte

Palm Haven at Cape Leyte
2.0 star property
Siesta Key
Palm Haven at Cape Leyte
4 bedrooms

Sarasota Family Home Private Heated Pool Relax

Sarasota Family Home Private Heated Pool Relax
2.0 star property
Whitfield Estates
Sarasota Family Home Private Heated Pool Relax
Interior

Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
The price is P49,349
P72,000 total
includes taxes & fees
Jul 23 - Jul 24
Siesta Heron 6 / Sunset
Interior

Unwind Poolside + Walk to Beach! Sarasota Retreat

Unwind Poolside + Walk to Beach! Sarasota Retreat
3.0 star property
South Village
8.0 out of 10, Very Good, (1 review)
"The location of the property was excellent. The home was clean and had everything we needed to prepare breakfast in the morning. The 3 bedrooms and 3 bathrooms made it easy for the six of us wash up and get ready for dinner after a fun fill day at the walkable beach. Beach was great. Having a pool at the property was great for the 2 youngsters. We also made use of the wagon that was available to carry items to the beach., The property is nothing fancy but a great value for the money. "
United States
Eleuterio
Unwind Poolside + Walk to Beach! Sarasota Retreat
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

Golden Host Resort - Sarasota

Golden Host Resort - Sarasota

10/10 Excellent
"We always stay here when we visit Sarasota because, it's very peaceful here, bed is comfy, the pool is nice (think that the hours should be extended cause 8pm is awfully too early to close), tiki hut on premises is a plus. Overall, we always have a nice time here"
Ngan 8-night trip
Posted 1 hour ago
Golden Host Resort - Sarasota

Find out more about Osprey

Search for holiday rentals in Osprey on Expedia! You can easily find your home rentals, villas, holiday 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 lively bars in this destination. While you're in the area, you can also enjoy the top-notch restaurants 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?

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 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.