Osprey Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 Aug

Our top choices for Osprey holiday rentals

Terrace/patio

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (272 reviews)
"Very clean & spacious pet friendly room. Would definitely stay there again."
United States
Brittany
The price is S$159
includes taxes & fees
1 Jun - 2 Jun
Kon Tiki Inn
Property grounds

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,466 reviews)
"Great place to stay, beach 2 minute walk."
United States
Joseph
The price is S$302
includes taxes & fees
25 May - 26 May
Tropical Beach Resorts
Premium bedding, pillow-top beds, individually decorated

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (630 reviews)
"Love this place"
United States
Marialis
The price is S$286
includes taxes & fees
27 May - 28 May
A Beach Retreat
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, pool loungers

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,306 reviews)
"Excellent location, great place to stay! "
United States
Lynn
The price is S$230
includes taxes & fees
18 May - 19 May
Hibiscus Suites - Gateway to Siesta Key
Balcony

Gulf View Condominiums

Gulf View Condominiums
3.5 star property
Manasota Key
The price is S$1,239
includes taxes & fees
6 May - 7 May
Gulf View Condominiums
Exterior

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
10.0 out of 10, Exceptional, (17 reviews)
"Great place and location "
United States
Cathy
The price is S$733
includes taxes & fees
7 May - 8 May
Chadwick Cove Resort & Marina
Living area

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (366 reviews)
"Cute place perfect for our holiday beach stay."
United States
Shelly
The price is S$297
includes taxes & fees
12 May - 13 May
Tiny House Siesta
Front of property – evening/night

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,245 reviews)
"Wonderful spot to stay! Traveled solo and Captiva was perfect "
United States
Angela
The price is S$280
includes taxes & fees
6 May - 7 May
Captiva Beach Resort
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, (273 reviews)
"Great place"
United States
tony
The price is S$318
includes taxes & fees
11 May - 12 May
Casey Key Resort - Gulf Shores
Private kitchen

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (66 reviews)
"Excellent location , minute walk to local bars and supermarket. Right across from beautiful siesta key beach."
United States
Alessandra
Siesta Key Island Rentals
Living area

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very good, (42 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is S$407
includes taxes & fees
12 May - 13 May
Siesta Heron Suites & Villas
Exterior

Minorga Sand Dollar on the Key

Minorga Sand Dollar on the Key
3.5 star property
Siesta Key Village
The price is S$693
includes taxes & fees
20 May - 21 May
Minorga Sand Dollar on the Key
In-room safe, iron/ironing board, free WiFi

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (118 reviews)
"Amazing staff, and beautiful property. Very nice place to visit and kid friendly."
United States
Ahmad
The price is S$419
includes taxes & fees
27 May - 28 May
SeaSpray Resort
4 bedrooms

Sarasota Family Home Private Heated Pool Relax

Sarasota Family Home Private Heated Pool Relax
2.0 star property
Whitfield Estates
The price is S$709
includes taxes & fees
27 May - 28 May
Sarasota Family Home Private Heated Pool Relax
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, (198 reviews)
"This property was everything we wanted...although not on the beach, it was a short walk to the beach and chairs, umbrellas, coolers and wagons were provided to the beach. The pool area was very comfortable and clean. We like that there were only 6 units...each was unique and very clean. We stayed in "The Nook" which was perfect for our getaway."
United States
Michele
The price is S$444
includes taxes & fees
10 May - 11 May
The Inn On Siesta Key
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
The price is S$688
includes taxes & fees
17 May - 18 May
Unwind Poolside + Walk to Beach! Sarasota Retreat
Outdoor pool

FANCY RETREREAT

FANCY RETREREAT
3.0 star property
Bradenton
The price is S$894
includes taxes & fees
26 May - 27 May
FANCY RETREREAT
Interior

Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
The price is S$1,003
includes taxes & fees
10 May - 11 May
Siesta Heron 6 / Sunset
Exterior

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 S$866
includes taxes & fees
3 Jun - 4 Jun
Lulu's Key House Leatherback 2/2 Downstairs
Interior

Outdoor Kitchen & Gaming Garage: Bradenton Retreat

Outdoor Kitchen & Gaming Garage: Bradenton Retreat
3.0 star property
Bradenton
The price is S$852
includes taxes & fees
21 May - 22 May
Outdoor Kitchen & Gaming Garage: Bradenton 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.
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

Golden Host Resort - Sarasota

Golden Host Resort - Sarasota

8/10 Good
"Room clean, pool area nice. Friendly service at concession desk. Checked in late at night, staff not as friendly. Went to wind down at bar and last call 5 minutes after arriving. Thought bar closed early for a Friday night. "
Steven 1-night trip
Posted 5 hours ago
Golden Host Resort - Sarasota

Explore a world of travel with Expedia

Frequently asked questions

Can I find holiday rentals in Osprey?

Yes, there are holiday rentals in Osprey close to Jim Neville Marine Preserve, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Osprey has to offer?

Siesta Key Island Rentals: This holiday home rental outside of Osprey comes with free WiFi so that you can feel at home during your trip. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals are there in Osprey?

With 18 Expedia holiday rentals, you're guaranteed 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 such as Siesta Key Beach and Lido Beach.

What’s a holiday rental in Osprey like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Osprey. Holiday rentals feature extras such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for families.