Osprey Holiday Rentals

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Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May

Our top choices for Osprey holiday rentals

Living area

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (349 reviews)
"Clean room, easy check in, beach nearby 15 minute walk, Florida Fun Rides scooter rental place nearby"
United States
Justice
The price is S$296
includes taxes & fees
3 Feb - 4 Feb
Tiny House Siesta
Living area

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very good, (39 reviews)
"Clean pool great apartment could use more seating in living room. Beach chairs was cool patio was awesome parking good water pressure great bed clean and comfy "
United States
jason
The price is S$738
includes taxes & fees
12 Feb - 13 Feb
Siesta Heron Suites & Villas
Exterior

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
10.0 out of 10, Exceptional, (16 reviews)
"Great place and location "
United States
Cathy
The price is S$952
includes taxes & fees
15 Feb - 16 Feb
Chadwick Cove Resort & Marina
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, (194 reviews)
"Very charming place! Great location for the beach and restaurants. Would definitely stay again."
United States
Blaine
The price is S$650
includes taxes & fees
10 Feb - 11 Feb
The Inn On Siesta Key
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, (2,247 reviews)
"Very clean, and staff was extremely nice. "
United States
Maribeth
The price is S$290
includes taxes & fees
3 Feb - 4 Feb
Hibiscus Suites - Gateway to Siesta Key
Property grounds

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,278 reviews)
"Wonderful stay!"
United States
Victoria
The price is S$296
includes taxes & fees
3 Feb - 4 Feb
Tropical Beach Resorts
Private kitchen

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (58 reviews)
"Wonderful stay,Great owners,Fun times"
United States
Cornelia
The price is S$587
includes taxes & fees
3 Feb - 4 Feb
Siesta Key Island Rentals
In-room safe, iron/ironing board, free WiFi

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (91 reviews)
"Very clean very quiet and a great location to the beach."
United States
Dave
The price is S$630
includes taxes & fees
3 Feb - 4 Feb
SeaSpray Resort
Terrace/patio

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (253 reviews)
"Great place! "
United States
Michelle
The price is S$418
includes taxes & fees
16 Feb - 17 Feb
Kon Tiki Inn
Front of property – evening/night

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,194 reviews)
"Excellent place and location, "
United States
Richard
The price is S$334
includes taxes & fees
3 Feb - 4 Feb
Captiva Beach Resort
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
"Is good"
Jaime 1-night trip
Posted 22 hours ago
Hyatt Place Sarasota/Bradenton Airport

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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 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 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 16 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.