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

Osprey Holiday Rentals

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Osprey holiday rentals

Property grounds

Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida

Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida
Sarasota
Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida
1 bedroom, desk, WiFi, bed sheets

Charming Secluded Tented Cabin in Sarasota, Florida

Charming Secluded Tented Cabin in Sarasota, Florida
Sarasota
Charming Secluded Tented Cabin in Sarasota, Florida
Property grounds

Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida

Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida
Sarasota
Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida
1 bedroom, desk, WiFi

Fantastic Tented Cabin with Fire Pit in Sarasota, Florida

Fantastic Tented Cabin with Fire Pit in Sarasota, Florida
Sarasota
Fantastic Tented Cabin with Fire Pit in Sarasota, Florida
Beach nearby, sun-loungers, beach towels, snorkelling

Manatee at Coastal Breeze | Waterfront | Dock & Fishing | Turtle Beach | Siesta Key

Manatee at Coastal Breeze | Waterfront | Dock & Fishing | Turtle Beach | Siesta Key
Sarasota
9.8 out of 10, Exceptional, (17 reviews)
"Wonderful location Perfect for what we wanted in a quick escape. "
United States
Antonio
Manatee at Coastal Breeze | Waterfront | Dock & Fishing | Turtle Beach | Siesta Key
Living area

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (381 reviews)
"Great place"
United States
Mario
The price is HK$559
HK$1,584 total
includes taxes & fees
3 Aug - 4 Aug
Tiny House Siesta
Property grounds

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,687 reviews)
"Great location, very close to the beach, very nice and helpful front desk."
United States
Airida
The price is HK$1,193
HK$1,552 total
includes taxes & fees
10 Aug - 11 Aug
Tropical Beach Resorts
Front of property – evening/night

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,290 reviews)
"Very helpful staff and excellent beach!"
United States
Vania
The price is HK$1,221
HK$1,512 total
includes taxes & fees
10 Aug - 11 Aug
Captiva Beach Resort
Premium bedding, pillow-top beds, iron/ironing board (on request)

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (655 reviews)
"The beach is right there, very clean and nice place."
United States
Maryna
The price is HK$1,445
HK$1,633 total
includes taxes & fees
5 Aug - 6 Aug
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, (2,376 reviews)
"Staff was friendly and room was clean"
United States
Maria
The price is HK$1,056
HK$1,194 total
includes taxes & fees
2 Aug - 3 Aug
Hibiscus Suites - Gateway to Siesta Key
Private kitchen

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (73 reviews)
"Great location, very clean and spacious."
United States
Jason
The price is HK$1,363
HK$3,212 total
includes taxes & fees
26 Jul - 27 Jul
Siesta Key Island Rentals
Coffee/tea maker, fridge, microwave, oven

[lounge like locals] walk to siesta beach +bikes

[lounge like locals] walk to siesta beach +bikes
Siesta Key
9.8 out of 10, Exceptional, (36 reviews)
"Only 10 mins walking from the Village, so easy to check in, great communication, super clean. "
United States
John
The price is HK$1,042
HK$2,857 total
includes taxes & fees
26 Jul - 27 Jul
[lounge like locals] walk to siesta beach +bikes
Beach nearby, beach umbrellas

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, (104 reviews)
"Awesome location and the staff was great!"
United States
John F.
The price is HK$1,262
HK$2,649 total
includes taxes & fees
16 Aug - 17 Aug
Couple’s Escape-Beach Club at Siesta Key 106C by RVA
Beach nearby, beach umbrellas

Relax & Unwind – 1BR Beach Club Siesta Key 110D RVA

Relax & Unwind – 1BR Beach Club Siesta Key 110D RVA
South Village
9.0 out of 10, Wonderful, (76 reviews)
"We enjoyed our stay, would stay again."
United States
Robert
The price is HK$1,388
HK$2,846 total
includes taxes & fees
9 Aug - 10 Aug
Relax & Unwind – 1BR Beach Club Siesta Key 110D RVA
Outdoor dining

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.
The price is HK$1,082
HK$3,147 total
includes taxes & fees
3 Aug - 4 Aug
Dolphin Villa - Pool - Steps to Siesta Key Village
On the beach

Jetties Pointe Cottage #5 - 408 “Casey Key”

Jetties Pointe Cottage #5 - 408 “Casey Key”
Casey Key
9.8 out of 10, Exceptional, (31 reviews)
"Amazing view and beach access, really great stay."
United States
Evan T.
The price is HK$1,421
HK$3,295 total
includes taxes & fees
3 Aug - 4 Aug
Jetties Pointe Cottage #5 - 408 “Casey Key”
On the beach, sun-loungers, beach towels

Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (128 reviews)
"We loved the cottage on the beach. The view was wonderful. Very peaceful location. The cottage was clean and had everything we needed. Highly recommend!"
United States
Virginia W.
The price is HK$1,945
HK$4,216 total
includes taxes & fees
14 Aug - 15 Aug
Casey Key Beachfront Escape: Charming 1BR Cottage
2 bedrooms, iron/ironing board, WiFi, bed sheets

[escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (31 reviews)
"Very clean and great location! Beds very comfortable and owner very responsive and accommodating! Highly recommend staying here!"
United States
Tim T.
The price is HK$945
HK$2,676 total
includes taxes & fees
26 Jul - 27 Jul
[escape to paradise] siesta key beach getaway
Beach nearby

Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
South Village
9.6 out of 10, Exceptional, (49 reviews)
"Everything was very clean, great location, perfect for a couple and enjoyed the pool area too"
United States
Dirk T
The price is HK$1,431
HK$2,837 total
includes taxes & fees
6 Aug - 7 Aug
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
Beach nearby

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, (168 reviews)
The price is HK$1,438
HK$2,459 total
includes taxes & fees
2 Aug - 3 Aug
Beachside Studio Located Across from Main Beach and Half Mile to Village
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

Embassy Suites by Hilton Sarasota, FL

Embassy Suites by Hilton Sarasota, FL

8/10 Good
"Clean room but needs some updates. Breakfast was nice pool is not in the most convenient place especially if your traveling with kiddos but has a nice view. Over all a good stay."
Valentina 2-night trip
Posted less than an hour ago
Embassy Suites by Hilton Sarasota, FL

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:

  • View our selection of featured holiday rentals in Osprey
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  • Enter your travel dates to view the best deals on holiday rentals in Osprey while they last

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

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 14 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.