Osprey Vacation Rentals

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Check prices for these dates

In two weeks
Oct 24 - Oct 26
In two months
Dec 5 - Dec 7
In three months
Jan 2 - Jan 4
In four months
Jan 30 - Feb 1

Vacation Rentals in Osprey

Charming Florida Beach Home w King Bed Patio
House | 2 bedrooms, Internet

Charming Florida Beach Home w King Bed Patio

2.0 star property
10.0 out of 10, Exceptional, (2)
"The best place to stay! Super clean home and friendly service. I would stay here again. "
Charming Florida Beach Home w King Bed Patio
Tropical Beach Resorts
Outdoor pool, a heated pool, open 8 AM to 10 PM, pool umbrellas

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (5021)
"Great place and loved the closeness to the beach!"
The price is ₩179,107
₩234,352 total
includes taxes & fees
Oct 9 - Oct 10
Tropical Beach Resorts
Captiva Beach Resort
Front of property - evening/night

Captiva Beach Resort

3.0 star property
9.0 out of 10, Wonderful, (1141)
"2nd time and excellent as always..close to the beach and great surroundings "
The price is ₩199,507
₩249,413 total
includes taxes & fees
Oct 12 - Oct 13
Captiva Beach Resort
Hibiscus Suites - Gateway to Siesta Key
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, sun loungers

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2179)
"Friendly staff, room was really clean!"
The price is ₩170,869
₩193,083 total
includes taxes & fees
Oct 9 - Oct 10
Hibiscus Suites - Gateway to Siesta Key
SeaSpray Resort
Deluxe Suite, 2 Bedrooms | Living area

SeaSpray Resort

4.0 star property
9.4 out of 10, Exceptional, (45)
"I love everything about this place so beautiful with walking distance to the beach "
The price is ₩291,465
₩329,365 total
includes taxes & fees
Oct 20 - Oct 21
SeaSpray Resort
The Ringling Beach House
Front of property

The Ringling Beach House

3.5 star property
9.0 out of 10, Wonderful, (327)
"We liked the stay very much "
The price is ₩259,798
₩437,395 total
includes taxes & fees
Oct 16 - Oct 17
The Ringling Beach House
The Residences at Siesta Key Beach by Hyatt Vacation Club
Property amenity

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
9.8 out of 10, Exceptional, (291)
"Loved our stay! "
The price is ₩574,586
₩721,193 total
includes taxes & fees
Oct 22 - Oct 23
The Residences at Siesta Key Beach by Hyatt Vacation Club
Sea Club I Beach Resort
On the beach, white sand

Sea Club I Beach Resort

3.0 star property
9.2 out of 10, Wonderful, (327)
"Amazing place, it’s the perfect place for relax and enjoy the beach. I love and I will come back again and again."
Sea Club I Beach Resort
Tiny House Siesta
Cabin (Tiny House - The Siesta) | Living area | Flat-screen TV, Netflix, streaming services

Tiny House Siesta

2.0 star property
8.4 out of 10, Very Good, (329)
"Clean space, with nice private patio. Excellent location! Plenty of eating options around. Will definitely stay at these Tiny Homes again!"
The price is ₩142,833
₩161,401 total
includes taxes & fees
Oct 9 - Oct 10
Tiny House Siesta
Siesta Palms By the Beach
Garden

Siesta Palms By the Beach

3.5 star property
9.2 out of 10, Wonderful, (132)
"We loved the condo. The distance to the beach was amazing. The wagon and beach chairs that were provided were so nice! The condo was clean and in great shape. The pool/ outdoor area was beautiful! We couldn’t have asked for a better place! "
Siesta Palms By the Beach
Bradenton Apartments by Landing
Exterior

Bradenton Apartments by Landing

4.5 star property
7.6 out of 10, Good, (46)
"Perfect place "
Bradenton Apartments by Landing
Kon Tiki Inn
Exterior

Kon Tiki Inn

2.5 star property
10.0 out of 10, Exceptional, (237)
"Charming, clean, and comfortable. Will definitely stay again when I'm the area. "
The price is ₩177,144
₩200,172 total
includes taxes & fees
Oct 9 - Oct 10
Kon Tiki Inn
Venice Beach Villas
Terrace/patio

Venice Beach Villas

3.0 star property
9.4 out of 10, Exceptional, (447)
"Staff was great. Room was very clean. Laundry onsite and the pool was wonderful! Will stay again!!!"
Venice Beach Villas
Siesta Key Island Rentals
322 Calle Miramar, Siesta Key, FL W/pool | Private kitchen

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (48)
"This place was incredible. We have traveled a lot with family and this was the best. Very comfortable and accommodating! I really cannot say enough good about this house. "
The price is ₩243,594
₩528,730 total
includes taxes & fees
Oct 9 - Oct 10
Siesta Key Island Rentals
The Inn On Siesta Key
Outdoor pool, a heated pool, open 8:00 AM to 8:00 PM, pool umbrellas

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (184)
"clean and close proximity to beach and restaurants"
The Inn On Siesta Key
Tropical Villas of Venice Beach
Beach nearby, beach umbrellas, beach towels

Tropical Villas of Venice Beach

3.5 star property
9.6 out of 10, Exceptional, (239)
"Great Location !!"
Tropical Villas of Venice Beach
Paradise Cove at Lemon Bay
Exterior

Paradise Cove at Lemon Bay

3.5 star property
8.2 out of 10, Very Good, (78)
"I loved the property and the host was also very professional. "
Paradise Cove at Lemon Bay
Siesta Heron Suites & Villas
Condo, Pool View | Private kitchen | Full-size fridge, microwave, oven, stovetop

Siesta Heron Suites & Villas

3.5 star property
8.4 out of 10, Very Good, (35)
"It was perfect for my family of 4 for our beach vacation!!"
The price is ₩136,797
₩439,031 total
includes taxes & fees
Oct 9 - Oct 10
Siesta Heron Suites & Villas
Chadwick Cove Resort & Marina
Property grounds

Chadwick Cove Resort & Marina

4.0 star property
10.0 out of 10, Exceptional, (14)
"Great place and location "
The price is ₩124,707
₩776,059 total
includes taxes & fees
Oct 15 - Oct 16
Chadwick Cove Resort & Marina
Casey Key Resort - Gulf Shores
Deluxe Studio, Bay View | View from room

Casey Key Resort - Gulf Shores

3.0 star property
8.4 out of 10, Very Good, (261)
"Cute place and property! Cozy, quiet and clean. The property manager was very nice. We enjoyed the private beach on the property. It is walking distance to 2 restaurants. Would def go back, we had a nice relaxing weekend. "
The price is ₩242,845
₩288,142 total
includes taxes & fees
Oct 19 - Oct 20
Casey Key Resort - Gulf Shores
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
"Staff was friendly and professional. It was quiet and clean. Very acommodating."
Mary 2-night trip
Posted 5 hours ago
Spark by Hilton Sarasota Siesta Key Gateway

Find out more about Osprey

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:

  • View our selection of featured Vacation rentals in Osprey
  • Use the map to find apartments and other Vacation homes in the Osprey neighbourhood you prefer
  • Enter your travel dates to view the best deals on Vacation 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 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?

Charming Florida Beach Home w King Bed Patio: Visitors give good reviews to this Osprey vacation home rental, which offers a garden and free WiFi to help you feel comfortable in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind.

How many vacation rentals are there in Osprey?

With 34 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.