Osprey Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Oct 5 - Oct 6
Tomorrow
Oct 6 - Oct 7
Next weekend
Oct 10 - Oct 12
In two weeks
Oct 17 - Oct 19

Vacation Rentals in Osprey

Charming Florida Beach Home w King Bed Patio
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, (5018)
"Great place and loved the closeness to the beach!"
The price is P7,329
P9,590 total
includes taxes & fees
Oct 6 - Oct 7
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 P8,164
P10,206 total
includes taxes & fees
Oct 6 - Oct 7
Captiva Beach Resort
SeaSpray Resort
Living area

SeaSpray Resort

4.0 star property
9.6 out of 10, Exceptional, (42)
"I love everything about this place so beautiful with walking distance to the beach "
The price is P11,927
P13,478 total
includes taxes & fees
Oct 6 - Oct 7
SeaSpray 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, (2178)
"Friendly staff, room was really clean!"
Hibiscus Suites - Gateway to Siesta Key
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 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
9.6 out of 10, Exceptional, (290)
"We celebrated my daughter’s 30th birthday and it was perfect. I can’t wait to stay again. The beach was truly amazing. This place has everything you need. "
The price is P23,513
P29,512 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
Living area

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 P5,093
P9,024 total
includes taxes & fees
Nov 3 - Nov 4
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, (236)
"Charming, clean, and comfortable. Will definitely stay again when I'm the area. "
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
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 P6,520
P15,910 total
includes taxes & fees
Oct 6 - Oct 7
Siesta Key Island Rentals
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
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
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
Private kitchen

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!!"
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 P4,024
P30,549 total
includes taxes & fees
Oct 6 - Oct 7
Chadwick Cove Resort & Marina
Casey Key Resort - Gulf Shores
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. "
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.
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

Ameniti Bay, BW Signature Collection

Ameniti Bay, BW Signature Collection

10/10 Excellent
"Great service as always willing to help make your stay the best "
alan 3-night trip
Posted 15 hours ago
Ameniti Bay, BW Signature Collection

Find out more about Osprey

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
  • Use the map to find apartments and other holiday homes in the Osprey neighbourhood you prefer
  • 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!

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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.