Osprey Vacation Rentals

    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
Aug 17 - Aug 18
Tomorrow
Aug 18 - Aug 19
Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31

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. "
The price is P6,919
P17,919 total
includes taxes & fees
Aug 25 - Aug 26
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, (4880)
"Very Nice Resort!"
The price is P7,957
P10,280 total
includes taxes & fees
Sep 1 - Sep 2
Tropical Beach Resorts
SeaSpray Resort
Living area

SeaSpray Resort

4.0 star property
9.4 out of 10, Exceptional, (17)
"Excellent place, awesome for families. The beach is spectacular, at walking distance. Our family strongly recommend this place"
The price is P11,929
P13,480 total
includes taxes & fees
Sep 1 - Sep 2
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, (2161)
"Bed comfort , great location, friendly staff. "
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, (318)
"We loved the Villa!! It was spacious and stocked with every kitchen item you can imagine. "
The Ringling Beach House
Tiny House Siesta
Living area

Tiny House Siesta

2.0 star property
8.4 out of 10, Very Good, (311)
"Super helpful staff."
The price is P4,566
P8,385 total
includes taxes & fees
Aug 18 - Aug 19
Tiny House Siesta
Captiva Beach Resort
Front of property - evening/night

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1123)
"Everything was great and a walking distance to the beach❤️❤️❤️❤️❤️. Everyone was very friendly and kind, thank you so much."
Captiva Beach Resort
Sea Club I Beach Resort
On the beach, white sand

Sea Club I Beach Resort

3.0 star property
9.0 out of 10, Wonderful, (320)
"just an amazing staff and clean rooms! it was paradise will go back next year for sure!!"
Sea Club I Beach Resort
Kon Tiki Inn
Exterior

Kon Tiki Inn

2.0 star property
10.0 out of 10, Exceptional, (224)
"We love everything about this place Debbie and her husband are awesome from check in to check out this is a 5 star resort and we will be back many more times"
The price is P7,944
P8,977 total
includes taxes & fees
Aug 24 - Aug 25
Kon Tiki Inn
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, (278)
"Great beach front property with amenities"
The price is P29,144
P35,835 total
includes taxes & fees
Aug 25 - Aug 26
The Residences at Siesta Key Beach by Hyatt Vacation Club
Siesta Key Island Rentals
Private kitchen

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (45)
"Quiet neighborhood, clean and well maintained property, responsive management."
The price is P7,874
P19,017 total
includes taxes & fees
Aug 18 - Aug 19
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, (182)
"Great place to stay! "
The price is P12,419
P16,162 total
includes taxes & fees
Aug 20 - Aug 21
The Inn On Siesta Key
Venice Beach Villas
Terrace/patio

Venice Beach Villas

3.0 star property
9.4 out of 10, Exceptional, (427)
"Easy walk or bike ride to beach. Property has plenty of bikes to borrow with locks. Overall just super place that I’ll stay again. "
Venice Beach Villas
Bradenton Apartments by Landing
Exterior

Bradenton Apartments by Landing

4.0 star property
7.4 out of 10, Good, (43)
"Absolutely beautiful location has everything you need n makes you feel like home"
Bradenton Apartments by Landing
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, (238)
"Great Location !!"
Tropical Villas of Venice Beach
Siesta Palms By the Beach
Garden

Siesta Palms By the Beach

3.5 star property
9.2 out of 10, Wonderful, (126)
"An outstanding experience — a place that leaves you with a strong desire to return."
Siesta Palms By the Beach
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!!"
The price is P11,247
P33,284 total
includes taxes & fees
Aug 23 - Aug 24
Siesta Heron Suites & Villas
Chadwick Cove Resort & Marina
Property grounds

Chadwick Cove Resort & Marina

4.0 star property
10.0 out of 10, Exceptional, (11)
"Nic place to stay and enjoy the area"
The price is P4,493
P30,717 total
includes taxes & fees
Aug 19 - Aug 20
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
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
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.
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

Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

10/10 Excellent
"Staff is awesome"
Ronald 2-night trip
Posted 3 hours ago
Casey Key Resorts - Mainland

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 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 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 31 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.