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

Osprey Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Osprey vacation rentals

A pool area with a waterfall feature, lounge chairs, and palm trees.

1. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,962 reviews)
"Amazing resort,"
United States
kurt
The price is P7,991
P10,662 total
includes taxes & fees
Oct 11 - Oct 12
Tropical Beach Resorts
A large orange armchair against a white wall with a 'Captiva' sign. There are two potted plants beside the chair.

2. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,318 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
The price is P9,808
P12,148 total
includes taxes & fees
Oct 11 - Oct 12
Captiva Beach Resort
An outdoor patio with a grill, white chairs, and a red umbrella.

3. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,465 reviews)
"This place was perfect!"
United States
Kat
The price is P8,473
P9,575 total
includes taxes & fees
Oct 18 - Oct 19
Hibiscus Suites - Gateway to Siesta Key
A compact living space with a kitchen, a dining area, and a sofa with cushions.

4. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (387 reviews)
"It's a very cute tiny house in a great location. Walking distance to Siesta Keys beach and numerous restaurants. I loved the decor in the sea turtle house. I would definitely stay here again next time I'm in Florida."
United States
Staci
The price is P3,635
P12,573 total
includes taxes & fees
Oct 16 - Oct 17
Tiny House Siesta
A living room with a view of the ocean, a ceiling fan, and a wooden coffee table.

5. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (688 reviews)
"Great stay!!"
United States
Genghis
The price is P11,576
P13,081 total
includes taxes & fees
Nov 4 - Nov 5
A Beach Retreat
A bathroom with a white vanity, a mirror, a shower with blue tiles, and a white toilet.

6. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (191 reviews)
"Best short vacation"
United States
Rommel
The price is P14,078
P15,909 total
includes taxes & fees
Nov 2 - Nov 3
SeaSpray Resort
A wooden structure with a thatched roof overlooking a beach.

7. Casey Key Resort

Casey Key Resort
3.0 star property
Casey Key
8.4 out of 10, Very good, (284 reviews)
"Nice little property,very well kept.Host was very nice and helpful.Will be back again."
United States
Greg
The price is P11,724
P14,421 total
includes taxes & fees
Oct 28 - Oct 29
Casey Key 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

Kompose Boutique Hotel

Kompose Boutique Hotel

10/10 Excellent
"Love staying at the Kompose! Great staff!! Amazing rooms!! Breakfast is 👍👍"
Jacqueline 2-night trip
Posted 6 hours ago
Kompose Boutique Hotel

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 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?

Tropical Villas of Venice Beach: This vacation home rental near Osprey is located near the beach and has an outdoor pool, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a microwave, and kitchenware. Make the most of the garden in this rental home to help you unwind.

How many vacation rentals are there in Osprey?

With 13 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?

Turtle Beach and Nokomis Beach are a couple of scenic spots to enjoy the outdoors, whereas Historic Spanish Point is one of the cultural attractions. 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.