Osprey Holiday Rentals

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Holiday Rentals in Osprey

Charming Florida Beach Home w King Bed Patio

2.0 star property
Bay Acres
10.0 out of 10, Exceptional, (2)
"The best place to stay! Super clean home and friendly service. I would stay here again. "
United States
Alyssa
Charming Florida Beach Home w King Bed Patio

Tropical Beach Resorts

3.5 star property
South Village
9.4 out of 10, Exceptional, (5136)
"Wonderful trip! Great location! Great staff!"
United States
Kevin
The price is AU$225
includes taxes & fees
7 Dec - 8 Dec
Tropical Beach Resorts

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
Sarasota
8.6 out of 10, Excellent, (2202)
"This place is a gem!! I only stayed one night but wish it was more. The room was very clean and the staff was fantastic. The area is beautiful and at an excellent price. I highly recommend you stay here if you are in Siesta Keys!!"
United States
Ryan
Hibiscus Suites - Gateway to Siesta Key

Captiva Beach Resort

3.0 star property
South Village
9.0 out of 10, Wonderful, (1171)
"Clean room, snd friendly staff. Great location "
United States
Stephanie
Captiva Beach Resort

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
South Village
9.6 out of 10, Exceptional, (298)
"Loved our stay! "
United States
Michelle
The price is AU$737
includes taxes & fees
11 Dec - 12 Dec
The Residences at Siesta Key Beach by Hyatt Vacation Club

SeaSpray Resort

4.0 star property
Siesta Key
9.4 out of 10, Exceptional, (72)
"Clean room, incredibly helpful staff. Will be staying here again"
United States
Caleb
The price is AU$426
includes taxes & fees
8 Dec - 9 Dec
SeaSpray Resort

The Ringling Beach House

3.5 star property
Siesta Key
9.0 out of 10, Wonderful, (341)
"Clean, friendly and beach!"
United States
Mary
The Ringling Beach House

Tiny House Siesta

2.0 star property
Sarasota
8.4 out of 10, Very good, (344)
"Enjoyable stay. "
United States
Lori
The price is AU$367
includes taxes & fees
13 Dec - 14 Dec
Tiny House Siesta

A Beach Retreat

2.5 star property
Casey Key
9.2 out of 10, Wonderful, (576)
"Location, very clean and comfortable. Nice efficiency."
United States
Chuck
A Beach Retreat

Kon Tiki Inn

2.5 star property
Venice Island
10.0 out of 10, Exceptional, (245)
"Staff was great, room was clean and comfortable. It was a short stay but we enjoyed our time there. We will be back!"
United States
Joan
The price is AU$278
includes taxes & fees
15 Dec - 16 Dec
Kon Tiki Inn

Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times

Siesta Key Village
9.8 out of 10, Exceptional, (25)
"The check in and kitchen environment was great no complaints "
United States
nicholas c.
Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times

Siesta Key Island Rentals

3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (52)
"Very nice place, we loved it. Great location. "
United States
Derrick
The price is AU$496
includes taxes & fees
7 Dec - 8 Dec
Siesta Key Island Rentals

Sea Club I Beach Resort

3.0 star property
Longboat Key
9.2 out of 10, Wonderful, (335)
"Very nice beach themed bungalow. Loved the quiet and the views. "
United States
Jennifer
Sea Club I Beach Resort

The Inn On Siesta Key

3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (190)
"Great place to stay! "
United States
Carlos
The price is AU$465
includes taxes & fees
9 Dec - 10 Dec
The Inn On Siesta Key

3-bedroom 2-bathroom Siesta Key townhome close to beaches, city and airport.

Siesta Key
8.0 out of 10, Very good, (4)
"Great location close to the beach. "
United States
David M.
The price is AU$312
includes taxes & fees
12 Dec - 13 Dec
3-bedroom 2-bathroom Siesta Key townhome close to beaches, city and airport.

Tropical Villas of Venice Beach

3.5 star property
Venice Island
9.6 out of 10, Exceptional, (240)
"Great Location !!"
United States
Orleys
Tropical Villas of Venice Beach

Siesta Palms By the Beach

3.5 star property
South Village
9.4 out of 10, Exceptional, (136)
"Comfy and clean, nice and close to the beach. Pool was very clean. Quiet, safe area. Would highly recommend!"
United States
Lynn
Siesta Palms By the Beach

Siesta Heron Suites & Villas

3.5 star property
Siesta Key
8.6 out of 10, Excellent, (38)
"It was perfect for my family of 4 for our beach vacation!!"
United States
Jesse
The price is AU$526
includes taxes & fees
17 Dec - 18 Dec
Siesta Heron Suites & Villas

Steps to Beach/Siesta Village-Resort Pool w/Slide

Siesta Key Village
10.0 out of 10, Exceptional, (40)
"This was the perfect place to stay for a large family with kids. The location to the beach and restaurants couldn't have been more convenient. Amazing vacation!"
United States
Frances E.
Steps to Beach/Siesta Village-Resort Pool w/Slide

THE BEACH CONDO #107 BEACHFRONT FULL VIEW

Longboat Key
9.8 out of 10, Exceptional, (80)
"Beautiful location and the beach is amazing "
United States
Heather A.
The price is AU$595
includes taxes & fees
9 Dec - 10 Dec
THE BEACH CONDO #107 BEACHFRONT FULL VIEW
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

Find out more about Osprey

Everything you need to know about Osprey holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Osprey holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Osprey holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Osprey holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Osprey. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Osprey holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Osprey holiday rentals we have selected for you start as low as AU$225 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Osprey rentals

At Expedia, we put the best Osprey holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Osprey rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Osprey holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Osprey. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 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 holiday rentals that Osprey has to offer?

Charming Florida Beach Home w King Bed Patio: This highly rated holiday home rental in Osprey offers a garden and free WiFi to help you feel comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals are there in Osprey?

With 20 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.