Osprey Holiday Rentals

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Holiday Rentals in Osprey

Charming Osprey Home
2.0 star property
The price is AU$499
includes taxes & fees
20 Oct - 21 Oct
Charming Osprey Home
Tiny House Siesta
2.0 star property
8.4 out of 10, Very good, (332)
"We had a great time at Tiny House, location can not be better and everything was as described."
United States
Elvia
The price is AU$267
includes taxes & fees
20 Oct - 21 Oct
Tiny House Siesta
Kon Tiki Inn
2.5 star property
10.0 out of 10, Exceptional, (238)
"Charming, clean, and comfortable. Will definitely stay again when I'm the area. "
United States
Carla
The price is AU$262
includes taxes & fees
18 Nov - 19 Nov
Kon Tiki Inn
Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (5041)
"Great place and loved the closeness to the beach!"
United States
Nadine
The price is AU$255
includes taxes & fees
20 Oct - 21 Oct
Tropical Beach Resorts
Hibiscus Suites - Gateway to Siesta Key
2.5 star property
8.6 out of 10, Excellent, (2180)
"Friendly staff, room was really clean!"
United States
Zasha
Hibiscus Suites - Gateway to Siesta Key
Chadwick Cove Resort & Marina
4.0 star property
10.0 out of 10, Exceptional, (14)
"Great place and location "
United States
Cathy
The price is AU$812
includes taxes & fees
26 Oct - 27 Oct
Chadwick Cove Resort & Marina
Gorgeous Pool house 5 min from the beach, shopping and restaurants I
9.0 out of 10, Wonderful, (62)
"Great host and close to the beach. We would definitely stay again at this location again."
United States
Natasha T.
The price is AU$539
includes taxes & fees
20 Oct - 21 Oct
Gorgeous Pool house 5 min from the beach, shopping and restaurants I
Captiva Beach Resort
3.0 star property
9.0 out of 10, Wonderful, (1143)
"Great place close to the beach"
United States
Yuditza
Captiva Beach Resort
The Oceanview Oasis
10.0 out of 10, Exceptional, (127)
"We loved our little island stay, the beach was as beautiful as the pictures! Clean and a such a short distance to everything, we will definitely be staying again! "
United States
Morgan A.
The price is AU$514
includes taxes & fees
31 Oct - 1 Nov
The Oceanview Oasis
Updated Spacious. 5 Min to Manasota Beach. Loaded w/amenities. Pets Welcome!
9.6 out of 10, Exceptional, (20)
"The house was renovated beautifully, was clean and filled with lots a little extras. Would love to stay again."
United States
Sherri B.
The price is AU$501
includes taxes & fees
21 Oct - 22 Oct
Updated Spacious. 5 Min to Manasota Beach. Loaded w/amenities. Pets Welcome!
SeaSpray Resort
4.0 star property
9.4 out of 10, Exceptional, (52)
"Pleasant stay, walk to beach and the Village. Good size mini apartment "
United States
Lisa L
The price is AU$398
includes taxes & fees
20 Oct - 21 Oct
SeaSpray Resort
1.3 Acres PETS Waterfront FUN! Caged/Heated Pool, 100' Pier, CANOES Kayaks incl!
9.4 out of 10, Exceptional, (83)
"We enjoyed the large property, being able to have plenty of parking for our cars and boat trailer and to be able to let our 2 small dogs safely walk around off leash outside. The dock was nice and we enjoyed being able to have easy access. The house was spacious and the kitchen had all the necessities. The pool was refreshing and was a nice size. The entire place needed a thorough cleaning, yards and the house. David, the owner was nice to work with. I realize this area has experienced 2...
United States
Joyce G.
The price is AU$689
includes taxes & fees
26 Oct - 27 Oct
1.3 Acres PETS Waterfront FUN! Caged/Heated Pool, 100' Pier, CANOES Kayaks incl!
Walk to Beach. Beautifully Renovated 3BR, 2BA Home w/Outdoor Shower & Grille
10.0 out of 10, Exceptional, (37)
"Great beach and restaurant access. Very clean and quaint house."
United States
Chad M.
The price is AU$646
includes taxes & fees
20 Oct - 21 Oct
Walk to Beach. Beautifully Renovated 3BR, 2BA Home w/Outdoor Shower & Grille
SEPT OCT NOV DISCOUNTS! IMG AMIsland BEACHES KAYAKS FISHING ON LAKE KIDS PETS OK
9.8 out of 10, Exceptional, (137)
"House and pool were great! Jackie is a great host! We really enjoyed our stay and plan to come again!"
United States
Brandi C.
The price is AU$789
includes taxes & fees
26 Oct - 27 Oct
SEPT OCT NOV DISCOUNTS! IMG AMIsland BEACHES KAYAKS FISHING ON LAKE KIDS PETS OK
[escape to paradise] siesta key beach getaway
10.0 out of 10, Exceptional, (22)
"Great place and location"
United States
Karen A.
The price is AU$413
includes taxes & fees
20 Oct - 21 Oct
[escape to paradise] siesta key beach getaway
Tiny House Yellow Lifeguard Stand- pet friendly
9.6 out of 10, Exceptional, (43)
"It was absolutely perfect like the photos show. We had a wonderful time. "
United States
Tiffanie D.
The price is AU$319
includes taxes & fees
20 Oct - 21 Oct
Tiny House Yellow Lifeguard Stand- pet friendly
Large Venice Studio, 8 Min To Manasota Beach / King Bed On Beautifu Acrage !
9.4 out of 10, Exceptional, (36)
"We enjoyed our stay, the location was great and all the amenities you need."
United States
Marlene E.
The price is AU$210
includes taxes & fees
20 Oct - 21 Oct
Large Venice Studio, 8 Min To Manasota Beach / King Bed On Beautifu Acrage !
Bradenton Breeze
4.0 star property
6.0 out of 10, (2)
"It was good! "
United States
Shayna
The price is AU$462
includes taxes & fees
20 Oct - 21 Oct
Bradenton Breeze
Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach
9.8 out of 10, Exceptional, (99)
"The Oystercatcher cottage was an A+! It has great amenities. The screened porch with the fans was very comfortable. We enjoyed the games in the evenings after dinner. The beach cart was very functional and hauled all the provided beach supplies easily. Today we are going to try the kayaks! "
United States
Kathleen
Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach
Fantastic Shorewalk Vacation 2 bed/2 bath condo/Lake view/close to IMG, beaches
9.8 out of 10, Exceptional, (59)
"It was clean, comfy and ideal locarion. Close to beaches AMI and the pool was great. "
United States
Marge G.
The price is AU$603
includes taxes & fees
20 Oct - 21 Oct
Fantastic Shorewalk Vacation 2 bed/2 bath condo/Lake view/close to IMG, beaches
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 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 33 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.