Holiday Rentals in Osprey

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Holiday Rentals in Osprey

Holiday Home in Bay Acres

2.0 star property
The price is €310
includes taxes & fees
8 Dec - 9 Dec
Charming Osprey Home

Mobile Home in Sarasota

2.0 star property
8.4 out of 10, Very good, (343)
"Enjoyable stay. "
United States
Lori
The price is €210
includes taxes & fees
27 Nov - 28 Nov
Tiny House Siesta

Aparthotel in South Village

3.5 star property
9.4 out of 10, Exceptional, (5118)
"The room was clean and the staff was very nice."
United States
Jill
The price is €121
includes taxes & fees
1 Dec - 2 Dec
Tropical Beach Resorts

Aparthotel in Sarasota

2.5 star property
8.6 out of 10, Excellent, (2199)
"Excellent location! Friendly staff, clean and updated rooms."
United States
Elba
Hibiscus Suites - Gateway to Siesta Key

Aparthotel in Venice Island

2.5 star property
10.0 out of 10, Exceptional, (244)
"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 €159
includes taxes & fees
2 Dec - 3 Dec
Kon Tiki Inn

Condo in South Village

3.0 star property
9.0 out of 10, Wonderful, (1163)
"Very good stay, clean, safe, and steps from the beach"
United States
Brandon
Captiva Beach Resort

Cottage in Manasota Key

9.6 out of 10, Exceptional, (169)
"Close to the beach and room was decorated very cute. Enjoyed our stay. "
United States
Wendy
The price is €169
includes taxes & fees
4 Dec - 5 Dec
Island Life! King Bed Studio-Steps to beach

Holiday Home in Siesta Key

3.0 star property
9.6 out of 10, Exceptional, (51)
"Very nice place, we loved it. Great location. "
United States
Derrick
The price is €244
includes taxes & fees
3 Dec - 4 Dec
Siesta Key Island Rentals

Holiday Home in Olde Englewood Village

9.8 out of 10, Exceptional, (60)
"Very good, great location 👍👍"
United States
James M.
The price is €223
includes taxes & fees
29 Nov - 30 Nov
Old Floridian cottage in Historic Gulf Village

Holiday Home in South Venice

9.4 out of 10, Exceptional, (29)
"Nice quiet home , very clean. "
United States
David M.
The price is €294
includes taxes & fees
3 Dec - 4 Dec
Mimosa Memories

Aparthotel in South Village

3.5 star property
9.6 out of 10, Exceptional, (297)
"Loved our stay! "
United States
Michelle
The price is €393
includes taxes & fees
11 Dec - 12 Dec
The Residences at Siesta Key Beach by Hyatt Vacation Club

Holiday Home in Siesta Key

10.0 out of 10, Exceptional, (22)
"Great place and location"
United States
Karen A.
The price is €270
includes taxes & fees
30 Nov - 1 Dec
[escape to paradise] siesta key beach getaway

Condo in Bradenton

9.8 out of 10, Exceptional, (146)
"Nice clean condo. Situated in a good location for multiple beach days."
United States
victoria c.
The price is €207
includes taxes & fees
8 Dec - 9 Dec
Beautifully furnished condo

Cottage in Casey Key

9.2 out of 10, Wonderful, (69)
"Quiet beautiful beachfront location! We had a wonderful stay and plan on coming back! Thank you very much!"
United States
Katherine Z.
The price is €421
includes taxes & fees
1 Dec - 2 Dec
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms

Condo in Casey Key

2.5 star property
9.2 out of 10, Wonderful, (574)
"Location, very clean and comfortable. Nice efficiency."
United States
Chuck
A Beach Retreat

Condo in Bayou Oaks

9.2 out of 10, Wonderful, (39)
"Excellent place to stay"
United States
garry s.
The price is €109
includes taxes & fees
1 Dec - 2 Dec
Riverside Oasis 1Bed/1Bath

Condo in Indian Beach Sapphire Shores

9.8 out of 10, Exceptional, (84)
"We loved our stay here, it was a perfect location with lots to do within even walking distance! "
United States
Austin S.
The Sapphire Suite 1Bed/1Bath

Condo in Bradenton

9.8 out of 10, Exceptional, (60)
"It was clean, comfy and ideal locarion. Close to beaches AMI and the pool was great. "
United States
Marge G.
The price is €356
includes taxes & fees
6 Dec - 7 Dec
Fantastic Shorewalk Vacation 2 bed/2 bath condo/Lake view/close to IMG, beaches

Cottage in Siesta Key

9.2 out of 10, Wonderful, (5)
"We really enjoyed the cleanliness and location. Pool was great. Having our own deck was nice. Great views. Highly recommend. "
United States
Rolly N.
The price is €263
includes taxes & fees
7 Dec - 8 Dec
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Condo in Sarasota

9.6 out of 10, Exceptional, (44)
"The location of the property could not have been better. A very short walk to the quietest beach on Siesta Key. The manager was very attentive when we called with a minor issue and had it resolved quickly. The property could use a pretty thorough cleaning of the baseboards and other nooks and crannies but overall it was pretty clean. We would stay again."
United States
Mel S.
The price is €218
includes taxes & fees
30 Nov - 1 Dec
POOL VIEW Walk to beach King bed Heated pool DAILY WEEKLY SPECIALS villa 3
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, apart-hotels, 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 favorite 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 depends 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 €121 per night. Entering your travel dates in the search wizard you might find 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 34 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.