Osprey Holiday Rentals

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Our top choices for Osprey holiday rentals

Holiday Home in Bay Acres

Charming Osprey Home
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"Upon entering the property, we felt it was clean, bright and very welcoming. We loved the decor and the nice spaces in this two bedroom, two bath home. We thought the location was perfect, right across the main street is Walmart for quick grocery items, and we liked the amenities including a kettle for hot tea, a coffeemaker and a fully equipped kitchen! We would have liked to have more than two beach towels, but we made do with two. The laundry room was convenient for washing clothes and did...
United States
Van-Ha N.
The price is AU$614
includes taxes & fees
24 Jan - 25 Jan
Charming Osprey Home

Mobile Home in Sarasota

Tiny House Siesta
2.0 star property
8.4 out of 10, Very good, (347 reviews)
"Clean room, easy check in, beach nearby 15 minute walk, Florida Fun Rides scooter rental place nearby"
United States
Justice
The price is AU$351
includes taxes & fees
20 Jan - 21 Jan
Tiny House Siesta
9.2 out of 10, Wonderful, (12 reviews)
"Property was perfect for the price."
United States
William M.
The price is AU$253
includes taxes & fees
30 Jan - 31 Jan
Charming cottage for 2 across warm mineral springs park

Condo in Manasota Key

Chadwick Cove Resort & Marina
4.0 star property
10.0 out of 10, Exceptional, (15 reviews)
"Great place and location "
United States
Cathy
The price is AU$864
includes taxes & fees
27 Jan - 28 Jan
Chadwick Cove Resort & Marina
9.2 out of 10, Wonderful, (36 reviews)
"Very nice place, easy check in, and communicative host"
United States
Cristopher M.
The price is AU$261
includes taxes & fees
20 Jan - 21 Jan
Near to the Beach, UTC mall, SCF, IMG, Airport, Ringling Museum and much more
10.0 out of 10, Exceptional, (50 reviews)
"Beautiful and immaculate property. Had everything we needed, uncluttered and so comfortable. Will definitely stay here again. "
United States
christine w.
The price is AU$490
includes taxes & fees
20 Jan - 21 Jan
Waterfront Getaway, a Boating Paradise

Holiday Home in Siesta Key

Siesta Heron Suites & Villas
3.5 star property
8.6 out of 10, Excellent, (38 reviews)
"It was perfect for my family of 4 for our beach vacation!!"
United States
Jesse
The price is AU$858
includes taxes & fees
17 Feb - 18 Feb
Siesta Heron Suites & Villas

Holiday Home in Olde Englewood Village

Old Floridian cottage in Historic Gulf Village
9.8 out of 10, Exceptional, (60 reviews)
"Very good, great location 👍👍"
United States
James M.
The price is AU$466
includes taxes & fees
1 Feb - 2 Feb
Old Floridian cottage in Historic Gulf Village
10.0 out of 10, Exceptional, (23 reviews)
"Everything was great!"
United States
Lisa and Colin M.
The price is AU$520
includes taxes & fees
20 Jan - 21 Jan
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!
9.8 out of 10, Exceptional, (25 reviews)
"Clean and comfortable. "
United States
Laney
The price is AU$416
includes taxes & fees
20 Jan - 21 Jan
[escape to paradise] siesta key beach getaway

Aparthotel in Venice Island

Kon Tiki Inn
2.5 star property
10.0 out of 10, Exceptional, (252 reviews)
"Great place! "
United States
Michelle
The price is AU$289
includes taxes & fees
26 Jan - 27 Jan
Kon Tiki Inn

Aparthotel in South Village

Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (5,245 reviews)
"Wonderful stay!"
United States
Victoria
The price is AU$320
includes taxes & fees
21 Jan - 22 Jan
Tropical Beach Resorts
9.2 out of 10, Wonderful, (5 reviews)
"We really enjoyed the cleanliness and location. Pool was great. Having our own deck was nice. Great views. Highly recommend. "
United States
Rolly N.
Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
3.5 star property
9.6 out of 10, Exceptional, (308 reviews)
"The rooms were perfect, and the staff was great. The location was perfect and peaceful"
United States
Marybeth
The price is AU$635
includes taxes & fees
28 Jan - 29 Jan
The Residences at Siesta Key Beach by Hyatt Vacation Club

Cottage in Siesta Key

The Inn On Siesta Key
3.5 star property
10.0 out of 10, Exceptional, (193 reviews)
"Great place to stay! "
United States
Carlos
The price is AU$502
includes taxes & fees
21 Jan - 22 Jan
The Inn On Siesta Key

Aparthotel in Siesta Key

SeaSpray Resort
4.0 star property
9.4 out of 10, Exceptional, (85 reviews)
"Very clean very quiet and a great location to the beach."
United States
Dave
The price is AU$573
includes taxes & fees
20 Jan - 21 Jan
SeaSpray Resort
10.0 out of 10, Exceptional, (32 reviews)
"It ia a very nice property on a quiet street. Close to all things in Venice. "
United States
Shiela H.
Beautiful home with very private heated pool minutes from the beach
9.8 out of 10, Exceptional, (35 reviews)
"This is our 3rd year staying at this property. We love the location and convince of a quiet neighborhood off university road. We also appreciate the updated amenities and the bed topper is a huge plus for us! "
United States
Cecillia C.
The price is AU$297
includes taxes & fees
20 Jan - 21 Jan
Beautiful University Pines Studio in Sarasota
9.8 out of 10, Exceptional, (137 reviews)
"everything was great had everything we need and more, would book again for sure."
United States
Kyrese S.
The price is AU$773
includes taxes & fees
20 Jan - 21 Jan
IMG Lake & Beach Home HOT Pool White Sand Beaches Kid&Pets OK Great Location!
2.5 star property
8.6 out of 10, Excellent, (2,236 reviews)
"Nice pool very spacious room"
United States
John W
The price is AU$296
includes taxes & fees
20 Jan - 21 Jan
Hibiscus Suites - Gateway to Siesta Key
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$289 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 17 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.