Osprey Vacation Rentals

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Our top choices for Osprey vacation rentals

Vacation 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.
$357 nightly
The price is $398
Jan 24 - Jan 25
Total with taxes and fees
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
$213 nightly
The price is $240
Jan 21 - Jan 22
Total with taxes and fees
Tiny House Siesta
9.2 out of 10, Wonderful, (12 reviews)
"Property was perfect for the price."
United States
William M.
$150 nightly
The price is $167
Jan 20 - Jan 21
Total with taxes and fees
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
$537 nightly
The price is $577
Jan 27 - Jan 28
Total with taxes and fees
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.
$155 nightly
The price is $173
Jan 20 - Jan 21
Total with taxes and fees
Near to the Beach, UTC mall, SCF, IMG, Airport, Ringling Museum and much more

Vacation Home in Englewood

Waterfront Getaway, a Boating Paradise
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.
$289 nightly
The price is $322
Jan 20 - Jan 21
Total with taxes and fees
Waterfront Getaway, a Boating Paradise

Vacation 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
$306 nightly
The price is $346
Jan 20 - Jan 21
Total with taxes and fees
Siesta Heron Suites & Villas

Vacation 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.
$278 nightly
The price is $310
Feb 1 - Feb 2
Total with taxes and fees
Old Floridian cottage in Historic Gulf Village
10.0 out of 10, Exceptional, (23 reviews)
"Everything was great!"
United States
Lisa and Colin M.
$300 nightly
The price is $335
Jan 20 - Jan 21
Total with taxes and fees
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
$267 nightly
The price is $272
Jan 20 - Jan 21
Total with taxes and fees
[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
$175 nightly
The price is $198
Jan 26 - Jan 27
Total with taxes and fees
Kon Tiki Inn

Aparthotel in South Village

Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (5,246 reviews)
"Wonderful stay!"
United States
Victoria
$189 nightly
The price is $214
Jan 21 - Jan 22
Total with taxes and fees
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
$375 nightly
The price is $424
Jan 28 - Jan 29
Total with taxes and fees
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
$299 nightly
The price is $338
Jan 21 - Jan 22
Total with taxes and fees
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
$339 nightly
The price is $383
Jan 20 - Jan 21
Total with taxes and fees
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.
$419 nightly
The price is $467
Feb 8 - Feb 9
Total with taxes and fees
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.
$172 nightly
The price is $192
Feb 10 - Feb 11
Total with taxes and fees
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.
$448 nightly
The price is $501
Jan 20 - Jan 21
Total with taxes and fees
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
$158 nightly
The price is $178
Jan 25 - Jan 26
Total with taxes and fees
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Osprey vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Osprey vacation 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 low season months. For more hustle and bustle, you may prefer to visit Osprey in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $178 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Osprey rentals

At Expedia, we put the best Osprey vacation 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 vacation.

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 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?

Charming Florida Beach Home w King Bed Patio: Visitors give good reviews to this Osprey vacation home rental, which offers a garden and free WiFi to help you feel comfortable in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind.

How many vacation rentals are there in Osprey?

With 17 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?

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 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.