Osprey Vacation Rentals

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Our top choices for Osprey vacation rentals

Charming Osprey Home

Charming Osprey Home
Bay Acres
10.0 out of 10, Exceptional, (2 reviews)
"We had a positive experience staying at Linda’s duplex in Osprey. Linda was a lovely host and even furnished us with beach chairs and a cabana . The place was spotless & location was convenient for us as we explored most of the Sarasota, Venice & Naples area. Highly recommended staying at this lovely duplex. "
United States
Diane S.
$309 nightly
The price is $344
May 1 - May 2
Total with taxes and fees
Charming Osprey Home

Sunny Coastal Escape

Sunny Coastal Escape
Bay Acres
10.0 out of 10, Exceptional, (6 reviews)
"Great location for exploring north & south! House was very clean and comfy. We appreciated the excellent communication with our nice host, Lynn."
United States
Kaja F.
$355 nightly
The price is $396
May 1 - May 2
Total with taxes and fees
Sunny Coastal Escape

Nestled in North Port. Updated 2 Bed / 1 Bath.

Nestled in North Port. Updated 2 Bed / 1 Bath.
North Port
10.0 out of 10, Exceptional, (23 reviews)
"Great place loved how clean and put together everything was would definitely stay here again"
United States
Jacob
$198 nightly
The price is $221
May 2 - May 3
Total with taxes and fees
Nestled in North Port. Updated 2 Bed / 1 Bath.

Path to Paradise.

Path to Paradise.
Olde Englewood Village
$276 nightly
The price is $308
May 1 - May 2
Total with taxes and fees
Path to Paradise.

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
10.0 out of 10, Exceptional, (17 reviews)
"Great place and location "
United States
Cathy
$508 nightly
The price is $545
May 8 - May 9
Total with taxes and fees
Chadwick Cove Resort & Marina

Beautiful University Pines Studio in Sarasota

Beautiful University Pines Studio in Sarasota
Sarasota
9.8 out of 10, Exceptional, (40 reviews)
"Perfect area, close to all the stores and restaurants"
United States
Maria B.
$171 nightly
The price is $191
May 4 - May 5
Total with taxes and fees
Beautiful University Pines Studio in Sarasota

Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
Southgate
10.0 out of 10, Exceptional, (74 reviews)
"Wonderful Stay"
United States
Christopher R.
$234 nightly
The price is $261
May 3 - May 4
Total with taxes and fees
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (271 reviews)
"Very clean & spacious pet friendly room. Would definitely stay there again."
United States
Brittany
$127 nightly
The price is $143
May 13 - May 14
Total with taxes and fees
Kon Tiki Inn

Lakefront Condo · IMG Academy 5 Min · Anna Maria Island 15 Min· Pools & Hot Tubs

Lakefront Condo · IMG Academy 5 Min · Anna Maria Island 15 Min· Pools & Hot Tubs
Bradenton
9.8 out of 10, Exceptional, (120 reviews)
"Perfect spot and host "
United States
Dee B.
$268 nightly
The price is $299
May 3 - May 4
Total with taxes and fees
Lakefront Condo · IMG Academy 5 Min · Anna Maria Island 15 Min· Pools & Hot Tubs

Sunset and beach view from your balcony Unit 403

Sunset and beach view from your balcony Unit 403
Longboat Key
9.8 out of 10, Exceptional, (113 reviews)
"Beach view with sunset!!"
United States
joseph l.
Sunset and beach view from your balcony Unit 403

Cozy Beach House Just Minutes From Siesta Key

Cozy Beach House Just Minutes From Siesta Key
Sarasota
8.8 out of 10, Excellent, (14 reviews)
"Great location, family friendly! "
United States
Lyna T.
$307 nightly
The price is $343
May 2 - May 3
Total with taxes and fees
Cozy Beach House Just Minutes From Siesta Key

Beautifully furnished condo

Beautifully furnished condo
Bradenton
9.8 out of 10, Exceptional, (157 reviews)
"We would stay there again."
United States
Connie S.
$266 nightly
The price is $297
May 1 - May 2
Total with taxes and fees
Beautifully furnished condo

[escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (30 reviews)
"Very clean and great location! Beds very comfortable and owner very responsive and accommodating! Highly recommend staying here!"
United States
Tim T.
$356 nightly
The price is $365
May 7 - May 8
Total with taxes and fees
[escape to paradise] siesta key beach getaway

3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf

3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf
Manasota Key
9.4 out of 10, Exceptional, (82 reviews)
"Beautiful condo and perfect location for a relaxing beach getaway! We celebrated my husband’s 50th birthday and it was perfect! We will definitely book again! "
United States
Yasamin G.
$393 nightly
The price is $435
May 3 - May 4
Total with taxes and fees
3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf

Cozy 2BR Condo · IMG Academy 5 Min · Anna Maria Island 15 Min · Pools & Hot Tubs

Cozy 2BR Condo · IMG Academy 5 Min · Anna Maria Island 15 Min · Pools & Hot Tubs
Bradenton
9.8 out of 10, Exceptional, (156 reviews)
"Very clean condo , we enjoyed closeness of the beaches."
United States
Joanna M.
$281 nightly
The price is $313
May 3 - May 4
Total with taxes and fees
Cozy 2BR Condo · IMG Academy 5 Min · Anna Maria Island 15 Min · Pools & Hot Tubs

Lavish Corner Condo! IMG Academy 5 Min · Anna Maria Island · Pools & Hot Tubs

Lavish Corner Condo! IMG Academy 5 Min · Anna Maria Island · Pools & Hot Tubs
Bradenton
10.0 out of 10, Exceptional, (127 reviews)
"We enjoyed our stay. Is as shown in pictures and description. "
United States
Erin M.
$284 nightly
The price is $316
May 9 - May 10
Total with taxes and fees
Lavish Corner Condo! IMG Academy 5 Min · Anna Maria Island · Pools & Hot Tubs

Luxury House Walking Distance to Ocean - Sleeps 12

Luxury House Walking Distance to Ocean - Sleeps 12
Central Sarasota
9.8 out of 10, Exceptional, (16 reviews)
"Great place perfect location to the marina, and downtown area. Highly recommended thanks "
United States
Domingo B.
$471 nightly
The price is $471
May 1 - May 2
Total with taxes and fees
Luxury House Walking Distance to Ocean - Sleeps 12

Paradise Retreat with HEATED POOL-- Need We Say More

Paradise Retreat with HEATED POOL-- Need We Say More
South Bradenton
10.0 out of 10, Exceptional, (183 reviews)
"Maggie ,the hostess, was great. Responsive and very accommodating for our needs. "
United States
David S.
$354 nightly
The price is $395
May 10 - May 11
Total with taxes and fees
Paradise Retreat with HEATED POOL-- Need We Say More

Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.

Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.
The Meadows
10.0 out of 10, Exceptional, (24 reviews)
"Fun place "
United States
Maureen
$234 nightly
The price is $261
May 17 - May 18
Total with taxes and fees
Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.

Two Miles to Siesta Key

Two Miles to Siesta Key
Gulf Gate Estates
10.0 out of 10, Exceptional, (52 reviews)
"Easy location to find. Clean room"
United States
Jennifer
$128 nightly
The price is $142
May 4 - May 5
Total with taxes and fees
Two Miles 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 $143 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 lively bars in this destination. While you're in the area, you can also enjoy the top-notch restaurants and shops.

What are some of the best vacation rentals in Osprey?

Siesta Key Island Rentals: This vacation home rental near Osprey comes with free WiFi so you can feel at home during your trip. This vacation rental also comes with free parking to give you added peace of mind.

How many vacation rentals are there in Osprey?

With 19 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 Venice 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.