Osprey Vacation Rentals

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In two weeks
Jan 23 - Jan 25
In two months
Mar 6 - Mar 8
In three months
Apr 3 - Apr 5
In four months
May 1 - May 3

Our top choices for Osprey vacation rentals

Beach towels
Charming Osprey Home

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.
$326 nightly
The price is $364
Jan 10 - Jan 11
Total with taxes and fees
Charming Osprey Home
Cabin (Tiny House - The Siesta) | Living area | Flat-screen TV, Netflix, streaming services
Tiny House Siesta

Mobile Home in Sarasota

Tiny House Siesta
2.0 star property
8.4 out of 10, Very Good, (346 reviews)
"Enjoyable stay. "
United States
Lori
$208 nightly
The price is $235
Jan 13 - Jan 14
Total with taxes and fees
Tiny House Siesta
Interior
Charming cottage for 2 across warm mineral springs park

Cottage in Warm Mineral Springs

Charming cottage for 2 across warm mineral springs park
9.2 out of 10, Wonderful, (10 reviews)
"Property was perfect for the price."
United States
William M.
$150 nightly
The price is $167
Jan 16 - Jan 17
Total with taxes and fees
Charming cottage for 2 across warm mineral springs park
House, Lakeside | Living area | 39-inch flat-screen TV with digital channels, TV, streaming services
Siesta Heron Suites & Villas

Vacation Home in Siesta Key

Siesta Heron Suites & Villas
3.5 star property
8.6 out of 10, Excellent, (38 reviews)
"Clean pool great apartment could use more seating in living room. Beach chairs was cool patio was awesome parking good water pressure great bed clean and comfy "
United States
jason
$308 nightly
The price is $349
Jan 13 - Jan 14
Total with taxes and fees
Siesta Heron Suites & Villas
Property grounds
Tropical Beach Resorts

Aparthotel in South Village

Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (5,214 reviews)
"Great place to stay. Very nice getaway. "
United States
Joyeeta
$164 nightly
The price is $185
Jan 11 - Jan 12
Total with taxes and fees
Tropical Beach Resorts
Deluxe Suite, 2 Bedrooms | In-room safe, iron/ironing board, free WiFi
SeaSpray Resort

Aparthotel in Siesta Key

SeaSpray Resort
4.0 star property
9.4 out of 10, Exceptional, (84 reviews)
"Very clean very quiet and a great location to the beach."
United States
Dave
$339 nightly
The price is $383
Jan 11 - Jan 12
Total with taxes and fees
SeaSpray Resort
Exterior
Chadwick Cove Resort & Marina

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
$505 nightly
The price is $542
Jan 12 - Jan 13
Total with taxes and fees
Chadwick Cove Resort & Marina
Living area
Nestled in North Port. Updated 2 Bed / 1 Bath.

Vacation Home in North Port

Nestled in North Port. Updated 2 Bed / 1 Bath.
10.0 out of 10, Exceptional, (15 reviews)
"Great place loved how clean and put together everything was would definitely stay here again"
United States
Jacob
$187 nightly
The price is $209
Jan 11 - Jan 12
Total with taxes and fees
Nestled in North Port. Updated 2 Bed / 1 Bath.
Terrace/patio
Kon Tiki Inn

Aparthotel in Venice Island

Kon Tiki Inn
2.5 star property
10.0 out of 10, Exceptional, (250 reviews)
"Great place! "
United States
Michelle
$179 nightly
The price is $202
Jan 13 - Jan 14
Total with taxes and fees
Kon Tiki Inn
Beach nearby, sun loungers, beach towels
HAPPY FUN BLUE HOUSE for 8 people kids, pets friendly, 3 miles from the beach🏖️

Vacation Home in South Venice

HAPPY FUN BLUE HOUSE for 8 people kids, pets friendly, 3 miles from the beach🏖️
9.8 out of 10, Exceptional, (48 reviews)
"Great place to stay especially if you have dogs "
United States
Erica R.
$339 nightly
The price is $378
Jan 10 - Jan 11
Total with taxes and fees
HAPPY FUN BLUE HOUSE for 8 people kids, pets friendly, 3 miles from the beach🏖️
On the beach, sun loungers, beach towels
Direct Beachfront 2BR Cottage on Casey Key!

Cottage in Casey Key

Direct Beachfront 2BR Cottage on Casey Key!
9.2 out of 10, Wonderful, (69 reviews)
"The Cottage is simple and in need of a few updates, but it is a beach cottage and the salt air is not kind. Overall, the location is fantastic, the Cottage is clean and comfortable and our stay was great."
United States
Bob T.
$419 nightly
The price is $468
Jan 11 - Jan 12
Total with taxes and fees
Direct Beachfront 2BR Cottage on Casey Key!
Fridge, microwave, oven, stovetop
Myakka River

Vacation Home in Venice

Myakka River
9.8 out of 10, Exceptional, (18 reviews)
"We loved everything about the property it’s nice and quiet. Nicely decorated and has a nice outdoor area and dock. The bed was a little firm for my taste but not terrible. 10/10 would stay here again "
United States
Ty
$415 nightly
The price is $462
Jan 10 - Jan 11
Total with taxes and fees
Myakka River
Interior
Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.

Vacation Home in The Meadows

Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.
10.0 out of 10, Exceptional, (19 reviews)
"Fun place "
United States
Maureen
$229 nightly
The price is $256
Jan 12 - Jan 13
Total with taxes and fees
Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.
Property grounds
The Residences at Siesta Key Beach by Hyatt Vacation Club

Aparthotel in South Village

The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5 star property
9.6 out of 10, Exceptional, (306 reviews)
"The rooms were perfect, and the staff was great. The location was perfect and peaceful"
United States
Marybeth
$384 nightly
The price is $434
Jan 19 - Jan 20
Total with taxes and fees
The Residences at Siesta Key Beach by Hyatt Vacation Club
Interior
The Mermaid at Tiny House Siesta

Vacation Home in Sarasota

The Mermaid at Tiny House Siesta
2.0 star property
10.0 out of 10, Exceptional, (2 reviews)
"It was exactly as listed on here. No problems with the check in it was very smooth as well as the check out process. Location was AMAZING, we were able to walk just 10 minutes to a longhorn to eat dinner and right next to it there was a bar near the beach and we were able to go back to the property just by walking. Really calm the area and the tiny house is very comfortable."
United States
Jackeline R.
$187 nightly
The price is $209
Jan 14 - Jan 15
Total with taxes and fees
The Mermaid at Tiny House Siesta
Fridge, microwave, oven, stovetop
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

Vacation Home in Southgate

Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
10.0 out of 10, Exceptional, (69 reviews)
"Enjoyed our stay. Great location close to everything we needed"
United States
Christine M.
$272 nightly
The price is $303
Jan 12 - Jan 13
Total with taxes and fees
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
Beach nearby, beach towels
Old Floridian cottage in Historic Gulf Village

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.
$280 nightly
The price is $312
Jan 11 - Jan 12
Total with taxes and fees
Old Floridian cottage in Historic Gulf Village
Smart TV, books, offices
Waterfront Getaway, a Boating Paradise

Vacation Home in Englewood

Waterfront Getaway, a Boating Paradise
10.0 out of 10, Exceptional, (49 reviews)
"Beautiful and immaculate property. Had everything we needed, uncluttered and so comfortable. Will definitely stay here again. "
United States
christine w.
$308 nightly
The price is $343
Jan 10 - Jan 11
Total with taxes and fees
Waterfront Getaway, a Boating Paradise
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, sun loungers
Hibiscus Suites - Gateway to Siesta Key

Aparthotel in Sarasota

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
8.6 out of 10, Excellent, (2,227 reviews)
"Very nice place !"
United States
Ivette
$144 nightly
The price is $163
Jan 11 - Jan 12
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key
Sun loungers, beach towels
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

Cottage in South Village

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
9.6 out of 10, Exceptional, (81 reviews)
"Wonderful experience! It was perfect for a girls’ weekend which included me, my mother & my 12 yr old daughters. There was enough restaurants in walking distance, the beach was in walking distance and we appreciated the trolley and frog hopper to get to Turtle Beach for kayaking. "
United States
Michelle A.
$269 nightly
The price is $300
Jan 13 - Jan 14
Total with taxes and fees
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
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

Kompose Boutique Hotel

Kompose Boutique Hotel

10/10 Excellent
"Great place a liter expensive for that place "
Ariel 2-night trip
Posted 20 hours ago
Kompose Boutique Hotel

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 $163 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.

Explore a world of travel with Expedia

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 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 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.