Osprey Vacation Rentals

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Vacation Rentals in Osprey

Beach towels
Charming Osprey Home

Vacation Home in Bay Acres

2.0 star property
$302 nightly
The price is $336
Dec 9 - Dec 10
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

2.0 star property
8.4 out of 10, Very Good, (343)
"Enjoyable stay. "
United States
Lori
$215 nightly
The price is $242
Nov 26 - Nov 27
Total with taxes and fees
Tiny House Siesta
Outdoor pool, a heated pool, open 8 AM to 10 PM, pool umbrellas
Tropical Beach Resorts

Aparthotel in South Village

3.5 star property
9.4 out of 10, Exceptional, (5115)
"The room was clean and the staff was very nice."
United States
Jill
$124 nightly
The price is $140
Nov 30 - Dec 1
Total with taxes and fees
Tropical Beach Resorts
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, sun loungers
Hibiscus Suites - Gateway to Siesta Key

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
$106 nightly
The price is $120
Dec 1 - Dec 2
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key
Exterior
Kon Tiki Inn

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
$140 nightly
The price is $159
Dec 2 - Dec 3
Total with taxes and fees
Kon Tiki Inn
Front of property - evening/night
Captiva Beach Resort

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
$136 nightly
The price is $152
Dec 10 - Dec 11
Total with taxes and fees
Captiva Beach Resort
Beach nearby
Island Life! King Bed Studio-Steps to beach

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
$171 nightly
The price is $190
Dec 4 - Dec 5
Total with taxes and fees
Island Life! King Bed Studio-Steps to beach
Exterior
Siesta Key Island Rentals

Vacation Home in Siesta Key

3.0 star property
9.6 out of 10, Exceptional, (50)
"Very nice place, we loved it. Great location. "
United States
Derrick
$249 nightly
The price is $281
Dec 3 - Dec 4
Total with taxes and fees
Siesta Key Island Rentals
Property grounds
Old Floridian cottage in Historic Gulf Village

Vacation Home in Olde Englewood Village

9.8 out of 10, Exceptional, (60)
"Very good, great location 👍👍"
United States
James M.
$226 nightly
The price is $252
Nov 26 - Nov 27
Total with taxes and fees
Old Floridian cottage in Historic Gulf Village
Fridge, microwave, oven, stovetop
Mimosa Memories

Vacation Home in South Venice

9.4 out of 10, Exceptional, (29)
"Nice quiet home , very clean. "
United States
David M.
Mimosa Memories
Property amenity
The Residences at Siesta Key Beach by Hyatt Vacation Club

Aparthotel in South Village

3.5 star property
9.6 out of 10, Exceptional, (297)
"Loved our stay! "
United States
Michelle
$384 nightly
The price is $434
Dec 17 - Dec 18
Total with taxes and fees
The Residences at Siesta Key Beach by Hyatt Vacation Club
Dining
[escape to paradise] siesta key beach getaway

Vacation Home in Siesta Key

10.0 out of 10, Exceptional, (22)
"Great place and location"
United States
Karen A.
$270 nightly
The price is $275
Nov 26 - Nov 27
Total with taxes and fees
[escape to paradise] siesta key beach getaway
Sun loungers, beach towels
Beautifully furnished condo

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.
$209 nightly
The price is $234
Dec 8 - Dec 9
Total with taxes and fees
Beautifully furnished condo
On the beach, sun loungers, beach towels
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms

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.
$427 nightly
The price is $476
Dec 1 - Dec 2
Total with taxes and fees
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
On the beach, white sand
A Beach Retreat

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
$184 nightly
The price is $208
Nov 30 - Dec 1
Total with taxes and fees
A Beach Retreat
Exterior detail
Riverside Oasis 1Bed/1Bath

Condo in Bayou Oaks

9.2 out of 10, Wonderful, (39)
"Excellent place to stay"
United States
garry s.
$109 nightly
The price is $121
Dec 1 - Dec 2
Total with taxes and fees
Riverside Oasis 1Bed/1Bath
Interior
The Sapphire Suite 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
Exterior
Fantastic Shorewalk Vacation 2 bed/2 bath condo/Lake view/close to IMG, beaches

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.
$339 nightly
The price is $379
Nov 26 - Nov 27
Total with taxes and fees
Fantastic Shorewalk Vacation 2 bed/2 bath condo/Lake view/close to IMG, beaches
Beach
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

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.
$297 nightly
The price is $297
Dec 7 - Dec 8
Total with taxes and fees
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
A heated pool
POOL VIEW Walk to beach King bed Heated pool DAILY WEEKLY SPECIALS villa 3

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.
$191 nightly
The price is $213
Nov 26 - Nov 27
Total with taxes and fees
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

Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

10/10 Excellent
"Room was clean, staff friendly "
Darlene 2-night trip
Posted 22 hours ago
Casey Key Resorts - Mainland

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 $120 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 34 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.