Best Resorts in Osprey

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28
In one month
Jan 9 - Jan 11
In two months
Feb 6 - Feb 8

Resorts in Osprey

Smart TV, fireplace, table tennis, printers
Newly updated in family/pet friendly resort with all the amenities - near beach!

Newly updated in family/pet friendly resort with all the amenities - near beach!

Nokomis
10.0 out of 10, Exceptional, (5)
"Each year our son competes in a skimboarding competion at Nokomis Beach. This property was only a short distance away and was convenient to travel back in forth to the beach over the long weekend. The residence was very clean, comfortable and either had (or in the resort) every possible amenity you could think of within arms reach. The VRBO description is very accurate and our family had zero issues during our stay. We recommend 100% and will consider staying again next year. "
United States
Har G.
$206 nightly
The price is $230
Dec 12 - Dec 13
Total with taxes and fees
Newly updated in family/pet friendly resort with all the amenities - near beach!
Outdoor pool, open 9 AM to 9 PM, sun loungers
Siesta Key Beach Resort and Suites

Siesta Key Beach Resort and Suites

2.5 star property
Siesta Key Village
9.0 out of 10, Wonderful, (1023)
"We enjoyed our stay very much "
United States
Simi
$247 nightly
The price is $279
Dec 9 - Dec 10
Total with taxes and fees
Siesta Key Beach Resort and Suites
Breakfast, lunch and dinner served
Zota Beach Resort

Zota Beach Resort

4.0 star property
Longboat Key
9.0 out of 10, Wonderful, (1004)
"Lovely poolside lanai area off room & white sandy beach"
United States
Courtney
$269 nightly
The price is $304
Jan 5 - Jan 6, 2026
Total with taxes and fees
Zota Beach Resort
Fridge, microwave, oven, stovetop
Beautiful Venice Resort Home close to Beaches & Warm Mineral Springs, Cozy

Beautiful Venice Resort Home close to Beaches & Warm Mineral Springs, Cozy

Venice
10.0 out of 10, Exceptional, (5)
"Niche place with it's own unique flavor. "
United States
Hari R.
$431 nightly
The price is $480
Dec 9 - Dec 10
Total with taxes and fees
Beautiful Venice Resort Home close to Beaches & Warm Mineral Springs, Cozy
2 outdoor pools, sun loungers
Lido Beach Resort

Lido Beach Resort

4.0 star property
Lido Key
8.8 out of 10, Excellent, (1003)
"Beautiful place, beautiful view, wonderful staff, super convenient location"
United States
Patricia Kathleen
$299 nightly
The price is $338
Dec 14 - Dec 15
Total with taxes and fees
Lido Beach Resort
Exterior
The Resort at Longboat Key Club

The Resort at Longboat Key Club

4.0 star property
Longboat Key
9.0 out of 10, Wonderful, (689)
"Amazing staff, Sherman the concierge was the absolute best making our experience the greatest it could possibly be! We will be back again and again!"
United States
Jared
$489 nightly
The price is $553
Dec 14 - Dec 15
Total with taxes and fees
The Resort at Longboat Key Club
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Osprey Hotel Reviews

Carlisle Inn

Carlisle Inn

10/10 Excellent
"I will definitely stay here again. Breakfast until 10:30! Great hotel"
Anne 1-night trip
Posted 5 hours ago
Carlisle Inn

Find out more about Osprey

Osprey Resorts information

Number of reviews
3,719
Accommodation
17 Resorts
Lowest Price
$230
Highest Price
$553

Frequently asked questions

What can I expect from a resort vacation in Osprey?
You deserve a vacation, and a resort is the ideal place to treat yourself to the amenities and services you need for a relaxing stay in Osprey. One of the comfortable resorts in the area might be just what you're looking for, whether you're hoping for great restaurants on site, shopping possibilities, or fun activities to try.
What's a top resort for my stay in Osprey?
Our highest-rated resorts around Osprey: Lido Beach Resort - Beach resort, 5-minute walk from Lido Beach. 9.5 mi (15.2 km) from Osprey. Features 2 outdoor pools, a private beach, and a fitness center. Highly rated for its great beach location. Zota Beach Resort - Beach resort. 17.1 mi (27.5 km) from Osprey. Has a private beach, a fitness center, and a terrace. Guests love the pool. Siesta Key Beach Resort and Suites - Situated just a 5-minute walk from Siesta Key Beach. 7 mi (11.3 km) from Osprey. Popular for its pool. Enjoy the terrace, pool loungers, and a car charging station. The Resort at Longboat Key Club - Beach resort. 11.3 mi (18.2 km) from Osprey. Amenities include 6 restaurants, a private beach, and 4 bars.
What can I do in Osprey?
Travelers love exploring the beaches in Osprey, and say that there are lots of great bars here. Get some time by the water at Turtle Beach, or bring the kids to Jim Neville Marine Preserve for some family fun. Siesta Key Beach and Lido Beach are a couple additional top attractions in the area.
What's the weather like in Osprey?
The hottest months are usually August and July with an average temp of 82°F, while the coldest months are January and February with an average of 66°F. Average annual precipitation for Osprey is 44 inches.
What's the best way to get to and around Osprey?
Fly into Sarasota-Bradenton Intl. Airport (SRQ), which is located 13.8 mi (22.2 km) from the city center. If you'd like to venture out around the area, consider renting a car to take in more sights.

Explore a world of travel with Expedia