Osprey Vacations

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Where to stay in Osprey

Find the best Osprey areas and neighborhoods for the activities you enjoy most. Learn more about Osprey
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Sorrento Shores

When in Sorrento Shores, you can plan a visit to Oscar Scherer State Park and Nokomis Beach, some noteworthy sights in the nearby area.

Find hotels in Sorrento Shores

Find the Best Osprey Vacation Packages

Osprey Hotel Deals

Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

2.5 out of 5
1650 South Tamiami Trail, Osprey, FL
Fully refundableReserve now, pay when you stay
The price is ₩140,257 per night from Aug 17 to Aug 18
₩140,257
₩158,483 total
Aug 17 - Aug 18
includes taxes & fees
8.6/10 Excellent! (1,046 reviews)
"Easy"

Reviewed on Aug 11, 2025

Casey Key Resorts - Mainland
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
965 University Pkwy, Sarasota, FL
Fully refundableReserve now, pay when you stay
The price is ₩68,776 per night from Aug 17 to Aug 18
₩68,776
₩94,384 total
Aug 17 - Aug 18
includes taxes & fees
9/10 Wonderful! (4,247 reviews)
"Decent hotel close to the airport"

Reviewed on Aug 13, 2025

Kompose Boutique Hotel
Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
6717 Sara Sea Circle, Siesta Key, FL
Fully refundableReserve now, pay when you stay
The price is ₩193,794 per night from Sep 1 to Sep 2
₩193,794
₩250,389 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (4,858 reviews)
Spectacular mini stay !
"The resort was truly fantastic! The pool was stunning, and we captured some breathtaking photos. The service was excellent, making our stay even more enjoyable. My only minor issue was with the shower—the water didn't get cool enough, and the faucet didn't fully switch to the showerhead. Aside from ..."

Reviewed on Aug 12, 2025

Tropical Beach Resorts
See all 10,466 properties in Osprey
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.

Frequently asked questions

How much does an Osprey vacation package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a vacation to Osprey costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Osprey?
August, September and November are great times to look for cheap Osprey vacation packages. Traveling in less busy periods means you can usually find lower prices on hotels and flights.
How many days is enough for Osprey?
Dedicate at least 3 days for your Osprey vacation to really immerse yourself in everything that makes this place special. Stroll around popular areas, including Laurel and Casey Key. Then make a beeline for major sights such as Oscar Scherer State Park and The Oaks Club. With a clever itinerary, you'll be kept busy with room for some relaxation too. Want to venture beyond Osprey? Consider squeezing in a day trip or two.
Is it worth booking a vacation package to Osprey?
Osprey has everything you need for an amazing trip. Get your Osprey vacation off to a flying start by checking out major attractions like Oscar Scherer State Park.
How to find the best Osprey package deals?
Bagging a cheap Osprey package deal is easy with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget range, apply some filters and browse what's available. You can personalize your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Order the results by "Price: low to high" to view the most wallet-friendly Osprey package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are usually lower.
Is it cheaper to book an Osprey vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll generally get a better deal than booking each component individually. And you'll still have the flexibility to create a customized Osprey vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Osprey?
Score incredible bargains by reserving your flights ahead of time with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for an impromptu Osprey getaway.
How to plan a trip to Osprey?

  1. Choose the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to visit Osprey.
  2. Budget wisely: On top of the cost of your hotel, you'll need to consider other expenses too. These include transportation, food and flights. Also, set aside a little extra for unexpected expenses that may crop up during your trip to Osprey.
  3. Decide how long to go away for: Now that you're more familiar with Osprey, you can work out the ideal length of your break. Put together a rough itinerary and allocate enough time for all the things you want to do.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to choose an Osprey vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.