Osprey Vacations from ₩350,332

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The Latest Osprey Vacation Packages

Price found within the past 48 hours. Click for updated prices.
OASIS BAY SUITES, Tampa, Busch Gardens, USF

OASIS BAY SUITES, Tampa, Busch Gardens, USF

2 out of 5
Terrace Park
per person
Oct 27 - Oct 29
found 11 hours ago
Roundtrip flight included
New York (LGA) to Sarasota (SRQ)
8.4/10 Very Good! (1,289 reviews)
Stayed for the weekend while visiting Busch Gardens. Hot breakfast. Clean, convenient & reasonably priced. Would definitely stay here again.

Reviewed on Aug 1, 2025

Holiday Inn Express & Suites Tampa East - Ybor City by IHG

Holiday Inn Express & Suites Tampa East - Ybor City by IHG

2.5 out of 5
per person
Oct 27 - Oct 29
found 11 hours ago
Roundtrip flight included
New York (LGA) to Sarasota (SRQ)
9.4/10 Exceptional! (1,015 reviews)
My stay was excellent. The room was comfortable and clean, friendly hotel staff.

Reviewed on Aug 4, 2025

Hotel Haya

Hotel Haya

4 out of 5
Ybor City
per person
Oct 27 - Oct 29
found 11 hours ago
Roundtrip flight included
New York (LGA) to Sarasota (SRQ)
9.2/10 Wonderful! (1,602 reviews)
This is a beautiful property located in a great area. It is half a block from a free trolly that runs every fifteen minutes and will take you all the way into town (11 stops total). The staff are excellent. I only deducted one start because our room, while cool enough, was quite humid.

Reviewed on Aug 4, 2025

Aloft Tampa Midtown

Aloft Tampa Midtown

3 out of 5
Midtown Tampa
per person
Oct 27 - Oct 29
found 11 hours ago
Roundtrip flight included
New York (LGA) to Sarasota (SRQ)
8/10 Very Good! (458 reviews)
Got it mixed up with the one Downtown but glad it turned into a running joke with the receptionist. So fun and different from hotels I’m accustomed too. Its in a great location 10/10 highly recommend. Very clean, all the staff were friendly and helped me out with any problems. A lot of great places surrounding it!

Reviewed on Jul 30, 2025

The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
Rocky Point
per person
Oct 27 - Oct 29
found 11 hours ago
Roundtrip flight included
New York (LGA) to Sarasota (SRQ)
8.4/10 Very Good! (1,001 reviews)
Check in was not a great experience. The receptionist was rude and not very informative. Our grievances were handled at check-out with a different receptionist and the manager. They were very apologetic. The toilet in our room had a broken handle. Overall, the hotel was great. Comfortable bed. Nice water pressure. Bellhop service was great. There’s a Starbucks inside of the hotel and it’s close to other convenient locations.

Reviewed on Aug 4, 2025

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 ₩139,729 per night from Aug 6 to Aug 7
₩139,729
₩157,895 total
Aug 6 - Aug 7
includes taxes & fees
8.6/10 Excellent! (1,051 reviews)
"easy access to the beach."

Reviewed on Aug 4, 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 ₩77,691 per night from Aug 6 to Aug 7
₩77,691
₩104,396 total
Aug 6 - Aug 7
includes taxes & fees
9/10 Wonderful! (4,217 reviews)
"Clean, cute, would have preferred private bathroom/shower"

Reviewed on Aug 4, 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 ₩193,065 per night from Sep 1 to Sep 2
₩193,065
₩249,447 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (4,825 reviews)
"The hotel is an good location close to restaurants and bars.the beach is an waliking distance. What we don't like.. we found a roach on our room.."

Reviewed on Aug 3, 2025

Tropical Beach Resorts
See all 10,455 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 from ₩350,332 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.