Osprey Vacation Packages
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Your Osprey Vacation
When a getaway to the city is calling, answer it with a Osprey vacation package. The neighborhood of Main Street Merchants, which is great for cafes, markets and shopping, makes a fantastic base for your adventures. Siesta Key Beach, Turtle Beach and Nokomis Beach are just a few of the sights worth exploring during your trip to Osprey. Check out Expedia's extensive range of travel options and book your dream vacation to Osprey now.
Top Osprey Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Landing Palmetto Apartments
CA $1,018
per person
Oct 22 - Oct 27
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Sarasota (SRQ)
9/10 Wonderful! (68 reviews)
Great option if you’re looking for a comfortable, home-like stay. The only downside was that there wasn’t a coffee maker, which would have been a nice addition (just Kuerig). The kitchen could also be better stocked with basic cooking utensils, such as a can opener and other essentials. We ended up having to run out and buy several basic items that we only needed for a one-time use.
Reviewed on Aug 5, 2026
Where to stay in Osprey
Find the best Osprey areas and neighborhoods for the activities you enjoy most. Learn more about Osprey
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.
Rivendell
Rivendell might not have many top sights, but Oscar Scherer State Park and Jim Neville Marine Preserve are two attractions nearby that you can check out.
Bay Acres
If you're looking for some top things to see and do in Bay Acres and surrounding area, you can visit Oscar Scherer State Park and Jim Neville Marine Preserve.
Ready to book your vacation to Osprey?
Osprey Hotel Deals
Casey Key Resorts - Mainland
1650 South Tamiami Trail Osprey FL
Fully refundableReserve now, pay when you stay
CA $123
CA $156 total
Aug 21 - Aug 22
includes taxes & fees
Kompose Boutique Hotel
965 University Pkwy Sarasota FL
Fully refundableReserve now, pay when you stay
CA $62
CA $100 total
Aug 23 - Aug 24
includes taxes & fees
9.2/10 Wonderful! (5,881 reviews)
"Great staff. Great management. Favorite hotel in Sarasota."
Reviewed on Aug 20, 2026
Tropical Beach Resorts
6717 Sara Sea Circle Siesta Key FL
Fully refundableReserve now, pay when you stay
CA $176
CA $234 total
Aug 23 - Aug 24
includes taxes & fees
9.4/10 Exceptional! (5,775 reviews)
"This is my Every Year.."
Reviewed on Aug 20, 2026
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.
Stay near popular Osprey attractions
Photo by Frank Methling
Oscar Scherer State Park
8.8/10 (83 reviews)
You can take time to visit Oscar Scherer State Park during your travels to Osprey. Attend a sporting event or simply enjoy the lively bars while you're in the area.
Photo by Jessica M Dobbins
Historic Spanish Point
9.0/10 (42 reviews)
You can spend time exploring the galleries in Historic Spanish Point in Osprey. Attend a sporting event or simply enjoy the lively bars while you're in the area.
Nancy's Consignments
6.8/10 (11 reviews)
Enjoy an outing to Nancy's Consignments during your stay in Osprey Village. Attend a sporting event or simply enjoy the lively bars while you're in the area.
What to do in Osprey
Siesta Key Electric Bike Sunset Tour
CA $100
per adult
98% of travellers recommend
Mangrove Tunnel & Manatee Kayak Eco-Tour
CA $83
per adult
94% of travellers recommend
Sarasota Guided Mangrove Tunnel Kayak Tour
CA $83
per adult
96% of travellers recommend
Frequently asked questions
How much does an Osprey vacation package cost?
You'll find cheap prices from CA $953 on Expedia for your Osprey escape. However, a range of factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Osprey costs.
What are the cheapest months to go to Osprey?
You can generally find lower rates and greater availability in August, September and November. Explore our cheap Osprey vacation packages and you could score some excellent off-season deals.
How many days is enough for Osprey?
To fully enjoy an Osprey vacation, we recommend booking for 3 days. Split your time between visiting Nokomis Beach, Crescent Beach and other well-known attractions, as well as exploring neighbourhoods like Laurel and Casey Key. If you've got some spare time, add a day trip or tour to your Osprey vacation itinerary.
Is it worth booking a vacation package to Osprey?
Osprey is a good vacation destination with attractions like Oscar Scherer State Park among the many things to keep you entertained. Whether you're heading away with the family or planning a trip with friends, an Osprey vacation promises fun for everyone.
How to find the best Osprey package deals?
Landing a cheap Osprey package deal is a cinch with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget range, add a couple of filters and see what's available. You can tweak your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to discover the most affordable Osprey package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book an Osprey vacation as a package?
You can enjoy significant savings on your next Osprey break by booking a customized vacation package. Check the "Package" heading, then enter your destination and travel dates to view some great flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Osprey?
If you've got your Osprey vacation dates confirmed, book as early as you can to grab some terrific deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for jetting off on a whim.
How to plan a trip to Osprey?
- Choose when to get away: Check your calendar and get your bags packed. Your favourite season and the activities available will also help you decide when to visit Osprey.
- Calculate your budget: Ensure you have enough money to cover everything from meals and transportation to flights and activities. Your hotel will likely be the largest expense during your trip to Osprey.
- Set the duration of your trip: Start by making a list of all the attractions and activities you'd like to experience in Osprey. Then, estimate how long you'll need for each, along with any travel time.
- Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to find 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.
