Osprey Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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.
Sleeps 6 Hot Tub Fenced Yard Cozy Chic

Sleeps 6 Hot Tub Fenced Yard Cozy Chic

3 out of 5
Town 'n' Country
per person
Sep 13 - Sep 16
found 12 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Sarasota (SRQ)
2/10 (2 reviews)
Twin Palms at Siesta

Twin Palms at Siesta

3 out of 5
per person
Oct 3 - Oct 10
found 11 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Sarasota (SRQ)
9.6/10 Exceptional! (545 reviews)
Property was very nice, room was beautifully decorated and very clean and comfortable. Nice kitchenette. The pool and pool area very nice. The location is great. Close to the beach and some restaurants and bars. Each room was provided a wagon, cooler, chairs and umbrella to use for the beach which was so nice. I would definitely stay there again!

Reviewed on Jun. 29, 2025

Captiva Beach Resort

Captiva Beach Resort

2 out of 5
per person
Oct 3 - Oct 10
found 11 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Sarasota (SRQ)
9/10 Wonderful! (1,113 reviews)
We love the property, beautiful, clean and we love that you can walked to the beach, that is a plus.

Reviewed on Jul. 13, 2025

Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
per person
Sep 5 - Sep 11
found 9 hours ago
Roundtrip flight included
Montreal (YMQ) to Sarasota (SRQ)
9/10 Wonderful! (837 reviews)
The hotel is ideally located for IMG Academy visitors and offers updated, comfortable rooms. It’s a practical and safe choice, with fair pricing and unbeatable proximity to the Academy. While the property isn’t brand new, the core essentials are solid. I would love to see improvements in room cleanliness—some fixtures and finishes showed wear, and more attention here would elevate the overall experience. Still, given the options in the area, this hotel provides the best balance of convenience and value. I look forward to returning.

Reviewed on Jul. 23, 2025

Venice Beach Villas

Venice Beach Villas

3 out of 5
per person
Oct 3 - Oct 10
found 11 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Sarasota (SRQ)
9.4/10 Exceptional! (420 reviews)
Everything was great. Great people to work with.

Reviewed on Jul. 22, 2025

Where to stay in Osprey

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

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

Ready to book your vacation to Osprey?

 

Choose your dates

Osprey Hotel Deals

Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

3 out of 5
1650 South Tamiami Trail, Osprey, FL
Fully refundableReserve now, pay when you stay
The price is CA $152 per night from Jul 27 to Jul 28
CA $152
CA $172 total
Jul 27 - Jul 28
includes taxes & fees
8.4/10 Very Good! (1,061 reviews)
"Rooms are clean. Staff is pleasant and efficient. The restaurant is excellent and so is the staff. As for the facilities I cannot pronounce myself as I did not get to use them."

Reviewed on Jul. 21, 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 CA $82 per night from Aug 7 to Aug 8
CA $82
CA $109 total
Aug 7 - Aug 8
includes taxes & fees
9/10 Wonderful! (4,188 reviews)
Brand new
"Everything is brand new, clean and perfect. I like the decoration and design. Great location and near the airport."

Reviewed on Jul. 23, 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 CA $195 per night from Aug 24 to Aug 25
CA $195
CA $252 total
Aug 24 - Aug 25
includes taxes & fees
9.2/10 Wonderful! (4,793 reviews)
"The staff was amazing, providing needed accommodations for my elderly mother's visit. Resourceful customer service and Nate, the five-star employee who ensured that our visit was a memorable vacation."

Reviewed on Jul. 24, 2025

Tropical Beach Resorts
See all 10,465 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Osprey

Oscar Scherer State Park

Oscar Scherer State Park

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.

Oscar Scherer State Park

What to do in Osprey

Private Luxury Boat Charter

Private Luxury Boat Charter

CA $513
per traveller
100% of travellers recommend
Private Luxury Boat Charter
Kayak Tour through Mangrove Tunnels

Mangroves, Manatees, and a Hidden Beach: Kayak Tour

CA $75
per adult
88% of travellers recommend
Mangroves, Manatees, and a Hidden Beach: Kayak Tour
See all activities in Osprey

Frequently asked questions

How much does an Osprey vacation package cost?
You'll find cheap prices from CA $717 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.