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.
Venice Beach Villas
Price was CA $1,022, price is now CA $712 per person
CA $712
per person
Oct 30 - Nov 5
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Sarasota (SRQ)
9.4/10 Exceptional! (433 reviews)
Very clean. Very comfortable. Location. They have everything you need. Bikes chairs umbrellas. Walkable to downtown with good restaurants and close to the beach. It also is very quiet and safe area.
Reviewed on Sep 6, 2025
The Residences at Siesta Key Beach by Hyatt Vacation Club
Price was CA $1,794, price is now CA $1,084 per person
CA $1,084
per person
Nov 2 - Nov 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Sarasota (SRQ)
9.8/10 Exceptional! (285 reviews)
Beautiful apartment! Great city view on the balcony. Pool area was lovely.
Reviewed on Aug 27, 2025
Cedar Cove Resort and Cottages
Price was CA $3,687, price is now CA $2,338 per person
CA $2,338
per person
Nov 15 - Nov 22
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Sarasota (SRQ)
9.2/10 Wonderful! (456 reviews)
My daughter and I loved staying here. The staff, beach and room were wonderful!! Thank you.. 😊
Reviewed on Sep 2, 2025
Captiva Beach Resort
Price was CA $1,196, price is now CA $795 per person
CA $795
per person
Dec 5 - Dec 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Sarasota (SRQ)
9/10 Wonderful! (1,127 reviews)
Captiva is in walking distance from the beach. Beds are very comfortable. Nice patio settings. Our kids enjoyed the pool.
Reviewed on Sep 3, 2025
Hampton Inn Tampa Downtown Channel District
Downtown Tampa
Price was CA $1,435, price is now CA $970 per person
CA $970
per person
Dec 4 - Dec 9
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Sarasota (SRQ)
9.4/10 Exceptional! (1,817 reviews)
Staff was great especially Captain T her service was exceptional.
Reviewed on Sep 10, 2025
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.
Osprey Hotel Deals
Casey Key Resorts - Mainland
1650 South Tamiami Trail, Osprey, FL
Fully refundableReserve now, pay when you stay
The price is CA $154 per night from Sep 11 to Sep 12
CA $154
CA $174 total
Sep 11 - Sep 12
includes taxes & fees
Kompose Boutique Hotel
965 University Pkwy, Sarasota, FL
Fully refundableReserve now, pay when you stay
The price is CA $71 per night from Sep 14 to Sep 15
CA $71
CA $97 total
Sep 14 - Sep 15
includes taxes & fees
Tropical Beach Resorts
6717 Sara Sea Circle, Siesta Key, FL
Fully refundableReserve now, pay when you stay
The price is CA $193 per night from Sep 11 to Sep 12
CA $193
CA $249 total
Sep 11 - Sep 12
includes taxes & fees
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.
Discover the most popular places to visit in Osprey
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.
What to do in Osprey
Private Luxury Boat Charter
CA $515
per traveller
100% of travellers recommend
HydroCats - 2 Hour CraigCat Sightseeing Tour
CA $200
per adult
100% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
