
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.

Holiday Inn Express & Suites Nokomis Sarasota South by IHG
Price was CA $976, price is now CA $956 per person
CA $956
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Sarasota (SRQ)
9.4/10 Exceptional! (522 reviews)
This was below the typical Holiday Inn Express standard. Seemed new and clean enough and breakfast was OK, but also was off. The room had a funky smell. We had to ask for toilet paper since they barely left any in the room upon arrival and did not add any after the first day of cleaning. Then, 2 days later they took the dirty towels and did not give clean ones, so another trip down to the front desk. Check in seemed to have more questions and was longer than most places are now. It was OK, but not the usual Holiday Inn Express from my 6 nights there. Location was good for us. Across the street from WaWa was a bonus.
Reviewed on Jun 30, 2026

Landing Palmetto Apartments
Price was CA $1,207, price is now CA $1,029 per person
CA $1,029
per person
Sep 2 - Sep 7
found 4 hours ago
Roundtrip flight included
Toronto (YYZ) to Sarasota (SRQ)
9/10 Wonderful! (64 reviews)
Great place to stay with a family
Pool has always hot water plus the grills are right next to it so yea what else do you need room was cleab
Reviewed on Jun 10, 2026


Casey Key Resorts - Mainland
Price was CA $1,130, price is now CA $978 per person
CA $978
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Sarasota (SRQ)
8.8/10 Excellent! (1,192 reviews)
The room was clean. Staff were very friendly and helpful. The location is conveniently located between Venice and Siesta Key.
Reviewed on Jun 29, 2026

Palmetto Marriott Resort & Spa
Price was CA $1,046, price is now CA $959 per person
CA $959
per person
Aug 24 - Aug 28
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Sarasota (SRQ)
9.2/10 Wonderful! (447 reviews)
The staff was awesome. The hotel was awesome. No complaints at all. I will stay here again.
Reviewed on Jun 29, 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 Turtle 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 $144 per night from Jul 2 to Jul 3
CA $144
CA $182 total
Jul 2 - Jul 3
includes taxes & fees
8.8/10 Excellent! (1,189 reviews)
"The room was clean. Staff were very friendly and helpful. The location is conveniently located between Venice and Siesta Key."
Reviewed on Jun 29, 2026

Kompose Boutique Hotel
965 University Pkwy Sarasota FL
Fully refundableReserve now, pay when you stay
The price is CA $95 per night from Jul 8 to Jul 9
CA $95
CA $138 total
Jul 8 - Jul 9
includes taxes & fees
9.2/10 Wonderful! (5,604 reviews)
"Nice breakfast. Clean room."
Reviewed on Jun 30, 2026

Golden Host Resort - Sarasota
4675 N Tamiami Trl Sarasota FL
Fully refundable
The price is CA $105 per night from Jul 26 to Jul 27
CA $105
CA $119 total
Jul 26 - Jul 27
includes taxes & fees
8.6/10 Excellent! (2,576 reviews)
"Pretty good for the price"
Reviewed on Jun 30, 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.
What to do in Osprey

Mangrove Tunnel & Manatee Kayak Eco-Tour
CA $82
per adult
94% of travellers recommend

Sarasota Guided Mangrove Tunnel Kayak Tour
CA $82
per adult
96% of travellers recommend

Sarasota - Clear Kayak LED Night Glass Bottom Tour
CA $90
per adult
74% of travellers recommend
Frequently asked questions
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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.











