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 $1,200, price is now CA $1,100 per person
CA $1,100
per person
Jul 16 - Jul 23
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Sarasota (SRQ)
9.6/10 Exceptional! (481 reviews)
Very happy to have stayed here for the first time. Rooms and property were clean and well maintained. Staff were all amazing and helpful. Breakfast was very good with many options. Pool area was clean and the location was perfect.
Reviewed on May 8, 2026
Landing Palmetto Apartments
Price was CA $1,712, price is now CA $1,237 per person
CA $1,237
per person
Jun 29 - Jul 6
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Sarasota (SRQ)
8.8/10 Excellent! (60 reviews)
The property was amazing for the price. nice clean and spacious I would recommend this over the inns or hotels felt like being home in privacy.
Reviewed on Apr 20, 2026
Casey Key Resorts - Beachfront
Price was CA $2,459, price is now CA $2,019 per person
CA $2,019
per person
Jul 17 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Sarasota (SRQ)
8.8/10 Excellent! (1,000 reviews)
Perfect location! We had our dogs with us and being 30 seconds from the beach was a treat for sure.
Reviewed on May 15, 2026
Palmetto Marriott Resort & Spa
Price was CA $1,470, price is now CA $1,223 per person
CA $1,223
per person
Jun 29 - Jul 6
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Sarasota (SRQ)
9.2/10 Wonderful! (423 reviews)
Very friendly staff made the check in process very easy. The room was clean and the bed very comfortable. Will stay again!
Reviewed on May 14, 2026
Casey Key Resorts - Mainland
Price was CA $1,309, price is now CA $1,162 per person
CA $1,162
per person
Jul 16 - Jul 23
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Sarasota (SRQ)
8.8/10 Excellent! (1,131 reviews)
I was a bit surprised that the hotel charged for morning coffee.
Reviewed on May 13, 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.
Osprey Hotel Deals
Casey Key Resorts - Mainland
1650 South Tamiami Trail Osprey FL
Fully refundableReserve now, pay when you stay
The price is CA $133 per night from Jun 14 to Jun 15
CA $133
CA $169 total
Jun 14 - Jun 15
includes taxes & fees
8.8/10 Excellent! (1,151 reviews)
Great stay
Reviewed on May 14, 2026
Kompose Boutique Hotel
965 University Pkwy Sarasota FL
Fully refundableReserve now, pay when you stay
The price is CA $73 per night from May 17 to May 18
CA $73
CA $112 total
May 17 - May 18
includes taxes & fees
9.2/10 Wonderful! (5,362 reviews)
Immaculate and friendly staff!
Reviewed on May 16, 2026
Golden Host Resort - Sarasota
4675 N Tamiami Trl Sarasota FL
Fully refundable
The price is CA $102 per night from May 17 to May 18
CA $102
CA $115 total
May 17 - May 18
includes taxes & fees
8.4/10 Very Good! (2,474 reviews)
Family run operation providing a great lodging experience at a fair rate. Bar on-site! Would for sure stay again!
Reviewed on May 15, 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.
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
Mangrove Tunnel & Manatee Kayak Eco-Tour
CA $81
per adult
94% of travellers recommend
Sarasota Guided Mangrove Tunnel Kayak Tour
CA $81
per adult
96% of travellers recommend
Sarasota - Clear Kayak LED Night Glass Bottom Tour
CA $89
per adult
74% 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.
