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.
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 1 day 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
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 1 day 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 $2,098, price is now CA $1,863 per person
CA $1,863
per person
Jun 26 - Jun 30
found 10 hours ago
Roundtrip non-stop flight included
Montreal (YUL) 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
Holiday Inn Express & Suites Nokomis Sarasota South by IHG
Price was CA $1,454, price is now CA $1,358 per person
CA $1,358
per person
Jul 1 - Jul 8
found 12 hours ago
Roundtrip non-stop flight included
Montreal (YUL) 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
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 May 30 to May 31
CA $133
CA $169 total
May 30 - May 31
includes taxes & fees
8.8/10 Excellent! (1,155 reviews)
Super clean hotel, friendly staff and the pool is amazing! Always the perfect temperature. Chef Rolf’s food is made from scratch and there’s always music, bands and things going on for the weekend. Quiet and peaceful location with daily shuttles to and from their private beach. What’s not to ...
Reviewed on May 16, 2026
Kompose Boutique Hotel
965 University Pkwy Sarasota FL
Fully refundableReserve now, pay when you stay
The price is CA $82 per night from May 19 to May 20
CA $82
CA $123 total
May 19 - May 20
includes taxes & fees
Golden Host Resort - Sarasota
4675 N Tamiami Trl Sarasota FL
Fully refundable
The price is CA $102 per night from May 31 to Jun 1
CA $102
CA $115 total
May 31 - Jun 1
includes taxes & fees
8.4/10 Very Good! (2,478 reviews)
Buenas muy linda la decoración, es playera ,y todo en general muy bien.
Reviewed on May 17, 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.
