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

Holiday Inn Express & Suites Nokomis Sarasota South by IHG

2.5 out of 5
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

Landing Palmetto Apartments

4.5 out of 5
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

Escape Coastal Resort on Casey Key

Escape Coastal Resort on Casey Key

2.5 out of 5
Price was CA $1,571, price is now CA $1,342 per person
CA $1,342
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Sarasota (SRQ)
9.8/10 Exceptional! (281 reviews)
Everything was great.

Reviewed on May 30, 2026

Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

4 out of 5
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

Palmetto Marriott Resort & Spa

4.5 out of 5
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
An aerial view of a coastal area with a sandy beach, a road, and scattered buildings.

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.

Find hotels in Sorrento Shores

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Osprey Hotel Deals

Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

4 out of 5
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

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 $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

Kompose Boutique Hotel
Golden Host Resort - Sarasota

Golden Host Resort - Sarasota

3 out of 5
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

Golden Host Resort - Sarasota
See all 11,375 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.
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Stay near popular Osprey attractions

A forest with tall trees and a dirt path.
Photo by Frank Methling
Open Photo by Frank Methling

Oscar Scherer State Park

8.8/10 (83 reviews)
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.
See properties

What to do in Osprey

Mangroves, Manatees & a Hidden Beach Kayak Tour

Mangrove Tunnel & Manatee Kayak Eco-Tour

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

Sarasota Guided Mangrove Tunnel Kayak Tour

CA $82
per adult
96% of travellers recommend
Sarasota Guided Mangrove Tunnel Kayak Tour
Sarasota - Clear Kayak LED Night Glass Bottom Tour

Sarasota - Clear Kayak LED Night Glass Bottom Tour

CA $90
per adult
74% of travellers recommend
Sarasota - Clear Kayak LED Night Glass Bottom Tour
See all activities in Osprey

Frequently asked questions

How much does an Osprey vacation package cost?
You'll find cheap prices from CA $956 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.

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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.