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

Palmetto Marriott Resort & Spa

4.5 out of 5
Price was CA $1,053, price is now CA $930 per person
CA $930
per person
Aug 21 - Aug 25
just found
Roundtrip non-stop flight included
Toronto (YTO) to Sarasota (SRQ)
9.2/10 Wonderful! (452 reviews)
Amazing stay!!! Clean rooms, staff was great!!! Breakfast was actually real good food. Staff was very patient with my son. Parking was easy and valet even offered to help us take our luggage up. Pool area amazing, had some spa vouchers but didnt get a chance to use them. Everyone seems really happy doing their job at this location. Next yr planning a longer stay, as we loved it so much!!! Worth every penny!!!

Reviewed on Jul 4, 2026

Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

4 out of 5
Price was CA $1,458, price is now CA $1,245 per person
CA $1,245
per person
Aug 20 - Aug 27
found 5 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Sarasota (SRQ)
8.8/10 Excellent! (1,189 reviews)
The room was huge, the bathroom was spotless and very spacious, and we had direct access to the pool from our room.

Reviewed on Jul 6, 2026

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 $1,261, price is now CA $1,211 per person
CA $1,211
per person
Aug 20 - Aug 27
found 5 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Sarasota (SRQ)
9.4/10 Exceptional! (522 reviews)
Perfect place to stay !! Very comfy, super clean and staff is amazing . Check out their breakfast bar it is sooo good !!!

Reviewed on Jul 6, 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 $134 per night from Jul 11 to Jul 12
CA $134
CA $169 total
Jul 11 - Jul 12
includes taxes & fees
8.8/10 Excellent! (1,203 reviews)
"The room was huge, the bathroom was spotless and very spacious, and we had direct access to the pool from our room."

Reviewed on Jul 6, 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 $66 per night from Jul 9 to Jul 10
CA $66
CA $105 total
Jul 9 - Jul 10
includes taxes & fees
9.2/10 Wonderful! (5,636 reviews)
"It was a very short stay but the property was an amazing deal for the price and we are already planning a longer stay here. Breakfast was great and pool was perfect per my wife."

Reviewed on Jul 6, 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 12 to Jul 13
CA $105
CA $119 total
Jul 12 - Jul 13
includes taxes & fees
8.6/10 Excellent! (2,589 reviews)
"I would stay again as the location is great!!!!"

Reviewed on Jul 5, 2026

Golden Host Resort - Sarasota
See all 11,378 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 $84
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 $84
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 $92
per adult
78% 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 $930 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.