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Osprey flight + hotel packages

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The Capri at Siesta

The Capri at Siesta

3 out of 5
per person
Aug. 9 - Aug. 12
Roundtrip flight included
Vancouver (YVR) to Sarasota (SRQ)
Stay at this 3-star beach hotel in Siesta Key. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the clean rooms in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Twin Palms at Siesta

Twin Palms at Siesta

3 out of 5
per person
Jun. 20 - Jun. 24
Roundtrip non-stop flight included
Montreal (YUL) to Sarasota (SRQ)
Stay at this 3-star beach hotel in Siesta Key. Enjoy free WiFi, free parking, and private pools. Our guests praise the pool and the clean rooms in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Tropical Breeze Resort

Tropical Breeze Resort

3 out of 5
Siesta Key Village
per person
Jun. 20 - Jun. 24
Roundtrip non-stop flight included
Montreal (YUL) to Sarasota (SRQ)
Stay at this 3-star beach hotel in Siesta Key. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
per person
Jun. 20 - Jun. 24
Roundtrip non-stop flight included
Montreal (YUL) to Sarasota (SRQ)
Stay at this 3.5-star beach aparthotel in Siesta Key. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Venice Beach Villas

Venice Beach Villas

3 out of 5
per person
Jun. 20 - Jun. 24
Roundtrip non-stop flight included
Montreal (YUL) to Sarasota (SRQ)
Stay at this 3-star business-friendly condo in Venice. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the clean rooms and the property condition in our reviews. Popular attractions Venice Beach and Nokomis Beach are located nearby.

Top Osprey hotels deals

Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

3 out of 5
1650 South Tamiami Trail, Osprey, FL
Free cancellation
Reserve now, pay when you stay
The price is CA $159 per night
CA $159
per night
May 19 - May 20
Stay at this 3-star business-friendly hotel in Osprey. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular attractions Nokomis Beach and Turtle Beach are located nearby.
Pet-friendly
Pool
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
965 University Pkwy, Sarasota, FL
Free cancellation
Reserve now, pay when you stay
The price is CA $94 per night
CA $94
per night
May 20 - May 21
Stay at this 3-star business-friendly hotel in Sarasota. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions St. Armands Circle and Lido Beach are located nearby.
Hot tub
Pet-friendly
Hyatt Regency Sarasota

Hyatt Regency Sarasota

4 out of 5
1000 Blvd Of The Arts, Sarasota, FL
Free cancellation
The price is CA $184 per night
CA $184
per night
May 27 - May 28
Book a stay at this eco-certified hotel in Sarasota. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions St. Armands Circle and Lido Beach are located nearby.
Hot tub
Pet-friendly
Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway

3 out of 5
6600 S Tamiami Trl, Sarasota, FL
Free cancellation
Reserve now, pay when you stay
The price is CA $174 per night
CA $174
per night
May 29 - May 30
Stay at this 3-star business-friendly hotel in Sarasota. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Hot tub
Pet-friendly
Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
6717 Sara Sea Circle, Siesta Key, FL
The price is CA $184 per night
CA $184
per night
May 21 - May 22
Stay at this 3.5-star beach aparthotel in Siesta Key. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Pool
Parking included
Siesta Key Beach Resort and Suites

Siesta Key Beach Resort and Suites

2.5 out of 5
5311 Ocean Blvd, Siesta Key, FL
The price is CA $268 per night
CA $268
per night
May 27 - May 28
Book a stay at this beach motel in Siesta Key. Enjoy free WiFi, free bicycles on site, and parking (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Siesta Key Beach and Lido Beach are located nearby.
Hot tub
Pet-friendly
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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.

Popular places to visit

Image for Oscar Scherer State Park

Oscar Scherer State Park

Enjoy the beautiful sunsets and explore Oscar Scherer State Park, a lovely green space in Osprey. Attend a sporting event or simply enjoy the lively bars while you're in the area.

Oscar Scherer State Park
Image for Historic Spanish Point

Historic Spanish Point

You can spend time exploring the galleries in Historic Spanish Point in Osprey. Attend a sporting event or simply enjoy the lively bars while you're in the area.

Historic Spanish Point
Image for The Oaks Club

The Oaks Club

Enjoy a round of golf in Osprey at The Oaks Club. Wander the area's beautiful beaches or simply enjoy one of its top-notch restaurants.

The Oaks Club

Osprey Vacations

We get it, geography isn't everyone's forte. If you're not sure where Osprey is situated, you'd be wise to learn about its location before you head off!

A neighborhood in the fabulous city of Sarasota, Osprey is 11 miles (18 kilometers) to the south of the heart of the action.

At last count, the population of Sarasota was 52,000.

Places to visit in Osprey

Getting out on the green is one of the best ways to enjoy the fresh air and have a real blast. Challenge yourself with a friendly round at Stoneybrook Golf & Country Club. Want some more close by options? Time spent with nature has been shown to be beneficial to both your physical and emotional state of being. Visit Oscar Scherer State Park and experience the benefits of connecting with the natural environment. But that's not all. Healthy oceans play a critical role in sustaining life on Earth. Spend a day at Jim Neville Marine Preserve and find out more about how this nature reserve is working to protect our waters for the future.

Where do you fly into for Osprey?

Grab your bags and your passport and get set for an unforgettable adventure. When you touch down at Sarasota-Bradenton International Airport (SRQ), you'll be just 14 miles (23 kilometers) north of Osprey.

Frequently asked questions

How much are vacation packages to Osprey?
Your vacation daydreams can come true in Osprey for only CA $762. Package deals include flights and hotels, and they’ll make your booking nice and easy. The only thing you’ll have to worry about is having a good time.
Where can I get the best vacation package deals for Osprey?
It’s hard to top Travelocity when it comes to piecing together your Osprey package deal. There are at least 400 partner airlines and 665,000 properties worldwide to select from. Secure your trip now and get ready to tick another exciting place off your must-visit list.
Why should I purchase my Osprey vacation bundle via Travelocity?
By booking your hotel, flights, activities and car rental all in the one place, you’ll save both time and money. We offer a dedicated team of experts available 24/7, and you’ll know that you’ll always score the lowest price possible with our Price Match Guarantee. So, what are you waiting for? Book that dream vacation today and get packing!
Can I save money on my Osprey car rental if I book it with hotels and flights?
Booking an Osprey vacation package with Travelocity is one of the simplest ways to save cold, hard cash. You can combine a hotel, car and flight, or any combination of them, and land awesome discounts. It’s also possible to throw in experiences and activities. Once you’ve collected the keys to your rental car, head out of the neighborhood and see what this place has to offer. Roughly 159 kilometersfrom Osprey, Walt Disney World® is certainly worth a road trip.
What is the best time of year to go to Osprey?
If you’re saving your pennies, is the perfect month to see this part of the world, while is the priciest time of the year. is generally regarded as high season. If you prefer to avoid the crowds, tend to be quieter.
What is there to do in Osprey?
As you’re roaming about Osprey, pay a visit to Oscar Scherer State Park and Historic Spanish Point. You won’t be short of things to do!
Where should I stay when visiting Osprey?
After a fun-filled day of sightseeing around Osprey, relax and unwind at the Bentley’s Boutique Hotel, BW Premier Collection. This top option will make your stay comfortable.
Can I go on vacation to Osprey at this time?
Discover all the info you need to know about quarantine policies and travel restrictions before you head for Osprey. Our Covid-19 Travel Advisor is full of advice to help make your trip relaxed and stress-free.