Deals on vacations and trips to Osprey

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Osprey flight + hotel vacation packages

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Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

4 out of 5
Price was $561, price is now $488 per person
$488
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
This hotel features an outdoor pool, a gym, and a restaurant. Unwind with a drink at the bar/lounge and enjoy perks like free self parking and a free beach shuttle. There's a poolside bar on site, and a 24-hour front desk and laundry facilities are also provided.
Landing Palmetto Apartments

Landing Palmetto Apartments

4.5 out of 5
Price was $898, price is now $693 per person
$693
per person
Oct 17 - Oct 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
This aparthotel features an outdoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, barbecue grills, and a virtual front desk are also on offer.
Palmetto Marriott Resort & Spa

Palmetto Marriott Resort & Spa

4.5 out of 5
Price was $897, price is now $752 per person
$752
per person
Oct 17 - Oct 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
A full-service spa, 2 restaurants, and 3 outdoor pools are all featured at this luxury hotel. Enjoy a meal in one of the 2 coffee shops/cafes and perks like free WiFi. 2 poolside bars and 3 bars/lounges are featured at this hotel, along with a 24-hour gym.
Casey Key Resorts - Beachfront

Casey Key Resorts - Beachfront

3 out of 5
Price was $695, price is now $596 per person
$596
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
This hotel features free self parking and free WiFi in public areas. Take the free beach shuttle and relax with sun loungers and beach umbrellas. A free beach shuttle is offered as well.
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 $668, price is now $575 per person
$575
per person
Oct 4 - Oct 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the 2 conference rooms, free WiFi in public areas, and express check-in. Enjoy the free buffet breakfast each morning.

Top Osprey hotels deals

Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

4 out of 5
1650 South Tamiami Trail Osprey FL
Free Cancellation
Reserve now, pay when you stay
$96 nightly
The price is $108 total per night
$108 total
Aug 15 - Aug 16
Total with taxes and fees
This hotel features an outdoor pool, a gym, and a restaurant. Unwind with a drink at the bar/lounge and enjoy perks like free self parking and a free beach shuttle. There's a poolside bar on site, and a 24-hour front desk and laundry facilities are also provided.
Pool
Pet friendly
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
965 University Pkwy Sarasota FL
Free Cancellation
Reserve now, pay when you stay
$77 nightly
The price is $87 total per night
$87 total
Aug 16 - Aug 17
Total with taxes and fees
This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.
Pool
Hot Tub
Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
6717 Sara Sea Circle Siesta Key FL
Free Cancellation
Reserve now, pay when you stay
$158 nightly
The price is $179 total per night
$179 total
Aug 18 - Aug 19
Total with taxes and fees
This aparthotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, a library, and a picnic area are also on offer.
Pool
Kitchen
Lido Beach Resort

Lido Beach Resort

4 out of 5
700 Benjamin Franklin Dr Sarasota FL
Free Cancellation
Reserve now, pay when you stay
$369 nightly
The price is $417 total per night
$417 total
Aug 16 - Aug 17
Total with taxes and fees
This smoke-free resort features a private beach, 2 outdoor pools, and a restaurant. Spend a day at the beach surfing, or relax with beach cabanas and sun loungers. Enjoy the gym and perks like free WiFi.
On private beach
Pool
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
$88 nightly
The price is $99 total per night
$99 total
Aug 30 - Aug 31
Total with taxes and fees
This hotel features a bar/lounge, a poolside bar, and an outdoor pool. Business travelers can take advantage of the free WiFi in public areas. Enjoy the hot tub and free perks like continental breakfast and free self parking.
Pool
Hot Tub
Zota Beach Resort

Zota Beach Resort

4 out of 5
4711 Gulf of Mexico Dr Longboat Key FL
Free Cancellation
Reserve now, pay when you stay
$279 nightly
The price is $315 total per night
$315 total
Aug 16 - Aug 17
Total with taxes and fees
A private beach and an outdoor pool are featured at this smoke-free resort. Traveling on business? Take advantage of the business center and free WiFi in public areas. There's a restaurant and a bar/lounge for dining and drinks, and also a gym on site.
On private beach
Pool
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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.

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

Frequently asked questions

How much are vacation packages to Osprey?
Travelocity offers great package deals to Osprey, including hotels and flights, from an impressive $488. With all the extra cash, you could book some interesting tours or maybe also tack on some extra nights to your vacation.
How long should my Osprey vacation be?
Around 3 nights is the average amount of time travelers vacation in Osprey. But the perfect trip length all comes down to how many cherished memories you want to make. Why not allow a little more time and uncover some of the lesser-known spots?
Where can I get the best vacation package deals for Osprey?
With around 400 airlines and 1,000,000 properties all over the world, you can't go wrong with Travelocity. Look through our extensive range and create the perfect Osprey package deal. Isn't it great when travel is that easy?
Why should I book my Osprey vacation bundle with Travelocity?
Because you'll never wander on your own if you lock in your vacation through us, and we offer round-the-clock customer support and excellent service to boot. Add to that our Price Match Guarantee and a huge range of experiences and destinations to select from. We're here to help you have the vacation of a lifetime.
Can I save on my Osprey car rental if I book it with my hotel or flight?
Combining your flight, hotel and car into an Osprey vacation package is a surefire way to land the best prices. Plus, having your own wheels gives you freedom to make your way to all those landmarks you're hoping to check out. Situated 110 mi from Osprey, Universal Studios Florida is one place that should be on your can't-miss list. Fasten your seat belt and make a day trip of it.
Which airport is best for Osprey?
Tampa Intl. Airport (TPA) is one of the top airports for Osprey. It's about 55 mi north of the downtown area. Other choices include Sarasota-Bradenton Intl. Airport (SRQ) (14 mi away from central Osprey) and St. Petersburg-Clearwater Intl. Airport (PIE) (50 mi away from central Osprey).
What is there to do in Osprey?
There's a certain kind of magic as you wander through the streets of Osprey. Oscar Scherer State Park and The Oaks Club are just a couple of landmarks that make this city such a sought-after destination, so put them on your itinerary.
Where should I stay when visiting Osprey?
Many people opt to hit the hay at the Casey Key Resorts - Mainland. It's an excellent base for your Osprey vacation.

Photos of local treasures

Browse Osprey vacation photos for more inspiration

A marina with boats docked, a man walking on a path, and a building with red roofs in the background.
A marina with several boats docked, surrounded by palm trees and buildings with orange roofs.
A marina with docked boats, a wooden bridge, and a building with a red roof.
A river with lush greenery and a lamp post.
A residential street lined with palm trees and houses with red-tiled roofs.

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