Deals on vacations and trips to Osprey

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Osprey flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

4 out of 5
Price was $728, price is now $569 per person
$569
per person
Dec 22 - Dec 26
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 Beautiful 2bd, Gym

Landing Beautiful 2bd, Gym

3 out of 5
Save 100% on your flight
Price was $1,082, price is now $813 per person
$813
per person
Dec 24 - Dec 27
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to Sarasota (SRQ)
This apartment features a 24-hour gym and a seasonal outdoor pool. Guests will appreciate free perks like free self parking and WiFi in public areas. Barbecue grills and a virtual front desk are also provided.
Landing Palmetto Apartments

Landing Palmetto Apartments

4.5 out of 5
Price was $1,383, price is now $1,042 per person
$1,042
per person
Dec 22 - Dec 28
found 1 hour ago
Roundtrip non-stop 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
Save 100% on your flight
Price was $1,880, price is now $1,522 per person
$1,522
per person
Nov 18 - Nov 23
found 23 hours 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.
Escape Coastal Resort on Casey Key

Escape Coastal Resort on Casey Key

2.5 out of 5
Price was $745, price is now $615 per person
$615
per person
Nov 2 - Nov 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
A marina and an outdoor pool are featured at this hotel. Enjoy the gym and perks like free WiFi. A grocery/convenience store, express check-in, and express check-out are also on offer.

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
$102 nightly
The price is $115 total per night
$115 total
Sep 30 - Oct 1
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
$62 nightly
The price is $71 total per night
$71 total
Oct 6 - Oct 7
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
$158 nightly
The price is $179 total per night
$179 total
Sep 30 - Oct 1
Total with taxes and fees
This aparthotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A library, a picnic area, and luggage storage are also on offer.
Pool
Kitchen
The Westin Sarasota

The Westin Sarasota

4 out of 5
100 Marina View Drive Sarasota FL
Free Cancellation
Reserve now, pay when you stay
$183 nightly
The price is $206 total per night
$206 total
Sep 30 - Oct 1
Total with taxes and fees
A full-service spa, 2 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Enjoy the 24-hour gym and perks like a free beach shuttle. You'll appreciate the a rooftop terrace, bar/lounge, and laundry facilities.
Pool
Spa
Siesta Key Beach Resort and Suites

Siesta Key Beach Resort and Suites

2.5 out of 5
5311 Ocean Blvd Siesta Key FL
$195 nightly
The price is $220 total per night
$220 total
Sep 30 - Oct 1
Total with taxes and fees
This resort features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the hot tub and perks like free WiFi. Self parking, a terrace, and a garden are also offered.
Pool
Hot Tub
Carlisle Inn

Carlisle Inn

3.5 out of 5
3727 Bahia Vista Sarasota FL
Free Cancellation
Reserve now, pay when you stay
$144 nightly
The price is $162 total per night
$162 total
Sep 30 - Oct 1
Total with taxes and fees
This hotel features an outdoor pool, a 24-hour gym, and a restaurant. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. A 24-hour business center, a coffee shop, and a terrace are also on offer.
Pool
Breakfast included
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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 $569. 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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