Osprey Vacation Packages 2026 from $468

Osprey flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Legacy Hotel at IMG Academy

$468

per person

May 7 - May 10

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Sarasota (SRQ)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free self parking and free WiFi. You'll appreciate the area shuttle, valet parking, and coffee shop/cafe.

Captiva Beach Resort

South Village

Save 100% on your flight

$648

per person

May 13 - May 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

A private beach and an outdoor pool are featured at this smoke-free condo. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area, laundry facilities, and barbecue grills are also on offer.

Hampton Inn & Suites Sarasota/Lakewood Ranch

Save 100% on your flight

$698

per person

Jun 11 - Jun 14

found 3 hours ago

Roundtrip flight included

Chicago (ORD) to Sarasota (SRQ)

This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.

Cedar Cove Resort and Cottages

Save 100% on your flight

$1,238

per person

May 13 - May 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

This resort doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a snack bar/deli are also on offer.

Top Osprey hotels deals

Casey Key Resorts - Mainland

1650 South Tamiami Trail Osprey FL

Free Cancellation

Reserve now, pay when you stay

$184 nightly

$208 total

Apr 1 - Apr 2

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

965 University Pkwy Sarasota FL

Free Cancellation

Reserve now, pay when you stay

$152 nightly

$172 total

Apr 30 - May 1

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

Golden Host Resort - Sarasota

4675 N Tamiami Trl Sarasota FL

Free Cancellation

$79 nightly

$89 total

Apr 26 - Apr 27

Total with taxes and fees

This hotel features an outdoor pool and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Free self parking, a terrace, and a garden are also offered.

Tropical Beach Resorts

6717 Sara Sea Circle Siesta Key FL

$226 nightly

$256 total

Apr 29 - Apr 30

Total with taxes and fees

An outdoor pool, free self parking, and laundry facilities are featured at this aparthotel. WiFi in public areas is free. A garden, a library, and a picnic area are also on offer.

Tropical Breeze Resort

140 Columbus Blvd. Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$345 nightly

$390 total

Apr 28 - Apr 29

Total with taxes and fees

This hotel's 2 outdoor pools and hot tub are among the featured amenities. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a garden, and luggage storage are also on offer.

Azul Resort Siesta Key

1105 Point of Rocks Rd Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$344 nightly

$389 total

Apr 26 - Apr 27

Total with taxes and fees

An outdoor pool is featured at this hotel, along with free self parking. WiFi in public areas is free. A terrace is also provided.

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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

Oscar Scherer State Park

4/5(9 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.

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.

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 lively bars.

Frequently asked questions

How much are vacation packages to Osprey?

Travelocity offers great package deals to Osprey, including hotels and flights, from an impressive $468. 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.