Osprey Vacation Packages 2026 from $578

Osprey flight + hotel vacation packages

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

Captiva Beach Resort

South Village

Save 100% on your flight

$578

per person

Apr 11 - Apr 14

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.

Seaside at Anna Maria Island Inn

Save 100% on your flight

$2,029

per person

Apr 16 - Apr 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

An outdoor pool is featured at this hotel, along with free WiFi in public areas and a safe deposit box.

The Residences at Siesta Key Beach by Hyatt Vacation Club

South Village

Save 100% on your flight

$1,821

per person

Apr 20 - Apr 24

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 hotel. Relax with free beach cabanas, sun loungers, and beach umbrellas. Enjoy the gym and free perks like continental breakfast and valet parking.

Cedar Cove Resort and Cottages

$1,352

per person

Apr 9 - Apr 14

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.

Legacy Hotel at IMG Academy

$740

per person

Apr 9 - Apr 14

found 1 day ago

Roundtrip 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.

Top Osprey hotels deals

Casey Key Resorts - Mainland

1650 South Tamiami Trail Osprey FL

Free Cancellation

Reserve now, pay when you stay

$223 nightly

$252 total

Feb 15 - Feb 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.

Kompose Boutique Hotel

965 University Pkwy Sarasota FL

Free Cancellation

Reserve now, pay when you stay

$182 nightly

$205 total

Feb 16 - Feb 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.

Golden Host Resort - Sarasota

4675 N Tamiami Trl Sarasota FL

Free Cancellation

$110 nightly

$125 total

Feb 17 - Feb 18

Total with taxes and fees

This hotel features a restaurant, 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.

Pool

Parking included

Tropical Beach Resorts

6717 Sara Sea Circle Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$349 nightly

$395 total

Feb 18 - Feb 19

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.

Lido Beach Resort

700 Benjamin Franklin Dr Sarasota FL

Free Cancellation

Reserve now, pay when you stay

$589 nightly

$666 total

Feb 19 - Feb 20

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.

Spark by Hilton Sarasota Siesta Key Gateway

6600 S Tamiami Trl Sarasota FL

Free Cancellation

Reserve now, pay when you stay

$237 nightly

$268 total

Feb 15 - Feb 16

Total with taxes and fees

This hotel features an outdoor pool, a hot tub, and a restaurant. Business travelers can take advantage of the free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy free perks like continental breakfast and free self parking.

Don't see what you're looking for?

See all available properties in Osprey

View all properties

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

One of the best RV parks yet!! Great price, great location, fantastic wild life right outside your door!

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 top-notch restaurants.

Frequently asked questions

How much are vacation packages to Osprey?

Travelocity offers great package deals to Osprey, including hotels and flights, from an impressive $578. 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.