Osprey Vacation Packages 2026 from $649

Osprey flight + hotel vacation packages

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

Family Home Tampa

Forest Hills

Save 100% on your flight

$649

per person

Mar 16 - Mar 21

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Sarasota (SRQ)

This guesthouse includes a garden and a virtual front desk. Take advantage of the free self parking.

Sleeps 6 Hot Tub Fenced Yard Cozy Chic

Town 'n' Country

$709

per person

Mar 4 - Mar 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

A full-service spa, free self parking, and laundry facilities are featured at this villa. Barbecue grills and a virtual front desk are also provided.

The Residences at Siesta Key Beach by Hyatt Vacation Club

South Village

Save 100% on your flight

$1,964

per person

Feb 1 - Feb 8

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Sarasota (SRQ)

A private beach and an outdoor pool are featured at this smoke-free aparthotel. Relax with free beach cabanas, sun loungers, and beach umbrellas. Enjoy the gym and free perks like continental breakfast and valet parking.

Hotel Tampa Riverwalk

Downtown Tampa

Save 100% on your flight

$887

per person

Mar 4 - Mar 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

This hotel features 2 bars/lounges, a poolside bar, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Enjoy the outdoor pool and conveniences like a 24-hour front desk and wedding services.

The Barrymore Hotel Tampa Riverwalk

Downtown Tampa

Save 100% on your flight

$852

per person

Mar 4 - Mar 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like a free area shuttle.

Top Osprey hotels deals

Casey Key Resorts - Mainland

1650 South Tamiami Trail Osprey FL

Free Cancellation

Reserve now, pay when you stay

$140 nightly

$159 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Relax with a drink at the poolside bar and enjoy perks like free self parking and free WiFi. A business center, a terrace, and a snack bar/deli are also on offer.

Pool

Pet friendly

Kompose Boutique Hotel

965 University Pkwy Sarasota FL

Free Cancellation

Reserve now, pay when you stay

$138 nightly

$156 total

Jan 5 - Jan 6, 2026

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

6717 Sara Sea Circle Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$164 nightly

$185 total

Jan 4 - Jan 5, 2026

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.

Pool

Kitchen

Carlisle Inn

3727 Bahia Vista Sarasota FL

Free Cancellation

Reserve now, pay when you stay

$197 nightly

$223 total

Jan 5 - Jan 6, 2026

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

Golden Host Resort - Sarasota

4675 N Tamiami Trl Sarasota FL

Free Cancellation

$80 nightly

$91 total

Jan 4 - Jan 5, 2026

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

Hibiscus Suites - Gateway to Siesta Key

1735 Stickney Point Rd Sarasota FL

Free Cancellation

Reserve now, pay when you stay

$145 nightly

$163 total

Jan 4 - Jan 5, 2026

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 terrace, a garden, and a picnic area are also on offer.

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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

Great national park to take your RV and lots of hiking and biking trails.

Oscar Scherer State Park

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 $649. 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.