Osprey Vacation Packages 2025 from $568

Osprey flight + hotel vacation packages

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

Captiva Beach Resort

Save 100% on your flight

per person

Aug 16 - Aug 21

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.

Cedar Cove Resort and Cottages

Save 100% on your flight

per person

Aug 16 - Aug 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

Free WiFi in public areas, a terrace, and a garden are available at this resort. A snack bar/deli, a picnic area, and luggage storage are also on offer.

Twin Palms at Siesta

Save 100% on your flight

per person

Aug 16 - Aug 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

An outdoor pool, free self parking, and barbecue grills are featured at this hotel. Guests will appreciate perks like free WiFi and a free beach shuttle. A terrace, a garden, and a picnic area are also on offer.

Resort Sixty-Six

Save 100% on your flight

per person

Sep 13 - Sep 20

found 8 hours ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

A restaurant and an outdoor pool are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a garden, and a picnic area are also on offer.

Palmetto Marriott Resort & Spa

Save 100% on your flight

per person

Aug 16 - Aug 21

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.

Top Osprey hotels deals

Casey Key Resorts - Mainland

1650 South Tamiami Trail, Osprey, FL

Free Cancellation

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This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with a drink at the poolside bar and enjoy perks like free self parking.

Pool

Pet friendly

Kompose Boutique Hotel

965 University Pkwy, Sarasota, FL

Free Cancellation

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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. Enjoy the hot tub and perks like free self parking.

Spark by Hilton Sarasota Siesta Key Gateway

6600 S Tamiami Trl, Sarasota, FL

Free Cancellation

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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.

Pool

Hot Tub

Tropical Beach Resorts

6717 Sara Sea Circle, Siesta Key, FL

Free Cancellation

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This aparthotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Spend a day at the beach surfing, or relax with sun loungers and beach umbrellas. There's an outdoor pool on site, and laundry facilities and concierge services are also offered.

Pool

Kitchen

Embassy Suites by Hilton Sarasota, FL

202 North Tamiami Trail, Sarasota, FL

Free Cancellation

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

Pool

Breakfast included

Golden Host Resort - Sarasota

4675 N Tamiami Trl, Sarasota, FL

Free Cancellation

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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

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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

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 $568. 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.