Osprey Vacation Packages 2025/2026 from $758

Osprey flight + hotel vacation packages

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

The Barrymore Hotel Tampa Riverwalk

Downtown Tampa

Save 100% on your flight

$758

per person

Feb 2 - Feb 9

found 1 day ago

Roundtrip flight included

Cincinnati (CVG) 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.

The Residences at Siesta Key Beach by Hyatt Vacation Club

South Village

$1,533

per person

Feb 7 - Feb 12

found 14 hours ago

Roundtrip non-stop flight included

Pittsburgh (PIT) 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

$857

per person

Feb 2 - Feb 9

found 1 day ago

Roundtrip flight included

Cincinnati (CVG) 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.

Sailport Waterfront Suites

Rocky Point

Save 100% on your flight

$834

per person

Feb 2 - Feb 9

found 1 day ago

Roundtrip flight included

Cincinnati (CVG) to Sarasota (SRQ)

This aparthotel features a restaurant, an outdoor pool, and a bar/lounge. You'll appreciate the gym, poolside bar, and snack bar/deli.

DoubleTree by Hilton Tampa Rocky Point Waterfront

Rocky Point

Save 100% on your flight

$1,154

per person

Feb 2 - Feb 9

found 1 day ago

Roundtrip flight included

Cincinnati (CVG) to Sarasota (SRQ)

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. There's a 24-hour gym on site, and a 24-hour front desk and a terrace are also provided.

Top Osprey hotels deals

Casey Key Resorts - Mainland

1650 South Tamiami Trail, Osprey, FL

Free Cancellation

Reserve now, pay when you stay

$128 nightly

$145 total

Nov 30 - Dec 1

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

$79 nightly

$89 total

Nov 16 - Nov 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.

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

Nov 16 - Nov 17

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

Tropical Breeze Resort

140 Columbus Blvd. Siesta Key FL

Free Cancellation

Reserve now, pay when you stay

$237 nightly

$267 total

Nov 18 - Nov 19

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.

Pool

Hot Tub

Spark by Hilton Sarasota Siesta Key Gateway

6600 S Tamiami Trl, Sarasota, FL

Free Cancellation

Reserve now, pay when you stay

$103 nightly

$117 total

Nov 23 - Nov 24

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.

Pool

Hot Tub

The Westin Sarasota

100 Marina View Drive Sarasota FL

Free Cancellation

Reserve now, pay when you stay

$281 nightly

$318 total

Nov 30 - Dec 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

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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 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 $758. 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.