Osceola County Vacation Packages 2026 from $304

Search vacation packages deals in Osceola County's top destinations

Located south of Kissimmee FL, the area is being brought back to its natural state, there is a couple of walking trails and scientific studies are also done here.

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Vacations

Osceola County flight + hotel vacation packages

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

Westgate Vacation Villas Resort

Save 100% on your flight

$304

per person

Mar 26 - Mar 30

found 16 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

This smoke-free resort features a water park, a marina, and 2 restaurants. There's fun for all ages with a children's club and a children's pool, and families will appreciate the onsite laundry facilities. Enjoy the 14 outdoor pools and get free self parking.

Westgate Town Center Resort

Save 100% on your flight

$352

per person

Mar 26 - Mar 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This smoke-free resort features a water park, a marina, and 2 restaurants. There's fun for all ages with a children's club and mini golf, and families will appreciate the onsite laundry facilities. Enjoy the 14 outdoor pools and perks like free self parking and free WiFi.

Summerville Vacation Homes by Columbia Management

$623

per person

Feb 26 - Mar 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This vacation home features an outdoor pool and a gym. Bring the family and enjoy the free kid's club, playground, and arcade/game room. Enjoy the hot tub and perks like free self parking and free WiFi.

Westgate Leisure Resort

International Drive District

Save 100% on your flight

$373

per person

Feb 25 - Mar 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

2 outdoor pools, a hot tub, and a gym are all featured at this smoke-free hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A business center, a garden, and a grocery/convenience store are also on offer.

The Shores Resort & Spa

Save 100% on your flight

$471

per person

Mar 25 - Mar 29

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Orlando (MCO)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. There's fun for all ages with a children's pool and an arcade/game room, and complimentary bicycles are available on site. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.

Top Osceola County hotels deals

Kompose Boutique Resort at Theme Parks

7491 W Irlo Bronson Memorial Hwy Kissimmee FL

Free Cancellation

Reserve now, pay when you stay

$68 nightly

$77 total

Jan 9 - Jan 10

Total with taxes and fees

2 hot tubs, an outdoor pool, and a 24-hour gym are all featured at this smoke-free resort. Enjoy the sauna and free perks like buffet breakfast and WiFi in public areas. A bar/lounge, a 24-hour front desk, and a poolside bar are also provided.

Pool

Hot Tub

Margaritaville Resort Orlando

8000 Fins Up Circle Kissimmee FL

Free Cancellation

Reserve now, pay when you stay

$188 nightly

$213 total

Jan 12 - Jan 13

Total with taxes and fees

This smoke-free resort features free water park access, a full-service spa, and 3 restaurants. Bring the family and enjoy the lazy river, waterslide, and arcade/game room. Enjoy the 3 outdoor pools and perks like free WiFi.

Pool

Hot Tub

Hilton Vacation Club Mystic Dunes Orlando

7600 Mystic Dunes Lane Kissimmee FL

Free Cancellation

Reserve now, pay when you stay

$130 nightly

$148 total

Jan 15 - Jan 16

Total with taxes and fees

A golf course, 4 outdoor pools, and 2 outdoor tennis courts are all featured at this smoke-free property. There's fun for all ages with mini golf and a children's pool, and barbecue grills are available on site. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas.

Pool

Parking included

Gaylord Palms Resort & Convention Center

6000 West Osceola Parkway Kissimmee FL

Free Cancellation

Reserve now, pay when you stay

$347 nightly

$394 total

Jan 11 - Jan 12

Total with taxes and fees

This smoke-free hotel features a full-service spa, a water park, and 6 restaurants. There's fun for all ages with a children's pool and a waterslide, and families will appreciate the onsite laundry facilities. Traveling on business? Take advantage of the business center, express check-in, and airport shuttle.

Pool

Hot Tub

Comfort Inn & Suites Kissimmee by the Parks

7675 W Irlo Bronson Hwy Kissimmee FL

Get rates

This hotel features an outdoor pool, a hot tub, and a restaurant. Enjoy the gym and free perks like buffet breakfast and free self parking. A 24-hour business center, free WiFi in public areas, and a terrace are also on offer.

Pool

Hot Tub

Ramada by Wyndham Hotel & Water Park

Kissimmee FL

Free Cancellation

Reserve now, pay when you stay

$69 nightly

$78 total

Jan 19 - Jan 20

Total with taxes and fees

Free water park access and a restaurant are featured at this smoke-free hotel. Bring the family and enjoy the lazy river, children's pool, and kid-friendly dining. Enjoy the gym and free perks like continental breakfast and a theme park shuttle.

Hot Tub

Breakfast 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.

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Frequently asked questions

How much are vacation packages to Osceola County?

Travelocity offers package deals to Osceola County, including flights and hotels, starting from an impressive $304. With the money you save, you could include some awesome tours or maybe even add on a few extra nights to your vacation.

Where can I get the best vacation package deals for Osceola County?

You'll find a fantastic range of Osceola County package deals on Travelocity. With 400 airlines and 1,000,000 properties around the globe, arranging a dream getaway will be simple.

Why should I book my Osceola County vacation package via Travelocity?

We offer 24/7 support, top-notch service and a Price Match Guarantee. Travel is all about the journey — and we have amazing destinations for you to journey to in every nook and cranny of the globe. Explore with us and make your hip pocket happy.

Can I save on my Osceola County car rental if I bundle it with a hotel or flight?

Combining your bookings into an Osceola County vacation package will certainly save you money. Book a flight and car; a hotel, car and flight; or a car and hotel. You won't find a better way to discover the greater Osceola County area than from the comfort of your own rental car. You can also add experiences and activities to your Travelocity package.

Which airport is best for Osceola County?

Orlando Intl. Airport (MCO) and Orlando Sanford Intl. Airport (SFB) are the top options for touching down in Osceola County.

What is there to do in Osceola County?

A diverse and inspiring destination, Osceola County is home to some fantastic sights and attractions. Lake Tohopekaliga and Disney Wilderness Preserve are just two of the top picks.