Osceola County Vacation Packages 2025/2026 from $334

Osceola County flight + hotel vacation packages

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

Westgate Palace Hotel / Universal / I-Drive

International Drive District

Save 100% on your flight

$334

per person

Dec 11 - Dec 14

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Orlando (MCO)

This resort features an outdoor pool, a gym, and a restaurant. Bring the family and enjoy the children's pool, free theme park shuttle, and kid-friendly dining. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi.

Westgate Lakes Resort & Spa Universal Studios Area

Save 100% on your flight

$485

per person

Nov 17 - Nov 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This smoke-free hotel features a full-service spa, a water park, and a marina. There's fun for all ages with a lazy river and a children's club, and barbecue grills are available on site. Enjoy the 7 outdoor pools and perks like free valet parking and a free theme park shuttle.

Hilton Daytona Beach Oceanfront Resort

Brush - Stewarts

Save 100% on your flight

$518

per person

Dec 8 - Dec 15

found 10 hours ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

4 restaurants, 2 outdoor pools, and 2 hot tubs are among this hotel's featured amenities. Traveling on business? Take advantage of the 24-hour business center, express check-in, and valet parking. Enjoy the 24-hour gym and visit the 2 beach bars and poolside bar for drinks.

Westgate River Ranch Resort & Rodeo

Save 100% on your flight

$487

per person

Dec 11 - Dec 14

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Orlando (MCO)

This smoke-free resort features free water park access, a marina, and 2 restaurants. There's fun for all ages with mini golf and a playground, and barbecue grills are available on site. Relax with a drink at one of the 3 bars/lounges and enjoy perks like free self parking.

Westgate Cocoa Beach Resort

Save 100% on your flight

$1,072

per person

Nov 25 - Nov 29

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

Free water park access and an outdoor pool are featured at this smoke-free condo resort. Spend a day at the beach surfing, or relax with sun loungers and beach umbrellas. There's fun for all ages with a lazy river and a children's pool, and barbecue grills are available on site.

Top Osceola County hotels deals

Palazzo Lakeside Hotel

4944 W. Irlo Bronson Memorial Highway, Kissimmee, FL

$74 nightly

$84 total

Oct 5 - Oct 6

Total with taxes and fees

This hotel features an outdoor pool, a gym, and a restaurant. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a picnic area are also on offer.

Pool

Breakfast included

Holiday Inn Resort Kissimmee by the Parks by IHG

3011 Maingate Ln, Kissimmee, FL

Free Cancellation

Reserve now, pay when you stay

$73 nightly

$83 total

Oct 12 - Oct 13

Total with taxes and fees

2 outdoor pools, a 24-hour gym, and a hot tub are all featured at this smoke-free hotel. Bring the family and enjoy the children's pool, playground, and kid-friendly dining. Enjoy a meal from the a restaurant and perks like free self parking.

Pool

Hot Tub

Margaritaville Resort Orlando with H2O Waterpark

8000 Fins Up Circle, Kissimmee, FL

Free Cancellation

Reserve now, pay when you stay

$169 nightly

$192 total

Oct 29 - Oct 30

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

Kompose Boutique Resort at Theme Parks

7491 W Irlo Bronson Memorial Hwy, Kissimmee, FL

Free Cancellation

Reserve now, pay when you stay

$68 nightly

$78 total

Oct 6 - Oct 7

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 perks like free WiFi. A bar/lounge, a 24-hour front desk, and a poolside bar are also provided.

Pool

Hot Tub

Hilton Vacation Club Mystic Dunes Orlando

7600 Mystic Dunes Lane, Kissimmee, FL

Free Cancellation

Reserve now, pay when you stay

$136 nightly

$155 total

Oct 12 - Oct 13

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

Magic Moment Resort and Kids Club

5200 West Irlo Bronson Memorial Highway, Kissimmee, FL

Free Cancellation

Reserve now, pay when you stay

$67 nightly

$76 total

Oct 5 - Oct 6

Total with taxes and fees

This hotel features an outdoor pool, a 24-hour gym, and a restaurant. There's fun for all ages with a theme park shuttle and a playground, and families will appreciate the onsite laundry facilities. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking.

Pool

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 $334. 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.