Kissimmee Vacation Packages 2025/2026 from $238

Kissimmee flight + hotel vacation packages

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

Westgate Towers Resort

$238

per person

Dec 5 - Dec 10

found 1 day ago

Roundtrip flight included

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

2 outdoor pools, 2 hot tubs, and a gym are all featured at this smoke-free hotel. There's fun for all ages with a children's pool and a playground, and barbecue grills are available on site. Relax with a drink at the bar/lounge and enjoy perks like free self parking.

Summerville Vacation Homes by Columbia Management

$1,194

per person

Dec 29 - Jan 5

found 1 day ago

Roundtrip non-stop 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.

Seasons Florida Resort

Save 100% on your flight

$268

per person

Dec 4 - Dec 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool and laundry facilities are also provided.

Westgate Blue Tree Resort in Lake Buena Vista

$594

per person

Jan 14 - Jan 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This hotel features an outdoor pool and a gym. There's fun for all ages with mini golf and a children's pool, and barbecue grills are available on site. Enjoy the hot tub and perks like free self parking.

Alhambra Villas

Solivita

Save 100% on your flight

$258

per person

Dec 4 - Dec 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This hotel features an outdoor pool and an outdoor tennis court. There's fun for all ages with a children's pool and a playground, and families will appreciate the onsite laundry facilities. WiFi in public areas is free.

Top Kissimmee hotels deals

Holiday Inn & Suites Orlando SW - Celebration Area by IHG

5711 W Irlo Bronson Memorial Hwy, Kissimmee, FL

Free Cancellation

$71 nightly

$81 total

Nov 2 - Nov 3

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Bring the family and enjoy the children's pool, free theme park shuttle, and playground. Enjoy the gym and perks like free self parking and 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

$128 nightly

$145 total

Nov 3 - Nov 4

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

Kompose Boutique Resort at Theme Parks

7491 W Irlo Bronson Memorial Hwy, Kissimmee, FL

Free Cancellation

Reserve now, pay when you stay

$61 nightly

$69 total

Oct 29 - Oct 30

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

Margaritaville Resort Orlando with H2O Waterpark

8000 Fins Up Circle, Kissimmee, FL

Free Cancellation

Reserve now, pay when you stay

$171 nightly

$194 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

Holiday Inn Resort Kissimmee by the Parks by IHG

3011 Maingate Ln, Kissimmee, FL

Free Cancellation

$76 nightly

$86 total

Nov 10 - Nov 11

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

Palazzo Lakeside Hotel

4944 W. Irlo Bronson Memorial Highway, Kissimmee, FL

$73 nightly

$82 total

Oct 29 - Oct 30

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

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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

Walt Disney World® Resort

Have a fun-filled day at Walt Disney World® Resort and find out why this is a popular theme park in Lake Buena Vista. Discover the top-notch restaurants and acclaimed theater scene in this walkable area.

Universal Studios Florida

Movie sets and thrill rides combine to create this internationally acclaimed theme park.

Universal Studios Orlando showing street scenes, a city and rides

Universal Orlando Resort

Have a fun-filled day at Universal Orlando Resort and see why people love this theme park in Orlando. Check out the shops and top-notch restaurants in this family-friendly area.

Frequently asked questions

How much are vacation packages to Kissimmee?

With a Travelocity vacation package, you could be living it up in Kissimmee for as little as $238. Hotels, flights and adventures — we've got you. You're bound to save loads just for bundling your bookings. And with all of that taken care of before you go, you won't have to worry about a thing.

How long should my Kissimmee vacation be?

Many travelers pack their suitcase and kick back in Kissimmee for about 4 nights. That's a good starting point, but don't be limited by it. Whether you only stay for a day or two to see the big attractions or settle in to discover the lesser-known sights, an unforgettable journey awaits.

Where can I get the best vacation package deals for Kissimmee?

No matter how you like to travel, Travelocity can help you snap up an unbeatable Kissimmee package deal. The only thing you need to do is pick and choose between our 400 partner airlines and 1,000,000 properties around the world.

Why should I book my Kissimmee vacation package via Travelocity?

With exceptional service, 24/7 customer support and some of the most incredible getaways imaginable, you'll never roam alone. And if you happen to find a better price, we'll match it. That's our Price Match Guarantee.

Can I save on my Kissimmee car rental if I bundle it with hotels and flights?

You certainly can — combine your flight, hotel and car into a Kissimmee vacation package and you can save a ton. With so many places to explore in Kissimmee, having your own ride will make exploring a joy. Once you're behind the wheel, get out on the wide open road and head to Daytona International Speedway, a must-see attraction about 65 mi from Kissimmee.

Which airport is best for Kissimmee?

Many travelers arrive at Orlando Intl. Airport (MCO). After you've landed and found your luggage, make your way 11 mi southwest to reach central Kissimmee. Orlando Sanford Intl. Airport (SFB) is your other option, 35 mi from the city center.

What is there to do in Kissimmee?

Kissimmee is overflowing with places to explore, including Old Town and Reunion Resort Golf Course. These two impressive attractions are at the top of most tourists' travel schedules.

Where should I stay when visiting Kissimmee?

If you're after someplace comfortable to base yourself, have a look at the Red Lion Hotel Orlando Lake Buena Vista South. It's the top pick for many travelers.