Kissimmee Vacation Packages 2026 from $333

Kissimmee flight + hotel vacation packages

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

Westgate River Ranch Resort & Rodeo

Save 100% on your flight

$333

per person

Oct 2 - Oct 4

found 1 day ago

Roundtrip flight included

San Juan (SJU) 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.

The Delaney Hotel

South Orange

Save 100% on your flight

$548

per person

Oct 30 - Nov 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a terrace, and a snack bar/deli are also offered.

Westgate Vacation Villas Resort

Save 100% on your flight

$333

per person

Oct 30 - Nov 3

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 a children's pool, and families will appreciate the onsite laundry facilities. Enjoy the 14 outdoor pools and get free self parking.

Florida Hotel & Conference Center in the Florida Mall

Save 100% on your flight

$689

per person

Nov 3 - Nov 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This traditional hotel includes 3 restaurants, an outdoor pool, and a gym. Bring the family and enjoy the free theme park shuttle and kid-friendly dining. Enjoy the hot tub and perks like free WiFi.

Virelli Apartments Upscale King Suite in the Heart of Orlando w Pool

Downtown Orlando

$1,899

per person

Nov 5 - Nov 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

An outdoor pool is available at this apartment. Take advantage of the free self parking.

Top Kissimmee hotels deals

Kompose Boutique Resort at Theme Parks

7491 W Irlo Bronson Memorial Hwy Kissimmee FL

Free Cancellation

Reserve now, pay when you stay

$75 nightly

$86 total

Aug 20 - Aug 21

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.

Vacation Village Orlando, Celebration

2975 Arabian Nights Blvd Kissimmee FL

Free Cancellation

Reserve now, pay when you stay

$95 nightly

$108 total

Sep 6 - Sep 7

Total with taxes and fees

7 outdoor pools, 7 hot tubs, and a gym are all featured at this smoke-free aparthotel. Bring the family and enjoy the children's pool, playground, and arcade/game room. WiFi in public areas is free.

Magic Moment Resort & Kids Club, Dazzler Select by Wyndham

5200 West Irlo Bronson Memorial Highway Kissimmee FL

Free Cancellation

Reserve now, pay when you stay

$56 nightly

$64 total

Aug 20 - Aug 21

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. Guests will appreciate freebies like continental breakfast and free self parking.

Margaritaville Resort Orlando with H2O Waterpark

8000 Fins Up Circle Kissimmee FL

Free Cancellation

Reserve now, pay when you stay

$187 nightly

$212 total

Aug 25 - Aug 26

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.

Palazzo Lakeside Hotel

4944 W. Irlo Bronson Memorial Highway Kissimmee FL

$58 nightly

$66 total

Aug 20 - Aug 21

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.

Holiday Inn Club Vacations at Orange Lake Resort by IHG

8505 W Irlo Bronson Memorial Hwy Kissimmee FL

Free Cancellation

Reserve now, pay when you stay

$144 nightly

$163 total

Aug 20 - Aug 21

Total with taxes and fees

This traditional resort features a golf course, free water park access, and 9 restaurants. 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 get free self parking.

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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.

Stay near popular Kissimmee attractions

A theme park entrance with a Ferris wheel and a roller coaster.

Old Town

8.6/10 (14,011 reviews)

Enjoy the excitement at Old Town and see why people love this theme park in Kissimmee. Check out the shops and top-notch restaurants in this family-friendly area.

See properties

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 $333. 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.