Deals on vacations and trips to Kissimmee, FL

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Kissimmee flight + hotel vacation packages

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flightPrice was $728, price is now $413 per person
per person
Feb 6 - Feb 12
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This smoke-free resort features a water park, a marina, and 3 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.
Westgate Palace a Two Bedroom Condo Resort

Westgate Palace a Two Bedroom Condo Resort

4 out of 5
Florida Center
Save 100% on your flightPrice was $884, price is now $525 per person
per person
Feb 17 - Feb 21
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
This resort features an outdoor pool, a gym, and a restaurant. Bring the family and enjoy the children's pool, playground, and kid-friendly dining. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi.
B Resort & Spa in the Disney Springs Resort Area

B Resort & Spa in the Disney Springs Resort Area

4 out of 5
Save 100% on your flightPrice was $899, price is now $575 per person
per person
Feb 6 - Feb 12
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This hotel features 4 outdoor tennis courts, an outdoor pool, and a restaurant. Families will appreciate the arcade/game room and onsite laundry facilities. Relax with a drink at the bar/lounge and enjoy perks like free WiFi.
Embassy Suites by Hilton Orlando Lake Buena Vista South

Embassy Suites by Hilton Orlando Lake Buena Vista South

3.5 out of 5
Save 100% on your flightPrice was $846, price is now $556 per person
per person
Feb 5 - Feb 12
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This smoke-free hotel includes 2 restaurants, an outdoor pool, and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Enjoy the spa tub and free full breakfast each morning.
CLC Regal Oaks Resort Vacation Townhomes

CLC Regal Oaks Resort Vacation Townhomes

4 out of 5
Save 100% on your flightPrice was $804, price is now $544 per person
per person
Feb 6 - Feb 12
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This Art Deco condo resort features free water park access, 2 outdoor pools, and a restaurant. Traveling on business? Take advantage of the 2 conference rooms, as well as the business center and free WiFi in public areas. Make the most of the gym and outdoor tennis court, and relax with drinks at one of the 2 bars/lounges.

Top Kissimmee hotels deals

Mystic Dunes Resort & Golf Club by Diamond Resorts

Mystic Dunes Resort & Golf Club by Diamond Resorts

3.5 out of 5
7600 Mystic Dunes Lane, Kissimmee, FL
Free Cancellation
Reserve now, pay when you stay
The price is $79 per night
A golf course, 4 outdoor pools, and 2 outdoor tennis courts are all featured at this smoke-free hotel. 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.
Wyndham Orlando Resort & Conference Center, Celebration Area

Wyndham Orlando Resort & Conference Center, Celebration Area

3.5 out of 5
3011 Maingate Ln, Kissimmee, FL
Free Cancellation
Reserve now, pay when you stay
The price is $81 per night
This smoke-free hotel features 2 outdoor pools, a bar/lounge, and a poolside bar. There's fun for all ages with a children's pool and a playground, and families will appreciate the onsite laundry facilities. Enjoy the 24-hour gym and perks like free self parking and free WiFi.
Magic Moment Resort and Kids Club

Magic Moment Resort and Kids Club

3 out of 5
5200 West Irlo Bronson Memorial Highway, Kissimmee, FL
Free Cancellation
Reserve now, pay when you stay
The price is $42 per night
This hotel features an outdoor pool and a 24-hour gym. There's fun for all ages with a free kid's club 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.
Margaritaville Resort Orlando

Margaritaville Resort Orlando

4 out of 5
8000 Fins Up Circle, Kissimmee, FL
Free Cancellation
Reserve now, pay when you stay
The price is $161 per night
A full-service spa, 3 restaurants, and 2 outdoor pools are all featured at this smoke-free resort. There's fun for all ages with a children's club and a playground, and supervised childcare is an added bonus. Relax with a drink at one of the 3 bars/lounges and get perks like free WiFi.
Red Lion Hotel Orlando Lake Buena Vista South

Red Lion Hotel Orlando Lake Buena Vista South

3.5 out of 5
5150 West Irlo Bronson Memorial Highway, Kissimmee, FL
Free Cancellation
Reserve now, pay when you stay
The price is $88 per night
This smoke-free hotel includes 2 restaurants, an outdoor pool, and a lazy river. There's fun for all ages with a waterslide and a playground, and families will appreciate the onsite laundry facilities. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like parking and WiFi in public areas.
The Grand Orlando Resort at Celebration

The Grand Orlando Resort at Celebration

3.5 out of 5
2900 Parkway Blvd, Kissimmee, FL
Free Cancellation
Reserve now, pay when you stay
The price is $65 per night
2 restaurants, 2 outdoor pools, and 2 outdoor tennis courts are among this hotel's featured amenities. There's fun for all ages with a children's pool and a waterslide, and families will appreciate the onsite laundry facilities. Enjoy the 2 spa tubs and perks like free WiFi.
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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 in Kissimmee

Image for Old Town

Old Town

4.5/5(2,047 reviews)

You can enjoy some retail therapy when you visit Old Town, a favorite shopping spot in Kissimmee. Discover the acclaimed theater scene and amusement park in this family-friendly area.

Old Town
Image for Mystic Dunes Golf Club

Mystic Dunes Golf Club

4/5(17 reviews)

Tee off at one of Orlando’s premier golf clubs and enjoy the championship course, the excellent facilities and the laid-back Florida vibe.

Mystic Dunes Golf Club
Image for Osceola Heritage Park

Osceola Heritage Park

4.5/5(6 reviews)

Explore the great outdoors with a trip to Osceola Heritage Park, a popular green space in Kissimmee. Attend a sporting event or visit the amusement park in this family-friendly area.

Osceola Heritage Park

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