Historic Downtown Kissimmee Vacation Packages 2025/2026 from $255

Historic Downtown Kissimmee flight + hotel vacation packages

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

Westgate Town Center Resort

Save 100% on your flight

$255

per person

Dec 4 - Dec 7

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.

Westgate Towers Resort

Save 100% on your flight

$363

per person

Nov 16 - Nov 22

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Westgate Vacation Villas Resort

Save 100% on your flight

$359

per person

Dec 7 - Dec 13

found 4 hours 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.

Westgate Lakes Resort & Spa Universal Studios Area

Save 100% on your flight

$428

per person

Oct 19 - Oct 25

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.

Westgate Cocoa Beach Resort

Save 100% on your flight

$1,099

per person

Nov 25 - Nov 29

found 1 day ago

Roundtrip non-stop 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 Historic Downtown Kissimmee hotels deals

Marriott's Grande Vista

5925 Avenida Vista, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$104 total

Sep 23 - Sep 24

Total with taxes and fees

This eco-certified hotel features a golf course, a full-service spa, and 3 restaurants. There's fun for all ages with mini golf and a children's pool, and barbecue grills are available on site. Enjoy a meal in one of the 2 coffee shops/cafes and perks like free WiFi.

Pool

Hot Tub

Universal's Cabana Bay Beach Resort

6550 Adventure Way, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$136 nightly

$153 total

Sep 29 - Sep 30

Total with taxes and fees

This smoke-free hotel features 2 restaurants, 2 outdoor pools, and 2 hot tubs. There's fun for all ages with a lazy river and a bowling alley, and families will appreciate the onsite laundry facilities. Unwind with a drink at one of the 2 poolside bars and enjoy freebies like WiFi in public areas and a theme park shuttle.

DoubleTree by Hilton Hotel Orlando at SeaWorld

10100 International Drive, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$99 nightly

$112 total

Sep 21 - Sep 22

Total with taxes and fees

This smoke-free resort features 2 restaurants, 2 outdoor pools, and a 24-hour gym. There's fun for all ages with mini golf and a children's pool, and families will appreciate the onsite laundry facilities. Relax with a drink at one of the 3 bars/lounges and get perks like free WiFi.

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

12401 International Dr, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$100 total

Oct 1 - Oct 2

Total with taxes and fees

This smoke-free hotel features 2 restaurants, 5 outdoor pools, and 2 outdoor tennis courts. Bring the family and enjoy the children's club, children's pool, and waterslide. Enjoy the 4 hot tubs and perks like free WiFi.

Rosen Inn at Pointe Orlando

9000 International Drive, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$65 nightly

$74 total

Oct 13 - Oct 14

Total with taxes and fees

This hotel features 3 outdoor pools, a gym, and a restaurant. Bring the family and enjoy the free theme park shuttle, playground, and kid-friendly dining. Enjoy a meal in one of the 2 coffee shops/cafes and perks like free WiFi.

DoubleTree by Hilton Orlando Airport

5555 Hazeltine National Drive, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$100 nightly

$113 total

Oct 4 - Oct 5

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free WiFi and a free airport shuttle. You'll appreciate the free area shuttle, valet parking, and 24-hour business center.

Pool

Free airport shuttle

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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

Kissimmee Lakefront Park

Kissimmee Lakefront Park is just one of the places to see in Kissimmee, so why not enjoy the other things to explore during your travels? Stroll along the lakeside or experience the entertainment choices in this family-friendly area.

Osceola County Clerk of the Court

After visiting Osceola County Clerk of the Court, make a plan to see the other sights and activities in Kissimmee. Discover the top-notch restaurants and entertainment choices in this family-friendly area.

Kissimmee Civic Center

Kissimmee Civic Center is just one of the places to see in Kissimmee, so why not enjoy the other things to explore during your travels? Discover the entertainment choices and shops in this family-friendly area.

Frequently asked questions

How much are vacation packages to Historic Downtown Kissimmee?

Starting from as low as $255, hotel and flight packages are an ideal way to make your vacation budget stretch further. Historic Downtown Kissimmee, here you come!

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

Travelocity can help you find an awesome Historic Downtown Kissimmee package deal. With more than 400 airlines and 1,000,000 properties across the world, you're sure to be able to put together the perfect itinerary.

Why should I purchase my Historic Downtown Kissimmee vacation package via Travelocity?

From our 24/7 customer support to our range of fantastic destinations, we're dedicated to giving you the most unforgettable escape. All you'll have to do is to click and book — our Price Match Guarantee will ensure you score the cheapest price.

Can I save money on my Historic Downtown Kissimmee car rental if I bundle it with a hotel or flight?

Booking a Historic Downtown Kissimmee vacation package with Travelocity is one of the simplest ways to save your hard-earned money. You can combine a hotel, car and flight, or any combination of them, and score great discounts. You might also want to throw in experiences. After you've collected the keys to your rental car, venture out of the neighborhood and uncover what this place has to offer. Around 65 mi from Historic Downtown Kissimmee, Daytona International Speedway justifies a road trip.

What is there to do in Historic Downtown Kissimmee?

Kissimmee Lakefront Park and Kissimmee Civic Center are much loved by many visitors. Cross these popular sights off your must-see list and see what the hype is about.