Historic Downtown Kissimmee Vacation Packages 2025 from $336

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

per person

Aug 27 - Sep 1

found 1 day ago

Roundtrip non-stop 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 Palace Hotel / Universal / I-Drive

Florida Center

per person

Aug 27 - Sep 1

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 River Ranch Resort & Rodeo

per person

Aug 14 - Aug 20

found 1 day ago

Roundtrip flight included

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

A marina, 2 restaurants, and an outdoor tennis court are all featured at this smoke-free resort. 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 Blue Tree Resort in Lake Buena Vista

Save 100% on your flight

per person

Aug 27 - Sep 1

found 1 day ago

Roundtrip non-stop 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.

Westgate Vacation Villas Resort

Save 100% on your flight

per person

Jul 19 - Jul 26

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.

Top Historic Downtown Kissimmee hotels deals

DoubleTree by Hilton at the Entrance to Universal Orlando

5780 Major Blvd, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

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This smoke-free hotel includes 2 restaurants, an outdoor pool, and a 24-hour gym. There's fun for all ages with a children's pool and an arcade/game room, and families will appreciate the onsite laundry facilities. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.

Pool

Hot Tub

Marriott's Grande Vista

5925 Avenida Vista, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

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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

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

8800 Vistana Centre Dr, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

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This smoke-free hotel features 3 restaurants, 6 outdoor pools, and 10 outdoor tennis courts. There's fun for all ages with a free kid's club and mini golf, and barbecue grills are available on site. Enjoy the 8 hot tubs and perks like free WiFi.

Pool

Hot Tub

Kompose Boutique Resort at Theme Parks

7491 W Irlo Bronson Memorial Hwy, Kissimmee, FL

Free Cancellation

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2 hot tubs, an outdoor pool, and a 24-hour gym are all featured at this smoke-free resort. Business travelers can take advantage of the free WiFi in public areas. Enjoy the sauna and free perks like buffet breakfast and free self parking.

Pool

Hot Tub

The Grove Resort & Water Park Orlando

14501 Grove Resort Avenue, Winter Garden, FL

Free Cancellation

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Free water park access, 3 restaurants, and 6 outdoor pools are all featured at this resort. Bring the family and enjoy the lazy river, children's club, and mini golf. Relax with a drink at one of the 3 poolside bars and enjoy the 2 hot tubs and 24-hour gym.

Pool

Hot Tub

Rosen Inn at Pointe Orlando

9000 International Drive, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

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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 free perks like free self parking and WiFi in public areas.

Pool

Pet friendly

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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

4/5(12 reviews)

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

5/5(1 review)

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 lively festivals and shops in this family-friendly area.

Frequently asked questions

How much are vacation packages to Historic Downtown Kissimmee?

Starting from as low as $336, 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.