Historic Downtown Kissimmee Vacation Packages from $276

Historic Downtown Kissimmee flight + hotel vacation packages

Prices and availability subject to change. Additional terms may apply.

Palazzo Lakeside Hotel

per person

May 25 - May 31

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

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.

Westgate Palace Hotel / Universal / I-Drive

Florida Center

per person

Jun 2 - Jun 8

Roundtrip 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 Lakes Resort & Spa Universal Studios Area

per person

May 25 - May 31

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 get free valet parking.

Alhambra Villas

Solivita

Save 100% on your flight

per person

May 29 - Jun 3

Roundtrip flight included

Philadelphia (PHL) 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.

Seasons Florida Resort

Save 100% on your flight

per person

May 25 - May 31

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.

Top Historic Downtown Kissimmee hotel deals

DoubleTree by Hilton at the Entrance to Universal Orlando

5780 Major Blvd, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$93

per night

May 13 - May 14

This hotel features 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.

Hot Tub

Breakfast available

The Grove Resort & Water Park Orlando

14501 Grove Resort Avenue, Winter Garden, FL

Free Cancellation

Reserve now, pay when you stay

$202

per night

May 12 - May 13

Free water park access, 3 restaurants, and 3 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 2 poolside bars and get perks like free WiFi.

Hyatt Regency Orlando International Airport

9300 Jeff Fuqua Boulevard, Orlando, FL

Free Cancellation

$199

per night

Apr 29 - Apr 30

This smoke-free aparthotel 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. There's a bar/lounge on site, and laundry facilities and concierge services are also provided.

Holiday Inn Resort Orlando Suites - Waterpark, an IHG Hotel

14500 Continental Gateway, Orlando, FL

Free Cancellation

$84

per night

Apr 28 - Apr 29

A water park, 2 outdoor pools, and 2 spa tubs are all featured at this smoke-free hotel. There's fun for all ages with mini golf and a waterslide, and families will appreciate the onsite laundry facilities. Enjoy the gym and perks like free WiFi.

Hot Tub

Pet friendly

Universal's Endless Summer Resort - Dockside Inn and Suites

7125 Universal Boulevard, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$144

per night

Apr 28 - Apr 29

This smoke-free hotel features 2 outdoor pools, a gym, and a restaurant. 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 3 bars/lounges and get perks like free WiFi.

Breakfast available

Pool

Universal's Cabana Bay Beach Resort

6550 Adventure Way, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$201

per night

Apr 28 - Apr 29

This smoke-free hotel features 2 restaurants, 2 outdoor pools, and 2 spa 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.

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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)

Explore the great outdoors at Kissimmee Lakefront Park, a lovely green space in Kissimmee. Amble around this family-friendly area's lakeside or experience its entertainment choices.

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.

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 lively festivals in this family-friendly area.

Frequently asked questions

How much are vacation packages to Historic Downtown Kissimmee?

Travelocity offers hotel and flight vacation packages starting from just $276. With these kinds of bargains, you’ll be exploring all of Historic Downtown Kissimmee in no time.

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

Travelocity is the place to go to score a terrific Historic Downtown Kissimmee package deal. Choose from as many as 400 air carriers and 1,000,000 properties around the world and create a travel itinerary that fits your style. With this amount of choice at your fingertips, it’s time to start booking your next great adventure.

Why should I book my Historic Downtown Kissimmee vacation bundle with Travelocity?

You’ll not only save loads, but you’ll also have access to our 24/7 support, top-notch service and a Price Match Guarantee. Explore every nook-and-cranny across the world, discover hidden gems and create lifelong memories — we’ll take care of the little details.

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

Booking a Historic Downtown Kissimmee vacation package with Travelocity is one of the simplest ways to save you money and time. Bundle a hotel, car and flight, or any combination of them, and score great discounts. You could also add in some activities and experiences. Once you’ve picked up the keys to the rental car, venture out of the neighborhood and find out what this place has to offer. Approximately 65 mi from Historic Downtown Kissimmee, Daytona International Speedway is worth a road trip.

What is the best time of year to go to Historic Downtown Kissimmee?

If a limited budget is what’s driving your travel decisions, you’ll score the best deals in . tends to be the dearest time of year. Most people come here around February, June and November. If you’d prefer to avoid peak season, you’ll find it calmer during March, August and December.

What is there to do in Historic Downtown Kissimmee?

Pull out your vacation itinerary and make time for Kissimmee Lakefront Park and Kissimmee Civic Center. They’re some of the best-known attractions in Historic Downtown Kissimmee.