Historic Downtown Kissimmee Vacation Packages 2025/2026 from $204

Historic Downtown Kissimmee flight + hotel vacation packages

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

Palazzo Lakeside Hotel

$204

per person

Dec 4 - Dec 7

found 1 day ago

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.

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

International Drive District

Save 100% on your flight

$390

per person

Nov 13 - Nov 18

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This hotel features an outdoor pool and a rooftop terrace. Enjoy the hot tub and free perks like continental breakfast and free self parking. A business center, free WiFi in public areas, and a terrace are also on offer.

Westgate Cocoa Beach Resort

Save 100% on your flight

$1,142

per person

Nov 26 - Nov 30

found 1 hour ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) 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.

Bryan’s Spanish Cove

$488

per person

Dec 1 - Dec 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

An outdoor pool, free self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. A garden, a picnic area, and concierge services are also on offer.

Alhambra Villas

Solivita

Save 100% on your flight

$289

per person

Oct 24 - Oct 31

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

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

$102 nightly

$115 total

Sep 22 - Sep 23

Total with taxes and fees

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

$87 nightly

$98 total

Oct 1 - Oct 2

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.

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

12401 International Dr, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$84 nightly

$95 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.

Pool

Hot Tub

DoubleTree by Hilton Hotel Orlando at SeaWorld

10100 International Drive, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$92 nightly

$104 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.

Pool

Pet friendly

Rosen Inn at Pointe Orlando

9000 International Drive, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$65 nightly

$74 total

Sep 14 - Sep 15

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.

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

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 $204, 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.