Historic Downtown Kissimmee Holidays

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Your Historic Downtown Kissimmee Holiday

From its shopping to its dining, there's a lot to love about Historic Downtown Kissimmee. Book a Historic Downtown Kissimmee holiday package and prepare to experience the delights of this neighbourhood. Kick off your trip to Historic Downtown Kissimmee with a visit to nearby attractions such as Osceola Heritage Park, Silver Spurs Arena and 192 Flea Market. Whatever your travel plans or budget, booking a perfect Historic Downtown Kissimmee holiday is quick and easy with Expedia.

Price found within the past 48 hours. Click for updated prices.
  • Water park
    Aug 29 - Sep 5

    Westgate Lakes Resort & Spa Universal Studios Area + Flight

    Orlando
    7 nights
    4.0 star property
    8.4/10 - Very good (6,567 reviews)
    "Super helpful staff! Clean rooms and in a great location!"
    Reviewed June 8, 2026
    Return • London (LHR) - Orlando (MCO)
    LHR - MCO • Direct MCO - LHR • Direct
    £1,122
    £710
    per traveller
    found 14 hours ago
    Westgate Lakes Resort & Spa Universal Studios Area
  • In-room safe, laptop workspace, blackout curtains, iron/ironing board
    Jul 13 - Jul 17

    Palazzo Lakeside Hotel + Flight

    Kissimmee
    4 nights
    3.0 star property
    8.2/10 - Very good (5,199 reviews)
    "Good"
    Reviewed June 8, 2026
    Return • London (LHR) - Orlando (MCO)
    LHR - MCO • Direct MCO - LHR • Direct
    £1,378
    £849
    per traveller
    found 1 day ago
    Palazzo Lakeside Hotel
  • Outdoor pool, open 7:00 AM to 11:00 PM, pool cabanas (surcharge)
    Jul 13 - Jul 17

    Meliá Orlando Celebration + Flight

    Celebration
    4 nights
    4.0 star property
    8.8/10 - Excellent (1,601 reviews)
    "Good breakfast with mickey waffles :) and very courteous staff. Room was clean will book again. Thanks melia ❤️"
    Reviewed June 6, 2026
    Return • London (LHR) - Orlando (MCO)
    LHR - MCO • Direct MCO - LHR • Direct
    £1,465
    £907
    per traveller
    found 1 day ago
    Meliá Orlando Celebration
  • Reception
    Aug 22 - Sep 5

    Florida Hotel & Conference Center in the Florida Mall + Flight

    Orlando
    14 nights
    3.5 star property
    9.2/10 - Wonderful (1,363 reviews)
    "The staff were all pleasant and friendly! Bed wasvery comfortable. The hotel was very comfortable and love that it was connected to The Florida Mall. It was a great experience for my granddaughter and I."
    Reviewed June 8, 2026
    Return • London (LGW) - Orlando (MCO)
    LGW - MCO • 2 stops MCO - LGW • 2 stops
    Save 100% on your flight
    £2,026
    £1,267
    per traveller
    found 1 day ago
    Florida Hotel & Conference Center in the Florida Mall
  • Aerial view
    Aug 26 - Sep 2

    Margaritaville Cottages Orlando by Vstays with H2O Waterpark + Flight

    Kissimmee
    7 nights
    4.0 star property
    9.2/10 - Wonderful (1,008 reviews)
    "Loved everything about it."
    Reviewed June 8, 2026
    Return • Edinburgh (EDI) - Orlando (MCO)
    EDI - MCO • Direct MCO - EDI • Direct
    Save 100% on your flight
    £2,336
    £1,472
    per traveller
    found 1 day ago
    Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Where to stay in Historic Downtown Kissimmee

Find the best Historic Downtown Kissimmee areas and neighborhoods for the activities you enjoy most. Learn more about Historic Downtown Kissimmee
International Drive District

International Drive District

Adventure activities, iconic attractions, shopping and world-class dining destinations make this famous street one of Orlando’s most popular tourist attractions.

Find hotels in International Drive District

Top hotels in Historic Downtown Kissimmee

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

4 out of 5
8800 Vistana Centre Dr Orlando FL
The price is £121 per night from 7 Jul to 8 Jul
£121
7 Jul - 8 Jul
includes taxes & fees
9.2/10 Wonderful! (5,729 reviews)
"Property was great having to pay extra to park kinda sucked."

Reviewed on 9 Jun 2026

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

4 out of 5
5780 Major Blvd Orlando FL
Fully refundable
The price is £90 per night from 6 Jul to 7 Jul
£90
6 Jul - 7 Jul
includes taxes & fees
8.6/10 Excellent! (6,985 reviews)
"Room was nice and big and clean."

Reviewed on 8 Jun 2026

DoubleTree by Hilton at the Entrance to Universal Orlando
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue Winter Garden FL
The price is £209 per night from 14 Jun to 15 Jun
£209
14 Jun - 15 Jun
includes taxes & fees
8/10 Very Good! (10,146 reviews)
"Great environment great environment"

Reviewed on 8 Jun 2026

The Grove Resort & Water Park Orlando
See all 53,392 properties in Historic Downtown Kissimmee
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Historic Downtown Kissimmee travel package cost?
Starting from as little as , you can create your own Historic Downtown Kissimmee package. Simply combine hotels, flights and car rentals and we'll reward you with discounts.
If I'm not able to travel, can I cancel my Historic Downtown Kissimmee travel package?
Plans can change unexpectedly, so yes, you can. You may be able to amend or cancel your Historic Downtown Kissimmee travel package for free within 24 hours of booking. For bookings made more than 24 hours ago, you can still make the necessary changes, but your car rental company, hotel or airline may impose a charge. Want more information? Check out our Customer Service Portal. We're here to help make sure your trip goes off without a hitch.
How do I get a cheap travel package to Historic Downtown Kissimmee?
Booking a Historic Downtown Kissimmee travel package with Expedia is a smart way to save. We have access to more than 550 air carriers and 1,000,000 hotels globally. With such a broad range to pick from, you'll have no difficulty pulling together your ideal adventure.
Does Expedia offer Book Now, Pay Later Historic Downtown Kissimmee holidays?
Expedia has partnered with online lender Klarna to make booking your next getaway easier on the purse strings. Paying by instalment means you can spread the costs of your next dream escape, leaving you with more cash to splash while you're away. Klarna has several payment plans to pick from, so you're sure to find something that falls within your budget. Browse these flexible payment options:

  • Pay monthly holidays: Klarna has easy monthly payment plans that work for all budgets, so you can take that well-earned holiday now.
  • Pay in instalments holidays: If you want to pay for your escape across multiple transactions, holidays paid in instalments might be right for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: Pressing the "book now" button is easier with this option. Just put down a small deposit on your holiday and then start packing your suitcase.

Where should I stay in Historic Downtown Kissimmee?
We recommend staying within walking distance of ChampionsGate Golf Club, one of this area's top attractions. It's the ideal spot for those eager to check out the local sights.
What are the top hotels in Historic Downtown Kissimmee?
Get your trip off to a fantastic start by booking a stay at Magic Moment Resort and Kids Club. It's one of most popular hotels in Historic Downtown Kissimmee. Another leading option is Red Lion Hotel Orlando Lake Buena Vista South.
How far in advance should I book my Historic Downtown Kissimmee holiday?
While prices change frequently, we generally advise booking your holiday as soon as possible. Most international fares can be found on Expedia up to 12 months in advance. If circumstances have left you booking last minute, you might still be lucky. Low prices to Historic Downtown Kissimmee occasionally appear just weeks before departure.
What does an Expedia Historic Downtown Kissimmee travel package include?
Expedia has all you need to arrange your Historic Downtown Kissimmee escape, but what your package looks like is up to you. Select from any combination of hotels, rental cars and flights. Looking for some activities to keep you entertained? Once you've made your booking, you can add them too. Whatever your style, there's a deal to suit your needs.
What should I know before booking a Historic Downtown Kissimmee travel package?
Our prices are already low. However, you'll pick up an even better deal if you book your flights, hotels and car rentals together. With an Expedia package, you'll get transparent pricing and a terrific range of choice.
Can I choose my airline with a Historic Downtown Kissimmee Expedia travel package?
Expedia offers access to more than 550 airline partners globally, so you definitely can. Simply select the carrier you want and craft your ideal Historic Downtown Kissimmee holiday.

Popular places to visit

Kissimmee Lakefront Park Grassy waterfront park with walking paths, a fishing pier, picnic pavilions, and a shaded playground. children's playgrounds, splash pad

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 lively festivals in this family-friendly area.

Kissimmee Lakefront Park

Monument of States

Learn about the local history of Kissimmee when you take a trip to Monument of States. Amble around this family-friendly area's lakeside or experience its entertainment choices.

Monument of States

Things to do

Universal Orlando Resort Theme Park Tickets

Universal Orlando Resort Theme Park Tickets

£445
per adult
92% of travellers recommend
Universal Orlando Resort Theme Park Tickets
"Drawn to Life" presented by Cirque du Soleil and Disney

Drawn to Life presented by Cirque du Soleil and Disney

£62
per adult
96% of travellers recommend
Drawn to Life presented by Cirque du Soleil and Disney
Aquatica Orlando

Aquatica Orlando

£39
per traveller
84% of travellers recommend
Aquatica Orlando
See all activities in Orlando

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.