Search Deals onHistoric Downtown Kissimmee Vacation Packages
Historic Downtown Kissimmee Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Boardwalk Inn and Suites
Davis
Save 100% on your flight
per person
Feb 4 - Feb 11
found 22 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this beach hotel in Daytona Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Daytona International Speedway and Daytona Beach Boardwalk are located nearby.
Westgate Lakes Resort & Spa Universal Studios Area
per person
Feb 13 - Feb 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 4-star spa hotel in Orlando. Enjoy free parking, 7 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Universal Orlando Resort and Universal Studios Florida are located nearby.
Palazzo Lakeside Hotel
per person
Feb 13 - Feb 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this hotel in Kissimmee. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Old Town and Disney Springs™ are located nearby.
Westgate Town Center Resort
Save 100% on your flight
per person
Feb 13 - Feb 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 4-star family-friendly resort in Kissimmee. Enjoy free WiFi, free parking, and 14 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports are located nearby.
Westgate Vacation Villas Resort
Save 100% on your flight
per person
Feb 13 - Feb 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 4-star family-friendly resort in Kissimmee. Enjoy free parking, 14 outdoor pools, and 4 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports are located nearby.
Westgate Towers Resort
per person
Feb 5 - Feb 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 3.5-star family-friendly hotel in Kissimmee. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports are located nearby.
Westgate Blue Tree Resort in Lake Buena Vista
Save 100% on your flight
per person
Feb 2 - Feb 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 3.5-star family-friendly hotel in Orlando. Enjoy free parking, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Disney Springs™ and Epcot® are located nearby.
Westgate River Ranch Resort & Rodeo
Save 100% on your flight
per person
Feb 13 - Feb 17
found 13 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Stay at this 3.5-star family-friendly resort in River Ranch. Enjoy free parking, 2 restaurants, and a marina. Our guests praise the helpful staff in our reviews.
3-4 Night Vacations in Historic Downtown Kissimmee
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Historic Downtown Kissimmee
Price found within the past 48 hours. Click for updated prices.
Cheap Hotel Deals in Historic Downtown Kissimmee
The Grove Resort & Water Park Orlando
14501 Grove Resort Avenue, Winter Garden, FL
Stay at this 4-star family-friendly resort in Four Corners. Enjoy free WiFi, 3 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff ...
Hyatt Regency Orlando International Airport
9300 Jeff Fuqua Boulevard, Orlando, FL
Stay at this 4-star eco-certified hotel in Orlando. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the restaurant ...
Holiday Inn Resort Orlando Suites - Waterpark, an IHG Hotel
14500 Continental Gateway, Orlando, FL
Stay at this 3.5-star family-friendly hotel in Orlando. Enjoy 2 outdoor pools, 5 restaurants, and 2 spa tubs. Our guests praise the clean rooms and the family ...
Save an average of 15% on thousands of hotels when you're signed in
Rosen Inn Lake Buena Vista
8442 Palm Parkway, Orlando, FL
Stay at this 3.5-star family-friendly hotel in Orlando. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the breakfast and the pool in our ...
DoubleTree by Hilton at the Entrance to Universal Orlando
5780 Major Blvd, Orlando, FL
Stay at this 4-star family-friendly hotel in Orlando. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the pool and the helpful staff in ...
DoubleTree by Hilton Hotel Orlando at SeaWorld
10100 International Drive, Orlando, FL
Stay at this 4-star family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the breakfast and the pool in our ...
Universal's Cabana Bay Beach Resort
6550 Adventure Way, Orlando, FL
Stay at this 3.5-star family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
Avanti International Resort
8738 International Dr, Orlando, FL
Stay at this 4-star family-friendly hotel in Orlando. Enjoy free WiFi, breakfast (surcharge), and a free theme park shuttle. Our guests praise the pool and the ...
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.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Mon, Feb 3 - Thu, Feb 6
TTN
Mercer
MCO
Orlando Intl.
$68 Roundtrip, found 2 days ago
$68
Roundtrip
found 2 days ago
Wed, Jan 15 - Wed, Jan 22
LGA
LaGuardia
MCO
Orlando Intl.
$71 Roundtrip, found 11 hours ago
$71
Roundtrip
found 11 hours ago
Tue, Jan 21 - Wed, Jan 29
JFK
John F. Kennedy Intl.
MCO
Orlando Intl.
$78 Roundtrip, found 17 hours ago
$78
Roundtrip
found 17 hours ago
Sun, Jan 12 - Thu, Jan 16
ORD
O'Hare Intl.
MCO
Orlando Intl.
$81 Roundtrip, found 4 hours ago
$81
Roundtrip
found 4 hours ago
Discover Other Travel Deals
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- Monument of States Vacations
- Bataan-Corregidor Memorial Vacations
- Walt Disney World® Resort Vacations
- Universal Studios Florida Vacations
- Universal Orlando Resort Vacations
- Disney SpringsTM Vacations
- Magic Kingdom® Park Vacations