Search Deals onHistoric Downtown Kissimmee Vacation Packages
Historic Downtown Kissimmee Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Ocean Sands Beach Boutique Inn - 1 Acre Private Beach
Vilano Beach
Save 100% on your flight
per person
Jun 28 - Jul 3
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Orlando (MCO)
Stay at this 3.5-star beach hotel in St. Augustine. Enjoy free breakfast, free WiFi, and a private beach. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Vilano Beach and Castillo de San Marcos National Monument are located nearby.
Westgate Palace Hotel / Universal / I-Drive
Florida Center
per person
Jun 26 - Jul 1
found 13 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Stay at this 4-star family-friendly resort in Orlando. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Universal’s Volcano Bay and The Orlando Eye at ICON Park are located nearby.
Westgate Town Center Resort
Save 100% on your flight
per person
Jun 26 - Jul 2
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
Jun 26 - Jul 2
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
Save 100% on your flight
per person
Jun 26 - Jul 2
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
Jun 26 - Jul 2
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 Orlando Vineland Premium Outlets and Disney Springs™ are located nearby.
Costa d'Este Beach Resort and Spa
Central Beach
Save 100% on your flight
per person
Jun 13 - Jun 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 4-star beach hotel in Vero Beach. Enjoy a full-service spa, a beach locale, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Sexton Plaza Beach and Vero Beach Museum of Art are located nearby.
Travelodge by Wyndham Hotel & Cottages St Augustine/Historic
Greater Fullerwood
Save 100% on your flight
per person
Jun 28 - Jul 3
found 8 hours ago
Roundtrip flight included
Cleveland (CLE) to Orlando (MCO)
Stay at this 3-star motel in St. Augustine. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Castillo de San Marcos National Monument and Vilano Beach are located nearby.
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
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 ...
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 by IHG
14500 Continental Gateway, Orlando, FL
Stay at this 3.5-star family-friendly hotel in Orlando. Enjoy 2 outdoor pools, 5 restaurants, and 2 hot tubs. Our guests praise the clean rooms and the family ...
Save an average of 15% on thousands of hotels when you're signed in
Westgate Lakes Resort & Spa Universal Studios Area
9500 Turkey Lake Rd, Orlando, FL
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 ...
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 ...
Rosen Inn at Pointe Orlando
9000 International Drive, Orlando, FL
Stay at this 3-star family-friendly hotel in Orlando. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the pool and the helpful staff in ...
The Grove Resort & Water Park Orlando
14501 Grove Resort Avenue, Winter Garden, FL
Stay at this 4-star family-friendly resort in Winter Garden. Enjoy free WiFi, 5 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful ...
Kompose Boutique Resort at Theme Parks
7491 W Irlo Bronson Memorial Hwy, Kissimmee, FL
Stay at this 4-star business-friendly resort in Kissimmee. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Disney's Animal Kingdom® Theme ...
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.
Sat, May 31 - Wed, Jun 4
DTW
Detroit Metropolitan Wayne County
MCO
Orlando Intl.
$73 Roundtrip, found 5 days ago
$73
Roundtrip
found 5 days ago
Tue, Jun 10 - Sat, Jun 14
TTN
Mercer
MCO
Orlando Intl.
$75 Roundtrip, found 5 days ago
$75
Roundtrip
found 5 days ago
Sat, May 31 - Thu, Jun 5
ORD
O'Hare Intl.
MCO
Orlando Intl.
$91 Roundtrip, found 3 days ago
$91
Roundtrip
found 3 days ago
Wed, Jun 4 - Wed, Jun 4
BOS
Logan Intl.
MCO
Orlando Intl.
$96 Roundtrip, found 3 days ago
$96
Roundtrip
found 3 days ago
Discover Other Travel Deals
- Kissimmee Lakefront Park Vacations
- Osceola County Clerk of the Court Vacations
- Kissimmee Civic Center Vacations
- First United Methodist Church Vacations
- Bataan-Corregidor Memorial Vacations
- Monument of States Vacations
- Lanier's Historic Downtown Marketplace Vacations
- Walt Disney World® Resort Vacations
- Universal Studios Florida Vacations
- Disney SpringsTM Vacations
- Universal Orlando Resort Vacations
- Magic Kingdom® Park Vacations