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
Price was $525, price is now $326 per person
$326
per person
Jul 14 - Jul 18
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 Beach Boardwalk and Daytona International Speedway are located nearby.
Westgate Palace Hotel / Universal / I-Drive
International Drive District
Price was $1,416, price is now $558 per person
$558
per person
Jul 15 - Jul 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this family-friendly resort in Orlando. Enjoy free WiFi, free parking, and a free theme park shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Universal’s Volcano Bay and The Orlando Eye are located nearby.
Westgate Lakes Resort & Spa Universal Studios Area
Price was $1,112, price is now $608 per person
$608
per person
Jul 15 - Jul 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this 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 Orange County Convention Center and Aquatica are located nearby.
Westgate Town Center Resort
Price was $628, price is now $350 per person
$350
per person
Jul 30 - Aug 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this 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 Complex are located nearby.
Seasons Florida Resort
Price was $648, price is now $367 per person
$367
per person
Jul 15 - Jul 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this business-friendly hotel in Kissimmee. Enjoy free WiFi, free parking, and laundry facilities. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Disney Springs™ and ESPN Wide World of Sports Complex are located nearby.
Palazzo Lakeside Hotel
Save 100% on your flight
Price was $644, price is now $388 per person
$388
per person
Jul 28 - Aug 2
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 Disney Springs™ and ESPN Wide World of Sports Complex are located nearby.
Hilton Daytona Beach Oceanfront Resort
Brush - Stewarts
Save 100% on your flight
Price was $1,815, price is now $1,116 per person
$1,116
per person
Jul 31 - Aug 7
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Orlando (MCO)
Book a stay at this beach hotel in Daytona Beach. Enjoy 2 outdoor pools, 4 restaurants, 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 Vacation Villas Resort
Price was $700, price is now $437 per person
$437
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this family-friendly resort in Kissimmee. Enjoy free parking, 14 outdoor pools, and 2 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 Complex 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
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
8800 Vistana Centre Dr Orlando FL
Book a stay at this family-friendly aparthotel in Orlando. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff ...
DoubleTree by Hilton at the Entrance to Universal Orlando
5780 Major Blvd Orlando FL
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the pool and the helpful staff in ...
The Grove Resort & Water Park Orlando
14501 Grove Resort Avenue Winter Garden FL
Book a stay at this family-friendly resort in Four Corners. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff ...
Save an average of 15% on thousands of hotels when you're signed in
Universal's Cabana Bay Beach Resort
6550 Adventure Way Orlando FL
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in ...
Walt Disney World Dolphin
1500 Epcot Resort Blvd Lake Buena Vista FL
Book a stay at this beach hotel in Lake Buena Vista. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the restaurant ...
Westgate Lakes Resort & Spa Universal Studios Area
9500 Turkey Lake Rd Orlando FL
Book a stay at this 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 ...
Avanti International Resort
8738 International Dr Orlando FL
Book a stay at this family-friendly hotel in Orlando. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the pool and the helpful ...
Holiday Inn Resort Orlando Suites - Waterpark by IHG
18000 International Dr S. Orlando FL
Book a stay at this family-friendly hotel in Orlando. Enjoy 2 outdoor pools, 5 restaurants, and 2 hot tubs. Our guests praise the clean rooms and the family ...
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.
Tue, Aug 25 - Tue, Sep 8
TTN
Mercer
MCO
Orlando Intl.
$119 Roundtrip, found 15 hours ago
$119
Roundtrip
found 15 hours ago
Tue, Oct 6 - Fri, Oct 16
PHL
Philadelphia Intl.
MCO
Orlando Intl.
$124 Roundtrip, found 1 day ago
$124
Roundtrip
found 1 day ago
Tue, Aug 25 - Thu, Aug 27
ORD
O'Hare Intl.
MCO
Orlando Intl.
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
Thu, Jul 23 - Sun, Aug 2
BOS
Logan Intl.
MCO
Orlando Intl.
$154 Roundtrip, just found
$154
Roundtrip
just found
Discover Other Travel Deals
- Kissimmee Lakefront Park Vacations
- Osceola County Clerk of the Court Vacations
- Bataan-Corregidor Memorial Vacations
- Monument of States Vacations
- Kissimmee Civic Center Vacations
- First United Methodist Church Vacations
- Walt Disney World® Resort Vacations
- Universal Studios Florida Vacations
- Disney SpringsTM Vacations
- Universal Orlando Resort Vacations
- Magic Kingdom® Park Vacations
- Disney's Animal Kingdom® Theme Park Vacations