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Kissimmee Vacation Packages

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Kissimmee Flight + Hotel Packages

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

Flamingo Inn Beachfront

2 out of 5
Save 100% on your flight
Price was $340, price is now $174 per person
$174
per person
Jan 31 - Feb 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this beach hotel in Daytona Beach Shores. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Daytona International Speedway and Beach at Daytona Beach are located nearby.
The Shores Resort & Spa

The Shores Resort & Spa

4 out of 5
Price was $851, price is now $301 per person
$301
per person
Feb 26 - Mar 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this beach hotel in Daytona Beach Shores. Enjoy free WiFi, a full-service spa, and a beach locale. Our guests praise the pool and the restaurant in our reviews. Popular attractions Daytona International Speedway and Beach at Daytona Beach are located nearby.
Residence Inn by Marriott Daytona Beach Oceanfront

Residence Inn by Marriott Daytona Beach Oceanfront

3 out of 5
Price was $1,474, price is now $599 per person
$599
per person
Jan 27 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this business-friendly hotel in Daytona Beach Shores. Enjoy free breakfast, free WiFi, and a beach locale. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Beach at Daytona Beach and Daytona Beach Boardwalk are located nearby.
Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was $2,091, price is now $916 per person
$916
per person
Mar 8 - Mar 12
just found
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this beach condo in Cocoa Beach. Enjoy free parking, a beach locale, and free water park access. Our guests praise the helpful staff in our reviews. Popular attractions Cocoa Beach Pier and Cocoa Beach are located nearby.
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Save 100% on your flight
Price was $810, price is now $386 per person
$386
per person
Mar 18 - Mar 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Orlando (MCO)
Book a stay at this 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 Islands of Adventure and Universal Orlando Resort are located nearby.
Parkway International Resort

Parkway International Resort

3 out of 5
Save 100% on your flight
Price was $834, price is now $426 per person
$426
per person
Feb 26 - Mar 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this family-friendly hotel in Kissimmee. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Old Town and ESPN Wide World of Sports Complex are located nearby.
Westgate Blue Tree Resort in Lake Buena Vista

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5
Save 100% on your flight
Price was $370, price is now $197 per person
$197
per person
Feb 28 - Mar 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this 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.
Boardwalk Inn and Suites

Boardwalk Inn and Suites

2.5 out of 5
Save 100% on your flight
Price was $330, price is now $177 per person
$177
per person
Jan 31 - Feb 4
found 1 day 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.

Kissimmee Vacation Packages 3-4 Night Stays

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

Palazzo Lakeside Hotel

3 out of 5
Price was $682, price is now $168 per person
$168
per person
Feb 28 - Mar 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
The Shores Resort & Spa

The Shores Resort & Spa

4 out of 5
Price was $443, price is now $172 per person
$172
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was $2,091, price is now $916 per person
$916
per person
Mar 8 - Mar 12
just found
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Save 100% on your flight
Price was $810, price is now $386 per person
$386
per person
Mar 18 - Mar 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Orlando (MCO)

Kissimmee Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
CoCo Key Hotel and Water Resort 

CoCo Key Hotel and Water Resort 

3.5 out of 5
International Drive District
Price was $640, price is now $260 per person
$260
per person
Feb 26 - Mar 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $1,374, price is now $289 per person
$289
per person
Jan 27 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
The Shores Resort & Spa

The Shores Resort & Spa

4 out of 5
Price was $759, price is now $262 per person
$262
per person
Jan 27 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Residence Inn by Marriott Daytona Beach Oceanfront

Residence Inn by Marriott Daytona Beach Oceanfront

3 out of 5
Price was $1,474, price is now $599 per person
$599
per person
Jan 27 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Spirit Airlines
Tue, Jan 20 - Sat, Jan 31
BOS
Logan Intl.
MCO
Orlando Intl.
$55 Roundtrip, found 2 hours ago
$55
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Tue, Jan 20 from Logan Intl. to Orlando Intl., returning Sat, Jan 31, priced at $55 found 2 hours ago
Spirit Airlines
Sun, Jan 18 - Thu, Jan 22
EWR
Newark Liberty Intl. Airport
MCO
Orlando Intl.
$58 Roundtrip, found 1 hour ago
$58
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sun, Jan 18 from Newark Liberty Intl. Airport to Orlando Intl., returning Thu, Jan 22, priced at $58 found 1 hour ago
Spirit Airlines
Thu, Jan 22 - Tue, Jan 27
LGA
LaGuardia
MCO
Orlando Intl.
$60 Roundtrip, found 2 hours ago
$60
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Thu, Jan 22 from LaGuardia to Orlando Intl., returning Tue, Jan 27, priced at $60 found 2 hours ago
Frontier Airlines
Mon, Jan 12 - Thu, Jan 22
JFK
John F. Kennedy Intl.
MCO
Orlando Intl.
$68 Roundtrip, found 1 hour ago
$68
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Mon, Jan 12 from John F. Kennedy Intl. to Orlando Intl., returning Thu, Jan 22, priced at $68 found 1 hour ago