Enjoy year-round warm weather and hundreds of things to do in Kissimmee!

Kissimmee is not only the gateway to the Everglades but is also just minutes away from everything you could ever want to create your perfect escape. Let loose, relax, and enjoy a vacation you will never forget.

Pair your Kissimmee golf escape with the most magical place on Earth. Find your happy place in Walt Disney World and create unforgettable memories with the whole family.

Kissimmee Vacation Packages

Flights to Kissimmee | Hotels & Resorts in Kissimmee

Vacations to Kissimmee, Florida - redtag.ca has made it easy for you to find Cheap Vacations to Kissimmee from Canada or Hotel and Resorts in Kissimmee. Book your Cheap Vacations to Kissimmee Today & Save! redtag.ca has the latest and Best Travel Deals to Kissimmee

Florida Condos
May 15, 2023 (4 days)
May 15, 2023 (4 days)
No Meals/Drinks
No Meals/Drinks
3 Bedroom Condo Windsor Hills
Book with Deposit
$50 Amazon Gift Card
$50 Amazon Gift Card
$50 Amazon Gift Card
Get 33 Miles
was $1,252 Save 46%
$674PP
taxes & fees
Book with Deposit
Westgate Town Center Resort And Spa
Oct 20, 2022 (4 days)
Oct 20, 2022 (4 days)
No Meals/Drinks
No Meals/Drinks
Double Guest Room
Get 28 Miles
was $990 Save 42%
$570PP
taxes & fees
Comfort Suites Maingate East
Oct 28, 2022 (3 days)
Oct 28, 2022 (3 days)
No Meals/Drinks
No Meals/Drinks
Suite
Get 33 Miles
was $1,125 Save 40%
$670PP
taxes & fees
Holiday Inn Orlando Sw Celebration Area
Oct 28, 2022 (3 days)
Oct 28, 2022 (3 days)
No Meals/Drinks
No Meals/Drinks
Room
Get 34 Miles
was $1,115 Save 39%
$681PP
taxes & fees
Comfort Inn Maingate
Comfort Inn Maingate Toronto Kissimmee - Orlando
Only Breakfast
Only Breakfast
Room
Nov 14, 2022 (3 days)
Nov 14, 2022 (3 days)
Only Breakfast
Only Breakfast
Room
Get 19 Miles
was $538 Save 29%
$384PP
taxes & fees
Seralago Hotel And Suites Maingate East
Nov 25, 2022 (3 days)
Nov 25, 2022 (3 days)
No Meals/Drinks
No Meals/Drinks
Room
Get 22 Miles
was $619 Save 27%
$453PP
taxes & fees
Melia Orlando Hotel At Celebration
Nov 14, 2022 (3 days)
Nov 14, 2022 (3 days)
No Meals/Drinks
No Meals/Drinks
Deluxe Room
Get 19 Miles
was $447 Save 13%
$389PP
taxes & fees
Wyndham Cypress Palms
Nov 14, 2022 (3 days)
Nov 14, 2022 (3 days)
No Meals/Drinks
No Meals/Drinks
1 Bedroom Suite
Get 23 Miles
was $535 Save 11%
$474PP
taxes & fees
Legacy Vacation Club Kissimmee
Nov 03, 2022 (3 days)
Nov 03, 2022 (3 days)
No Meals/Drinks
No Meals/Drinks
Mini Suite
Get 28 Miles
was $605
$565PP
taxes & fees
Florida Homes Deluxe
Jan 04, 2023 (6 days)
Jan 04, 2023 (6 days)
No Meals/Drinks
No Meals/Drinks
6 Bedroom Home Windsor Westside
Book with Deposit
$50 Amazon Gift Card
$50 Amazon Gift Card
$50 Amazon Gift Card
Get 71 Miles
was $1,479
$1,421PP
taxes & fees
Book with Deposit

Hotels & Resorts in Kissimmee

Kissimmee Flight Deals

Vacations to Kissimmee

Great travel deals and cheap vacation packages to Kissimmee, Florida. Get redtag.ca prices on vacations to Kissimmee, Florida also the biggest & best selection on Kissimmee.