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By Huuk Team

Road trip from Leesburg to Kissimmee

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Show more (4+)

ITINERARY

1h 8m54 miles28 stops
1
MetroWest Golf Club
2100 S Hiawassee Rd, Orlando, FL 32835-6307
MetroWest Golf Club, voted the best golf course in Orlando, is located just minutes away from Universal Orlando Resort. The club provides a fair, yet demanding challenge to make a pleasurable golf experience for players of all skill levels.
2
Marion Theatre
50 S Magnolia Ave, Ocala, FL 34471-1153
3
Island H2O Water Park
3230 Inspiration Dr, Kissimmee, FL 34747
Island H2O Water Park is your place for family fun! Tube slides, raft riding & splash zones, plus luxury cabana rentals at a sprawling water park.
4
The Woodhouse Day Spa
7513 West Sandlake Road, Orlando, FL 32819
The Woodhouse Day Spa offers treatments for men and women including facials, massages, body treatments in a Vichy shower, microdermabrasion, hand and foot treatments, and exquisite baths. 6,000 square feet of Victorian decor featuring 16 private guest treatment rooms, men’s & women’s quiet rooms, duet massage room, bath & massage room, private pedicure rooms, and more! The Woodhouse is the perfect place for spa parties & corporate events.
5
Tinker Field
287 S Tampa Ave, Orlando, FL 32805-2157
6
Istanbul Lounge
8395 International Dr I-Drive 360, Home of the Coca-Cola, Orlando Eye, Orlando, FL 32819-9300
7
Lake Rianhard
701 Front St Em frente a Market Street, Celebration, Orlando, FL 34747-4915
8
Corpus Christi Catholic Church
1050 Celebration Ave, Celebration, Orlando, FL 34747-4867
9
DayDreams Day Spa
1463 Town Center Dr, Lakeland, FL 33803-7966
10
The Legends Walk Course
8505 W Irlo Bronson Memorial Hwy Orange Lake Resort, Kissimmee, FL 34747-8217
11
Cleopatra Hookah Lounge
7733 Turkey Lake Rd, Orlando, FL 32819-5221
12
Teatro Martini
6400 Carrier Dr, Orlando, FL 32819-8260
When the sun goes down at the circus, the acts get hotter, the laughs get bigger, and everything gets a whole lot crazier. Award winning acts from around the world will amaze and astound while the best of the best perform on the stage and all around you. Laugh till you can’t breath, watch till you can’t believe, and celebrate what happens when you finally get to see Teatro Martini. Located in Orlando, Florida, in the heart of I-Drive, this highly interactive show features circus performers from around the world including comedy magician, clowns, acrobats and performing puppies!
13
Cinemark Artegon Marketplace and XD
5150 International Dr, Orlando, FL 32819-9423
14
Inter & Co Stadium
655 W Church St, Orlando, FL 32805-2207
Exploria Stadium is a brand new, state-of-the-art stadium located in downtown Orlando, FL. Opened in 2017, the stadium is home to MLS team Orlando City and NWSL team Orlando Pride. Visit the stadium for an Orlando City or Orlando Pride match! Plus, you can now tour the stadium with the new Orlando City Stadium Tours program.
15
1001 Transportation
6401 Time Square Ave Cu-20 #1022, Orlando, FL 32819-9118
Airport Transportation Affordable flat rate Orlando & Miami ground transportation with over 20 years of combined experience. Our chauffeurs have earned an excellent reputation for exceptional standard of safety, reliability and professionalism Transportation in Orlando & Miami Florida.
16
Chef Nite
47 E Robinson St Building 608 B, Orlando, FL 30349-1923
Custom Expierences with your own Personal Chef. The CHEF NIGHT Expierence Has a few options. You can choose to have a Chef host your own Privated Dinner party or you can Choose the PICNIC in the PARK
17
Orange County Convention Center
9800 International Dr, Orlando, FL 32819-8111
18
Wally's On Mills
1001 N Mills Ave, Orlando, FL 32803-3231
19
Ocala Palms Golf & Country Club
5174 NW 26th St, Ocala, FL 34482-3250
20
Greenwood Cemetery
1603 Greenwood St, Orlando, FL 32801-4112
21
Timucua Arts Foundation
2000 S Summerlin Ave just South of Kaley Street, across from the Boone High School athletic field, Orlando, FL 32806
The mission of the Timucua Arts Foundation is to present and inspire great music and art in Central Florida through performance and education.
22
American Girl Orlando
8001 S Orange Blossom Trl, Orlando, FL 32809-7654
Discover a place like no other, where lifelong memories are made, time together counts, and girls can be girls! Enjoy casual dining in the Bistro, where dolls are always welcome.
23
New Balance Factory Store
5881 W Irlo Bronson Memorial Hwy, Kissimmee, FL 34746-4717
24
Kissimmee Lakefront Park
201 Lakeview Drive, Kissimmee, FL 34741
25
Kissimmee Bay Country Club
2801 Kissimmee Bay Blvd, Kissimmee, FL 34744-3949
Kissimmee Bay Country Club Just 15 minutes from Orlando International Airport and 25 minutes from downtown Orlando, as well as all major tourist attractions in the area, Kissimmee Bay Country Club provides a convenient break from the hustle and bustle of everyday life. Here, you can ease into a relaxing round of golf in a casual setting surrounded by the gorgeous Florida landscape. Within one visit to Kissimmee Bay, you will understand why it was nominated one of America's "Best New Courses" by Golf Digest. The course, opened in 1990 and designed by Lloyd Clifton, is a traditional 6,830-yard, par-71, southern-style championship golf course. The layout was cut from an old oak forest, and features lofty cypress trees, a dozen intriguing and challenging water hazards, and the presence of friendly Sandhill Cranes. While you're here, take a free visit to our extensive golf museum, or step into our clubhouse for a unique sense of culture you will find nowhere else in Central Florida. Our
26
Escapology
210 E Pine St, Lakeland, FL 33801-4967
Escape Rooms are a fun, immersive, & entertaining indoor activity that’s great for families, friends, co-workers, couples, and corporate team building! Each of our escape rooms challenge your team to collaborate, communicate, & problem solve within a certain time limit, while still maintaining that sense of fun! Located in Downtown Lakeland next door to Gent’s Classic Cuts, guests will be challenged in this new attraction by working together to find clues, solve puzzles, and decode locks that will free them from the escape room within the hour. All of our Escape Games are Private and can book a room with a minimum of 2 guests up to 8 guests per escape game. We have four different themed games to choose from: Antidote, Arizona Shootout, Budapest Express, & Th3 Cod3! DO YOU HAVE WHAT IT TAKES TO ESCAPE? BOOK AN ESCAPE ROOM TODAY!
27
Frances Langford Promenade
501 E Main St, Lakeland, FL 33801
28
Orlando Speed World Dragway
19164 E Colonial Dr, Orlando, FL 32820-3701
Customize this Trip

OVERVIEW

Leesburg to Kissimmee
1
Start:MetroWest Golf Club
Orlando, Florida·
3.0
(96) review
MetroWest Golf Club, voted the best golf course in Orlando, is located just minutes away from Universal Orlando Resort. The club provides a fair, yet demanding challenge to make a pleasurable golf experience for players of all skill levels.
2100 S Hiawassee Rd, Orlando, FL 32835-6307
2
Marion Theatre
Ocala, Florida·
4.5
(90) review
50 S Magnolia Ave, Ocala, FL 34471-1153
3
Island H2O Water Park
Kissimmee, Florida·
3.5
(96) review
Island H2O Water Park is your place for family fun! Tube slides, raft riding & splash zones, plus luxury cabana rentals at a sprawling water park.
3230 Inspiration Dr, Kissimmee, FL 34747
4
The Woodhouse Day Spa
Orlando, Florida·
4.5
(93) review
The Woodhouse Day Spa offers treatments for men and women including facials, massages, body treatments in a Vichy shower, microdermabrasion, hand and foot treatments, and exquisite baths. 6,000 square feet of Victorian decor featuring 16 private guest treatment rooms, men’s & women’s quiet rooms, duet massage room, bath & massage room, private pedicure rooms, and more! The Woodhouse is the perfect place for spa parties & corporate events.
7513 West Sandlake Road, Orlando, FL 32819
5
Tinker Field
Orlando, Florida·
3.5
(9) review
287 S Tampa Ave, Orlando, FL 32805-2157
6
Istanbul Lounge
Orlando, Florida·
2.5
(9) review
8395 International Dr I-Drive 360, Home of the Coca-Cola, Orlando Eye, Orlando, FL 32819-9300
7
Lake Rianhard
Celebration, Orlando, Florida·
4.5
(95) review
701 Front St Em frente a Market Street, Celebration, Orlando, FL 34747-4915
8
Corpus Christi Catholic Church
Celebration, Orlando, Florida·
5.0
(99) review
1050 Celebration Ave, Celebration, Orlando, FL 34747-4867
9
DayDreams Day Spa
Lakeland, Florida·
4.5
(90) review
1463 Town Center Dr, Lakeland, FL 33803-7966
10
The Legends Walk Course
Kissimmee, Florida·
4.0
(96) review
8505 W Irlo Bronson Memorial Hwy Orange Lake Resort, Kissimmee, FL 34747-8217
11
Cleopatra Hookah Lounge
Orlando, Florida·
3.0
(9) review
7733 Turkey Lake Rd, Orlando, FL 32819-5221
12
Teatro Martini
Orlando, Florida·
4.5
(960) review
When the sun goes down at the circus, the acts get hotter, the laughs get bigger, and everything gets a whole lot crazier. Award winning acts from around the world will amaze and astound while the best of the best perform on the stage and all around you. Laugh till you can’t breath, watch till you can’t believe, and celebrate what happens when you finally get to see Teatro Martini. Located in Orlando, Florida, in the heart of I-Drive, this highly interactive show features circus performers from around the world including comedy magician, clowns, acrobats and performing puppies!
6400 Carrier Dr, Orlando, FL 32819-8260
13
Cinemark Artegon Marketplace and XD
Orlando, Florida·
4.5
(95) review
5150 International Dr, Orlando, FL 32819-9423
14
Inter & Co Stadium
Orlando, Florida·
4.5
(91) review
Exploria Stadium is a brand new, state-of-the-art stadium located in downtown Orlando, FL. Opened in 2017, the stadium is home to MLS team Orlando City and NWSL team Orlando Pride. Visit the stadium for an Orlando City or Orlando Pride match! Plus, you can now tour the stadium with the new Orlando City Stadium Tours program.
655 W Church St, Orlando, FL 32805-2207
15
1001 Transportation
Orlando, Florida·
5.0
(98) review
Airport Transportation Affordable flat rate Orlando & Miami ground transportation with over 20 years of combined experience. Our chauffeurs have earned an excellent reputation for exceptional standard of safety, reliability and professionalism Transportation in Orlando & Miami Florida.
6401 Time Square Ave Cu-20 #1022, Orlando, FL 32819-9118
16
Chef Nite
Orlando, Florida·
3.0
(9) review
Custom Expierences with your own Personal Chef. The CHEF NIGHT Expierence Has a few options. You can choose to have a Chef host your own Privated Dinner party or you can Choose the PICNIC in the PARK
47 E Robinson St Building 608 B, Orlando, FL 30349-1923
17
Orange County Convention Center
Orlando, Florida·
4.5
(957) review
9800 International Dr, Orlando, FL 32819-8111
18
Wally's On Mills
Orlando, Florida·
4.0
(9) review
1001 N Mills Ave, Orlando, FL 32803-3231
19
Ocala Palms Golf & Country Club
Ocala, Florida·
4.5
(9) review
5174 NW 26th St, Ocala, FL 34482-3250
20
Greenwood Cemetery
Orlando, Florida·
4.5
(9) review
1603 Greenwood St, Orlando, FL 32801-4112
21
Timucua Arts Foundation
Orlando, Florida·
5.0
(9) review
The mission of the Timucua Arts Foundation is to present and inspire great music and art in Central Florida through performance and education.
2000 S Summerlin Ave just South of Kaley Street, across from the Boone High School athletic field, Orlando, FL 32806
22
American Girl Orlando
Orlando, Florida·
4.5
(98) review
Discover a place like no other, where lifelong memories are made, time together counts, and girls can be girls! Enjoy casual dining in the Bistro, where dolls are always welcome.
8001 S Orange Blossom Trl, Orlando, FL 32809-7654
23
New Balance Factory Store
Kissimmee, Florida·
4.0
(9) review
5881 W Irlo Bronson Memorial Hwy, Kissimmee, FL 34746-4717
24
Kissimmee Lakefront Park
Kissimmee, Florida·
4.5
(904) review
201 Lakeview Drive, Kissimmee, FL 34741
25
Kissimmee Bay Country Club
Kissimmee, Florida·
3.5
(93) review
Kissimmee Bay Country Club Just 15 minutes from Orlando International Airport and 25 minutes from downtown Orlando, as well as all major tourist attractions in the area, Kissimmee Bay Country Club provides a convenient break from the hustle and bustle of everyday life. Here, you can ease into a relaxing round of golf in a casual setting surrounded by the gorgeous Florida landscape. Within one visit to Kissimmee Bay, you will understand why it was nominated one of America's "Best New Courses" by Golf Digest. The course, opened in 1990 and designed by Lloyd Clifton, is a traditional 6,830-yard, par-71, southern-style championship golf course. The layout was cut from an old oak forest, and features lofty cypress trees, a dozen intriguing and challenging water hazards, and the presence of friendly Sandhill Cranes. While you're here, take a free visit to our extensive golf museum, or step into our clubhouse for a unique sense of culture you will find nowhere else in Central Florida. Our
2801 Kissimmee Bay Blvd, Kissimmee, FL 34744-3949
26
Escapology
Lakeland, Florida·
5.0
(909) review
Escape Rooms are a fun, immersive, & entertaining indoor activity that’s great for families, friends, co-workers, couples, and corporate team building! Each of our escape rooms challenge your team to collaborate, communicate, & problem solve within a certain time limit, while still maintaining that sense of fun! Located in Downtown Lakeland next door to Gent’s Classic Cuts, guests will be challenged in this new attraction by working together to find clues, solve puzzles, and decode locks that will free them from the escape room within the hour. All of our Escape Games are Private and can book a room with a minimum of 2 guests up to 8 guests per escape game. We have four different themed games to choose from: Antidote, Arizona Shootout, Budapest Express, & Th3 Cod3! DO YOU HAVE WHAT IT TAKES TO ESCAPE? BOOK AN ESCAPE ROOM TODAY!
210 E Pine St, Lakeland, FL 33801-4967
27
Frances Langford Promenade
Lakeland, Florida·
4.5
(9) review
501 E Main St, Lakeland, FL 33801
28
Orlando Speed World Dragway
Orlando, Florida·
4.5
(9) review
19164 E Colonial Dr, Orlando, FL 32820-3701

CHECKLIST

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FAQ
Frequently Asked Questions
What's the driving distance between Leesburg and Kissimmee?
The distance is 54 miles
What's the travel time between Leesburg and Kissimmee?
The driving time can vary depending on traffic conditions, but it is typically 1h 8m mins in normal traffic
What are some of the best cities to visit between Leesburg and Kissimmee?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Kissimmee?
There are plenty! Here are some stops you shouldn’t miss on your way to Kissimmee
What’s the weather like in Kissimmee?
The weather in Kissimmee is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Kissimmee in January
Weather in Kissimmee in February
Weather in Kissimmee in March
Weather in Kissimmee in April
Weather in Kissimmee in May
Weather in Kissimmee in June
Weather in Kissimmee in July
Weather in Kissimmee in August
Weather in Kissimmee in September
Weather in Kissimmee in October
Weather in Kissimmee in November
Weather in Kissimmee in December
Interested in a detailed plan for your time in Kissimmee?
Plan your dream Kissimmee trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Kissimmee
A 2-day itinerary in Kissimmee
A 3-day itinerary in Kissimmee
A 4-day itinerary in Kissimmee
A 5-day itinerary in Kissimmee
A 6-day itinerary in Kissimmee
Where else can I travel to if I'm starting my trip in Leesburg?
We have a lot of great trip options for Leesburg! See the links below for all the itineraries we created for you