Mad Men Vacation Rentals

Our Top 10 Kissimmee Recommendations

Here are our favorite things to see and do in and around Kissimmee, Florida.
Some are well know, some not so well known. Have a look around as we have included photos, videos, information and links.
They are in no particular order

1. Island Grove Wine Company

It’s Kissimmee and Orlando’s best kept secret! Plus it’s less than 5 minutes from Mad Men Magic Kingdom House!

Island Grove Wine Company at Formosa Gardens is Kissimmee's best kept secret

Island Grove Wine Company at Formosa Gardens is a family-friendly agritourism destination. Tour our wine-making area and taste unique fruit wines, traditional grape wines, and local craft beers. Explore our 7+ acres of botanical gardens. Host business meetings and classes here. Formosa Winery is also a wedding venue, with a variety of outdoor and indoor event spaces. Check out their events page to see what’s going on there on your next trip to Mad Men Magic Kingdom House or just drop into the Bistro for a delicious bite to eat. And defiantly be sure to try their speciality Blueberry Wines! Yum! 


The 150-acre interactive theme park dedicated to families with children between the ages of 2 and 12. With more than 50 rides, shows and attractions and the all-new water park, LEGOLAND is geared towards family fun! Here you’ll find a creative collection of LEGO®-inspired rides and attractions that promise fun for everyone, from the “pink knuckle” thrills of roller coasters such as The Dragon, Project X and Flying School to interactive adventures including Quest for CHI and Lost Kingdom Adventure

Legoland Florida what to do and see on vacation

Check out whats just opening in 2019, guests are invited to Bricksburg where the immersive world of THE LEGO MOVIE comes to life through three new rides, a taco stop and character meet-and-greets. Brave the family-friendly Unikitty-themed drop tower, rocket into a daring flying theater and battle through the waters against DUPLO® aliens to save the day.

Make no mistake, diehard LEGO fanatics might want to head straight to MINILAND USA, which features LEGO recreations of famous cities — including Orlando! — and key scenes from Star Wars movies. Nature-lovers will find much to enjoy at LEGOLAND Florida, too, thanks to the park’s Cypress Gardens section.

Visiting LEGOLAND Florida in the summer? There’s no better way to beat the heat than with a visit to the onsite LEGOLAND Water Park, entry to which is available as an upgrade to standard admission. And at the adjacent Pirate’s Cove, you can catch a live water show starring Brickbeard.

Address: 1 Legoland Way, Winter Haven, FL 33884

Phone: (888) 690-5346 

3. Golfing in Central Florida

The fairest of fairways and the greenest of greens. Any way you slice it, the golf courses in and surrounding Kissimmee are some of the best in the country.  Putt around on championship layouts architected by legendary golfers. With year-round Florida sunshine and 365 days of play, this is a golf vacation you’ll book again and again. It’s always tee time in Kissimmee!

Here are some the best places to check out in and around Kissimmee:

Falcons Fire Golf Club:  3200 Seralago Boulevard, Kissimmee, FL 34746

Falcon’s Fire Golf Club is recognized both regionally and nationally as one of the finest public golf courses in Orlando. This Rees Jones designed championship golf course and the spacious Clubhouse offer guests a spectacular venue for any occasion. From an immaculate golf course featuring the highest level of service and amenities, to the exquisite dining at the Falcon’s Nest Restaurant, to the latest technology, equipment, and apparel at the award-winning Golf Shop, Falcon’s Fire Golf Club is a premier Florida golf destination. https://www.falconsfire.com/

Celebration Golf Club: 701 Golfpark DrCelebration, FL 34747

The famed father-son team of Robert Trent Jones, Sr. and Jr. designed this 18-hole championship course that features a park-like atmosphere with a natural wetland environment. https://celebrationgolf.com/

The Ritz-Carlton Golf Club: 4048 Central Florida PkwyOrlando, FL 32837

Embark on a course to become one with nature when you set out to play 18 holes at The Ritz-Carlton Golf Club(R) Orlando, Grande Lakes. A Certified Audubon Cooperative Sanctuary, the golf course blends into the natural landscape, protecting natural resources and habitats while enhancing the overall golf experience. Designed by two-time British Open Champion Greg Norman, the course blends a variety of hazards to provide a challenging but fair test of a golfer’s abilities resulting in an atmosphere reminiscent of a private course. https://www.ritzcarlton.com/en/hotels/florida/orlando/area-activities/golf

And you don’t want to miss out on the Walt Disney World Resort’s Famous Courses while you are in town:

Palm Course:1950 Magnolia PalmOrlando, FL 32830

Experience the natural beauty of the Florida woodlands at Disney’s Palm Golf Course. This majestic course is both a pleasure to play, as well as an exciting test of skill. Golfers will appreciate the course design, which features shimmering lakes and tropical sands, all across a golf landscape that’s dotted with strategically placed palm trees.https://www.golfwdw.com/courses/disneys-palm-golf-course 

Magnolia Course: 1950 Magnolia PalmOrlando, FL 32830

Named for its majestic magnolia trees, this course features elevated tees, spacious greens and challenging water hazards. Wide fairways invite you to hit the ball and hit it long, but beware-11 of the 18 holes boast water hazards and 97 bunkers dot the landscape. Certified by Audubon International as a Cooperative Wildlife Sanctuary and rated 4 stars by Golf Digest, Disney’s Magnolia Golf Course represents a paradise for serious golfers, as well as a thrilling challenge for players at all levels. https://www.golfwdw.com/courses/disneys-magnolia-golf-course

Oak Trail Course: 1950 Magnolia Palm DriveOrlando, FL 32830-8418

Disney’s Oak Trail Golf Course is a beautiful 9-hole course with rolling greens and exciting challenges. Certified by Audubon International as a Cooperative Wildlife Sanctuary, Disney’s Oak Trail Golf Course lets you test your skills with holes ranging from 132 to 517 yards from the white tees; holes 5, 6 and 7 are routed around a deep canal and a picturesque pond. Operated by Arnold Palmer Golf Management and featuring junior tees for younger golfers, this walking course is fun for the whole family. We do not allow golf carts on Disney’s Oak Trail Golf Course. Disney’s Oak Trail Golf Course is walking only.https://www.golfwdw.com/courses/disneys-oak-trail-golf-course

Lake Buena Vista Course: 2200 Golf DrOrlando, FL 32830

Disney’s Lake Buena Vista Golf Course presents meandering fairways that wind their way through pastel villas, pine forests, palmettos and sparkling lakes. Experience the pleasures of a classic country-club course with a distinctive atmosphere. Tee off next to boats, navigating scenic canals while taking in views of an enchanting lighthouse. Disney’s Lake Buena Vista Golf Course is rated an impressive 4 stars by Golf Digest.Disney’s Lake Buena Vista Golf Course is one of the few courses that have hosted PGA Tour, LPGA Tour and USGA events. The course most notably features elevated bunkered greens that put a premium on accurate approach shots. You can also test your skills and fortitude at the demanding 7th hole with its inviting island green. https://www.golfwdw.com/courses/disneys-lake-buena-vista-golf-course


4. Miniature Golf

One thing is for sure, Kissimmee is not lacking on Miniature golf courses! This is a fun non-park day out!

miniature golf central Florida vacation activities

Pirate’s Cove Adventure Golf: Pirate’s Island offers a unique “Adventure Golf” experience for ages 3 to 93.  Follow in the footsteps of notorious pirates like Blackbeard and Captain Kidd.  Begin your themed adventure at our seaside village and depart along the shores of the tidal lagoon.  Continue through the caves where pirates buried their booty and explore the mountain to view a panorama of our entire pirate adventure.  Extraordinary landscapes, waterfalls, streams and bridges await, as you stroll through this themed setting.  Join us for an experience the entire family can enjoy.

Address: 2845 Florida Plaza BlvdKissimmee, FL 34746-4701
Telephone: 407-396-7484

Congo River Golf: Welcome to Congo River Golf! Play award-winning miniature golf at Congo River Golf. With eight locations in Florida to choose from, there’s an adventure for everyone. It’s fun for the whole family! Experience tranquil waterfalls, mysterious caves, tropical rainforests, challenging golf holes and more as you follow in the footsteps of Stanley and Livingstone on an unforgettable African adventure. It’s fun exploring the Congo during the day and at night, under the stars! Search for lost artifacts, feed live gators, mine for gemstones and challenge your skills in the arcade. Birthday celebrations and group parties provide fun for all ages. Grab a putter and get ready for the adventure of a lifetime!

Address: 4777 W Irlo Bronson Memorial Hwy, Kissimmee, FL
Website: https://www.congoriver.com/
Telephone: 407-396-6900

Mighty Jungle Golf:Located in the Formosa Gardens Village West 192, Guide Marker 4 Two 18 Hole Courses. Pro Putting Turf, Life Like animals, picnic area with tables and chairs. Pepsi products Philadelphia Water Ice & Ice Cream Voted Best in Mini Golf by Orlando Weekly Readers Poll. GREAT place to Host a Birthday Party or your next Business Team Building Event.

Address: 7792 W Irlo Bronson Memorial HwyKissimmee, FL 34747
Website: http://www.mightyjunglegolf.com/
Telephone: 407-390-6453

5. Old Town

Old Town is a unique 18-acre walking featuring over 70 unique and affordable shops, restaurants, bars, rides and family friendly attractions.  Relax as you stroll down our beautiful, tree-lined brick streets and discover why Old Town has become a beloved family tradition for over 30 years.

Old Town Kissimmee Fl Family Friendly activities for vacation

Old Town is a unique 18-acre walking featuring over 70 unique and affordable shops, restaurants, bars, rides and family friendly attractions.  Relax as you stroll down our beautiful, tree-lined brick streets and discover why Old Town has become a beloved family tradition for over 30 years.

Old Town is the perfect destination for an afternoon or night of fun with friends and family. Mine for gold at Black Market Minerals, stroll through one-of-kind stores, catch a magic show at the Great Magic Hall, test your fears at Mortem Manor, try a classic game of Skee-Ball at Happy Days Family Amusement Center or relax with your favorite cocktail while enjoying free live entertainment on Trophy Row Stage.

Old Town is more than your average shopping experience.  We are host to weekly events including America’s longest running weekly car show and cruise every Saturday.  Step back in time and experience a car show like no other with hundreds of classic cars followed by our Saturday Nite Classic Car Cruise starting at 8:30 pm.

We invite you to enjoy the simple pleasures of classic American fun.

6. Shopping, Shopping and More Shopping

Don’t waste your time in the parks shopping for souvenirs! Take a park break day and make a day of shopping, eating and enjoying at Disney Springs!  

No trip to Kissimmee would be complete without a visit to Disney Springs complex which boasts numerous restaurants, cinemas, an indoor interactive theme park and some world class shopping to boot! Anchored by the largest Disney store in the world selling everything from the latest Disney costumes to home wares and souvenirs, you will find many specialized stores in Disney Springs so it’s well worth the trip.               

Website: https://www.disneysprings.com/?CMP=OKC-wdw_TA_415

7. Boggy Creek Airboat Rides

Uniquely the best airboat tour in Florida for 25 years! Cruise the swamps by day, sunset or night on an airboat with an expert who knows wetlands like the back of their hand. See wildlife including gators, exotic birds & turtles in plentiful measure. Visit the Native American Village: Deeply rooted appreciation for their Native American heritage is brought to life for guests through the traditional stories & techniques such as cooking, tool making, weapons and more.View the gator pond for an up-close & personal view of Florida’s favorite reptiles. GO MINING! Infinite possibilities of finding precious gems & rare fossils in our 70 foot mine. You will feel like a true miner discovering various gems stones, shells, shark or alligator teeth, fossils & more! Rent family friendly all-terrain bicycles & explore our historic park with opportunities to view wildlife. Stop at the old swamp shack & take a fun family photo or try our scrumptious restaurant with an unforgettable lakeside view

Phone: 407-344-9550

Address: 2001 E Southport Rd, Kissimmee, FL 34746

8. The Disney Wilderness Preserve

At The Disney Wilderness Preserve, nature offers you a front-row seat to conservation at its best.

The Nature Conservancy’s 11,500-acre Disney Wilderness Preserve near Kissimmee stands as a testament not only to Disney’s love of nature, but also to the power of cooperation, perseverance and innovative thinking. Perhaps most significant, the preserve has become a national model for sustainable development and state-of-the-art conservation management.

Home to more than 1,000 species of plants and animals, The Disney Wilderness Preserve is an essential part of the Everglades ecosystem and contains 3,500 acres of restored wetlands that act as nature’s “sponges,” capturing rain, filtering out nutrients and replenishing our groundwater. Admission is free but donations are accepted. This is NOT a Disney owned property.

Hours: 9 a.m.–4:30 p.m. November–March: Open daily, including weekends April–October: open Monday-Friday, closed weekends 

Address: 2700 Scrub Jay Trail, Poinciana, FL 34759

Phone: 407-935-0002

9. The Florida Coasts

Disney World is located within around an hour’s drive of both of Florida’s coastlines. A trip to the sea can provide much needed rest and relaxation after a hard few days at the parks! Each “beach resort” has its own attractions.  

Cocoa Beach: This is the closest beach to Kissimmee and is located along the Space coast so it is ideal to tie in with a trip to The Kennedy Space Center. A laid back atmosphere, an excellent range of restaurants and shops and the historic Cocoa Beach Pier make for an enjoyable day trip.

Clearwater Beach: Pristine white sand beaches and crystal clear water is the order of the day at Clearwater! You can enjoy a range of water sports and cruise experiences including a dolphin encounter or simply soak up the warm sunshine!

St. Petersburg Beach: There is a wide range of museums, art galleries and shops all within close range of St Pete’s Beach as well as the sun, sea and sand as standard! If you get a chance, visit Spinners Restaurant which is located on the top (12th) floor of the Grand Plaza Hotel and revolves a full 360 degrees over the course of nearly 2 hours. An amazing view not to be missed! Many of the beaches in the area have nightlife to rival the daytime activities and it is well worth staying on “after dark” to experience all these resorts have to offer.

10. ESPN Wide World of Sports

More than 200 events take place each year at the ESPN Wide World of Sports Complex. With an unparalleled roster of facilities and partners, you can watch athletes committed to taking sports and competition to the next level!

ESPN Wide World Of Sports Fun Kissimmee Activity for Villa Vacationers

Something magical occurs when ESPN innovation combines with the guest service of Walt Disney World® Resort. Since 1997, ESPN Wide World of Sports Complex has seen sports dreams come true for athletes and fans of all ages. 

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