Trip Ideas for Your Kissimmee Vacation

Find inspiration for your trip to Central Florida with articles, lists and itineraries featuring things to do and places to explore.

Located minutes from Orlando, Kissimmee is your gateway to Central Florida’s must-do adventures: thrilling airboat rides, vibrant local festivals, family-friendly theme parks, and all the shopping and dining options you could dream of. The hard part is deciding where to start, but that’s where we come in.

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11 - 20 of 23 results

11 - 20 of 23 results

Girl sitting in a rocket ship bed at a Kissimmee vacation home.

Themed Vacation Rentals in Kissimmee

With game rooms, bedrooms, and in-house theaters, these vacation home rentals in Central Florida make for a magical place to stay.

A man unloads his car in front of a vacation home as his family enters the home. — Plan your next stay in Kissimmee at one of our many vacation homes.

Where to Stay in Kissimmee

Kissimmee offers lodging to fit any need, from 4-star resorts to motels to vacation rentals. Learn more about all the ways you can stay in Central Florida!

Wooden boardwalk winding through a peaceful cypress swamp surrounded by tall trees at Gatorland near Kissimmee, Florida. — Explore the natural side of Gatorland along its scenic boardwalk, where towering cypress trees and still waters showcase the beauty of Florida’s wetlands.

Outdoor Adventure & Indoor Leisure in Kissimmee

Discover how Florida Instagrammer Angela Jones and her husband, Matthew Lewis, embraced the best of Kissimmee—from serene vacation-home downtime to standout moments in nature, dining, and after-dark fun. Their trip showcases just how effortlessly a Kissimmee getaway can balance relaxation with adventure.

Woman relaxing on a massage table wrapped in a white towel, surrounded by soft lighting, flowers, and candles in a tranquil spa setting. — Unwind and recharge with a soothing spa experience in Kissimmee.

Babymoon in Kissimmee

Calling all moms-to-be! Plan the ultimate babymoon in Kissimmee with this three-day itinerary filled with relaxation, pampering, and gentle adventures. From spa treatments to scenic nature spots, discover why Kissimmee is the perfect destination for a blissful pre-baby escape.

Kimberly J. Brown smiles in surprise as two baby goats hop onto the table while she paints during a painting with goats experience at Alaska Farms. — A little goat interference never hurt the creative process! Kimberly J. Brown gets a surprise assist from some curious kids at Alaska Farms.

A Touch of Kissimmee Magic with Kimberly J. Brown

Being normal is vastly overrated, and so is a basic vacation. Actress Kimberly J. Brown casts a spell of fun over Kissimmee with castles, goats, and Halloween-ready adventures.

Three pizza's on a wooden table beside a jar full of salt and a glass full of juice. — Explore endless pizza opportunities in Central Florida / @kndvg

10 of the Best Pizza Places in Kissimmee

Find your perfect slice at these top spots for pizza across the Kissimmee area.

A family enjoys a sunny afternoon at a Kissimmee vacation home pool, with a father and son jumping in while two women relax on inflatable floats. — Making a splash! Enjoy poolside fun and relaxation at a spacious Kissimmee vacation home.

Kissimmee’s Most Enticing Vacation Home Pools

Here in Kissimmee, your dream vacation home comes with its very own splash zone! Forget cramped hotel pools and crowded water parks, these seven spectacular homes offer private pools that turn any day into a tropical getaway.

Modern two-story vacation home in Kissimmee at sunset, with warm exterior lighting, a spacious driveway, and an upper-level balcony. — A golden-hour welcome. This is what arriving in the Vacation Home Capital of the World feels like.

Top 5 Most Unique Amenities at The Bear’s Den Resort Orlando

Whether you’re visiting Central Florida to escape the cold weather or planning your next vacation with the whole family, The Bear’s Den Resort Orlando is the ideal spot for luxury accommodations.

A beautiful vacation home rental in Kissimmee — A Kissimmee Vacation Home is your home away from home

How to Pick a Vacation Home Rental in Kissimmee

At a Glance

Spacious Vacation Homes for Every Group: Choose from thousands of vacation home rentals in Kissimmee, Florida, ranging from two-b

The exterior of The One by Magical Vacation Homes features a large horseshoe paved driveway, a large entryway, and a couple balconies. — The One at Magical Vacation Homes

Unforgettable Vacation Homes for Your Next Florida Getaway

Explore exceptional homes from Magical Vacation Homes, where luxury, unique amenities, and affordability come together for an unforgettable vacation experience in Kissimmee.