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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21 - 28 of 28 results

21 - 28 of 28 results

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.

Outdoor lawn at Gaylord Palms Resort & Convention Center at sunset. — Enjoy the artfully crafted outdoor spaces when you stay at Gaylord Palms Resort

4 Reasons to Meet in Kissimmee - The Big, Bold Heart of Florida

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.

Family eating a meal together next to a pool at their vacation home in Kissimmee, Florida. — Find the perfect home-away-from-home with Jeeves Florida Vacation Rentals.

Kissimmee’s Affordable Vacation Homes

Planning an affordable Central Florida vacation? No problem! Vacation homes don’t have to break the bank and can often offer more value than a hotel.

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

Luxurious Vacation Home Rentals in Kissimmee

When it comes to vacation home rentals, you may think you’ve seen it all, but have you ever seen a vacation rental with its own indoor basketball court? Elevate your expectations with the crème de la crème of Central Florida's vacation home rentals!

Two men and a woman walk the water front in Celebration. — Enjoy your next meeting or event in sunny Florida.

9 Hotels in Kissimmee for Hosting Your Next Meeting or Event

Where business meets innovation — and a bit of fun! Discover top meeting hotels in Kissimmee with flexible spaces, modern amenities, and unique venues for your next event.