Guest Houses in Kissimmee

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Next weekend
14 Aug - 16 Aug
In two weeks
21 Aug - 23 Aug
In one month
4 Sept - 6 Sept
In two months
2 Oct - 4 Oct

Guest Houses in Kissimmee

Hallway

Enchanted Fantasy

Enchanted Fantasy
2.0 star property
Kissimmee
6.8 out of 10, (13 reviews)
The price is £86
includes taxes & fees
10 Aug - 11 Aug
Enchanted Fantasy
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
See more propertiesforward arrow

Top neighbourhoods in Kissimmee

A golf course with bunkers, water hazards, and a large lake.

Reunion

Reunion is a golfer's paradise just outside Orlando with three legendary courses designed by Palmer, Nicklaus, and Watson. After teeing off, splash around at the resort water park or lounge by multiple pools scattered throughout this upscale community. When you're ready for theme parks, Disney and Universal are just 20 minutes away. Holiday homes with private pools dominate the accommodation scene, giving families plenty of space to spread out. Resort restaurants serve upscale meals, though you'll need a car to explore beyond the community's Mediterranean-style grounds. The quiet, manicured setting feels worlds away from Orlando's tourist bustle.

A street sign reading "Welcome to Kissimmee, Florida" with a mural of horses on a building.

Historic Downtown Kissimmee

Historic City centre Kissimmee captures Florida's past with its stunning 1890s courthouse and Victorian shopfronts along Broadway Street. Stroll under heritage oaks while exploring unique shops filled with antiques and local crafts. Weekend farmers markets and street festivals bring the area to life, celebrating the region's cowboy heritage and diverse community. The lakefront area offers peaceful fishing spots and scenic views of Lake Tohopekaliga. A mix of Southern comfort food, Cuban cafes, and barbecue joints fuel your adventures. Most attractions are within the walkable six-block historic core, making it easy to explore this charming slice of old Florida.

An aerial view of a residential area with numerous houses, roads, and several lakes.

Windsor Hills

Windsor Hills offers a perfect home base for Disney adventures with resort-style amenities just minutes from major attractions. Families love the gated communities with pools, game rooms, and themed holiday rentals ranging from cosy condos to luxury villas. After exhilarating theme park days, this quiet residential haven provides a peaceful retreat. Dining options are limited within the area, so most visitors drive 10-15 minutes to nearby tourist areas for meals. Rental cars are essential for getting around, though rideshares are readily available. The Mediterranean-style properties with private pools make Windsor Hills ideal for groups seeking comfort between park visits.

A sunset over a marshy landscape with a wooden pier extending into the water.

Orange Lake

Orange Lake revolves around holiday vibes with the massive Orange Lake Resort at its centre. Championship golf courses, sparkling pools, and family-friendly recreation areas keep visitors entertained without leaving the area. Disney World is just minutes away, making this Four Corners spot perfect for theme park enthusiasts who want amenities galore after a day of adventure. Resort shuttles and rideshares make getting to attractions easy since public transit is limited. Dining options stick mostly to resort restaurants and nearby chains. Holiday villas and timeshare units dominate the accommodation scene, offering spacious digs with full kitchens and multiple bedrooms for families.

A lakeside town with a prominent white building, lush greenery, and a distant city skyline.

Lake Berkley

Kissimmee's Lake Berkley neighbourhood offers attractions, including beach near Lake Berkley.

Top landmarks in Kissimmee

A theme park entrance with a Ferris wheel and a roller coaster.

Old Town

8.6/10 (14,011 reviews)
Why not give yourself a treat with a trip to Old Town, one of the most popular family attractions located 7.1 mi (11.4 km) from central Kissimmee? It's also full of great shops and restaurants, so you can spend the afternoon having a wander. If you have fun at Old Town, you'll love Fun Spot America, just a short walk away.
See properties

Learn more about Kissimmee

Immerse yourself in the magic of theme parks, from Disney's enchanted kingdoms to Universal's movie-inspired thrills. Airboat through gator-filled swamps or soar above it all in a hot air balloon for unforgettable Florida adventures.

See all hotels in Kissimmee
A large, historic building with a tower, reflecting on a calm lake with lily pads, surrounded by trees and a sunset sky.

Find out more about Kissimmee

People go to Kissimmee for fun-filled days at Disney's Animal Kingdom® Theme Park, as well as many other top attractions like Walt Disney World® Resort. This sunny city is also known for its festivals and restaurants. Families visiting Kissimmee will enjoy attractions like Old Town. While you're here, make time to enjoy other sights such as Reunion Resort Golf Course.

Keep exploring