Villas 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

In two weeks

In one month

In two months

Villas in Kissimmee

A covered patio area with wicker furniture, a glass table, and a view of a swimming pool.

A residential area with multiple two-story houses, a curved road, and a body of water in the background.

A hotel room with two beds, a ceiling fan, a nightstand with a lamp, a framed quote on the wall, and a door with a picture frame.

A modern living room with a flat-screen TV, a ceiling fan, a sliding glass door to a balcony, and a brown sofa with yellow cushions.

1. Enchanting 4BR Villa / Family Vacation Home Near Disney

Kissimmee

$95

$379 total

includes taxes & fees

Oct 22 - Oct 23

A modern kitchen with wooden cabinets, stainless steel appliances, and a central island.

A hot tub area with a pool, surrounded by palm trees and a clear sky.

A basketball court with a blue surface, surrounded by palm trees and a building with a red roof in the background.

2. 8 Mi to Disney: Villa w/ Screened Pool & Lanai

Kissimmee

$149

$412 total

includes taxes & fees

Oct 21 - Oct 22

A two-story house with a garage, a covered entryway, and a well-maintained lawn.

An outdoor patio with a glass-top table and wicker chairs, beige walls, and a door leading to the interior.

A dining area with a glass table, chairs, and a kitchen in the background.

A modern kitchen with granite countertops, stainless steel appliances, and wooden cabinets.

3. 261 Lasso Drive 6bed

Kissimmee

$622

$1,448 total

includes taxes & fees

Nov 13 - Nov 14

A modern kitchen with white cabinets, stainless steel appliances, and a red rug.

A fountain with multiple water jets, surrounded by a well-manicured lawn and palm trees.

4. Emerald Garden - Resort - 15 Min to Disney - Pets

Kissimmee

An outdoor lounge area with multiple seating options, ceiling fans, and large windows offering views of palm trees and a beach.

A spacious dining area with long tables and chairs, large windows, and a modern ceiling design.

5. Upstay Modern Solara Retreat w Games Room & Pool

Kissimmee

$127

$359 total

includes taxes & fees

Oct 18 - Oct 19

A two-story house with a front porch, a mailbox, and a well-maintained garden with various plants and a palm tree.

A kitchen with granite countertops, a dishwasher, a sink, and a pendant light.

A living room with a sofa, coffee table, dining table with chairs, a TV, and artwork on the walls.

A modern living room with a flat-screen TV, a dining area with chairs, a kitchen with white cabinets, and a staircase leading to another floor.

6. Upstay Modern 3BR Townhome With Pool Near Disney

Kissimmee

$93

$275 total

includes taxes & fees

Nov 4 - Nov 5

A covered outdoor seating area with sofas and chairs, large windows, and a ceiling fan.

A spacious conference room with a long table, multiple chairs, and large windows.

A modern kitchen with a built-in oven, microwave, and dishwasher. There is a large island with a sink and a seating area in the background.

A gym with treadmills, weight machines, and free weights.

7. Solara Resort Home With Private Pool Near Disney

Kissimmee

$93

$320 total

includes taxes & fees

Oct 25 - Oct 26

A water park with a large pool, palm trees, and a view of a lake.

A modern living room with a sofa, a coffee table, a TV on a wall, and a staircase.

A patio area with a round wooden table and chairs, a swimming pool, and a view of buildings in the background.

A modern hotel room with a large bed, a dresser, a television, and a window with curtains.

8. Upstay Modern Home Near Disney With Pool

Kissimmee

$133

$365 total

includes taxes & fees

Oct 19 - Oct 20

A two-story building with a red-tiled roof, a central entrance with a clock, and a palm tree in the foreground.

A spacious lobby with a large seating area, a reception desk, and a view of the outdoors through large windows.

9. Spacious 4BR Family Townhouseprivate Pool & BBQ

Bellavida

$148

$382 total

includes taxes & fees

Nov 2 - Nov 3

A two-story house with a front porch, palm trees, and a well-maintained garden.

A hammock between palm trees on a sandy beach, with a pool and chairs in the background.

An aerial view of a resort with multiple swimming pools, a water park, and a parking area.

A modern kitchen with a central island, a dining area with a white table and blue chairs, and a large sliding glass door leading to an outdoor patio.

10. Upstay Resort Home w Private Pool Near Disney

Kissimmee

$138

$371 total

includes taxes & fees

Oct 18 - Oct 19

11. Rustic Hideaway - Great Location + Pet Friendly!

Windermere

$144

$590 total

includes taxes & fees

Oct 18 - Oct 19

A row of townhouses with green awnings, a curved pathway, and well-maintained landscaping.

A living room with a black leather sofa, a coffee table, a ceiling fan, and a painting on the wall.

A bedroom with a large bed, a ceiling fan, a dresser, and a painting on the wall.

A pool area with a pergola overhead, lounge chairs, and a view of the pool.

12. Family Vacation Home Near Disney w Pool & Spa

Orlando

$94

$375 total

includes taxes & fees

Oct 18 - Oct 19

13. Family Townhome Near Disney w Pool & Resort Access

Orlando

$105

$387 total

includes taxes & fees

Oct 25 - Oct 26

A two-story residential building with a stone facade, multiple windows, and a well-maintained garden.

A residential building with a stone facade, a black metal gate, and a glass door with a metal handle.

A dining area with a wooden table set for six, surrounded by chairs, in a modern kitchen with wooden cabinets and a built-in oven.

A bathroom with a shower, toilet, and sink.

14. 4 BD Townhome Close to Disney!

Orlando

$94

$375 total

includes taxes & fees

Oct 18 - Oct 19

A modern bathroom with dual sinks, a shower area, and a window providing natural light.

A chessboard set up outdoors with a pergola and lounge chairs in the background.

A swimming pool with a wooden pergola overhead, surrounded by tropical plants and a clear sky.

15. Family Disney Getaway With Pool, Spa and Billiards

Orlando

$94

$375 total

includes taxes & fees

Oct 18 - Oct 19

A hotel room with a bed, a dresser, a painting, and a wall-mounted light fixture.

A spacious living area with a black sectional sofa, a dining table with chairs, and a kitchen in the background.

A dining area with a wooden table set for four, chairs, and a ceiling fan.

16. Family Townhome Near Disney With Pool & Billiards

Orlando

$105

$387 total

includes taxes & fees

Nov 1 - Nov 2

A neatly made bed in a room with a large window and a framed picture on the wall.

A modern bathroom with a double sink vanity, a large mirror, and a window with a view of greenery.

A dining area with a wooden table set for four, flanked by chairs, a chandelier, and a wall-mounted painting.

A modern kitchen with stainless steel appliances, wooden cabinets, and a dining area with a table set for four.

17. Family Vacation Home Near Disney With Resort Pool

Orlando

$94

$375 total

includes taxes & fees

Oct 18 - Oct 19

See more properties

Top neighborhoods in Kissimmee

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

A golf course with sand bunkers, a water hazard, and a clubhouse in the background.

A large body of water surrounded by green vegetation and trees under a partly cloudy sky.

A white bird flying over a body of water with dense green foliage in the background.

A waterfront hotel with a prominent tower and multiple buildings along the shore.

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. Vacation 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.

See properties

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

A yellow vintage car driving down a brick-paved street lined with a black metal fence and green benches.

A lighthouse by a calm lake, surrounded by trees and a grassy area.

A green-roofed building with a covered porch, surrounded by trees and a well-maintained lawn.

A castle-like structure with the words "Medieval Times" on the top.

Historic Downtown Kissimmee

Historic Downtown Kissimmee captures Florida's past with its stunning 1890s courthouse and Victorian storefronts 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.

See properties

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

A tree with hanging moss and green leaves against a clear blue sky.

A city skyline reflected in a calm lake with modern buildings and trees along the shore.

A palm tree with a brown trunk and red foliage, surrounded by green leaves and red flowers.

Orlando skyline with fireworks, theme park rides, and a castle.

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 vacation rentals ranging from cozy condos to luxury villas. After exhilarating theme park days, this quiet residential haven provides a peaceful retreat. Dining options are limited within the neighborhood, 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.

See properties

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

An aerial view of a resort with multiple buildings, a lake, and golf courses.

A sunset over a calm lake with a pier and reeds in the foreground.

A sunset over a calm body of water with a silhouette of trees in the background.

A sunset over a lake with a boat and a forested shoreline.

Orange Lake

Orange Lake revolves around vacation vibes with the massive Orange Lake Resort at its center. Championship golf courses, sparkling pools, and family-friendly recreation areas keep visitors entertained without leaving the neighborhood. 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. Vacation villas and timeshare units dominate the accommodation scene, offering spacious digs with full kitchens and multiple bedrooms for families.

See properties

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

Lake Berkley

Kissimmee's Lake Berkley neighborhood offers attractions including beach near Lake Berkley.

See properties

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

A golf course with sand bunkers, trees, and a flagstick.

Mystic Dunes Golf Club

7.8/10 (4,134 reviews)

You might want to play some rounds at Mystic Dunes Golf Club, located 2 mi (3.3 km) from central Four Corners. If Mystic Dunes Golf Club doesn't quite scratch your golfing itch, Orange Lake Golf, and Reunion Resort Golf Course are also nearby.

See properties

A water park with a pool, palm trees, and a statue of a horse.

Kissimmee Lakefront Park

8.4/10 (2,921 reviews)

Kissimmee Lakefront Park is worth a pic or two when discovering Historic Downtown Kissimmee.

See properties

Three heraldic shields on a wall covered in ivy.

Medieval Times

8.0/10 (3,178 reviews)

Medieval Times is 3.5 mi (5.6 km) from central Kissimmee, why not stop by during your stay. It's also full of great shops and restaurants, so you can spend the afternoon having a wander. If you want to experience more of the culture Kissimmee has to offer, head to 192 Flea Market, Give Kids the World Village, and Lake Buena Vista Factory Stores.

See properties

Silver Spurs Arena

7.8/10 (3,021 reviews)

You can catch an event at Silver Spurs Arena, located 2.3 mi (3.7 km) from central Kissimmee. If you think Silver Spurs Arena is cool, you also might like Osceola Heritage Park and The Ice Factory of Central Florida, both located nearby.

See properties

A landscape with a clear blue sky, a large body of water with lily pads, and a distant horizon.

Boggy Creek Airboat Rides

7.8/10 (463 reviews)

Why not give yourself a treat with a trip to Boggy Creek Airboat Rides, one of the family attractions located 11 mi (17.6 km) from central Kissimmee. If you'd also like to explore some of the parks in Kissimmee, head to Lakefront Park.

See properties

Vintage cars parked on grass under a cloudy sky.

Osceola Heritage Park

7.8/10 (3,681 reviews)

You can catch an event at Osceola Heritage Park, located 2.4 mi (3.9 km) from central Kissimmee. Want to stretch your legs some more? Head to Kissimmee Lakefront Park and Brinson Park, both nearby.

See properties

Reunion Resort Golf Course

7.6/10 (3,040 reviews)

You might want to play some rounds at Reunion Resort Golf Course, located 11.1 mi (17.9 km) from central Kissimmee. If Reunion Resort Golf Course doesn't quite scratch your golfing itch, ChampionsGate Golf Club, and Mystic Dunes Golf Club are also nearby.

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 shops. Families visiting Kissimmee will enjoy attractions like Old Town. In the surrounding area, popular sights include Disney Springs™ and Orlando Vineland Premium Outlets.

Keep exploring

More ways to book

Book Villas in Kissimmee on Hotels.com