Villas in Kissimmee

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Villas in Kissimmee

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 sofa, coffee table, dining table, and kitchen area with appliances.

1. Upstay Modern 3BR Townhome With Pool Near Disney

Kissimmee

$81

$261 total

includes taxes & fees

Nov 18 - Nov 19

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

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

Kissimmee

$114

$413 total

includes taxes & fees

Oct 26 - Oct 27

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

A residential area with a swimming pool and water slides.

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

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

3. 261 Lasso Drive 6bed

Kissimmee

$622

$1,448 total

includes taxes & fees

Nov 13 - Nov 14

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.

4. Upstay Modern Solara Retreat w Games Room & Pool

Kissimmee

$133

$365 total

includes taxes & fees

Nov 1 - Nov 2

A resort with a large pool area, water slides, and a view of surrounding residential buildings.

A modern kitchen with white cabinets, a stainless steel refrigerator, and a microwave.

A modern kitchen with white cabinets, stainless steel appliances, a central island with bar stools, and a contemporary light fixture.

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

Kissimmee

$95

$379 total

includes taxes & fees

Oct 27 - Oct 28

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

A water park with multiple slides and a wave pool.

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.

6. Solara Resort Home With Private Pool Near Disney

Kissimmee

$93

$320 total

includes taxes & fees

Oct 26 - Oct 27

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

A covered outdoor swimming pool with a pergola, lounge chairs, and a hot tub.

7. Spacious 4BR Family Townhouseprivate Pool & BBQ

Bellavida

$115

$345 total

includes taxes & fees

Nov 18 - Nov 19

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

A modern kitchen with dark cabinets, stainless steel appliances, and a central island with bar stools.

A modern kitchen with a central island, built-in appliances, and a green accent wall.

A multi-story residential building with a symmetrical facade, multiple windows, and a well-maintained front yard with various plants.

8. Upstay Modern Home Near Disney With Pool

Kissimmee

$133

$365 total

includes taxes & fees

Oct 27 - Oct 28

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.

9. Upstay Resort Home w Private Pool Near Disney

Kissimmee

$147

$381 total

includes taxes & fees

Oct 27 - Oct 28

A modern bathroom with two sinks, wooden cabinets, and a glass shower enclosure.

A bedroom with a bay window, a chair, a small table with a plant, and a bed.

A spacious living area with a dining table, sofas, and a ceiling fan.

A modern kitchen with stainless steel appliances, wooden cabinets, and a window with blinds.

10. Family Vacation Home Near Disney With Resort Pool

Orlando

$105

$387 total

includes taxes & fees

Nov 1 - Nov 2

A staircase with white railings and wooden steps leading to an upper floor.

11. Rustic Hideaway - Great Location + Pet Friendly!

Windermere

$144

$590 total

includes taxes & fees

Oct 26 - Oct 27

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 modern living room with a sectional sofa, a coffee table, and a dining area with wooden furniture.

A spacious living area with a sofa, a dining table set for four, and a ceiling fan.

12. 4 BD Townhome Close to Disney!

Orlando

$94

$375 total

includes taxes & fees

Oct 26 - Oct 27

A two-story house with a paved driveway and a lawn.

A modern kitchen with stainless steel appliances, a granite island, and a built-in oven.

A spacious living area with a wooden rocking chair, a white console table, and a dining area in the background.

A modern living room with a sofa, coffee table, and a bookshelf filled with books.

13. The Farm House - Great Location + Pet Friendly!

Windermere

$160

$567 total

includes taxes & fees

Oct 26 - Oct 27

14. Family Townhome Near Disney w Pool & Resort Access

Orlando

$95

$376 total

includes taxes & fees

Oct 28 - Oct 29

A two-story residential building with a brick driveway, palm trees, and manicured landscaping.

A bedroom with a bed, nightstand, lamp, ceiling fan, and large windows.

A swimming pool with palm trees, a water slide, and a building with an arched entrance.

A hot tub in a room with a checkered floor, a glass door leading to another room, and a tiled wall.

15. Spacious Townhome Near Disney, Free Parking

Regal Palms

$78

$299 total

includes taxes & fees

Oct 29 - Oct 30

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

A modern bathroom with a walk-in shower, a bathtub, and a vanity with a sink.

A hotel room with a large bed, two bedside lamps, a chair, a desk, and a window with a view of greenery.

16. Family Townhome Near Disney With Pool & Billiards

Orlando

$105

$387 total

includes taxes & fees

Oct 28 - Oct 29

Outdoor wicker seating areas with cushions, a pergola structure, and a large planter.

A spacious living room with a black leather sofa, a coffee table, and a dining area with wooden furniture.

A modern living room with leather sofas, a coffee table, and a flat-screen TV.

17. Family Vacation Home Near Disney w Pool & Spa

Orlando

$94

$375 total

includes taxes & fees

Oct 28 - Oct 29

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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Give Kids the World Village

7.8/10 (1,311 reviews)

Why not give yourself a treat with a trip to Give Kids the World Village, one of the family attractions located 3.1 mi (5 km) from central Kissimmee. If you have fun at Give Kids the World Village, you'll love Old Town and Fun Spot America, both located nearby.

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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.

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