House vacation rentals in Kissimmee

4.9 out of 5 average rating, 126 reviews

Encanto at Emerald Island-Pool House by Disney

POOL HEATER OPTION!! Make some memories at this unique and family-friendly place. A guarded Resort- neighborhood awaits! As you enter this magical place you will fall in love with the unique landscaping full of palm trees surrounding the neighborhood. This secluded place has everything you need! 5 star location, security, private pool, and also a clubhouse with many activities for the young ones. You will be next to restaurants, shopping and more. Only 3 miles aways from Disney's exit & parks!

FamilyLocationCheckout

The villa features a modern exterior with a sloped roof and a two-car garage. Palm trees are landscaped around the front yard, which is bordered by well-maintained grass. A clear blue sky provides a bright backdrop to the welcoming entrance.

4.88 out of 5 average rating, 281 reviews

3 bedroom Villa in Kissimmee

The villa is in a residential area within a 5-min drive to local amenities including, a pharmacy, 3 supermarkets and 2 gas stations. The property is between 15 - 40 mins drive from Disney, Epic Universe, SeaWorld, Gatorland & Universal Studios. Orlando International Airport is only about 17 mins drive away. Osceola Heritage Park, the home of the world’s largest collector car auction is only 4 mins drive from the villa. The Florida Turnpike that runs through Miami is 6 mins from the property.

ValueLocationBathroom

4.99 out of 5 average rating, 158 reviews

10 Minutes to Disney | Heated Pool, Arcade, Kings

🏡 Tucked inside a gated community near Kissimmee’s top attractions, this bright, themed home is made for memorable family getaways. Enjoy friendly competition in the game room, unwind in the heated private pool (available upon request), or relax on the covered patio beneath the Florida sun. Just 11 minutes to Fun Spot America, 11 minutes to Old Town, and 12 minutes to Disney World, it’s the perfect home base for your Florida adventure. Book now and start creating unforgettable memories!

FamilyLocationPool

4.95 out of 5 average rating, 106 reviews

A single-story home showcases a well-maintained front lawn with lush green grass. The house features a welcoming entrance with a central door, flanked by large windows. A driveway leads to a two-car garage with decorative doors, while a fenced yard adds privacy.

Home in Davenport

Sunny-All-Day Pool Vacation Home

Welcome to our Sunny 3-Bedroom Retreat! This inviting home features 3 spacious bedrooms, a south-facing pool for all-day sun, and a private fenced yard. Enjoy the bright living space, modern kitchen, and outdoor oasis with comfortable seating. Conveniently located near local attractions, dining, and shopping. Additional amenities include high-speed Wi-Fi, smart TV, air conditioning, washer and dryer, and free parking. Book now for a perfect getaway! **No parties ($500 fine) and no smoking**

LocationValueKitchen

4.97 out of 5 average rating, 142 reviews

Lakeview Luxury Home 9BD|9BA Sleeps20/Near Disney

We have the largest driveway in the entire resort. 6000 SQ ft gated luxury home near Disney.Enjoy the sunset from our pool!Sonoma Resort is a perfect location, only 5 minutes to the LOOP,one of Florida`s finest shopping and entertainment destinations, in the resort it self, you`ll discover a amazing clubhouse with a gym and a large community pool.This 9 bedroom/9 bathroom home is well equipped to accommodate up to 20 guests. Our driveway will accommodate up to 8cars.Come enjoy your vacay Home!

LocationFamilyParking

Home in Buenaventura Lakes

A modern two-story house is showcased, featuring a bright exterior and a spacious driveway. Lush green grass surrounds the property, while palm trees add a tropical touch. Large windows on the upper level allow for ample natural light, highlighting the clean lines of the architecture.

Villa Resort Club

VILLA LUJOSA - BARRIO SÚPER HERMOSO POOL HEATER HOUSE - Diviértete con toda la familia en este alojamiento con estilo moderno , te encantará el área de picnic frente de la casa , el área de juegos y piscina con calentador , un espacioso lugar de hierba artificial para jugar tus niños y en una zona muy trankila cerca de los parques de Disney y del aereopuerto MCO . TE ENCANTARÁ LA CASA Local utility or county personnel may access exterior areas for maintenance without prior notice.

ValueLocationSleep quality

4.88 out of 5 average rating, 177 reviews

4.97 out of 5 average rating, 187 reviews

Near Disney | Heated Pool, King Bed, Arcade

✨ Family-Friendly Retreat Near Disney in a gated, safe & quiet community 🏰 Loved by guests for its cleanliness, comfort, and fast communication. 🏊‍♂️ Unwind after park days in your private HEATED pool 🍔 Enjoy the outdoor BBQ for easy family meals 🎮 Have fun in the upgraded game room with pool table, ping pong, foosball, and a retro arcade ⭐ Hosted by 3 experienced Superhosts known for quick, reliable replies. A perfect balance of fun and relaxation. Book now as dates fill fast!

LocationValueAir conditioning

4.91 out of 5 average rating, 282 reviews

Cozy House with Pool. Kissimmee/Orlando

Welcome to Your Kissimmee Getaway! 🏠 Enjoy a relaxing stay in beautiful Kissimmee, conveniently located near Orlando’s world-famous theme parks, restaurants, shopping, and entertainment -Pet friendly home🐾( pet fees may apply) Please make sure to include your pet(s) when making your reservation so any applicable fees can be reflected in your booking. -No parties or events of any kind -No smoking inside the property Please respect the home, neighbors, and community during the stay

ValueFamilyBackyard

A vibrant games room is equipped with various arcade machines, including SpongeBob Racing. A massage chair is positioned nearby, while a theater room features plush seating. An outdoor space highlights a screened-in pool area surrounded by palm trees, visible through large windows.

4.99 out of 5 average rating, 255 reviews

Windsor Orlando Private Arcades,Theater,Pool-Spa

Orlando, Disney, Arcade, Movie Theater, Massage Chair, Pool, Hot Tub, 2 King Beds, Kids Bunk Bed, Kissimmee. Upgraded games room IN the private home, theater for evenings home and your private lanai with pool and hot tub. Choose from including Pump It Up dance, Sponge Bob Racing, NASCAR racing, Legends 3, Pac-Man's Arcade Party, an 80-inch TV, and an Xbox 360. Watch your favorite movies on the 92-Inch projection screen, surround sound, and stadium style seating.

FamilyValueCondition

A private outdoor area features a pool with a spa, surrounded by a spacious deck. A basketball hoop is positioned nearby. A large inflatable swan floats in the water, while a hammock provides a cozy spot for relaxation. Lush greenery frames the scene under a colorful sky.

4.94 out of 5 average rating, 167 reviews

Luxury Encore Pool Spa Pets Game Rm Theater Gym

Amazing Brand New Modern Luxurious Home at Encore Resort Reunion. PET-FRIENDLY & Minutes to all Theme Parks. BRAND NEW HOME. Private Pool & Spa / Game Room / Movie Theater / Gym / Massage Chair / Fireplace / PS5 / Board Games & Much More. Embrace the extraordinary and book your stay at our home, where luxury, entertainment come together for an unforgettable vacation experience. ** Please review the rules before booking. Waterpark access is not included. **

LocationValueTV

4.96 out of 5 average rating, 118 reviews

A unique sleeping area features a round bed designed to resemble a giant clam shell. Vibrant murals depicting underwater scenes adorn the walls, complementing the ocean-themed decor. Soft curtains in shades of green flow down from the ceiling, adding color to the tranquil space.

Home in Davenport

Royal Retreat Disney Themed Pool Home, Arcade, Theater

Welcome to The Royal Retreat. Located just 10 miles away from the entrance of WDW, our rental is the perfect place to stay for your Disney vacation. Our 5 star home features 8 themed bedrooms and 5 bathrooms, a fully-equipped kitchen, private heated pool, private arcade, home theater & BBQ! Free Pool heat & the 1st tank of propane for the BBQ are included. Booking with us includes full access to the Champions Gate Clubhouse, Oasis Resort and Retreat Club!

ValueFamilyAmenities

4.99 out of 5 average rating, 181 reviews

Private Epcot-Themed Near Disney

Hello, my globetrotters! Welcome to your global getaway, where you will embark on a new experience in different countries from each room of the house. Countries featured at our home are Italy, Mexico, Paris, China, Japan, and Morocco Located in a quiet neighborhood, our vibrant house is equipped with fast wifi and comfortable beds. Perfect for families eager to travel without a passport. Step inside and let your family's adventure begin! 🌍✨

FamilyLocationIndoor spaces

Popular amenities for Kissimmee house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.86 out of 5 average rating, 100 reviews

Modern 12 BR 11.5 BA, Sleeps 32, 15 mins to Disney

ValueFamilyHot tub

The image displays the Summerville Resort sign, highlighting its proximity to Disney. A comfortable bedroom is shown, featuring two spacious beds and colorful wall art. An inviting patio area with outdoor seating is visible, alongside a community pool surrounded by lounge chairs and palm trees.

4.86 out of 5 average rating, 125 reviews

Comfy Family Villa|5min->Disney!

LocationValuePets

5.0 out of 5 average rating, 3 reviews

Magical Stay Near Disney

LocationFamilyKitchen

5.0 out of 5 average rating, 23 reviews

4BR Disney & Universal Themed Villa Reunion Resort

LocationFamilyComfort

4.82 out of 5 average rating, 60 reviews

Disney's Pool House

ValueFamilyKitchen

4.86 out of 5 average rating, 14 reviews

2026 Themed NEW 08 Bedrooms At Solara Resort

FamilyLocationBathroom

A private heated pool is surrounded by a screened patio, with two lounge chairs positioned nearby. A small dining area with a table and chairs is visible, enhancing the relaxing outdoor space. The backdrop features the home’s elegant design and a cozy seating area beyond.

4.91 out of 5 average rating, 74 reviews

Disney/Universal Villa w/ Pool

FamilyLocationDecor

4.8 out of 5 average rating, 10 reviews

Sleeps 13·Pvt Pool+Spa·Game Room·Clubhouse

FamilyLocationCleanliness

House rentals with free parking

4.93 out of 5 average rating, 71 reviews

Stylish 12BR 11.5BA, Sleeps 33, 15 mins to Disney

ValueFamilyAccuracy

A single-story home is presented with a light tan exterior and a welcoming front yard. Lush greenery surrounds the property, featuring neatly trimmed shrubs and palm trees. A paved driveway leads to a two-car garage with solar panels on the roof, providing an energy-efficient touch.

4.99 out of 5 average rating, 82 reviews

Family Vacay with Pool near WDW!

FamilyValueOutdoor spaces

4.98 out of 5 average rating, 58 reviews

A vibrant collage of themed spaces showcases the enchanting variety within the home. Featured are a luxurious bedroom with a grand bed, a playful winter-themed room, a themed home theater, and a pool area with a spa set against colorful lighting.

Home in Orlando

12BR Disney Luxury Retreat - Pool, Theater & Fun!

LocationFamilyWifi

The spacious living room features double-height ceilings with stylish pendant lighting. A large sectional sofa is arranged around a wall-mounted TV and an electric fireplace. Large sliding glass doors lead to a patio space, offering views of the outdoor area furnished with a dining set.

5.0 out of 5 average rating, 19 reviews

Magic Village new 4 suites BBQ 8 min Disney (7589)

LocationFamilyParks

An open-concept living area features a large sectional sofa in soft gray, arranged around a circular coffee table. A contemporary fireplace is integrated into the wall, providing a focal point. Glass doors lead to the outdoor pool area, enhancing natural light throughout the space.

4.98 out of 5 average rating, 86 reviews

Luxury Home w/ Pool & 6 Beds near Disney

LocationFamilyHospitality

A private screened pool area is presented, featuring a spacious pool with a gentle blue hue. Loungers line one side, inviting relaxation. The surrounding yard is visible beyond the screened enclosure, creating a serene outdoor space.

4.7 out of 5 average rating, 60 reviews

15BD Sonoma Resort DreamHouse Near Disney (SR2610)

LocationFamilyAccess

A well-maintained single-story home is framed by lush greenery and palm trees, with a clean walkway leading to a welcoming front porch. The house features a two-car garage, and the landscaped yard presents a neat appearance with evenly trimmed bushes.

4.97 out of 5 average rating, 29 reviews

Delightful private pool home near Disney!

LocationFamilyAccuracy

A game room features a billiard table surrounded by colorful murals depicting architectural landmarks. Entertainment options include two wall-mounted televisions displaying scenic views and a vintage arcade game. Ambient overhead lighting enhances the playful atmosphere, creating an inviting space for relaxation and enjoyment.

4.89 out of 5 average rating, 46 reviews

Main Street USA in Luxury Reunion Home

ValueLocationSleep quality

House rentals with a hot tub

4.81 out of 5 average rating, 187 reviews

Minutes to Disney: Resort Home w/ Private Pool,

FamilyValueHeating

The image showcases a vibrant game room filled with arcade machines and billiards, accompanied by a resort-style pool featuring a lazy river and splash park. The private heated pool and spa are visible in the outdoor area, surrounded by palm trees and comfortable lounge seating.

4.95 out of 5 average rating, 241 reviews

DISNEY 🎉 Game rm, heated Pool, Spa, Lazy rvr, BBQ

LocationValueLong stay

An outdoor space features a screened-in pool area with a clear blue pool and spa. Comfortable lounge chairs are positioned beside the pool, with a dining table set beside them. Lush greenery is visible beyond the fenced yard, creating a private and relaxing environment.

4.79 out of 5 average rating, 136 reviews

The Real Florida Whispering Oaks

FamilyLocationQuiet

The single-story home features a welcoming façade with a brick accent. Lush palm trees frame the entrance, which is highlighted by large windows allowing natural light to filter inside. A manicured lawn and a decorative white planter add charm to the front yard.

4.95 out of 5 average rating, 259 reviews

Disney Orlando vacation home with private pool 2

FamilyValueLaundry

4.98 out of 5 average rating, 133 reviews

Dream Vacation | Sleeps 18 | Themed Arcade & Rooms

ValueLocationKitchen

4.83 out of 5 average rating, 133 reviews

OI2836 - 4BR house with private pool in kissimmee

ValueLocationLong stay

4.96 out of 5 average rating, 74 reviews

Brand New 12br/33 ppl-Pool/Arcade/Theatre

ValueFamilyCondition

A private cinema room features plush reclining seats arranged for viewing a large screen. Blue and purple lights create a vibrant atmosphere, while a bar area with stools is visible in the background. The screen displays a scenic landscape, enhancing the entertainment experience.