House holiday 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!

4.99 out of 5 average rating, 159 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!

A private pool area is surrounded by a screened enclosure, featuring a well-shaped pool and a jetted hot tub. Lounge chairs are positioned nearby, with a grassy area beyond. The evening sky displays hues of pink, creating a serene atmosphere, enhanced by string lights that illuminate the space.

4.92 out of 5 average rating, 214 reviews

*Luxe Disney Home* Priv Pool/Spa- 6BR Sleeps 15

JUST ADDED! (Check out our other reviews) New Construction!!! 3000ft2! Welcome to our luxury 6-BR private pool home near Disney World, Universal Studios, and Sea World! With 8 beds, it sleeps 15 people comfortably. Enjoy the private heated pool, hot tub, and game room with ping pong, cornhole, and arcade. Located in Veranda Palms community, you also have access to a large pool, clubhouse, gym, and splash pad. Perfect for large families or groups seeking a memorable Orlando stay. Book now!

4.97 out of 5 average rating, 188 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!

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!

Summerville Resort is a new and prestigious collection of town-home villas just 5 miles from the entrance to Walt Disney World! Be among the first to stay in this contemporary vacation rental with pristine finishes & amenities. No need to wait in line to shower here; each of the 4 bedrooms has its own attached bath. After a day exploring the parks, come home to indulgence at the Resort, which features a community hot tub, heated pool, fitness center, playground, and a sleek Clubhouse.

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!

Welcome to our magical vacation home in Orlando, just minutes from Universal Studios, located on International Dr, less than 2 miles from SeaWorld! Featuring 12 themed bedrooms inspired by beloved movies like Harry Potter, Frozen, and Aladdin, and a Tiana-themed kitchen, every detail is designed to delight guests of all ages. With 21 beds, it’s perfect for families and groups. Enjoy a prime location, unique decor, and ultimate comfort for an unforgettable stay. All themed environments.

4.96 out of 5 average rating, 119 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!

4.86 out of 5 average rating, 101 reviews

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

Welcome to this modern 12-bedroom, 11.5-bath home—perfect for your next family getaway! Comfortably sleeping up to 32 guests, this centrally located retreat is just 15 minutes from the Disney parks. Enjoy fantastic amenities including a private pool and spa, a home theater for movie nights, and a fun-filled game room. With plenty of space and entertainment for all ages, it’s the ideal spot for family reunions, group vacations, and special get togethers.

A welcoming living area features a large screen TV mounted on the wall above a stylish cabinet. Comfortable seating options include a brown leather couch and a fabric armchair. Natural light filters through the sheer curtains, while a green plant adds a touch of nature to the space.

4.9 out of 5 average rating, 138 reviews

Wonderfull home near Disney & FREE Waterpark 2421

STOREY LAKE RESORT. A premier vacation community just 8 miles from Disney and minutes from Universal & SeaWorld, this community is surrounded by restaurants, shops, and top malls. Only 30 minutes from Orlando Airport, it offers easy access to everything you need. Book your stay for 7 days or more and unlock an exclusive 5% discount ! Stay 30+ nights and save 10% (Discount will apply on selected stays) Reserve now! we would love to be your host!

4.97 out of 5 average rating, 101 reviews

12BR Disney Beach house 34 ppl Pool Theater Arcade

Stay near Walt Disney World in this luxury 12-bedroom Orlando vacation home, perfect for large families and groups. Enjoy a private pool and hot tub, movie theater, Transformers game room, poker table, outdoor kitchen, and themed Minions, Moana, Scooby-Doo, Inside Out, and Lilo & Stitch bedrooms. With multiple king suites and space to relax, play, and reconnect, it’s the perfect Disney-area getaway for reunions and unforgettable group vacations.

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

Welcome to Villa Resort Club! Lovely 4BR/2.5BA for 8 with screened private pool and game room. Full kitchen, workspace, washer/dryer, parking, WiFi. Pet-friendly. Minutes from Disney. Quiet, comfy home base! ¡Bienvenidos a Villa Resort Club! Casa 4 hab/2.5 baños para 8, piscina con enclosure y juegos. Cocina completa, trabajo, lavadora/secadora, parking, WiFi. Mascotas OK. Minutos de Disney. ¡Tranquila y cómoda!

4.88 out of 5 average rating, 177 reviews

A bright living area features large glass windows that provide views of the outdoors. A white sofa is positioned near two teal chairs, complemented by a light rug. A coffee table and an accent table add functionality to the space, with warm lighting from stylish fixtures above.

4.79 out of 5 average rating, 232 reviews

4418 Le Reve 4BDRM townhouse close to Disney

Our townhouse can accommodate up to 8 people, with 4 bedrooms and 3.5 bathrooms and has a small jacuzzi for you to relax after a long day at the parks or outlets. Our property is only 10 miles to Disney’s theme parks and 15 miles to Universal Studios and major Outlets. It has many restaurants and supermarkets (Walmart, Target, Sam’s Club) nearby. Walmart Superstore is just 0.2 miles or 5 minutes walk.

Popular amenities for Kissimmee house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.99 out of 5 average rating, 136 reviews

Disney Villa w/ Priv Pool & Lake View~12 Mi parks!

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

A modern living area features a comfortable sofa in neutral tones alongside two vibrant orange chairs. A round glass coffee table is positioned in front of the sofa, while a large television is mounted on a wooden accent wall. Floor-to-ceiling windows allow natural light to fill the space.

4.92 out of 5 average rating, 132 reviews

Modern 4bdr Storey Lake w/themed rooms near disney

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, 256 reviews

Windsor Orlando Private Arcades,Theater,Pool-Spa

An aerial view presents the resort-style community with a turquoise pool surrounded by lush greenery and tropical landscaping. A bright children's room features cheerful wall art and themed bedding. A cozy living area shows comfortable seating under tall windows, while a private patio reveals outdoor seating overlooking a spacious green lawn.

4.94 out of 5 average rating, 118 reviews

Spacious 4BR/3.5BA Home. Private Balcony & Patio!

5.0 out of 5 average rating, 23 reviews

4BR Disney & Universal Themed Villa Reunion Resort

4.82 out of 5 average rating, 60 reviews

Disney's Pool House

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

Weekly house rentals

4.88 out of 5 average rating, 8 reviews

6 miles from Disney ! Private pool ! 4 bedrooms

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, 87 reviews

Luxury Home w/ Pool & 6 Beds near Disney

4.96 out of 5 average rating, 25 reviews

Lakeview Themed Home w/ Pool & Theater Near Disney

4.71 out of 5 average rating, 28 reviews

Luxury 7BR/8BA Retreat Near Attractions w/ Pool

5.0 out of 5 average rating, 5 reviews

Home in Davenport

Remodeled 5BR | Pool, Theater & Themed Rooms

4.82 out of 5 average rating, 11 reviews

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

5.0 out of 5 average rating, 8 reviews

Luxury Disney Villa | Game Room | Pool Heat

4.95 out of 5 average rating, 19 reviews

Montego Bay Retreat | 15 Min to Disney

Private house rentals

4.89 out of 5 average rating, 55 reviews

2319 7BD Beautiful Family Home with Private Cinema

A two-story home with a tiled roof and extensive outdoor living space is showcased. The property features a swimming pool surrounded by palm trees and a fenced patio area. Lush landscaping and open green spaces are visible, enhancing the inviting surroundings.

4.83 out of 5 average rating, 36 reviews

Luxury Retreat at Reunion Resort

The exterior of a two-story house features Mediterranean-style architecture with a terracotta roof and balconies. A private pool area, surrounded by a brick patio, is visible in one image. Another image shows a themed bedroom with bunk beds and decor inspired by popular movies.

4.83 out of 5 average rating, 89 reviews

Reunion Resort Theme Home, Pool, Arcade, Golf View

An open living area features a modern sectional sofa facing a large television mounted above a sleek fireplace. Pendant lighting hangs from the ceiling, and a stylish wooden ladder leans against the wall. The space is complemented by natural light from the adjacent kitchen.

4.93 out of 5 average rating, 54 reviews

Magic Village Resort Gated Community Disney World

4.98 out of 5 average rating, 91 reviews

15 Min to Disney•Cozy Home Heated Pool & Game Room

Home in Davenport

Palms & Pixie Dust Villa Pool

New place to stay

Home in Buenaventura Lakes

Comfy Home with Hot Tub at Kissimmee/Orlando area!

4.95 out of 5 average rating, 73 reviews

An inviting private pool area is shown within a screened enclosure, featuring clear blue water and a rounded pool shape. Comfortable outdoor seating is placed beside the pool, with lush greenery decoratively lining the wall, enhancing the tranquil space.