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!

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, 215 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!

The exterior view showcases a well-appointed home with a paved walkway leading to the entrance. A manicured lawn and driveway provide an inviting atmosphere. An outdoor BBQ grill overlooks a private, screened pool area, surrounded by a peaceful lake view and tropical landscaping.

4.82 out of 5 average rating, 101 reviews

5390 Vacation Sunset House Private Pool Grill

Relax in this calm, stylish and FULLY RENOVATED residential HOME. Enjoy with the whole family our PRIVATE POOL & BBQ GRILL with LAKE VIEW. Located in Kissimmee Florida, in a quiet residential neighborhood. Master Suite with view to Pool & BBQ outdoor area. 3 bedrooms, 2 bathrooms, fully equipped kitchen, 2 car garage, 3 Smart TV's and strong Wi-Fi all around the house. Have unforgettable moments at our BBQ area next to our private screened pool. Sunsets by the lake are breathtaking.

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!

4.97 out of 5 average rating, 101 reviews

An outdoor area features a private pool surrounded by a paved patio. Blue lounge chairs offer seating, while a basketball hoop stands at the pool's edge. Lush palm trees line the space, and a neighboring building is visible in the background against a clear blue sky.

Home in Four Corners

Magical 6BR at Encore Resort next to Disney - 453

Modern 3,300sf luxury home, with 6 en-suites, at world's renowned Encore Resort at Reunion. It features a movie room with PS4, a beautiful backyard, a private pool and spa, and a garage with ping-pong and foosball tables. 6 Minutes away from Super Walmart and Publix supermarket 15 Minutes away from Disney Parks 15 minutes away from Disney Springs 15 Minutes away from Premium Outlets 20 Minutes away from Universal Studios 20 Minutes away from International Drive attractions

5.0 out of 5 average rating, 4 reviews

Luxe Family Escape | Pool Oasis Near Disney

Welcome to your Luxe Family Escape near Disney! ✨ Located in one of Kissimmee’s exclusive golf communities, this home offers the perfect mix of relaxation and fun. Enjoy your private screened pool, hammock, ping pong, and charming backyard gazebo. Inside, you’ll find stylish bedrooms, a fully equipped kitchen, and comfortable living spaces. The perfect private oasis for families and groups looking to enjoy Disney, Orlando’s attractions, and a relaxing Florida getaway. 🌴🏊

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. **

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.

4.89 out of 5 average rating, 157 reviews

Private Heated Pool & BBQ Included Near Disney

Stay close to Orlando’s top attractions in this modern 4-bedroom, 3.5-bath vacation home for up to 10 guests. Enjoy your own private heated pool and built-in BBQ, both included with your stay, plus a bright open living area, full kitchen, fast Wi-Fi, laundry, and family-friendly sleeping spaces. This home is a great fit for families, extended families, and groups who want more space, privacy, and comfort than multiple hotel rooms.

4.82 out of 5 average rating, 60 reviews

Disney's Pool House

Magical family retreat in Central Florida! Just minutes from Disney, this spacious home features fun Disney-themed decor, a private screened pool, game room with pool table and air hockey, smart TVs, full kitchen, free Wi-Fi, and washer/dryer. Close to Universal, SeaWorld, CityWalk, and International Drive—perfect for families looking to relax, explore, and create unforgettable memories in the heart of all the action!

Popular amenities for Kissimmee house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A spacious living area features a large sectional sofa, paired with a round coffee table. Natural light floods in through sliding glass doors that open to the pool area. Decorative accents include coastal-themed artwork and soft lighting fixtures, enhancing the inviting ambiance.

4.84 out of 5 average rating, 150 reviews

Park Place! 7 Min from Disney, Pool, Theater

4.97 out of 5 average rating, 101 reviews

12BR Disney Beach house 34 ppl Pool Theater Arcade

4.87 out of 5 average rating, 15 reviews

2026 Themed NEW 08 Bedrooms At Solara Resort

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!

4.83 out of 5 average rating, 18 reviews

Orlando Dream Escape | Private Pool | Disney

A vibrant game room is highlighted by colorful Mario-themed wall art, featuring interactive gaming stations equipped with racing chairs. Adjacent, a home theater is presented with luxurious seating and a large screen, surrounded by atmospheric LED lighting. A resort-style pool and relaxing outdoor space are seen, complemented by poolside lounge chairs.

4.98 out of 5 average rating, 42 reviews

NEW Modern Villa Near Disney w/ Pool & Spa!

5.0 out of 5 average rating, 9 reviews

Amazing Home Near Parks w/ Pool & Spa

4.82 out of 5 average rating, 90 reviews

A screened patio showcases a crystal-clear pool and inviting spa, surrounded by comfortable lounge chairs. Sunlight reflects off the water, creating a serene ambiance. The backdrop features the house's exterior, with large windows allowing views of the interior spaces.

Home in Celebration

12BR | 11.5 BA > Sports Game Room!

House rentals with free parking

4.82 out of 5 average rating, 11 reviews

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

4.86 out of 5 average rating, 83 reviews

The Denmark

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

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, 83 reviews

Family Vacay with Pool near WDW!

4.98 out of 5 average rating, 42 reviews

*Modern Condo Resort/Pool/Spa/15 Min to Disney*

5.0 out of 5 average rating, 8 reviews

Luxury Disney Villa | Game Room | Pool Heat

4.74 out of 5 average rating, 73 reviews

Orlando Lake-House with Pool, Spa & Game Room!

4.96 out of 5 average rating, 25 reviews

Lakeview Themed Home w/ Pool & Theater Near Disney

House rentals with a hot tub

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

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

4.93 out of 5 average rating, 166 reviews

Private Pool + Spa Game Room •4m Disney •Pinball

5.0 out of 5 average rating, 126 reviews

The image features a private pool surrounded by lounge chairs, with a basketball hoop and a lush green backdrop. An entertainment area is visible in the foreground, showcasing a game table, a digital pinball machine, and a large screen for movies and games, including a fun tube slide.

Home in Four Corners

*NEW* Space Odyssey: Pool, Spa, Cinema, Games+PS5

Aerial view of the resort showcases a large pool with lounge chairs and palm trees surrounding a tranquil pond. Colorful amenities, including slides, are visible, enhancing the outdoor recreational area.

4.99 out of 5 average rating, 123 reviews

Fabulous 2BR Home With Hot tub

4.88 out of 5 average rating, 162 reviews

A vibrant superhero-themed bedroom features colorful LED lighting and playful decor. Two sets of bunk beds accommodate guests, with a children's slide providing an engaging entryway. Cozy seating areas invite relaxation, while windows allow natural light to fill the space.

Home in Four Corners

Captivating home 12 minutes from Disney world Fl

A home theater room is equipped with red stadium seating for eight, positioned toward a large screen displaying vibrant visuals. An arcade game machine is set beside the screen, with ambient blue lighting accentuating the dark walls, creating an engaging entertainment space.

4.85 out of 5 average rating, 158 reviews

Resort Home 3.5 miles to Disney with home theater