House vacation rentals in Kissimmee

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

House for rent next to DISNEY Windsor at Westside features a grand 10,000 square foot resort clubhouse FREE FOR GUEST USE filled with amenities for active families that include multiple sports courts, children's playgrounds as well as a resort-style swimming pool and lazy river with splash water park. Tu Casa is an onsite restaurant and bar and there's even an ice cream shop to refresh yourself with some sweet treats. GAME ROOM- air hockey, basketball, themed rooms, billiards, designer bedrooms!

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!

4.94 out of 5 average rating, 108 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**

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!

4.98 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.

4.97 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. 🌴🏊

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.

Popular amenities for Kissimmee house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.83 out of 5 average rating, 133 reviews

OI2836 - 4BR house sleeps 8 with private pool

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!

4.93 out of 5 average rating, 72 reviews

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

5.0 out of 5 average rating, 23 reviews

4BR Disney & Universal Themed Villa Reunion Resort

5.0 out of 5 average rating, 21 reviews

2026 NEW 06 Bedrooms at Solara Resort/Private Pool

5.0 out of 5 average rating, 5 reviews

Home in Davenport

Remodeled 5BR | Pool, Theater & Themed Rooms

4.83 out of 5 average rating, 18 reviews

Orlando Dream Escape | Private Pool | Disney

4.88 out of 5 average rating, 8 reviews

6 miles from Disney ! Private pool ! 4 bedrooms

House rentals with free parking

4.71 out of 5 average rating, 28 reviews

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

4.86 out of 5 average rating, 83 reviews

The Denmark

4.92 out of 5 average rating, 13 reviews

15BR w/ Game Room, Themed Rooms & Pool

4.97 out of 5 average rating, 36 reviews

Spacious Home | Near Disney | Perfect for families

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!

4.98 out of 5 average rating, 42 reviews

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

The exterior of the villa features a two-story structure with a light-colored facade and a welcoming entrance. Palm trees are positioned on either side of the pathway leading to the front door, and a driveway leads toward a two-car garage.

4.86 out of 5 average rating, 29 reviews

Spectacular 7 Br, 4.5 Ba Retreat With Pool (166)

5.0 out of 5 average rating, 8 reviews

Luxury Disney Villa | Game Room | Pool Heat

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

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

4.99 out of 5 average rating, 184 reviews

An expansive outdoor pool deck is featured, surrounded by lounge seating and shaded areas. A giant outdoor chess set stands nearby, along with a view of the scenic forest and pond. A brightly decorated game area showcases themed decor and entertainment options.

Home in Four Corners

*Luxurious Paradise Mansion: Pool, Spa & Cinema

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

4.93 out of 5 average rating, 166 reviews

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

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

5.0 out of 5 average rating, 44 reviews

9BR Family Villa | Pool, Games, Spa | Near Disney