Holiday rentals with a pool in Kissimmee

4.83 out of 5 average rating, 320 reviews

A private movie theater features a 150-inch screen displaying a Disney image. Black walls and hardwood flooring create a modern atmosphere. Comfortable reclining seats with cup holders are arranged for a cinematic experience, ensuring a cozy and immersive viewing environment.

Villa in Kissimmee

150 Inch 4K Movie Theater Pool & Spa sleeps 16

"Just 3 miles from Disney up to 16 guests! Unwind in the pool & jacuzzi. A private cutting-edge Movie Theater, featuring a 150-inch screen, 4K projector, and immersive surround sound. Relive your favorite movie moments like never before! Stream on Roku, game on PS5, and enjoy high-speed Wi-Fi for endless fun. The well-equipped kitchen is perfect for large families and with 6 bedrooms and 4 en-suite baths, privacy is guaranteed. A Star Wars and a Disney-themed rooms so the kids will feel at home.

A lush outdoor water complex showcases a winding lazy river surrounded by palm trees and landscaped greenery. Lounge chairs are positioned alongside the water, providing ample space for relaxation. In the background, a clubhouse and scenic waterfront can be seen under a bright blue sky.

4.96 out of 5 average rating, 176 reviews

Disney 5BR • Private Pool Free Heat • Pet Friendly

Welcome to this gem near all major attractions: Disney (5 miles), SeaWorld (7 miles), Universal (12 miles), Convention Center (9 miles), and Airport (20 miles). Nearby are outlets, restaurants, and supermarkets. This luxurious home features 5 bedrooms, 4 bathrooms, a private heated pool/spa, fully equipped kitchen, laundry, and free stroller, playpen, and highchair. Resort amenities include a water complex, lazy river, bar, fitness center, mini golf, kayaking, and more! Pets friendly & welcome!

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!

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!

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.

4.97 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

4.97 out of 5 average rating, 266 reviews

Near Disney • 4BR • Perfect for Families

Guests love this home! It’s usually fully booked! Location is incredible! Heart our property and save it to your wishlist! IMPORTANT: parking available only for one car. 9 min - Hollywood Studios (6 mi) 10 min - Animal Kingdom (8 mi) 12 min - Disney Springs (5 mi) 15 min - Magic Kingdom (10 mi) Just 3’ from Walmart, Publix, and a big strip mall full of restaurants, grocery stores, and shopping! Experienced host, 10 years on Airbnb!

Superhost

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.

Home in Buenaventura Lakes

Villa Resort Club

Welcome to Villa Resort Club! Lovely 4BR/2.5BA for 8 with a screened private pool and game room. Full kitchen, workspace, washer/dryer, parking, and Wi-Fi. Pet-friendly. Minutes from Disney. Quiet, comfy home base! Welcome to Villa Resort Club! House with 4 bedrooms/2.5 bathrooms for 8, pool with enclosure and games. Full kitchen, workspace, washer/dryer, parking, Wi-Fi. Pets OK. Minutes from Disney. Quiet and comfortable!

4.88 out of 5 average rating, 177 reviews

Superhost

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.

4.95 out of 5 average rating, 109 reviews

A wooden pier extends towards a gazebo, surrounded by calm waters reflecting shades of orange and purple from a vibrant sunset. The structure is bordered by wooden railings, enhancing the serene atmosphere of the setting.

Hotel room in Orlando

Modern Rock Star Suite

Located at the gates of Walt Disney World, this modern Rockstar Suite offers easy access to area theme parks, and entertainment venues in the surrounding area, including Walt Disney World, Universal Studios, Sea-world, Legoland + Restaurants, Shopping and many more. Wonderful lake / pool view with sunrise. Enjoy!

Popular amenities for Kissimmee rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.86 out of 5 average rating, 101 reviews

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

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

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

4.99 out of 5 average rating, 136 reviews

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

4.93 out of 5 average rating, 149 reviews

Entire Modern Home near Disney • Pool & Game Room

4.97 out of 5 average rating, 101 reviews

12BR Disney Beach house 34 ppl Pool Theater Arcade

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!

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!

Apartment rentals with a pool

A cozy bedroom features a spacious bed adorned with light-colored linens, complemented by decorative pillows. The living area offers comfortable seating arranged around a flat-screen TV, while soft natural light filters through sheer curtains. The Mickey-themed room presents vibrant wall art and two plush beds with coordinating bedding.

4.89 out of 5 average rating, 172 reviews

207_ Sparkle Apartment Close to Disney Free Waterp

A master bedroom features a spacious bed with a white quilted coverlet, accented by a blue tufted headboard. Two bedside tables with lamps provide soft lighting. A ceiling fan hangs above, while light-colored walls and flooring enhance the room's bright atmosphere.

4.85 out of 5 average rating, 123 reviews

Disney Retreat

4.84 out of 5 average rating, 108 reviews

Green View Condo near Disney

A balcony is depicted with four cushioned chairs arranged around a small table. The railing provides a view of a serene landscape with water and greenery in the background. Light fabric drapes softly from the sliding door frame.

4.9 out of 5 average rating, 165 reviews

Modern Condo with Lake View Near Disney 3151

The image features a spacious bedroom with two separate sleeping areas. One side includes a yellow-accented bed, while the other is themed with a starry wall mural. Light-colored tile flooring enhances the bright atmosphere, complemented by ample natural light from the nearby window.

4.82 out of 5 average rating, 228 reviews

Resort-Style Condo with free Waterpark!

Aerial view of a resort-style pool area features winding lazy river and miniature golf course set amidst lush greenery and palm trees. Bright blue water complements the surrounding landscaping, with lounge chairs and umbrellas positioned for relaxation. A community building is visible in the background.

4.97 out of 5 average rating, 123 reviews

Top Floor, 3bd, FREE Clubhouse, Kids Room, Disney

A bright living space is showcased, featuring a circular dining table set with four plates. A comfortable teal seating area is arranged against the wall, complemented by a nature-inspired wall art piece and greenery. Large glass doors provide a view of the outdoors and invite natural light.

4.87 out of 5 average rating, 148 reviews

Stylish Condo 20 mins to Disney/King Bed

A modern kitchen space is highlighted, featuring stainless steel appliances, white cabinetry, and a large island with seating for three. A dining area with a round table accommodates four, illuminated by soft overhead lighting. Neutral tones and textured tiles create a clean and open atmosphere.

4.94 out of 5 average rating, 249 reviews

BRAND NEW CONDO- 2 BR 2 Bath-Great location!

Other holiday rentals with a pool

4.85 out of 5 average rating, 321 reviews

6 miles from Disney ! Private pool

4.95 out of 5 average rating, 60 reviews

Flat in Orlando

Epic stay at Vista Cay!

5.0 out of 5 average rating, 46 reviews

Disney Theme Rooms | Private Pool | Storey Lake

4.93 out of 5 average rating, 15 reviews

Villa in Kissimmee

6BR Home w/ Priv Pool Near Disney Gated Resort

5.0 out of 5 average rating, 12 reviews

5 Bd/ 3.5 Ba Sleeps 16! Cumbrian Lakes (4645 CL)

4.82 out of 5 average rating, 17 reviews

Orlando Dream Escape | Private Pool | Disney

Superhost

5.0 out of 5 average rating, 3 reviews

Themed Stay with PS5 + Poolside TV | W. Westside