Villa holiday rentals in Kissimmee

A screened-in pool area features inviting turquoise water, complemented by a sunken hot tub. Outdoor furniture, including a dining set and lounge chairs, is arranged beneath soft, ambient lighting. A basketball hoop is positioned near the pool, with lush greenery visible beyond the enclosure.

5 out of 5 average rating, 119 reviews

Villa Sol Peaceful private Pool/Hot tub Home

Close to all major attractions, and airport sits this private villa. It has a little something for all ages! Your family can play in the pool or relax in the hot tub. Enjoy fun game nights with a cabinet full of games, or play a game of basketball, pickleball, or tennis right outside our pool. Fun on the playground or enjoy the clubhouse gym. All of your needs for the beach trips or the ball games. All of your baby's needs are covered as well. Ask about Stroller and cart rentals. We have it all

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.

4.82 out of 5 average rating, 267 reviews

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 home cinema room features a large flat-screen TV displaying a film scene. The walls are painted blue and red, and plush seating is arranged in front of the screen. Decor includes framed posters and a Mickey Mouse silhouette, creating an engaging entertainment space.

4.86 out of 5 average rating, 424 reviews

OMG! Disney Area, Movie Theater, Game Room & Pool!

"Guest favorite" - This home is in the top 10% of eligible listings based on ratings, reviews, and reliability. Comfort and Space in an Elegant home with a lot of amenities, 4Bed/3Bath. Private Movie Theater, Game Room, Pool and Themed Rooms. A well equipped Kitchen, Laundry, 3 parking spaces, WiFi, Smart TVs. Located at Crystal Cove Resort, a gated community, close to Disney. Few minutes to Walmart, Target, Sams Club, Publix, Outlets, Restaurants, Disney, Sea World, OCCC, EPIC and Universal.

An inviting outdoor pool area is featured, surrounded by a protective screen enclosure. The pool water is a clear turquoise, reflecting the evening sky. Comfortable seating is arranged nearby, alongside a BBQ grill. Soft lighting enhances the tranquil atmosphere.

4.94 out of 5 average rating, 123 reviews

❤NEW Gorgeous 5br/3.5ba|POOL| Game ROOM| Disney

Nestled in the peaceful 4 Corners community close to Disney & top rated attractions, Target, Publix & restaurants. Newly updated, inviting and modern 2 level, 5 bedroom/3.5 bath with comfortable luxurious beds! Equipped with a private pool (heat for an extra fee), game room, BBQ grill & free Nespresso. Out back is a mini golf putting green, corn hole and fire pit for the family to gather around under the warm vibe of string lights. A place for the family to retreat, relax, reset and have fun!

4.99 out of 5 average rating, 130 reviews

A private pool features a spacious deck and a whimsical swan float. Adjacent is a covered dining area with views of landscaped grounds. Inside, a kids’ tube slide and superhero-themed decor are seen, along with a game area featuring a billiards table and arcade console.

Villa in Osceola County

*Private Resort Oasis: Golf-Front, Pool/Spa/Cinema

The perfect balance of STYLISH DESIGN, LUXURIOUS COMFORT, & ENDLESS ENTERTAINMENT, beautifully situated with stunning views in the sprawling 3.5 square mile Reunion Resort. You will have your own private pool, spillover spa, STAR WARS cinema-game room with pinball, classic arcade games, and karaoke, MARVEL kids room with tube slide and double bunks, the latest Xbox Series S, a sprawling 2000 ft2 pool deck, fire pit, and even a HARRY POTTER cupboard hidden under the stairs, minutes to Disney.

A private pool deck is enclosed with mesh, providing a clear view of the surrounding greenery. Two comfortable loungers are arranged beside the inviting swimming pool, adorned with orange striped towels. The peaceful outdoor space is well-lit by natural sunlight.

4.87 out of 5 average rating, 119 reviews

Sunny Family Retreat ~ Peaceful Pool ~ Game Room

Unwind in this sunny 4 Bedroom 3 Bath house nestled in a serene family-friendly neighborhood. This prime location allows quick access to nearby restaurants and shops while being just a short drive away from Disney World, Universal, Legoland, and more. The lively pool deck and entertaining game room offer various relaxing and fun amenities. ✔ 4 Comfortable Bedrooms ✔ 3 Large Bathrooms ✔ Fully Equipped Kitchen ✔ Swimming Pool ✔ Game Room ✔ Six TVs w/ Roku ✔ Sun Loungers Learn more below!

4.97 out of 5 average rating, 114 reviews

15min2parks! 9B, Pool/Spa/Theatre/Karaoke/Vgames

Sleeps 20, this luxury 9 bedroom will check all the boxes and more! Located 4 miles from Disney in the popular Storey Lake community, you will be within minutes of any of the theme parks without all of the crazy traffic on the other side of WDW. No detail has been overlooked...Smart home features, to upgraded hot water heater, to Sleep Number Beds with luxury linens, Houz of Bluz has it all! Designed with fun, luxury and relaxation in mind. HOB IS your ultimate "Resort within a Resort"!

A large wooden dining table is surrounded by eight wooden chairs, set against a backdrop of stone-like walls with arched windows. A metal chandelier hangs overhead, while a decorative knight statue stands in the corner, adding character to the atmospheric space.

4.87 out of 5 average rating, 540 reviews

Magical 5-Bedroom Villa Near Universal's Wizarding

Ensure an enchanted holiday in Orlando. Inspired by everyone’s favorite castle, this magical home provides an immersive experience with 5 bedrooms, common room with large screen TV with Netflix & Nintendo Switch, dining hall, fully equipped kitchen, swimming pool, patio with grill and laundry room. Located in a quiet residential community, 10 miles to the Wizarding World of Harry Potter, 6 miles to Disney, 5 miles from Celebration, 4 miles from Old Town and 18 miles from downtown Orlando.

The outdoor living space features a cozy seating area surrounding a fire pit and a large dining table. A private swimming pool is illuminated in blue, with sun loungers lining the edge. The backyard is framed by palm trees, creating a tropical ambiance at dusk.

5 out of 5 average rating, 110 reviews

8 BR Villa, Private Pool, Theater, Min to Disney!

Big and Beautiful Themed Vacation Villa in premium gated Encore Resort. Spacious main floor for entertaining large groups - bring the family and friends! Enjoy the included resort amenities a minute's walk from the front door. Or, relax around your private pool and custom summer kitchen. Enjoy big-screen movies and sound in the theater in premium loungers, and play classic arcade games! 10-15 min from Disney, one of the closest villa resorts. Tons of shopping and dining nearby!

A recreational game room is presented, featuring an air hockey table and a pool table centered in the space. Two gaming chairs are positioned near flat-screen monitors on the wall. Colorful LED lighting creates an engaging atmosphere in the room.

4.96 out of 5 average rating, 145 reviews

Mr. Clean's Cozy Disney Home w/ Luxury Finishes

• Newest house in the #1 resort community in the Disney Area, Windsor Hills • ALL Mattresses & Pillows are encased in waterproof SANITIZED covers. • 2 FUN children themed rooms (Star Wars, & Frozen) • Onsite, driveway parking for 3 vehicles • FREE pool heat + BBQ with ALL rentals • Fully equipped + stocked kitchen; including Keurig machine • Self check-in with digital lock • Super FAST Wi-Fi wireless internet speed at +1,000 Mbps!! • Property is managed directly by owner

4.91 out of 5 average rating, 240 reviews

House by the Mouse: Something for Everyone!

Welcome to our completely remodeled solar four bedroom, three bath villa, less then four miles to Disney World, and only a short drive to Universal, Sea World, Lego Land, and other local attractions. Designed themed bedrooms include Harry Potter, Mickey and Minnie Mouse, Star Wars, and a romantic master bedroom that allows you to relax in comfort. The pool, spa, and the entire villa is just for you, no need to share with anyone else, so kick back and enjoy!

A private screened patio features a heated swimming pool and a Jacuzzi surrounded by a spacious deck. Outdoor seating is provided, with a dining table and lounge chairs positioned for relaxation. Sunlight glimmers on the water, creating a serene atmosphere.

4.91 out of 5 average rating, 114 reviews

Gorgeous 3 bed, 2 bath villa w/ pool and jacuzzi

Gorgeous 3 bedroom, 2-bathroom villa set on a 1/4 acre of land, with our own screened, private, heated swimming pool & Jacuzzi, and high speed internet. Situated in a quiet residential community on the sought after Sunridge Woods in Davenport, only 9 miles from Disney. Please note smoking or parties are NOT allowed in house premises. No pool heater available during May through October. **You also MUST be 21 or older to rent this property**

Popular amenities for villa rentals in Kissimmee

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Private villa rentals

4.96 out of 5 average rating, 51 reviews

EPIC 10 min Disney Villa~Mini Golf~Arcade~Theater

Superhost

The exterior of the house is shown, featuring a light grey facade and dark double front doors. The driveway is lined with bricks, complementing the neatly trimmed grass and shrubs. Palm trees and a blue sky with scattered clouds enhance the inviting appearance of the property.

4.9 out of 5 average rating, 60 reviews

4 BED 3 BATH LAKE VIEW & POOL/SPA (sleeps 8) 4681

The image captures a view from the pool, showcasing the villa's large glass windows and covered outdoor seating area. Loungers are positioned around the pool, offering ample space for relaxation. The sparkling water reflects the modern architecture above, framed by a screened enclosure.

4.94 out of 5 average rating, 93 reviews

Private Pool & Free Heat - Close to Disney!

4.84 out of 5 average rating, 49 reviews

A heated swimming pool is enclosed by screen protection, providing a clear view of the water. Surrounding greenery adds privacy, while a patio area features sun loungers and a grill for outdoor dining. Sunlight reflects off the water, creating a bright atmosphere.

Villa

South facing Modern villa in quiet gated estate

An open-concept living area showcases a modern beige sofa accompanied by a stylish area rug. Bright natural light filters through large sliding doors leading to the pool area. The adjoining kitchen features high stools at a breakfast bar, providing a casual dining option.

4.95 out of 5 average rating, 65 reviews

Luxury Villa w/ Hot Tub-Grill-Private Heated Pool

The pool deck features a spacious swimming pool surrounded by a screened enclosure. Four sun loungers are positioned nearby, accompanied by a cantilevered umbrella for shade. The tranquil conservation area is visible in the background, providing a peaceful setting.

4.98 out of 5 average rating, 47 reviews

Beautiful 4 bedrooms with South/West facing pool

The open living area features high ceilings, large windows, and a cozy seating arrangement with a sofa and armchairs. Decorative wall art and plants enhance the design, while an elegant dining space and modern kitchen are visible in the background.

4.99 out of 5 average rating, 82 reviews

The Balmoral Manor: Luxurious & Bright 5BR Oasis

4.99 out of 5 average rating, 96 reviews

Amazing Villa near DisneyWorld FREE heated-pool

Luxury villa rentals

A spacious themed room is depicted, featuring an imaginative design with a dark, cosmic ceiling. The room includes a large blue slide and a staircase, adjacent to cozy bean bag chairs for seating. Colorful space-themed murals enhance the playful atmosphere.

4.98 out of 5 average rating, 120 reviews

4mi to Disney | Games | Private Pool

The outdoor pool area features a spacious swimming pool with a spa, surrounded by paved decking. Lounge chairs are arranged around the pool, while a colorful float and a hammock invite relaxation. Palm trees line the background against a vibrant sky.

4.94 out of 5 average rating, 50 reviews

Luxury 8BD Theater Game Pool Golf Firepit - Disney

A vibrant themed room showcases a blue slide and bunk beds, enhancing playfulness. Adjacent, a cozy bedroom features rich curtains and themed decor. A home theater room displays a large projector screen and comfortable seating. The private pool area is highlighted with seating, a projector, and colorful inflatables.

4.97 out of 5 average rating, 116 reviews

Pickleball PoolsideMovies |WalkToWaterpark| Arcade

4.95 out of 5 average rating, 65 reviews

A spacious pool area features a large, inviting swimming pool surrounded by a screened enclosure. Poolside loungers are positioned under large umbrellas, while an outdoor dining table is visible in the background, enhancing the relaxing atmosphere.

Villa in Orlando

Villa w/ Pool + Cinema & Game Room | Intl Drive

A lively game room is showcased, featuring bright blue flooring and vibrant wall colors of pink and green. Retro arcade machines line one side, while a play area includes a two-story playhouse and colorful seating, providing a fun retreat for guests of all ages.

4.96 out of 5 average rating, 104 reviews

Epic Disney Villa • Hidden Arcade & Playroom!

A game room features striking themed decor, with large flat-screen TVs and seating. The private pool area showcases a serene swimming pool surrounded by a screen enclosure, highlighted by comfortable lounge furniture. A cozy outdoor seating area is visible, offering a relaxing view.

4.95 out of 5 average rating, 157 reviews

"Disney Serenity": Luxe 8BR Villa/ Privacy/ Pool

Superhost

A themed game room features futuristic decor with a space-inspired mural depicting spacecraft. Capsule-like sleeping areas with glowing blue accents are positioned along one wall. A large table with integrated gaming elements occupies the center, while comfortable seating is present for relaxation.

4.84 out of 5 average rating, 105 reviews

Brand New Storey Lake 10 Bedroom Villa with Pool &

A private screened lanai features an inviting pool and hot tub surrounded by lounge chairs. A game room is seen with a pool table, seating areas, and colorful wall decor. Bedrooms are present, including a nursery with themed decor and shared spaces for relaxation.

4.92 out of 5 average rating, 120 reviews

Storey Lake•9BR•Fire Pit•Pool•Hot Tub•Game•EV

Villa rentals with a pool

4.91 out of 5 average rating, 56 reviews

Luxury Villa 6BR/6.5 BA Near Disney/Sleeps16/Pool

5 out of 5 average rating, 25 reviews

7BR Disney Villa Escape Room+ Pool +Cinema+Game Rm

A private pool area is framed by a screen enclosure, with views of the lake in the background. Clear blue skies and fluffy clouds reflect in the water. Surrounding greenery adds a natural touch, creating a serene outdoor space ideal for relaxation.

4.95 out of 5 average rating, 79 reviews

Lakefront Private Pool Villa, 10min to Disney

The image showcases a vibrant gaming area with a glowing dance floor, a relaxing outdoor space featuring lounge chairs near the pool, a themed sleeping area with bunk beds, and a foosball table positioned in a cozy game room filled with colorful lighting.

4.96 out of 5 average rating, 55 reviews

6 BD/4.5 Ba Sleeps 14! Lily Pad At Solterra Resort

A vibrant gaming room is highlighted with space-themed murals and wall art. A pool table sits centrally, flanked by a modern lighting fixture. The room includes two large television screens and multiple gaming chairs for comfortable play.

4.96 out of 5 average rating, 47 reviews

Private Family Villa w/ Pool, Game Room, Resort

A private pool and hot tub are surrounded by a screened enclosure, showcasing crystal-clear water. Comfortable lounge chairs are positioned along the edge of the pool deck, with large glass doors offering views of the adjoining living spaces. The sky displays soft colors of twilight.

4.93 out of 5 average rating, 42 reviews

Rest & Relax at Sunset by the Lake with SPA!

An outdoor dining area is presented under a screened enclosure, featuring a wooden table with seating for eight. A movie screen displays a scene from Disney Moana. The surrounding pool area includes lounge chairs, with vibrant colors reflecting in the evening sky.

5 out of 5 average rating, 23 reviews

Luxe Windsor Hills w/Poolside Theatre & GameRoom