Villa holiday rentals in Kissimmee

The villa features a distinct architectural style with a terracotta roof and a landscaped front yard. Lush palm trees are positioned around the entrance, while a spacious driveway leads to a three-car garage, all set against a tranquil evening sky.

5 out of 5 average rating, 120 reviews

Villa Sol Peaceful 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, 275 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 themed game room showcases a Batman-inspired design with a bright yellow slide leading to a two-level play area. An air hockey table is positioned prominently, surrounded by stylized dark walls, creating an immersive gaming environment.

4.99 out of 5 average rating, 135 reviews

Sleeps 21|Free Pool Heat|15 min to Disney|Hot Tub

Make memories to last a lifetime in our luxurious seven-bedroom home (sleeps 21) at Orlando's premier vacation community. Enjoy your own Batman cave game room, private pool (heated at no extra charge*), and hot tub. Our 100% Five-Star rating from previous guests and our generous cancellation policy means you can book with confidence. Only 15 minutes to Disney and a short walk to a fabulous resort clubhouse with free access to a lavish pool, kids waterpark, restaurant, playground, gym, and more!

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, 426 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!

An outdoor dining area features a large, custom-built wooden table surrounded by black chairs. Blue plates and glassware are meticulously arranged for an inviting meal. A bright blue pool glimmers in the background, enclosed by a mesh screen to ensure privacy.

4.97 out of 5 average rating, 139 reviews

*Brand New!* Minutes to Disney + Free Resort!

Closest FREE resort to Disney Parks! Hibiscus Hideaway is a 6 bedroom 4 bathroom luxury villa that sleeps 14. Completely renovated in October 2022! * Kitchen is loaded & all baby gear provided. * Custom game room with A/C, LED panel lighting & ROCK CLIMBING WALL! * New Roku smart TVs & NEST tech throughout. * Outdoor space includes your own private pool, hot tub, overhead lighting, NEW BBQ grill & 10' custom-built farmhouse table to seat the whole family! Every detail has been thought of!

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

Get ready to make memories of a lifetime just over 3 miles to Disney when you stay at this newly renovated Star Wars and Lego-themed private pool villa. Located in Formosa Gardens Estates, a prestigious gated community, our home is professionally furnished with multigenerational families in mind and can comfortably sleep up to 15 guests. After a trip to the parks, enjoy a refreshing dip in the private pool and rest those tired feet in the spa (pool heat included in stays after 10 Dec 2025!).

4.99 out of 5 average rating, 132 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.

Villa in Championsgate Village

A vibrant game room displays an air hockey table and foosball station, with colorful LED lights casting an engaging glow. An adjoining indoor theater features plush seating and a large screen, while a private pool area invites relaxation, surrounded by lush greenery and floatation devices.

4.97 out of 5 average rating, 102 reviews

Pool Movies|Water Park|Movie Theater|Arcade|Themed

Enjoy our Early Bird Sale and Save! ✨ Discover an enchanting escape at Ice Saber Manor-a stunning 6 bed Villa featuring FROZEN and SPIDER-MAN rooms, 4 gorgeous master suites and endless entertainment options! Immerse yourself in cinematic wonders with a Star Wars MOVIE THEATER, belt out your favorites in the KARAOKE area or revel in our POOLSIDE THEATER! Relax in your heated POOL&SPA or enjoy our WATERPARK! Discover Disney from the comfort of this modern home nestled in a beautiful resort!

The image showcases a vibrant collage of the villa's features. The top left displays a colorful Encanto-themed bedroom with a playful bed. The top right features the modern living area with large windows and comfortable seating. The bottom left presents a private pool area, and the bottom right highlights a Mario-themed game room with arcade games.

4.98 out of 5 average rating, 124 reviews

Magical 5BR Family Vacation Villa

Professional Hosts & Guest Favorite Home! Immaculate and well equipped Stargazer Villas vacation home at Windsor Island Resort now featuring Pickleball Court! This central Florida villa has heated pool included for your family to relax in after a busy day at the parks. Family friendly, featuring Star Wars, Harry Potter, & Encanto themed bedrooms, and a new Mario World game room! Stargazer Villas provides the perfect place to create unforgettable memories with your family.

A vibrant collage highlights the Tiki Tropical Oasis. The inviting pool is surrounded by lounge chairs under umbrellas. A colorful putting green and BBQ grill add to the outdoor appeal. The interior features thematic rooms, showcasing tropical decor and immersive environments designed for family enjoyment.

4.99 out of 5 average rating, 111 reviews

OMG Private Pool Oasis! LED Lights! Mini Golf!

This is the place! Look no further for the most magical immersive dream vacay! Welcome to your own private tropical paradise oasis minutes from Disney World! In Encore Resort by Reunion (gated community) enjoy your private pool, hot tub/jacuzzi, hammock swings, tiki bar, unique mini golf experience. The LED lighting in the backyard & throughout the house will wow you! Gorgeous decor and immersive themed rooms for the kids! The perfect place for your dream family vacation!

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, 117 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 Kissimmee villa rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Private villa rentals

5 out of 5 average rating, 21 reviews

Epic Escape/9Br/Theater, Game Rm/Theme Rm/Disney

A private pool area is enclosed with a screen, featuring a clear blue pool surrounded by lounge chairs. A dining table is positioned nearby, with green landscaping visible in the background. The expansive sky above is bright and clear, enhancing the outdoor leisure space.

4.66 out of 5 average rating, 146 reviews

Villa w/ Pvt Pool & BBQ + Resort | 10 min Disney

4.92 out of 5 average rating, 78 reviews

A playful room features a Moana-themed space with a custom tiki bed and artwork of Moana. Another area shows a Toy Story-themed room with a colorful slide and bunk beds. The outdoor view showcases a private pool in a screened lanai, while an arcade room features vibrant LED lighting and arcade cabinets.

Villa in Four Corners

Solara Villa – Themes, Arcade, Privacy | Sleeps 22

4.81 out of 5 average rating, 26 reviews

Amazing home 5 mins to Disney Orlando

4.91 out of 5 average rating, 45 reviews

A spacious living area features a modern sectional sofa and two accent chairs, arranged around a glass coffee table. A well-lit kitchen and dining area are visible in the background, connected through an open layout. Decorative lighting and potted plants add a touch of elegance.

Villa in Four Corners

Luxury, Fun & Comfort 7BD Home w/ Home Theater

The image showcases a vibrant outdoor area featuring a private pool and spa, with a large projector for outdoor movie viewing. Inside, two game rooms are filled with themed decor and various entertainment options, including virtual reality experiences and arcade games.

5 out of 5 average rating, 47 reviews

Rotating VR Machine, Arcade, Slide | 3mi to Disney

The exterior of a two-story home is showcased, featuring a well-manicured lawn and palm trees in the front yard. A spacious driveway leads to a garage with a white door, while the house displays a neutral color scheme and large windows allowing natural light.

4.93 out of 5 average rating, 106 reviews

Disney Dream Villa- 10 Minutes From Disney!

5 out of 5 average rating, 5 reviews

2817 Story Lakes

Luxury villa rentals

A vibrant game room inspired by space features several gaming options, including a foosball table, air hockey table, and arcade machines. The room is illuminated with blue LED lighting, and large screens are arranged for gaming, all set against a backdrop of starry wall designs.

4.99 out of 5 average rating, 76 reviews

Free Pool Heat & BBQ|Disney Nearby|Resort|Waffles

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

A collage showcases the vibrant features of the villa, including a two-lane bowling alley with colorful bowling balls, a private home theater with comfortable seating, and a pool area with a screened enclosure. Bright blue walls and space-themed decor create a playful atmosphere.

4.82 out of 5 average rating, 22 reviews

Bowling| video wall TV | theater| pool | sleeps 36

The image displays four themed bedrooms, each uniquely designed. A Moana-inspired room features vibrant ocean murals and a queen bed. The Toy Story room shows playful characters with a twin bunk bed. A Frozen-themed room highlights snowy landscapes with two twin beds, and a Mickey Mouse room displays bold colors and playful decor.

4.92 out of 5 average rating, 71 reviews

66+ 5 star reviews Villa@ StoreyLake mins 2 Disney

4.92 out of 5 average rating, 121 reviews

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

4.97 out of 5 average rating, 117 reviews

Luxury Themed Villa 9 BR | Close to Disney

4.84 out of 5 average rating, 32 reviews

6BR+Spa&Pool+Walk to Clubhouse+Theater+ThemedRooms

4.8 out of 5 average rating, 157 reviews

A modern dining area features a long table set for eight, complemented by comfortable gray chairs. A stylish lighting fixture hangs above, and a large television is mounted on the wall nearby. The open layout connects to a sleek kitchen visible in the background.

Villa in champions gate

Luxury 8BR w/ Pool, Theater & Game Room

Villa rentals with a pool

5 out of 5 average rating, 10 reviews

Casita Kissimmee!Family Vacation Villa! 8minDisney

The image showcases a private pool area encased in a screened enclosure, with a clear blue pool reflecting sunlight. Surrounding the pool are comfortable lounge chairs and a dining table set on a spacious deck, with greenery visible beyond the enclosure.

4.88 out of 5 average rating, 67 reviews

Disney Pool Home Kissimmee

A screened-in pool area is showcased, featuring a refreshing swimming pool adorned with colorful floats. Lounge chairs are positioned nearby, providing a space for relaxation. Lush greenery and blue skies create a tranquil outdoor setting, enhancing the inviting atmosphere for guests.

4.94 out of 5 average rating, 80 reviews

Family Clubhouse - Private Pool 5 Miles to Disney!

The newly renovated pool is visible within a screened enclosure, providing a safe area for enjoyment. The pool is shaped uniquely and features clear blue water, creating a refreshing focal point in the outdoor space surrounded by inviting patio areas.

4.92 out of 5 average rating, 64 reviews

Vacation 3 bedroom 2 bath Villa+pool

A single-story home with a light beige exterior features a well-kept lawn bordered by shrubs. The front porch, highlighted by four windows, leads to a dark front door framed by decorative elements. A clear blue sky completes the inviting outdoor scene.

4.82 out of 5 average rating, 11 reviews

Florida Cottage Getaway - (4958TV)

An inviting screened-in lanai features a private pool surrounded by paver decking, with vibrant sunset colors reflecting overhead. The large dining area showcases a long table set for gatherings, accompanied by stylish light fixtures. The game room is equipped with multiple entertainment options, including arcade games and a pool table.

4.84 out of 5 average rating, 94 reviews

Brand New Luxury 9BR Villa/ Pool/Spa/Game Room

A cozy media room is designed with a Harry Potter theme, featuring a large flat-screen TV mounted on a wall. Comfortable sofas with colorful cushions are arranged around a carpet, while gaming stations are visible in the background. Framed artwork and decorative elements enhance the themed atmosphere.

5 out of 5 average rating, 70 reviews

Mickey's Pool House

A spacious two-story vacation home is featured with a well-maintained façade. The exterior showcases a combination of light-colored siding and stone accents. A paved driveway leads to a two-car garage, with lush greenery surrounding the entrance and a manicured lawn enhancing the overall presentation.