Villa holiday rentals in Winter Garden

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, 121 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, 137 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!

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, 133 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.

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.

4.93 out of 5 average rating, 98 reviews

Private Pool & Free Heat - Close to Disney!

3 bed, 3 bath luxury villa in exclusive gated community 10 mins from Disney. Private pool & hot tub with free heat not overlooked by other homes. Main rooms open onto pool. Kitchen with granite counter tops. Outside bar, loungers, table & chairs. Master bedroom with double sink ensuite and twin with ensuite shower room. Queen is separate to main house providing additional privacy when travelling with friends/family. 32 inch tv's and comfortable beds with pillow top mattresses in all bedrooms

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!

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, 123 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!

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, 113 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! min from Disney, one of the closest villa resorts. Tons of shopping and dining nearby!

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 spacious private pool area is showcased, featuring colorful inflatable rafts and lounge chairs. A barbecue grill and outdoor dining set are visible nearby, surrounded by a screened enclosure that enhances the outdoor experience. Sunlight reflects pleasantly on the water's surface.

4.92 out of 5 average rating, 126 reviews

Villa with pool

Fabulous 4 bedroom villa,two bathrooms, with games room, BBQ and private pool. Fully equipped for your convenience! Centrally located. Only minutes away from Disney and the other amusement parks. 3 minutes away from Walmart, Publix and varied restaurants. Come with your family and have an unforgettable vacation!The house also has the enjoyment of an additional area in the area ,which has an extra pool,tennis courts a children's park and boat ramp and yeskit .

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, 162 reviews

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

**Exclusive Discount!** Mention **Disney Serenity** when booking 90+ days in advance for special savings! 🏡 **Welcome to Disney Serenity** – a family-friendly villa near Disney World! Enjoy a **private heated pool**, **game room**, and **cinematic home theater**. Plus, access resort amenities like a **lazy river, gym, and tiki bar**. **Wheelchair-friendly** and perfectly located for Disney & Universal adventures. Book now for a magical stay! ✨

Popular amenities for villa rentals in Winter Garden

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Private villa rentals

4.87 out of 5 average rating, 23 reviews

Playful villa near Disney w/ pool & Spa

4.96 out of 5 average rating, 90 reviews

The exterior of the house showcases a striking blend of wood and stone finishes, featuring large windows that illuminate the interior. An expansive, clear blue pool reflects the sky, with a bridge extending over the water leading to the main entrance.

Villa in Orlando

The Lakeview Oasis - XL Pool & Jacuzzi - Orlando

4.94 out of 5 average rating, 94 reviews

Cute N Cozy Villa near Disney, pool, Wi-Fi

A spacious living area features a modern sectional sofa, complemented by a circular coffee table and decorative plant. Bright natural light enters through window slats, enhancing the contemporary aesthetic, while the kitchen area is visible in the background with sleek cabinetry and appliances.

4.86 out of 5 average rating, 102 reviews

Charming 4 Bdr~ Villa near Disney

The outdoor pool area features a large swimming pool and a spa, both surrounded by a screened enclosure. Clear blue water reflects sunlight, while lush greenery accents the space, enhancing the views of the conservation area beyond.

5 out of 5 average rating, 3 reviews

Dog friendly, no rear neighbors, open field views.

A game room features various entertainment options, including a treadmill, exercise bike, and classic arcade machines. The decor showcases a 'Star Wars' theme with vibrant blue lighting and dark walls, creating an inviting atmosphere for guests to enjoy recreational activities.

4.95 out of 5 average rating, 96 reviews

Luxury Villa! /Game Room/ Pool Heater

The outdoor pool area is framed by a screened enclosure, reflecting the warm lights above. The pool water shimmers softly, and a colorful beach ball rests on the surface. A glimpse of the inviting interior, including white furniture, is visible through the large windows.

4.97 out of 5 average rating, 30 reviews

Luxury home | Lakeside Landing

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, 107 reviews

Disney Dream Villa- 10 Minutes From Disney!

Luxury villa rentals

A spacious dining area features a long glass table surrounded by white chairs, set for a large meal with blue and gold accents. A striking blue wall with geometric gold patterns creates a modern backdrop, while contemporary light fixtures illuminate the space.

4.94 out of 5 average rating, 111 reviews

Blue Paradise 15BR 11BA, Sleeps 36, Theater/GameRm

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, 117 reviews

Pickleball PoolsideMovies |WalkToWaterpark| Arcade

4.82 out of 5 average rating, 72 reviews

Villa in Orlando

4,800 sf Estate | Pool, Lake, Weddings and Events

4.94 out of 5 average rating, 67 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

Villa in Championsgate Village

An imaginative arcade and themed play area is displayed, featuring a blue slide and space-themed bunk beds. A princess-themed room with a carriage bed is highlighted. An arcade area with vintage game machines completes the vibrant layout, showcasing a unique blend of fantasy and entertainment.

4.94 out of 5 average rating, 178 reviews

Free Pool Heat! Disney Themes, Arcade, Sleeps 22

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, 48 reviews

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

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, 72 reviews

67+ 5 STAR reviews Villa@ StoreyLake mins 2 Disney

4.96 out of 5 average rating, 52 reviews

Luxury Villa | Pool, Spa, Game Room | Near Disney

Villa rentals with a pool

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, 66 reviews

Vacation 3 bedroom 2 bath Villa+pool

The exterior of a blue house is framed by manicured landscaping, featuring palm trees and neatly trimmed bushes. A welcoming red door serves as the focal point, complemented by large windows that allow natural light to fill the interior.

4.93 out of 5 average rating, 40 reviews

Cozy&Peaceful Family Getaway Near Disney and more!

4.81 out of 5 average rating, 26 reviews

Amazing home 5 mins to Disney Orlando

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, 51 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.

4.98 out of 5 average rating, 87 reviews

The Balmoral Manor: Luxurious & Bright 5BR Oasis

4.99 out of 5 average rating, 82 reviews

Enchanted Escape - 8 BR - Super Mario - Pool - Hot

4.99 out of 5 average rating, 99 reviews

Amazing Villa near DisneyWorld FREE heated-pool

A fire pit is surrounded by Adirondack chairs, creating an inviting space for gatherings. Marshmallows are being roasted over the flames, which are gently flickering. The background features greenery, providing a serene atmosphere as dusk approaches.