Villa holiday rentals in Winter Haven

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, 125 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!

4.98 out of 5 average rating, 200 reviews

The living area features a modern sectional sofa with colorful throw pillows in vibrant red and yellow. A matching ottoman sits in front, accompanied by stylish side tables with lamps. Bright blue walls create a lively backdrop, enhanced by a large abstract painting and adjacent dining space.

Villa in Lake Wales

Lakefront, Dock, 2 Kayaks, near Bok & Legoland

** New Construction ** Breathtaking view of lake, private dock (2 kayaks for guests included), beach/swim area, outdoor shower, large private balcony w/gas grill and gorgeous sunsets! 2 Bedrooms each w/walk in closet, two full baths, full kitchen w/all amenities. All new furnishings, (3) 4K Smart TV's, FAST free wifi. Gorgeous location, quiet street, private free parking, 2 private entrances. Villa is detached from main house. Near Disney, LegoLand, Bok Tower. WEEKLY & MONTLY DISCOUNTS

An entertainment area is visible with a pool table positioned under a modern light fixture. Nearby, a cozy seating arrangement surrounds a circular table, while large windows offer natural light. A vibrant themed room is accented with bunk beds, sporty decor, and a bold area rug.

4.96 out of 5 average rating, 155 reviews

Luxury Fun Stay w/Pool/Spa/WaterPark

This stunning 5BR pool home is in the sought-after Champions Gate resort. Just 12 miles to Disney and 19 miles to Universal Studios, it's a short 9-min walk to the clubhouse, offering free access to the lazy river, fitness center, water park, movie theater, and more. With exceptional facilities, the villa comfortably accommodates up to 14 guests, making it perfect for family fun and gatherings. Enjoy a relaxing retreat near top restaurants, attractions, landmarks, and the famous Disney World!

4.99 out of 5 average rating, 134 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 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!

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, 127 reviews

Villa con piscina

Fabulosa villa de 4 habitaciones ,dos baños, con sala de juegos, BBQ y piscina privada. Completamente equipada para su conveniencia! Lugar céntrico. Solo a minutos de Disney y de los demás parques de atracción. A 3 minutos de Walmart, Publix y restaurantes variados. Venga con su familia y pase unas vacaciones inolvidables!La casa también cuenta con el disfrute de un área adicional en el área ,que tiene una piscina extra,canchas de tenis un parque para niños y rampa para botes y yeskit .

A screened-in patio area features a private pool surrounded by comfortable lounge chairs. The inviting water reflects the colors of the sunset sky, and a small dining table is visible nearby. The home is designed for relaxation and outdoor enjoyment.

4.91 out of 5 average rating, 176 reviews

Beautiful 4 Bedroom Pool Villa Near Disney World

This sunny single story home has 4 beautiful bedrooms (2 master suites) and 3 full bathrooms with its own private screened pool. It is an ideal accommodation for 2 families to share, or one large family. This villa is located in the gated community, a small peaceful community set away from any main road traffic. The home is situated approximately 15 minutes from the Walt Disney World, and is conveniently located from all major Orlando attractions, nearby restaurants and shopping.

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, 114 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!

4.86 out of 5 average rating, 157 reviews

A well-maintained villa is showcased, featuring a welcoming entrance with a single-car garage. Lush greenery and colorful shrubs line the brick pathway, while tall palm trees and vibrant landscaping enhance the cheerful exterior. Bright clouds are visible in a clear blue sky.

Villa in Haines City

Sandy's Southern Dunes Villa

This villa is in the Southern Dunes Golf & Country Club, which is an immaculately kept, secure complex, which maintains a 24-hour manned gate, making this a safe place to stay. There are community swimming pools, tennis courts, a gym, library and children's playground for those days when meeting Mickey Mouse is just too much trouble. With a Super-Walmart a minute away plus Dicks and several well-known restaurants just further away, virtually everything is on hand.

A private pool area is surrounded by a screened enclosure, featuring a jacuzzi spa and lounge chairs. The pool is inviting, with light blue water reflecting the sky's pink and purple hues. A serene lake is visible beyond the pool, adding to the tranquil setting.

4.91 out of 5 average rating, 244 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!

Popular amenities for Winter Haven villa rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Private villa rentals

The exterior of the home presents a modern design, featuring a combination of blue stucco and elegant archways. Lush landscaping surrounds the entrance, with palm trees and greenery complementing the exterior. A spacious driveway leads to a three-car garage, all under a clear blue sky.

4.93 out of 5 average rating, 42 reviews

Golf Oasis-Game Room-Pool-Disney South Face Pool

5 out of 5 average rating, 38 reviews

The Citrus Villa | An Entertainer's Delight

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.

4.97 out of 5 average rating, 58 reviews

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

A modern coastal farmhouse is pictured, featuring a light-colored exterior with a covered porch. Lush green lawns surround the home, and a spacious driveway provides access to a two-car garage. Trees in the background add a natural touch to the setting.

4.91 out of 5 average rating, 115 reviews

Modern Coastal Farm House/Pool+Jacuzzi/near Disney

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

5 out of 5 average rating, 20 reviews

WaterView 4 miles to Disney 3Br 2Ba Pool Home

4.96 out of 5 average rating, 23 reviews

Epic Luxury Theme Home w/ Private Pool & Game Room

4.94 out of 5 average rating, 81 reviews

Disney Pool Retreat-Jacuzzi-Game Room-Cinema-BBQ

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

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, 112 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, 118 reviews

Pickleball PoolsideMovies |WalkToWaterpark| Arcade

A private pool area is illuminated in a soft green hue, surrounded by a screened enclosure. Comfortable lounge chairs are positioned nearby, with a table set under an umbrella. String lights create a warm ambiance as the evening sky darkens.

4.99 out of 5 average rating, 138 reviews

Magical Disney House-Pool & Hot Tub,Free Waterpark

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

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, 163 reviews

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

4.92 out of 5 average rating, 122 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

Villa rentals with a pool

5 out of 5 average rating, 10 reviews

Lux 4BD/2BAVilla/Heated Pool/Private Backyard

A light-filled living area showcases a white sofa adorned with decorative cushions in blue tones. An elegant round blue ottoman sits at the center on a patterned rug. A large mirror reflects natural light from the window, framed by navy curtains, with decorative elements adding style.

4.85 out of 5 average rating, 95 reviews

5bedroom,pool,18min to Disney, Kissimmee davenport

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

Superhost

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!

Superhost

A spacious dining area showcases a long wooden table surrounded by a mix of upholstered and ergonomic chairs. Large windows draped in sheer fabric allow natural light to flow in, while a modern light fixture adds an elegant touch to the room.

Villa in Four Corners

4.87 out of 5 average rating, 84 reviews

Game Room, Home Theater, Private Pool/Sleeps 15

Superhost

The outdoor area features a private pool and spa surrounded by a screened enclosure. Two sun loungers are positioned nearby, offering a place to relax. Lush greenery lines the background, complemented by a clear blue sky filled with clouds.

4.88 out of 5 average rating, 78 reviews

Spectacular 3b/2b With Private Pool And Spa

A private pool area is visible, featuring a clear blue pool surrounded by spacious lounge chairs. The pool deck is screened-in for comfort, with a dining area in the background under a ceiling fan, creating a serene setting for relaxation.

4.92 out of 5 average rating, 12 reviews

Disney Family Retreat w/screened-in patio & pool

The game room is designed with vibrant murals and lighting, featuring arcade machines and a pool table. An immersive children’s room showcases whimsical decor and themed artwork, including structures resembling natural elements, enhancing the playful environment.