Villa vacation 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, 136 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!

4.98 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

5 out of 5 average rating, 111 reviews

9BR Memory Making Villa with Free Pool Heat!

9BR Stargazer Villas Guest Favorite! Your family will love this vacation home in Champions Gate Resort just outside Orlando! Occupancy up to 16 beautifully decorated masterpiece. A short drive to Disney Magic Kingdom and close to attractions, shopping and dining. This villa has a heated pool (no extra charge) to relax in after a day at the parks. Themed rooms featuring Frozen, Guardians of the Galaxy, and Lilo & Stitch bedrooms as well as two primary suites & full size Harry Potter game room!

A private pool area features a sparkling blue pool surrounded by a screened enclosure. Comfortable lounge chairs are positioned on the pool deck, with tropical landscaping visible in the background under a clear blue sky.

4.93 out of 5 average rating, 138 reviews

South-Facing Pool & Spa | 4BR/4BA Near Disney

Minutes to Disney! Relax in our south-facing pool & spa after fun-filled days. Four spacious bedrooms each with private bath give every guest room to unwind. Fun for all ages: arcade games, pool table, hot tub, high-speed Wi-Fi and themed kids’ room keep everyone happy when you stay in. Fully stocked kitchen, washer/dryer and family gear (crib, highchair, safety gates, stroller) make travel easy. Just a short drive away from every attraction. Book your stay with Endless Summer Villa today!

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, 120 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, 125 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.

4.97 out of 5 average rating, 111 reviews

Delux Pirate Dream Vacation—Disney Magic Awaits!

Ahoy, mateys! Welcome to Your Custom-Crafted Pirate Dream Vacation! Among countless vacation rentals, our uniquely themed home offers an unparalleled experience for your family’s ultimate getaway. Every detail is thoughtfully curated to create a relaxing haven for you, while your kids discover adventure and excitement around every corner. We’ve brought the magic of Disney to you, ensuring unforgettable family memories that last a lifetime! Book now and set sail for memories!

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, 112 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.

Popular amenities for Winter Haven villa rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Private villa rentals

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 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, 57 reviews

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

A private pool and spa area is enclosed by a screen, offering views of a serene sunset through palm trees. The pool features a textured surface and a safety railing, with vibrant water reflecting the evening sky. A lush green lawn surrounds the space, contributing to the tranquil environment.

4.93 out of 5 average rating, 100 reviews

25%off/Close to Disney/Hot Tub/Private Pool/Fenced

Superhost

A two-story vacation home features a stone-accented façade and a welcoming entrance. A paved driveway leads to a garage, and colorful landscaping complements the exterior. Large windows provide natural light, while the blue sky adds a vibrant backdrop.

Villa in Haines City

4.77 out of 5 average rating, 47 reviews

Beautiful Lakeview 4 BR Vacation Home with Pool!

Superhost

An outdoor area is captured, featuring a screened-in patio with a sparkling pool and a spa. Lounge chairs are arranged around the pool, and a dining table sits nearby. Lush greenery and a tranquil lake are visible beyond the enclosure, enhancing the serene atmosphere.

4.65 out of 5 average rating, 83 reviews

Tranquility at Lake Wilson Preserve, lake view

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.

4.91 out of 5 average rating, 11 reviews

Disney Family Retreat w/screened-in patio & 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

The collage features four areas: the screened-in pool area showcasing a shimmering pool beneath a grid of roof panels; a game room with vibrant lighting highlighting several game tables; a colorful children’s bedroom with Mickey Mouse decor; and the welcoming facade of a modern home with a paved driveway.

5 out of 5 average rating, 49 reviews

25 Min to Disney-Gated Community-Free Hot Tub

Luxury 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, 41 reviews

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

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 themed bedroom features dark walls adorned with a space mural, creating an immersive atmosphere. A large bed is dressed in colorful bedding featuring popular characters. A wall-mounted television is positioned above a dresser, complementing the room's playful design.

4.97 out of 5 average rating, 255 reviews

Disney-Themed Home w/ Game Room & Private Hot Tub!

4.97 out of 5 average rating, 116 reviews

15 min2parks! 9B/Lakeview/Vgames/*Pool heat Promo

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, 161 reviews

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

A spacious dining area features a long wooden table surrounded by comfortable gray upholstered chairs. Tropical-themed artwork adds color to the walls, complemented by soft lighting from overhead fixtures. A mirror and sideboard enhance the open feel of the room, promoting a welcoming atmosphere.

4.87 out of 5 average rating, 113 reviews

Brand New 10Bd Mansion At Windsor Island Resort

4.8 out of 5 average rating, 169 reviews

A private pool area is enclosed by a screened lanai, featuring clear turquoise water reflecting sunlight. Surrounding tropical plants and a fenced area enhance privacy, while the pool deck offers ample space for relaxation.

Villa in Four Corners

Villa w/ PVT Pool & BBQ + Ping Pong | Near Disney

Villa rentals with a pool

5 out of 5 average rating, 10 reviews

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

4.92 out of 5 average rating, 12 reviews

The exterior view of a single-story home is presented, showcasing a vibrant orange facade with a welcoming entrance. Lush green landscaping, including palm trees and shrubs, frames the property. A two-car garage is visible, along with large windows that enhance the bright and inviting appearance.

Villa in Polk County

Fabulous 3 bed villa - Privacy & South facing pool

A single-story residence features a neat brick driveway leading to a two-car garage. Lush green landscaping includes palm trees and colorful plants, enhancing the curb appeal. The front porch is inviting, with symmetrical windows framing the entrance under a gently sloped roof.

4.93 out of 5 average rating, 69 reviews

Luxury 4 Bedrooms, 3.5 Bathrooms with pool.

The villa's exterior showcases a charming single-story design with a light beige facade. A well-manicured lawn is framed by mature palm trees and ornamental shrubs. The two-car garage features a beige door, while the welcoming front entrance is highlighted by decorative lighting fixtures.

4.95 out of 5 average rating, 55 reviews

The Dorset Shire

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

4.91 out of 5 average rating, 23 reviews

Gated Resort, Lake View, Pool/Spa, Games Room

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.

4.84 out of 5 average rating, 49 reviews

South facing Modern villa in quiet gated estate