Villa holiday rentals in Winter Haven

A living area showcases comfortable seating and a flat-screen TV, with a vibrant green wall accentuating the space. The pool area is visible, featuring floating devices in a clear blue pool under sunlight. An inviting bedroom with a spacious bed is complemented by light streaming through the window. A chilled bottle of champagne and glasses are set inside the refrigerator, enhancing the welcoming environment.

4.85 out of 5 average rating, 127 reviews

Emerald City, No AirBNB Fees, Heated Pool

Stylish 4BR, 3.5BA home w/ emerald & gold decor. Enjoy a private pool up to 6ft deep w/ floaties. Pool heat available for $30/night (2-night min) Starter items provided: 1 roll of paper towels, 3 kitchen garbage bags, 2 toilet rolls per bathroom, 2 laundry pods, & 2 dishwasher pods. We don’t restock Booking guest must be 25+ & stay on-site 11mi to Disney 22mi to Universal 27mi to MCO 4.2mi to golf 2.2mi to liquor/grocery Check-in after 4pm, check-out before 10am NO pets, smoking, or parties

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, 130 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 iconic castle structure is seen towering against a bright blue sky, complementing the clouds. The building features multiple spires and intricate architectural details, with a large clock prominently displayed. Colorful banners can be seen in the foreground, adding vibrancy to the scene.

4.77 out of 5 average rating, 103 reviews

Villa Near Parks/Hot Tub/Pool/Golf/Sunset Views

Stunning 5BR, 3BA Highlands Reserve Golf Resort Estate overlooking the golf course with breathtaking sunset views. The SW-facing pool maximizes sun exposure and offers stunning sunset vistas. Minutes from Disney (12 min) and MCO Airport (20 min), with nearby restaurants, bars, and outlets. Enjoy a 4-person hot tub poolside and Smart TVs throughout, for seamless streaming. Whether relaxation or adventure, this private pool home in a golf community promises an unforgettable getaway for all ages.

4.98 out of 5 average rating, 204 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

Villa in Championsgate Village

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, 159 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, 136 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, 107 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, 126 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 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.

4.9 out of 5 average rating, 188 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.

4.87 out of 5 average rating, 158 reviews

A game room is displayed, featuring a red pool table at center, surrounded by arcade games and two prominent Star Wars-themed characters on the walls. A large screen hangs at the back, enhancing the entertainment space, with modern lighting fixtures providing illumination.

Villa in Four Corners

Family-Friendly Pool Oasis, Arcade & Theatre

Enjoy our home theater, game room & fully equipped kitchen. Perfect for families and friends to spread out while enjoying quality time in the upscale Champions Gate Resort. Ideal for families and groups who appreciate a genuine 5-star home experience while visiting Orlando Disney - 9 miles Universal - 22 miles Sea World - 18 miles Legoland - 21 miles Airport - 24 miles Outlet Mall - 6 miles Supermarket - 1 miles * Professionally managed, inspected, and cleaned.

4.86 out of 5 average rating, 166 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 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.

4.92 out of 5 average rating, 125 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 Winter Haven

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Private villa rentals

The image reveals various areas of the home, including a modern kitchen with sleek appliances, a tastefully decorated bedroom featuring natural light, a welcoming living space with comfortable seating, and an outdoor area showcasing a private pool and bubbling spa, all within a screened enclosure.

4.77 out of 5 average rating, 53 reviews

Fun in the Sun-Dream Solterra Villa

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.

4.91 out of 5 average rating, 45 reviews

Cozy&Peaceful Family Getaway Near Disney and more!

4.77 out of 5 average rating, 73 reviews

Luxury Private Villa near Disney

4.92 out of 5 average rating, 26 reviews

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

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.

4.96 out of 5 average rating, 76 reviews

Resort Villa with Private Pool & Spa

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, 53 reviews

Beautiful 4 bedrooms with South/West facing pool

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.

4.94 out of 5 average rating, 16 reviews

Disney Family Retreat w/screened-in patio & pool

4.99 out of 5 average rating, 76 reviews

Quiet Villa w/ pool close to Theme Parks and golf!

Luxury villa rentals

Villa in Championsgate Village

5 out of 5 average rating, 11 reviews

Disney 8-bedroom Villa Pool Resort BBQ Game Room

A spacious living area is presented with a comfortable sectional sofa adorned with various cushions. A large, circular coffee table sits atop a soft rug, while a vibrant mural featuring a sunset over hills acts as a striking backdrop. Warm orange curtains frame the windows, enhancing the inviting ambiance.

4.89 out of 5 average rating, 129 reviews

3mi to Disney Star Wars Galaxy Edge 7BDRM Villa

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, 116 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.

4.98 out of 5 average rating, 125 reviews

Poolside Movies | 3Min.Walk to Waterpark| Game Roo

An interactive stage area is presented, featuring musical instruments including an electronic drum set and keyboard. A large mural of a guitar and palm trees creates a vibrant backdrop. The space is equipped with seating and surrounded by a lush green carpet.

4.97 out of 5 average rating, 116 reviews

Luxe Villa/15min2parks/Lakeview/Vgames/Theater

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.

4.86 out of 5 average rating, 116 reviews

Brand New 10Bd Mansion At Windsor Island Resort

4.92 out of 5 average rating, 127 reviews

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

4.97 out of 5 average rating, 121 reviews

Luxury Themed Villa 9 BR | Close to Disney

Villa rentals with a pool

A spacious living room features high ceilings and large windows that allow natural light to fill the area. Comfortable seating arrangements include a gray sectional sofa and two blue accent chairs. The open layout leads to a modern kitchen visible in the background.

4.87 out of 5 average rating, 52 reviews

Fun & Vibrant 5BD/5BA w/ FREE Resort Access!

4.87 out of 5 average rating, 23 reviews

Orlando Escape | Private Pool | Luxury Deal

4.9 out of 5 average rating, 20 reviews

Waterfront Luxury Villa - Fresh Updates!

The exterior of a Mediterranean-style villa is shown, featuring a spacious front yard with landscaped greenery. A brick driveway leads to a two-car garage. Golf course views are visible in the background, highlighting the peaceful surroundings of the property.

4.94 out of 5 average rating, 68 reviews

Executive Disney Home on Highlands Reserve

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, 51 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.

4.94 out of 5 average rating, 51 reviews

Rest & Relax at Sunset by the Lake with SPA!

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, 51 reviews

South facing Modern villa in quiet gated estate

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.