Villa vacation rentals in Winter Haven

Villa in Championsgate Village

A modern kitchen features sleek granite countertops and white cabinetry, with ample natural light filtering through large windows. The inviting pool area is visible through sliding glass doors, showcasing a private pool with floating beach balls. A vibrant children's bedroom is decorated with a whimsical theme and features colorful bedding. A game room is equipped with a pool table and illuminated by LED lights, enhancing the playful atmosphere.

4.93 out of 5 average rating, 121 reviews

Family Dream Vacation Villa w 6br + pool & Resort

The perfect family vacation destination! Champions Gate is just outside Orlando and a quick drive to Disney and other theme parks. Want to enjoy the Florida sunshine without having to leave the neighborhood? Enjoy your own private pool or take a walk to the Oasis Clubhouse or 2nd clubhouse where you can enjoy amazing resort amenities for free! Villa Features: Pool/Spa, GameRoom, VideoGames, Baby friendly. Clubhouses: Pools, Slides, LazyRiver, SplashPad, Gym, Restaurant, Bar, Tennis, Volleyball

The exterior of a spacious villa is showcased, featuring a combination of light gray siding and white trim. Large windows complement the entrance, which is adorned with a blue door. Lush greenery and a neatly landscaped yard enhance the inviting appearance against a vibrant sunset sky.

4.93 out of 5 average rating, 136 reviews

Rest Relax Unwind at Orista Endless Summer Villa

Endless Summer Villa is the perfect vacation destination. With a game room, 4 bedrooms & 4 bathrooms, our villa is handicap accessible and perfect for families. Take a splash in the private pool or relax in one of our two master suites, each outfitted with top-quality furnishings and bedding. Let our beautifully landscaped pool transport you to a tropical paradise, all while being just a short drive away from Disney, SeaWorld, and Universal. Book your stay with Orista Endless Summer Villa today!

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, 120 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, 199 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, 151 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!

Villa in Championsgate Village

5 out of 5 average rating, 106 reviews

9BR Epic 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!

4.99 out of 5 average rating, 128 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 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, 171 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.

4.86 out of 5 average rating, 152 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.

4.91 out of 5 average rating, 238 reviews

Villa in Kissimmee

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!

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, 114 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**

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.