Villa vacation 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

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.

4.92 out of 5 average rating, 127 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

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

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!

4.98 out of 5 average rating, 117 reviews

9BR Highly Themed 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, 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.

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, 140 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 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.

4.86 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**

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, 120 reviews

Modern Coastal Farm House/Pool+Jacuzzi/near Disney

Welcome to Florida!!! Have fun with the whole family at this stylish place, equipped with everything you need for your staying. Our gorgeous modern coastal farm house is sitting in one of the most desirable communities for those wishing to vacation around the Disney and Kissimmee/Orlando areas. Drive time to Disney is 10 to 15 minutes and the community is also nearby Hwy 192 with a variety of shopping, dining, and entertainment.

Popular amenities for Winter Haven villa rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Private villa rentals

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.

4.86 out of 5 average rating, 97 reviews

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

4.9 out of 5 average rating, 20 reviews

Waterfront Luxury Villa - Fresh Updates!

4.93 out of 5 average rating, 14 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

4.77 out of 5 average rating, 73 reviews

Luxury Private Villa near Disney

The image showcases a bright living area featuring a colorfully themed Mickey blanket draped over a spacious bed. A view of the outdoor pool and hot tub area is visible through a large window, with dining space in the background, highlighting seating arrangements and decor.

4.97 out of 5 average rating, 86 reviews

Disney, Pool, Hot Tub, Gym!

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

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

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, 122 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, 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

Luxury Villa/15min2parks/Lakeview/Vgames/Theater

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.

4.93 out of 5 average rating, 183 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, 170 reviews

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

A two-story home features a light blue and grey exterior with a welcoming front porch and large windows. A well-maintained lawn surrounds the property, with neatly arranged flower beds. A spacious driveway leads to a double garage, providing ample parking space.

4.84 out of 5 average rating, 107 reviews

Brand New 9Bd Mansion Pool/ Spa At Windsor Island

4.92 out of 5 average rating, 127 reviews

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

Villa rentals with a pool

5 out of 5 average rating, 12 reviews

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

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 private pool area is enclosed with a screen for safety and features a resort-style pool with an adjacent spa. Sun loungers are positioned nearby, surrounded by tall shrubs for added privacy while enjoying outdoor relaxation.

4.84 out of 5 average rating, 58 reviews

Magical✨️4b/3b Private Pool/Game Room Disney Area

4.85 out of 5 average rating, 88 reviews

The spacious living area features a comfortable sectional sofa arranged around a low table. A flat-screen TV is mounted on a rustic wooden accent wall. Bright lighting fixtures hang above an open kitchen area with modern appliances, enhancing a cozy atmosphere.

Villa in Four Corners

Lovely 3BD close to Disney - Waterpark

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

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.

4.64 out of 5 average rating, 84 reviews

Tranquility at Lake Wilson Preserve, lake view

The exterior of the two-story home features a paved driveway leading to a two-car garage. Lush landscaping, including trimmed shrubs and small trees, surrounds the entrance, enhancing the welcoming appearance of the property. The sky is clear, with fluffy clouds adding depth to the scene.