Villa holiday rentals in Winter Haven

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Top-rated villa rentals in Winter Haven

Guests agree: These villas are highly rated for location, cleanliness and more.

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Top Guest favourite
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.
Villa in Davenport
4.87 out of 5 average rating, 126 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

Guest favourite
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.
Villa in Davenport
4.94 out of 5 average rating, 128 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!

Top Guest favourite
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
4.98 out of 5 average rating, 203 reviews

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

Top Guest favourite
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
4.99 out of 5 average rating, 136 reviews

*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.

Top Guest favourite
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.
Villa in Davenport
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!

Top Guest favourite
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.
Villa in Davenport
4.91 out of 5 average rating, 186 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.

Guest favourite
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
4.87 out of 5 average rating, 156 reviews

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.

Guest favourite
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
4.87 out of 5 average rating, 165 reviews

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.

Top Guest favourite
The image showcases a private outdoor pool with a screened enclosure, surrounded by lush greenery. A cozy children's bedroom features themed bedding with characters from popular movies. A spacious master bedroom is highlighted with a view of the pool through large glass doors. An overhead shot reveals the entire property set within a landscaped community.
Villa in Kissimmee
4.96 out of 5 average rating, 113 reviews

Sunset Villa 4 miles from Disney w/ private pool!

Free pool heat! You and your family will absolutely fall in love with this stunning 4 bedroom 3 bathroom pool home backing onto a beautiful forest for complete privacy. The home is centrally located in the wonderful gated community of Sunset Lakes just a short drive from all of Orlando's world famous attractions! Disney World (4.7 miles), Sea World (13.2 miles), Universal Studios Florida, (18 miles). Not to mention dozens of fabulous restaurants within minutes!

Guest favourite
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.
Villa in Davenport
4.92 out of 5 average rating, 123 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**

Guest favourite
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.
Villa in Davenport
4.91 out of 5 average rating, 119 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.

Top Guest favourite
Villa in Davenport
4.99 out of 5 average rating, 103 reviews

Amazing Villa near DisneyWorld FREE heated-pool

Have fun with the whole family at this stylish place. Our home has everything you will need for you and your guest to have a great experience. This home is a short drive from Walt Disney World and Orlando Attractions!! Don’t wait book with us now and give you and your family the vacation you all deserve. We can’t wait to welcome you . BBQ ( free to use ) Heated pool (free) Dogs friendly! Extra fee $120 per stay

Popular amenities for Winter Haven villa rentals

Quick stats about villa rentals in Winter Haven

  • Nightly prices starting at

    Winter Haven holiday rentals start at $287 AUD per night before taxes and fees

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Winter Haven rentals

  • 5 Average rating

    Winter Haven stays are highly rated by guests—averaging 5 out of 5!

Destinations to explore

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  3. Florida
  4. Polk County
  5. Winter Haven
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