
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.

❤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!

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

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!

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!

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!

Magical Disney House-Pool & Hot Tub,Free Waterpark
Mickey Mouse & Star Wars bedrooms, gameroom, pool & hot tub with bbq, loungers,cozy couch and plenty of fun to be had under the sun or under the stars with outdoor lights over pool. 1st and 2nd floor master suites -great for two families. Our gated resort community at Solterra gives you access to FREE pool/lazy river/water slide/playground and much more Also own the house across the street for renting two homes at same time. ask about that home. Ask about our early check in/out options

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.

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!

Emerald City, No AirBNB Fees, Heated Pool
Stylish 4 bedroom and 3.5 bath home with emerald & gold decor. Outside you’ll cool down in an up-to 6ft pool with floaties. Pool heating is an extra feature for $30/night. Starter items provided: 2 toilet rolls/bathroom, 2 laundry pods & 2 dishwasher pods. ★ 11 mi from Disney ★ 22 mi from Universal ★ 27 mi from MCO Airport ★ 4.2 mi away from Golf course ★ 2.2 mi away from Liquor & Grocery ★ Check in after 4pm. Check out before 10am ★ NO PETS, NO SMOKING, & NO PARTIES

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.

Villa with pool
Fabulous 4 bedroom villa,two bathrooms, with games room, BBQ and private pool. Fully equipped for your convenience! Centrally located. Only minutes away from Disney and the other amusement parks. 3 minutes away from Walmart, Publix and varied restaurants. Come with your family and have an unforgettable vacation!The house also has the enjoyment of an additional area in the area ,which has an extra pool,tennis courts a children's park and boat ramp and yeskit .

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
Private villa rentals

Lakefront Victorian Hse for Time Travelers & Event

Villa w/ Pvt Pool & BBQ + Resort | 10 min Disney

Disney Family Fun Resort, Pool/Game Room

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

South facing Modern villa in quiet gated estate

Magical 5BR Themed Pool home + Game Room!

Beautiful Lakeview 4 BR Vacation Home with Pool!

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

Blue Paradise 15BR 11BA, Sleeps 36, Theater/GameRm

Pickleball PoolsideMovies |WalkToWaterpark| Arcade

The Golden Bear Villa | Private Pool & Theater

Epic Disney Villa • Hidden Arcade & Playroom!

Free Pool Heat! Disney Themes, Arcade, Sleeps 22

Brand New 9Bd Mansion Pool/ Spa At Windsor Island

Sleeps 24✦Free Pool Heat✦15 min to Disney✦Hot Tub

Luxury Themed Villa 9 BR | Close to Disney
Villa rentals with a pool

Disc rate Spacious View4bdrm SplashPool & Yoga Rm

Fabulous 3 bed villa - Privacy & South facing pool

Lovely 3BD close to Disney - Waterpark

Executive Disney Home on Highlands Reserve

Cozy&Peaceful Family Getaway Near Disney and more!

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

Epic 8BR Villa w/Free Arcade, Theater, Pool & Spa!

WaterView 4 miles to Disney 3Br 2Ba Pool Home
Quick stats about villa rentals in Winter Haven

Nightly prices starting at
Winter Haven holiday rentals start at € 155 per night before taxes and fees

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Winter Haven rentals

5 Average rating
Winter Haven stays are highly rated by guests – averaging 5 out of 5!
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- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Universal's Volcano Bay
- Disney Springs
- SeaWorld Orlando
- Disney's Animal Kingdom Theme Park
- Busch Gardens Tampa Bay
- Magic Kingdom Park
- Old Town Kissimmee
- Raymond James Stadium
- Walt Disney World Resort Golf
- Epcot
- ESPN Wide World of Sports
- Amway Center
- Reunion Resort Golf Courses - Palmer & Watson
- Discovery Cove
- Aquatica
- Amalie Arena
- Island H2O Water Park
- Disney's Hollywood Studios
- ICON Park
- Southern Dunes Golf and Country Club
- ZooTampa at Lowry Park




