
Vacation rentals in Windsor Hills
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Top-rated vacation rentals in Windsor Hills
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Disney Escape at Windsor Hills
This is a fantastic family vacation townhouse located just four miles from Walt Disney World! Inside, you'll find a full kitchen with a breakfast bar, a dining table for six, and a living area with a TV for streaming all your favorite channels! Right outside, take a refreshing swim in your private pool. Guests will be able to enjoy a wide variety of resort-style amenities close by including a community clubhouse with a game room, Olympic-size pool, children's waterpark, putting green, and more!

Private Gated Community 8 mins away from Disney!
Gorgeous brand NEW luxury condo gated w 24 hr security guard. 8 mins from Disney & all parks!! 2 bedrooms, 2 bathrooms (rain shower & tub) Therapeutic beds in every room, including full size pull out. Smart TVs in every room w/cable, Netflix, Wifi. Extra steps to clean & sanitize. 2 min walk to Super Walmart. Walking distance to food, shopping, gas, Starbucks & more. washer dryer, coffee, tea, toiletries Clubhouse Resort with pool, jacuzzi, playground, gym, tennis & volley ball court, lake.

★Completely New★ 3 miles to Disney + Free Resort!
Closest FREE resort to Disney Parks! Plumeria Place is a 6 bedroom 4 bathroom luxury villa that sleeps 14. Completely renovated in March 2022! * Kitchen is loaded & all baby gear provided. * Custom game room with A/C, LED panel lighting & ROCK CLIMBING WALL! * New Roku smart TVs & NEST tech throughout. * Outdoor space includes your own private pool, hot tub, overhead lighting, NEW BBQ grill & 9' custom-built farmhouse table to seat the whole family! Every detail has been thought of!

Jackies’s Jungle View Vacation Villa
ALL NEW fully remodeled and updated! One of the closest and newest communities to Walt Disney World! Located just 5 minutes from Disney, our freshly updated townhouse is the perfect location for your next Florida adventure. A fully equipped kitchen, super-fast Wifi, heated community pool, and a brand new Walmart just down the street are only a few of the many amenities you will find with this incredible rental. Our 1600 sq. ft. home is bright, fresh, and waiting to welcome our next guests.

🏖 Resort Condo | 🎢 2mi -> Disney | 💦 Waterpark Fun
Welcome to Mickasita @ Windsor Hill's! Our condo is the ideal family vacation spot, conveniently located just minutes away from Disney World and all your desired attractions. During your stay, our whole-condo dehumidifier will maintain a comfortable and healthy level of humidity. Recently upgraded, our condo is sparkling clean and offers many resort amenities with the convenience of a home. You'll find new beds with fresh linens, flat-screen TVs, high-speed internet, a gym, and more.

Chic Vibes Comfy King Bed Next to Parks/Food/shops
Welcome to our stylish oasis in Kissimmee, which seamlessly blends sophistication with a laid-back vibe. Your stay begins in a professionally cleaned apartment for your full enjoyment. Discover resort-style amenities – a sparkling pool, a fitness center, and hammocks, offering the luxuries of a five-star retreat. Conveniently located with in walking distance of theme parks, restaurants, and shopping. Book now. We can't wait to host you in our little slice of paradise!

It's too much like a elegant mini-hotel (3)
It's too much like a elegant mini hotel with rich artistic atmosphere! All the pictures on this page are a reflection of the real condition of the house. All the furniture has been carefully selected, and comfortable mattress and pillows will quickly accompany you into sweet dreams. The biggest feature of this house are comfort, economy and convenience. All of my houses have hosted countless friendly and courteous guests from Brazil. We will always welcome you!

Gorgeous Views: Golf Front, StarWars, XBox, 2Pools
This modern 3-bedroom luxury condo has one of the most PICTURESQUE VIEWS in the Reunion Resort of the Arnold Palmer PGA golf course. Combining STYLISH DESIGN and LUXURIOUS COMFORT, there are 2 KING bedrooms and a playful STAR WARS themed bedroom with a classic Arcade machine & Xbox. 4 TVs with DirecTV, free high-speed wifi, your own washer & dryer, access to 6 resort pools, 2 of which are only a 3 minute walk away, and only a short drive to Disney.

1BD Cottage "Limoncello" in Margaritaville
Welcome to your own island-inspired oasis. Our charming cottage is the perfect home base for your next dream Orlando vacation. The unit comes with all the comforts from home but worlds away. Conveniently located minutes from the Disney parks, a state-of-the art water park and newly opened 196,000 square foot shopping and dining district with multiple dining food and beverage options & brand-new movie theater. All Pets Must Be Preapproved :)

4BD 2BA Kissimmee Pool House near Disney
This 4BD 2BA house is in a quiet part of Kissimmee less than 5 miles south of Disney! The master suite features a king bed and attached bath with double sinks and walk-in shower. The second room contains a queen bed and the last two rooms have two twins each. There is a fully equipped kitchen and two work spaces, each containing a desk, office chair and computer monitor. Shops, entertainment, and restaurants are just a few minutes away.

"Ocean's Gate" - 2BD/2BA condo near Disney
Welcome to our beautiful ground-level condo! With the prime location at ChampionsGate Resort near Disney World and major parks, this 2BD/2BA condo unit is designed for your best accommodation. Spread out in 1,558 Sq. Ft., the unit offers a fully equipped kitchen, a cozy living room, a working station, and comfortable bedrooms. With access to the Clubhouse and resort amenities, you’ll spend amazing days in our home!

Themed Resort Condo | Pool | Spa | Mins to Disney
The Magic Galaxy – an affordable 3 bedroom, 2 bath condo in the gated Windsor Palms resort, known for its cleanliness and thematic charm. The retreat features themes from Star Wars, Mickey Mouse, Jurassic World, and Harry Potter. Enjoy resort amenities like a pool, spa, splash pad, courts for basketball, tennis, and volleyball, a movie theater, game room, gym, Tiki bar and grill, and a sundry shop.
Popular amenities for Windsor Hills, Four Corners vacation rentals
Stay near Windsor Hills's top sights
Private Windsor Hills, Four Corners vacation rentals

4 bedroom, south facing pool 3 miles to Disney

3 Miles 2 Disney | DisneyThemed | Fully Renovated

Everlasting Memories: 10 Min. From Disney!

Harry Potter • Windsor Hills + Pool• Near Disney

Toy Story Retreat Near Disney

Walt’s Vision – Disney-Inspired 3BR Condo

8 Mins To Disney W/Poolside Theater & Games Room

Westgate Vacation Villas - 1 Bedroom
Windsor Hills, Four Corners home rentals

Dream vacation, near Disney

Hibiscus Villa w/ themed rooms, game room and pool

Luxury and Perfect Family Vacay 3 min from Disney!

3 BR Private Pool Home 5 miles from Disney

Mickey's Lakefront Villa at Sunset Lakes

Your Cozy 3 BD Home w/ Private Hot Tub & BBQ Gril

Best Location! Best Location! Villa in Kissimmee

Spectacular Lake View - Game Room- Close to Disney
Windsor Hills, Four Corners condo rentals

Minutes to Disney best of Home, with a Resort feel

Heavenly Bliss - 3 bed 2 bath condo near Disney!

Magical Stay Near Disney & ESPN

Oakwater Resort, Kissimmee , 1.5 Miles to Disney

The Tree House, only 1.5 Miles From Disney!

Disney Oasis by the lake

Disney Oasis

Lovely well-furnished. See fireworks from balcony!
When is the best time to visit Windsor Hills?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ834 | ﺩ.ﺇ852 | ﺩ.ﺇ914 | ﺩ.ﺇ918 | ﺩ.ﺇ823 | ﺩ.ﺇ848 | ﺩ.ﺇ900 | ﺩ.ﺇ823 | ﺩ.ﺇ746 | ﺩ.ﺇ830 | ﺩ.ﺇ863 | ﺩ.ﺇ922 |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°C |
Quick stats about vacation rentals in Windsor Hills

Total vacation rentals
Explore 640 vacation rentals in Windsor Hills

Nightly prices starting at
Windsor Hills vacation rentals start at ﺩ.ﺇ184 per night before taxes and fees

Verified guest reviews
Over 13,540 verified reviews to help you choose

Family-friendly vacation rentals
590 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Vacation rentals with a pool
630 properties feature pools

Rentals with dedicated workspaces
380 properties have a dedicated workspace

Wi-Fi availability
640 of Windsor Hills vacation rentals include wi-fi access

Popular amenities for guests
Guests love Private bathroom, Self check-in, and Gym across Windsor Hills rentals

4.7 Average rating
Windsor Hills stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Fitness-friendly rentals Windsor Hills
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- Rentals with a washer and dryer Windsor Hills
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- Condo rentals Windsor Hills
- Family-friendly rentals Windsor Hills
- Rentals with pools Windsor Hills
- Villa rentals Windsor Hills
- Rentals with an EV charger Windsor Hills
- Rentals with a hot tub Windsor Hills
- Serviced apartment rentals Windsor Hills
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- Pet-friendly rentals Windsor Hills
- House rentals Windsor Hills
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Disney Springs
- SeaWorld Orlando
- Give Kids the World Village
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Discovery Cove
- ESPN Wide World of Sports
- Disney's Animal Kingdom Theme Park
- Epcot
- Old Town
- Kia Center
- Reunion Resort Golf Courses - Palmer & Watson
- Universal's Volcano Bay
- Aquatica
- Island H2O Live!
- Disney's Hollywood Studios
- ICON Park
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club
- Camping World Stadium




