
Vacation rentals in Windsor Hills
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Top-rated vacation rentals in Windsor Hills
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Poolside 3Br Windsor Hills, Waterpark, Disney 2mi
Your Windsor Hills Getaway starts here! This immaculate condo overlooks the resort pool & waterpark and is just minutes from Disney World! New appliances and updated furnishings, this 3rd floor condo sleeps 8, with plenty of parking. The screened-in balcony can’t be beat, overlooking the pool, hot tub, and waterpark with waterslides! The clubhouse is just steps away, with a store, food, drinks, game room, and fitness center. No resort, parking, or hidden fees. Full access to all amenities!

Tito's Beachy Townhouse, 1.5 miles from Disney
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 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. Absolutely the best unit in the entire community!

Family, Windsor Hills, Sleep In with 11AM Checkout
Walk into your home away from home. Enjoy a relaxing stay. Located on 4th floor. Enjoy morning coffee on a screened-in balcony or a late snack. Pet-free home. Please NO Smoking. Children are always welcome. Come enjoy all of the accommodating facilities at Windsor Hills with a top-notched 24/7 gated security. FREE parking & leisure activities! Maximum of 3 cars allowed per reservation. This includes all guest that are visiting. All unregistered drivers will be denied access by HOA.

🏖 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.

Disney Spring Break– Pool + Waterpark + Family Fun
Ideal for families traveling to Disney, our spacious 3 bedroom condo at Windsor Hills offers resort-style pools, waterpark access, and fun Disney-themed bedrooms just minutes from the parks. What Makes It Special: - Walk to the resort’s pool & waterpark - Complimentary fast Wi-Fi + free parking - No resort fees - Family & kid-friendly rooms with Disney themes - Fully equipped kitchen Superhost (nearly 100 reviews!) , Guest Favorite, free parking, no resort fees—perfect for families!

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!

Themed Pool Home 2 Miles to Disney
Welcome to your perfect getaway! - Newly remodeled 3 bedroom, 3 bathroom themed private pool home - Amazing theme rooms kids will LOVE - Private splash pool fully screened-in - Free Wifi and fast internet for your Zoom meetings - Access to Windsor Hills Resort amenities, including a NEW WATER PARK - 24-hour security in a gated community - Just 2 miles from Disney and close to shopping and dining - Don't let the fun end at the parks - Every bedroom is themed!

Mr. Clean's Cozy Disney Home w/ Luxury Finishes
• Newest house in the #1 resort community in the Disney Area, Windsor Hills • ALL Mattresses & Pillows are encased in waterproof SANITIZED covers. • 2 FUN children themed rooms (Star Wars, & Frozen) • Onsite, driveway parking for 3 vehicles • FREE pool heat + BBQ with ALL rentals • Fully equipped + stocked kitchen; including Keurig machine • Self check-in with digital lock • Super FAST Wi-Fi wireless internet speed at +1,000 Mbps!! • Property is managed directly by owner

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!

A Refined Modern Oasis next to Disney World
An architecturally stunning 2400 square foot corner villa next to Disney World Orlando that is privately owned and designed by the world-renowned Pininfarina Group of Italy embodies modern sophistication with open-concept living, high ceilings, 4 bedrooms (2 master bedrooms – one on each floor), 4 en-suite bathrooms, and a downstairs half bath. All bathrooms each have their own bath and shower supplies. THERE ARE NO CAMERAS ANYWHERE ON OR IN THE PROPERTY.

No Airbnb Fee | Newly Renovated 4BR w/ Pool!
**We offer EV Charger for FREE!!! The magic of Orlando starts at home! This incredible house has much more than you need; it has everything you WANT! We offer guests comfort, convenience and an amazing experience!! Transparency and communication is very important to us! We want to make it clear, that we are here at your disposal for any doubts or suggestions. We can't wait to have you here enjoying peace and quiet and having lots of fun!

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 :)
Popular amenities for Windsor Hills, Four Corners vacation rentals
Stay near Windsor Hills's top sights
Windsor Hills, Four Corners home rentals

4 bedroom, south facing pool 3 miles to Disney

Themed House • Arcade Room • Summerville Resort

10 Min to Disney • Cozy Townhome + Jacuzzi + BBQ

4BD 2BA Kissimmee Pool House near Disney

★Completely Renovated★ 3 mi to Disney+Free Resort!

Disney Escape at Windsor Hills

Home mins to Disney, pool, arcade, waterslides

Glamorous and Modern House 8 minutes to Disney
Other great vacation rentals in Windsor Hills

Gorgeous 5BR @Encore next to Disney - 7710

Relaxing Vacation Resort Villa

Themed villa wt Pvt Pool near Disney|Gameroom, BBQ

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

Tiki Palms | Game Room| Heated Pool | Themed

Mickey Train Bed, Free Waterpark, 10 min to Disney

*Pixie Dust Penthouse* Totally Remodeled, Luxury

Cozy Home close to Disney with a Heated pool!
When is the best time to visit Windsor Hills?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$47,460 GYD | G$48,505 GYD | G$52,059 GYD | G$52,268 GYD | G$46,832 GYD | G$48,296 GYD | G$51,223 GYD | G$46,832 GYD | G$42,442 GYD | G$46,205 GYD | G$50,805 GYD | G$58,122 GYD |
| 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 G$10,454 GYD 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
- Family-friendly rentals Windsor Hills
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- Rentals with pools Windsor Hills
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Disney Springs
- SeaWorld Orlando
- Orlando / Kissimmee KOA
- Give Kids the World Village
- 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
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!
- Camping World Stadium
- ChampionsGate Golf Club
- Southern Dunes Golf and Country Club




