Vacation rentals in Windsor Hills

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Top-rated vacation rentals in Windsor Hills

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Top guest favorite
A spacious pool area is featured, surrounded by palm trees and lounge chairs. The expansive waterpark includes vibrant waterslides, providing a lively atmosphere. A relaxing hot tub is also visible nearby, complemented by a well-maintained landscaping that enhances the resort's inviting ambiance.
Condo in Kissimmee
4.98 out of 5 average rating, 185 reviews

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!

Top guest favorite
A spacious living area is showcased, featuring a large sectional sofa with decorative pillows. A flat-screen TV is mounted on a media console, while a coffee table sits in the center. Light from nearby windows enhances the open atmosphere leading into the dining area.
Townhouse in Kissimmee
4.93 out of 5 average rating, 244 reviews

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!

Top guest favorite
The community pool area features a winding pool surrounded by palm trees and lounge chairs. A colorful water slide is visible, along with shaded cabanas. The well-maintained grounds include lush greenery and pathways leading to residential buildings in the background.
Condo in Kissimmee
4.98 out of 5 average rating, 114 reviews

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.

Top guest favorite
An inviting living space features a modern gray sofa centered around a round coffee table, set on a plush area rug adorned with a playful pattern. A wall-mounted fan circulates air beneath a vibrant Mickey Mouse artwork, while a dining table for four is positioned nearby.
Condo in Kissimmee
4.94 out of 5 average rating, 174 reviews

🏖 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.

Top guest favorite
Apartment in Kissimmee
4.96 out of 5 average rating, 91 reviews

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!

Top guest favorite
The living area features a comfortable gray sofa adorned with accent pillows, complemented by a wooden coffee table. A large TV is mounted on the wall, with a stylish chair placed nearby. Natural light enters through glass doors, which lead to a balcony.
Apartment in Kissimmee
4.99 out of 5 average rating, 134 reviews

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!

Superhost
A private splash pool is visible, surrounded by a fully screened-in area, providing a safe environment. Nearby, a vibrant water park can be seen, featuring colorful slides and play areas. The living space showcases modern furnishings, inviting family gatherings, and themed decor appealing to children.
Townhouse in Kissimmee
4.75 out of 5 average rating, 147 reviews

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!

Top guest favorite
A recreational game room is presented, featuring an air hockey table and a pool table centered in the space. Two gaming chairs are positioned near flat-screen monitors on the wall. Colorful LED lighting creates an engaging atmosphere in the room.
Villa in Kissimmee
4.96 out of 5 average rating, 151 reviews

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

Top guest favorite
A gold keypad lock is mounted on a white door frame, with the blurred outline of a spacious sleeping area behind it. Soft lighting from a nearby table lamp casts a warm glow, while green curtains hang in the background.
Guest suite in Kissimmee
4.96 out of 5 average rating, 184 reviews

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!

Guest favorite
A modern living area boasts high ceilings and large windows that invite natural light. Elegant furnishings include two gray sofas and a wooden dining table set against a backdrop of neutral tones. A flat-screen TV is mounted on the wall, and vibrant artwork decorates the space.
Townhouse in Kissimmee
4.95 out of 5 average rating, 103 reviews

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.

Top guest favorite
A game room is presented with a red and neutral color scheme, featuring a billiard table with a set of colorful pool balls arranged on it. A television is mounted on the wall, and a dartboard is visible. The space is accented with vibrant wall art and seating areas.
Home in Kissimmee
4.9 out of 5 average rating, 133 reviews

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!

Top guest favorite
The cottage features a charming exterior with bright yellow siding and a classic gabled roof. Lush palm trees and manicured hedges frame the entrance, which includes a welcoming porch with yellow chairs. Large windows allow natural light to enhance the inviting facade.
Cottage in Kissimmee
4.98 out of 5 average rating, 124 reviews

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

When is the best time to visit Windsor Hills?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$47,460 GYDG$48,505 GYDG$52,059 GYDG$52,268 GYDG$46,832 GYDG$48,296 GYDG$51,223 GYDG$46,832 GYDG$42,442 GYDG$46,205 GYDG$50,805 GYDG$58,122 GYD
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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

  1. Airbnb
  2. United States
  3. Florida
  4. Osceola County
  5. Four Corners
  6. Windsor Hills