Holiday rentals in Windsor Hills

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Top-rated holiday rentals in Windsor Hills

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Guest favourite
A townhouse exterior is shown beneath a gentle rainbow. Flanking palm trees provide a tropical setting, while the structure features multiple windows with white frames and dark shutters. A parked vehicle can be seen in front, enhancing the suburban feel.
Home in Kissimmee
4.88 out of 5 average rating, 124 reviews

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!

Top guest favourite
The living room features a comfortable sofa and an accent chair set around a central coffee table. A smart TV is mounted on the wall, while large windows allow natural light to fill the space, complementing the overall cozy atmosphere.
Flat in Kissimmee
4.98 out of 5 average rating, 52 reviews

Full Apt w/ Gym Pool 10m Disney

Welcome to Your Magical Gateway – Just 10 Minutes from Orlando's Parks! Discover the perfect retreat for your Orlando adventure! Our bright, modern apartment is ideally located for visiting Disney and Universal, offering a peaceful, resort-style escape with all the comforts of home. Whether you're here for the theme parks or a longer-term stay, you'll find this cozy space, which sleeps 4, is the perfect home base. CONTACT US TO INQUIRY ABOUT ADDITIONAL POTENTIAL DISCOUNTS FOR MULTI-DAY STAY

Top guest favourite
Apartment in Kissimmee
5 out of 5 average rating, 12 reviews

Adventurers Retreat | 3mi Disney | Walk to Walmart

Perched near the banks of the Oakwater Delta sits the Oakwater Outpost, a lesser-known destination of the Jungle Navigation Co. Our skippers have stepped out briefly (mumbling something about navigation training), but explorers are welcome to use our boathouse to rest and prepare for their adventures in the surrounding jungle. Our maps are about 70% accurate, our boats float most of the time, and our skippers are almost good with directions—assuming they find their way back to the boathouse.

Guest favourite
An open-plan living area features a spacious seating arrangement with two patterned chairs and a gray sofa. A large wooden dining table with blue chairs is visible, alongside a TV mounted on the wall. Light pours in through multiple windows, enhancing the inviting atmosphere.
Townhouse in Kissimmee
4.95 out of 5 average rating, 183 reviews

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.

Guest favourite
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.
Flat in Kissimmee
4.99 out of 5 average rating, 135 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!

Top guest favourite
The image features a collage of six photos showcasing various aspects of the condo. Highlights include a vibrant water park with dueling slides, a Star Wars themed bedroom with two beds and neon lights, a master bedroom with decorative bedding, a cozy living room with ample seating, and a modern kitchen equipped with stainless steel appliances and granite countertops.
Apartment in Four Corners
5 out of 5 average rating, 46 reviews

Windsor Hill Fun Condo Starwars, Moana, Pool, Spa

Welcome to your dream vacation getaway by FunStay Homes! - Beautifully furnished 3-bedroom, 2-bath condo - Spacious living areas with beautiful interior - Themed rooms: Moana, Star Wars, and Hollywood Tower Hotel - Fully equipped gourmet kitchen with granite countertops - Comfortable amenities including cozy bedding and ceiling fans - Free WiFi, air conditioning, and private entrance - Step outside to relax on the new patio furniture - Free Parking/Street Parking

Top guest favourite
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

Guest favourite
Townhouse in Kissimmee
4.94 out of 5 average rating, 17 reviews

Disney Escape - Private Pool & Full Resort Access

3-bed 3-bath Minutes to Disney Splash pool Huge 98" TV Bedrooms with ensuite bathroom Fully equipped kitchen Zootopia-themed kids' bedroom Video arcade with 60 games PS4 Pool child safety fencing Pool door alarm Stairway child safety gate Potty training seats

Guest favourite
A modern keypad lock is installed on a door, featuring illuminated numbers for easy access. Blurred in the background, a vibrant green plant adds a touch of nature to the entryway, enhancing the welcoming ambiance of the space.
Guest suite in Kissimmee
4.93 out of 5 average rating, 187 reviews

It's too much like a elegant mini-hotel (7)

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 favourite
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 favourite
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 :)

Guest favourite
Townhouse in Four Corners
4.9 out of 5 average rating, 10 reviews

3BR - Fun Themed Rooms Near Disney!

Highlights: 📍 Only 2 miles from Disney & minutes to shops and dining ✨ Awesome themed rooms kids will LOVE 📶 Free high-speed WiFi — great for streaming or Zoom calls 🏡 Windsor Hills Resort (No resort fee) with top amenities 💦 Brand-new Kids’ Water Park included FREE 🏊‍♂️ Private screened splash pool for your family 🔐 24/7 gated security for peace of mind

Popular amenities for Windsor Hills holiday rentals

When is the best time to visit Windsor Hills?

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Quick stats about holiday rentals in Windsor Hills

  • Total holiday rentals

    Explore 640 holiday rentals in Windsor Hills

  • Nightly prices starting at

    Windsor Hills holiday rentals start at £37 per night before taxes and fees

  • Verified guest reviews

    Over 13,540 verified reviews to help you choose

  • Family-friendly holiday rentals

    590 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 40 rentals that welcome pets

  • Holiday rentals with a pool

    630 properties feature pools

  • Rentals with dedicated workspaces

    380 properties have a dedicated workspace

  • Wifi availability

    640 of Windsor Hills holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Gym and BBQ grill across Windsor Hills rentals

  • 4.7 Average rating

    Windsor Hills stays receive an average rating of 4.7 out of 5 from guests

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  5. Four Corners
  6. Windsor Hills