
Holiday rentals in 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 €52 per night before taxes and fees

Verified guest reviews
Over 14,470 verified reviews to help you choose

Family-friendly holiday rentals
600 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

4.8 Average rating
Windsor Hills stays are highly rated by guests – averaging 4.8 out of 5!
Top-rated holiday rentals in Windsor Hills
Guests agree: these stays are highly rated for location, cleanliness and more.

New Luxury Condo near Disney
Steps from the swimming pool and water park. Covid-19 safe. 500 megabytes of Wi-Fi! The apartment has a privileged location: it is in the gated community of Windsor Hills, the closest to the parks. 10 minutes from Animal Kingdom, Epcot, Hollywood Studios and Magic Kingdom and 25 minutes from Universal parks. In addition, it has easy access to the airport (US 192, FL 417 and I-4), Downtown Orlando, Miami and all the attractions of the Central Florida region (Daytona Beach, Clearwater, St. Petersburg).
4.93 out of 5 average rating, 177 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!
4.86 out of 5 average rating, 145 reviews
Game & Theater Room, Castle Bunks, Pool & Spa
Vacation at Windsor’s Best located in Windsor Hills Resort just 2 miles from Walt Disney World. This one-story 4 bed, 4 bath vacation villa has everything you need for a wonderful getaway with family or friends. Situated on an elevated corner lot, this spacious villa with it's private pool and spillover spa offers a beautiful view overlooking the resort community. Plus, guests have access to the family-friendly Windsor Hills Resort amenities, including the water park, playgrounds, gym and more.
4.99 out of 5 average rating, 161 reviews
*Hibiscus Hideaway* Minutes to Disney+Free Resort!
Closest FREE resort to Disney Parks! Hibiscus Hideaway is a 6 bedroom 4 bathroom luxury villa that sleeps 14. Completely renovated in October 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 & 10' custom-built farmhouse table to seat the whole family! Every detail has been thought of!
4.97 out of 5 average rating, 175 reviews
Highest Rated Minutes to Disney! -Newly Renovated
• Newest house in the #1 community in the Disney Area, Windsor Hills • Only home with 7 bedrooms in the community (3 KING beds) • Extra privacy: only one side & no rear neighbors • 4 children themed bedrooms (Mickey, Star Wars, Toy Story, & Frozen) • Onsite, driveway parking for 4 vehicles • FREE pool heat + BBQ with all rentals • Fully equipped + stocked kitchen • Self check-in with digital lock • Super FAST Wi-Fi wireless internet speed at +1000 Mbps • Property is managed directly by owner
4.95 out of 5 average rating, 173 reviews
The Manatee Manor | 5 BR•Windsor Hills•Game Room
Welcome To The Manatee Manor - A 5 bedroom, 5 bath home located in Windsor Hills, right in the heart of Kissimmee's tourist area, and mere minutes to the gates of Disney! With a feel of 'Better than home', you'll never want to leave. Outfitted with all the standards that you come to expect (Pool, Hot Tub, plenty of space, and serene décor), in addition to themed rooms, big screen smart TVs, and complimentary pool/hot tub heat - life doesn't get any better than when you stay at "The Manor"!
4.94 out of 5 average rating, 110 reviews
Resort Home 3.5 miles to Disney with home theater
We welcome you to stay in our home located in the Windsor Hills community with a water park, slides, theatre and so much more! The house is just 3.5 miles from Disney’s Animal Kingdom. Our home has 6 large bedrooms including laundry in the home, an 8 seat home theatre, TVs in every room, a large swimming pool & spa with a large patio cover, plus a large kitchen fully equipped with everything you need for your stay. Please message us if you have any questions, we look forward to hosting you!
4.85 out of 5 average rating, 157 reviews
Disney Inspired 3 Bedroom Townhome w/Private Pool!
Our Mickey themed townhome is 15-20 minutes away from the Disney World parks giving YOU the best of both worlds. With 1 bedroom downstairs and two bedrooms upstairs, each with their own bathroom and shower, you'll have the perfect place to stay that gives a Disney Magic VIBE without the chaos of staying inside Disney World resort areas. Our townhome is located in the gated, guarded Windsor Hills Resort Club and is a 60 second walk from amenities like fitness center, pools and game room.
5.0 out of 5 average rating, 7 reviews
Cozy Themed Villa 6 BR | Close to Disney
🏖️☀️🏄♀️Stay just minutes from Disney in this spacious 6-bedroom home, perfect for a family getaway. It comfortably sleeps up to 14 guests and is designed for both kids and adults to enjoy. Located in Windsor Hills Resort — one of the closest communities to Disney World — you’ll have quick and easy access to the parks. Enjoy themed bedrooms, a game room, and your own private patio and pool — great for relaxing after a fun day at Disney.🌴👙🩳🥽🩴 ❤️❤️We'd love to welcome you here!
4.99 out of 5 average rating, 111 reviews
Splendid house 1, 5 miles to Disney
Crestwynd Bay condominium is only 1,5 miles to Disney Parks entrance. Walmart is 0,3 miles,very near. Beautiful and complete townhouse with 3 bedrooms, 3 bathrooms, kitchen equipped, laundry room, free WIFI, exterior area . Self check-in. This condo has community pool and children playground. Parking for car in front of the house. Is five minutes from target ,pharmacies , restaurants and fast foods. Ten minutes of outlets and 15 min from Universal parks and sea world. Great location!
4.87 out of 5 average rating, 402 reviews
*Windsor Hills Ohana Oasis* 4/4 Disney Pool Home
A house perfect for families, located just minutes from Disney and other attractions in the Orlando area. This beautiful Windsor Hills pool home follows all federal, state, county, & CDC guidelines. All of our properties are properly cleaned for your safety. Maximum of 9 guests. This nearly 2,000 sq ft air-conditioned home has 4 bedrooms 4 bathrooms and a private pool. The house sleeps up to 9 people. Price includes taxes. House rules prohibit parties, pets, and smoking indoors.
4.8 out of 5 average rating, 119 reviews
Windsor Orlando Private Arcades,Theater,Pool-Spa
Orlando, Disney, Arcade, Movie Theater, Massage Chair, Pool, Hot Tub, 2 King Beds, Kids Bunk Bed, Kissimmee. Upgraded games room IN the private home, theater for evenings home and your private lanai with pool and hot tub. Choose from including Pump It Up dance, Sponge Bob Racing, NASCAR racing, Legends 3, Pac-Man's Arcade Party, an 80-inch TV, and an Xbox 360. Watch your favorite movies on the 92-Inch projection screen, surround sound, and stadium style seating.
4.99 out of 5 average rating, 255 reviewsPopular amenities for Windsor Hills holiday rentals
Other great holiday rentals in Windsor Hills

Disney Family Fun Villa
5.0 out of 5 average rating, 28 reviews
Coastal Magic Retreat at Windsor Hills
5.0 out of 5 average rating, 12 reviews
Getaway Cove Villa
4.86 out of 5 average rating, 29 reviews
Top Floor Condo | Pool & Water Park View | Disney
5.0 out of 5 average rating, 7 reviews
Hibiscus Villa w/ themed rooms, game room and pool
4.9 out of 5 average rating, 31 reviews
Disney Pool&Spa Windsor Hills Privacy
4.91 out of 5 average rating, 23 reviews
Retreat w/ Game Room, Pool, Spa, BBQ | Near Disney
4.79 out of 5 average rating, 38 reviews
3BR First Floor | Free Water Park | 5 Min Disney
5.0 out of 5 average rating, 3 reviewsDestinations to explore
- Rentals with a hot tub Windsor Hills
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- Pet-friendly rentals Windsor Hills
- Serviced apartment rentals Windsor Hills
- Family-friendly rentals Windsor Hills
- Rentals with pools Windsor Hills
- Walt Disney World Resort
- Universal Studios Florida
- Universal Orlando Resort
- Disney Springs
- SeaWorld Orlando
- Orange County Convention Center
- Orlando / Kissimmee KOA
- Epcot
- Universal's Volcano Bay
- Kia Center
- Camping World Stadium
- University of Central Florida
- Disney's Animal Kingdom Theme Park
- Tinker Field
- Discovery Cove
- Reunion Resort Golf Courses - Palmer & Watson
- Old Town
- LEGOLAND Florida Resort
- ChampionsGate Golf Club
- ICON Park
- Disney's Hollywood Studios
- Epperson Lagoon
- Aquatica
- Southern Dunes Golf and Country Club





