Holiday houses in Windsor Hills, Four Corners

5 out of 5 average rating, 3 reviews

10 Min to Disney |Themed | Sauna | Pool | Golf Sim

This 6BR dream villa is just minutes from Disney and fully redesigned for comfort and fun! 3 elegant bedrooms plus 3 themed rooms: Minions, Avatar, and Guardians of the Galaxy—plus a hidden Mario-themed speakeasy game room. A brand-new kitchen, bathrooms, and living spaces complete this magical escape. Recently completed down-to-the-studs renovation—every detail thoughtfully curated with luxury, comfort, and style in mind. Be among the first to experience it! Book now for an unforgettable stay!

4.97 out of 5 average rating, 120 reviews

*Brand New!* 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!

5 out of 5 average rating, 13 reviews

Townhouse in Kissimmee

free waterpark-2 king suites-minutes to parks

- Animal Kingdom 4 miles - Magic Kingdom 8 miles - Epcot and Hollywood 5 miles - main floor king bed - upstairs king bed - upstairs queen & twin bed - Private Heated Pool: Enjoy your own private heated pool! Pool heat is provided seasonally from Dec-Mar – never an extra charge for pool heat - all new furniture&linens - Free community water park - short walk from house - community pool, hot tub, play to play arcade, playground, ping pong, pool table, theater, gym, pickleball & basketball court

Superhost

4.85 out of 5 average rating, 117 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!

4.98 out of 5 average rating, 128 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

4.94 out of 5 average rating, 36 reviews

ReDesigned | Windsor Hills | Location | Water Park

Discover the enchantment of our 6-bedroom Villa located in the vibrant Windsor Hills community, a stone's throw from Disney. Revel in our heated pool, or splash around in the community water park. Each room has been designed with guests in mind for an immersive experience. Embark on an adventure in our game room and relax in the comforting ambiance of our cozy sitting area. This home sleeps up to 14 people and is ideal for families desiring a magical and engaging retreat.

4.93 out of 5 average rating, 27 reviews

Family Disney Home | Pool | Game Room | Hot Tub

Enjoy a comfortable stay at this modern and clean home. With a private pool, a hot tub, a pool table, foosball, and air hockey, there is fun for the entire family. Create magical memories with easy access to Disney and other nearby attractions. Enjoy fast wifi, free parking, and complimentary access to the resort clubhouse, water parks, and more. Disney World – 7 min drive Old Town – 10 min drive Fun Spot America – 12 min drive Book For Lasting Memories In Kissimmee!

4.98 out of 5 average rating, 107 reviews

4mi to Disney | Games | Private Pool

Get ready to make memories of a lifetime just over 3 miles to Disney when you stay at this newly renovated Star Wars and Lego-themed private pool villa. Located in Formosa Gardens Estates, a prestigious gated community, our home is professionally furnished with multigenerational families in mind and can comfortably sleep up to 15 guests. After a trip to the parks, enjoy a refreshing dip in the private pool and rest those tired feet in the spa (pool heat included!).

5 out of 5 average rating, 221 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.

4.89 out of 5 average rating, 116 reviews

2584 - 6 Bedroom w/ Pool and Water Park Included

Welcome to Your Ultimate Vacation Escape at Windsor Hills Resort! This charming vacation home in Windsor Hills Resort offers six spacious bedrooms and is perfect for the entire family. Located in one of the finest gated communities in the area, Windsor Hills Resort features 24-hour security, ensuring only permitted guests have access to the neighborhood. We’re just a short distance from Disney parks, shopping, dining, and many of Orlando’s top attractions.

Superhost

5 out of 5 average rating, 3 reviews

Themed Rooms with Private Pool in Kissimmee

Welcome to this amazing house with unique themed rooms! - 5 themed bedrooms with private bathrooms - Private pool and spa - Game room for endless fun - Access to Windsor Hills Resort amenities, including a water park - 24/7 check-in at a gated community - No resort fees - Pool/Spa heat available for an additional fee It's important that the title is as close to 50 characters. You should use some of the other characteristics of the listing.

4.96 out of 5 average rating, 27 reviews

Apartment in Celebration

Mystic dunes resorts 1 bedroom apartment

Whether you're planning a short weekend getaway, a week-long family vacation, holiday stay, or a business trip mixed in with some fun, Mystic Dunes Resort is the perfect choice for families, couples travelling together, golf vacationers, groups and business travelers. With spacious villas, wide array of resort amenities and close proximity to Orlando theme parks, attractions and entertainment, This Resort provides so much more than a typical hotel.

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Other great holiday rentals in Windsor Hills, Four Corners

4.81 out of 5 average rating, 140 reviews

Villa with private Pool and Spa. Close to Disney.

KarissaRating, 5 stars1 week ago

Our family had a great stay at the Villa. We stayed for 7 days. Our trip was purely a Disney world vacation. House is close to all Disney parks. It’s in a great location to get to other outings. Our 2 teens loved the themed Disney rooms. Host is responsive and welcoming and gave clear instructions. The house and pool is beautiful.. Our only regret is that we didn’t book it for longer, we didn’t want to leave. Thank you Michel, our family had such a memorable family vacation.

5 out of 5 average rating, 18 reviews

Luxury 6 Bedroom Pool Home in Windsor Hills

ElizabethRating, 5 stars2 weeks ago

As an ex owner of a rental property in Florida I am fussy about where I stay. We travelled as a party of 13 and Steven’s place was superb for us. The house is clean, plenty of space, ideally suited for restaurants, things to do etc. We had two minor issues which we dealt with efficiently. I highly recommend Steven’s place.

5 out of 5 average rating, 19 reviews

Townhouse in Kissimmee

4miles to Disney/ Free Waterpark/ Private Pool

JohnRating, 5 stars2 days ago

Aya's place was perfect for our family. 3 bedrooms each with their own bathroom was what caught our eye. The place was very clean and modern. The grandchildren loved the pool and small water park. We would stay here again if we return to Orlando. Thank you Aya.

5 out of 5 average rating, 5 reviews

Windsor hills Amazing,6BDrm lakeview,3mi to WDW!

BeckiRating, 5 stars1 month ago

Our stay was amazing and even better than we imagined. This place is as described and more. Love all of the extra effort and thought that Mike and Meta put into making this place the perfect get away. Before you arrive you have the app they created with all info, when you get there everything is ready for you plus more than you usually get at an Airbnb (extra toilet paper, laundry, garbage bags, coffee, tons of towels for the bathrooms and pool)! Made such a difference for an amazing week stay. The house was spotless, the beds were comfy and every question or concern was immediately addressed. Great recommendations for pre-stocking the fridge and pantry with a service was also perfect. Would do this stay again in a heartbeat (and hopefully will again soon!) this location in Windsors hills was so quiet and walkable to the resort area too! Book this place you won’t regret it!!!

4.95 out of 5 average rating, 56 reviews

Disney Pool Villa | Windsor Hills | Sleeps 8

SarahRating, 5 stars3 days ago

We had a fantastic stay at this property! The place was spotless, comfortable, and had a very welcoming vibe. The location was ideal—close to restaurants, shops, and easy access to all things Orlando! One of the highlights was the pool area—it was beautiful, clean, and well-maintained, with plenty of lounge chairs and shaded spots to relax. I really appreciated the clear communication from the host and how easy the check-in process was. I would absolutely stay here again and highly recommend it to anyone looking for a relaxing and convenient place to stay!

5 out of 5 average rating, 4 reviews

Fun/Private + Game Room + Themed BRs + Pool/Spa

SteveRating, 5 stars2 months ago

Amazing space, best rental we’ve had for our annual visit in the area over the past 5 years. Kids loved the game room. House was spacious, great kitchen, new updates and appliances. We’ll be back.

5 out of 5 average rating, 13 reviews

Once upon a galaxy: Star Wars/fairytale retreat

CassandraRating, 5 stars3 weeks ago

We spent a week on vacation here and it was amazing! This was our first time staying at this property and we can’t wait to go back! The home is close to Disney so it was perfect for our Park days. On our off days, we took full advantage of the pool and the in-home theater. My children enjoyed our walks to the playground. The home was clean and very well stocked. The AC was great and kept the home cool. We were all able to shower at the end of a long day and had sufficient hot water. All appliances were in great shape so we were able to wash laundry and do minimal cooking with zero hesitation. The hosts were responsive and very helpful. We love the added security of being in a gated community. This really has been one of the top places we’ve had the privilege of staying at!