Holiday rentals with outdoor seating in Windsor Hills, Four Corners

4.99 out of 5 average rating, 137 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.

4.94 out of 5 average rating, 185 reviews

5 miles to Disney- Private Pool - Arcade Games

Just 4 miles from Disney, our luxury townhome is your family’s perfect escape! With a private splash pool, brand-new 65” Smart TV, and family-friendly gear (stroller, pack n’ play, high chair), you’ll have everything needed for a carefree stay. Located across from Windsor Hills Resort’s clubhouse, enjoy resort perks like a pool, splash pad, fitness center, and theater! Sleeps 8 comfortably with 3 en-suite bedrooms, including a themed Disney beach kids’ room. Fun, comfort, and convenience await!

4.97 out of 5 average rating, 130 reviews

Villa in Kissimmee

*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!

4.98 out of 5 average rating, 135 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, 164 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.

5 out of 5 average rating, 6 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

Superhost

4.75 out of 5 average rating, 12 reviews

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

Just 10 minutes from Disney, this 6BR home has it all—Minions, Avatar, and Guardians of the Galaxy-themed kids' rooms, a hidden Mario game room, and luxe king suites. Outside, enjoy a private screened pool and spa with free heat, a full outdoor kitchen, firepit lounge, movie screen, sauna, and dining for 8. Located in a gated resort with slides, arcade, gym, theater, and sports courts, it's the perfect blend of play and relaxation for families or groups.

Guest favourite

4.97 out of 5 average rating, 70 reviews

Fantastic home just 3 miles from Disney World!

Wishes and Dreams Villa, in the popular Windsor Hills Resort, is the perfect Disney area retreat! This home offers all the comforts you expect from a high end vacation home. Every spacious area has been professionally decorated & furnished. Challenge your family/friends to a friendly competition in the home's game room! You will also love having your own pool, relaxing on the private lanai and enjoying meals al fresco. Pool heat is FREE!

4.9 out of 5 average rating, 298 reviews

Disney fireworks new house - 5 minutes to Disney

Welcome to our beautifully decorated 2-store Townhouse only 6 miles away from the Disney Parks and many other attractions. You will have the entirely house for yourself and your family while enjoying your vacation in Florida. We have sought to equip our home to a high standard and to anticipate your needs for a luxurious stay. We truly believe that our home is special based on 4 main reasons: Location, Security, Decoration and Comfort.

Guest favourite

4.85 out of 5 average rating, 131 reviews

7754 Windsor Hills 6B Luxury Pool Home Near Disney

🌟 Welcome to Your Ultimate Windsor Hills Vacation Escape! 🌟 Discover the perfect blend of luxury, comfort, and fun in this newly renovated 6-bedroom, 4-bathroom villa at Windsor Hills Resort Orlando, located just 5 miles from Walt Disney World. With a private pool, game room, and access to world-class resort amenities, this home is designed for families and groups who want an unforgettable Orlando vacation.