Family-friendly holiday rentals in Windsor Hills, Four Corners

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Top-rated family-friendly rentals in Windsor Hills, Four Corners

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Top guest favourite

Home in Davenport

4.93 out of 5 average rating, 206 reviews

Orlando 5BD+Pool, Near Disney & ChampionsGate Golf

Spacious and cozy house, gated, quiet, safe community, private pool, and view of preservation. | 3 min | Publix & Aldi Groceries, TacoBell & Wendy's | 4 min | Olive Garden & LongHorn Steakhouse | 5 min | Panera Bread & Miller's Ale House | 6 min | ChampionsGate Golf Club | 14 min | Walmart & TARGET | 19 min | DISNEY AREA | 19 min | ESPN Sports | 29 min | UNIVERSAL and EPIC Universe | 30 min | ORLANDO Convention Center | 39 min | MCO Airport | 60 min | Bush Garden's | 90 min | Sarasota & Beaches

Top guest favourite

Townhouse in Kissimmee

4.94 out of 5 average rating, 177 reviews

Updated Pics | 5 Miles to Disney | Themed bunkroom

🎉 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 an Olympic 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 conveni

Guest favourite

Apartment in Kissimmee

4.84 out of 5 average rating, 134 reviews

2 miles to Disney.Mickey Mouse Condo-Windsor Hills

♥ 2/2 top floor condo (sleeps 6) in Windsor Hills Resort,2 miles from Disney World entrance ♥ Free access to resort pool & waterpark ♥ All amenities open 365 days ♥ Free parking ♥ Free wifi, Smart TVs in all 3 rooms ♥ Master bedroom w/ queen bed & 12" memory foam mattress ♥ Mickey kids bedroom w/ bunk bed, XBox One, air hockey & toys ♥ Strollers, mini crib, pack n play, high chair, step stool in unit ♥ Fully equipped kitchen ♥ Washer & dryer in unit ♥ 2 elevators in building ♥ Valet trash pickup

Superhost

Townhouse in Kissimmee

4.89 out of 5 average rating, 136 reviews

"Sunset Hideaway" - Enchanted Lakeside Retreat

Discover our luxurious 2100 sq ft, four-bedroom townhouse near Orlando's magic! A vast open-plan lounge meets a gourmet kitchen with a grand island. Step out to a sunlit pool deck facing a serene lake, perfect for Florida sunsets. Dine outdoors, watch TV, or sunbathe. Enjoy a ground-floor queen room with a spa-like ensuite. Upstairs, relax in a plush lounge with a TV and Xbox, sleep like royalty in the King En-Suite, or dive into themed rooms of Avatar and Mickey. Luxury and enchantment await!

Superhost

Townhouse in Kissimmee

4.78 out of 5 average rating, 101 reviews

With Resort Amenities 3BR/3BA home 2 mile Disney

If you are looking for a charming, clean and peaceful home with a private splash pool, Just two miles to Walt Disney World, you found it! The perfect place for your stay, Windsor Hills is an amazing community with a resort pool and waterpark. Staying in our townhouse you will have access to the clubhouse, pool, and community amenities. Enjoy three bedrooms, each with full bathrooms, a full-size washer & dryer, a fully stocked kitchen, high-speed Wifi, cable and smart TVs will make it fun!

Guest favourite

Home in Kissimmee

4.81 out of 5 average rating, 340 reviews

Tropical Villa,Private Pool, 3.5 miles from Disney

Beautiful 4 BR villa with extended south facing pool deck. It's situated just minutes away from the world-renowned theme parks, including Disney World, Universal Studios, and SeaWorld. Our cozy villa offer a perfect base for families and friends to enjoy all the attractions while enjoying the quiet surroundings and warm sunshine. The villa is well equipped with modern amenities to make your stay comfortable and enjoyable. Book your stay with us today and start making unforgettable memories!

Guest favourite

Apartment in Kissimmee

4.82 out of 5 average rating, 290 reviews

Beautiful 2/2 Gem, 2 mi to Disney with Water Park!

Brand new flooring, mattresses, AC, water heater and more! Disney SO close! Our Property Manager will see to any needs during your stay, a rental registration is required. Beautiful, clean and comfy condo in Windsor Hills Resort with a new WATER PARK and tons of amenities. Stainless appliances and granite, free wifi/cable, desk/charging station and PS 3 with games, Pack N play, stroller, high chair, wash/dryer, a starter kit of supplies. No hidden fees, free parking. Perfect for families!

Top guest favourite

Home in Kissimmee

4.87 out of 5 average rating, 220 reviews

RU Incredible Parents? Themed-7bed, 4mi. to Disney

One of a kind 7 bedroom themed home with pool, sleeps 15 close to Disney! (And, yes, location does matter.) Our clubhouse is designed to make your once in a lifetime vacation memorable. We spoke to Disney experts (children) about what they prefer and created a magical experience. There is something for everyone with surprises throughout! Why limit your experience only to the parks? Read our reviews and see why parents that book with our Magical Clubhouse are ‘Incredible’ to their families.

Guest favourite

Flat in Kissimmee

4.89 out of 5 average rating, 368 reviews

Superb Townhouse Newly Renovated 1 mile to Disney

This 2-bedroom rental in Kissimmee is just 1 mile from Walt Disney and only 14 miles from Universal. This home has been completely renovated as of May 2017 with all brand new furniture and linens. This gated community is ideal for families and features plenty of updated, modern conveniences. Take advantage of the many on-site resort amenities including a swimming pool, hot tub, fitness center, tennis and basketball courts, and a fully-equipped game room with a pool table and air hockey.

Guest favourite

Home in Kissimmee

4.95 out of 5 average rating, 168 reviews

🏰 Disney Princess Crownhouse! Closest to Disney!

*100% 5-star reviews in 2025* *End unit* South facing pool Magical 3 bed, 3 bath luxury crownhouse in 5 star gated Windsor Hills Resort. *2 miles from the gate of Walt Disney World! Enjoy our magical Mickey and Princess Rooms designed with both adults and kids in mind. Your little princess will love our Princess room with Disney collection princess furniture. *Resort pool, a fully equipped kitchen, you and your family will have a truly magical vacation! Princess-tastic!

Superhost

Apartment in Kissimmee

4.87 out of 5 average rating, 140 reviews

Steps to Disney Gated Luxury Condo, Best Location!

Spacious, 3 Bedroom, 2 Bath Vacation Condo in fantastic Gated Community, Unbeatable location within the Windsor Palms Resort. We have room for 4 adults and up to 3 children. NO RESORT FEES! The convenience of this location will save you money & time. Close to Theme parks, Restaurants, Grocery, retail shopping and anything else you need. Nicely furnished with full kitchen, air conditioning, TV's in all rooms, Full size Washer/Dryer, FREE WI-FI and much more.

Superhost

Home in Kissimmee

4.82 out of 5 average rating, 130 reviews

Magical Adv 5 Star Villa Movie Room Arcade Pool an

Experience enchantment at Magical Adventure Villa, a top-rated 6-bedroom and 4-bath home for 12 guests. Conveniently located in Windsor Hills Resort, just 2 miles from Disney World®. Experience the highly acclaimed getaway that has garnered rave reviews. Enjoy a private pool, home theater, and a thrilling arcade. Unleash your inner Jedi at the state-of-the-art Star Wars gaming center with a movie theater, Xbox One, Nintendo Switch, and immersive 3D designs.