
Condo vacation rentals in Windsor Hills
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Top-rated condo rentals in Windsor Hills
Guests agree: these condos are highly rated for location, cleanliness, and more.

Stylish Condo 20 mins to Disney/King Bed
Escape to our lovely vacation villa, nestled in the vibrant heart of Orlando's premier golfing destination. Just a 7-mile drive from Disney attractions and 30 minutes from Orlando International Airport. Discover the awe-inspiring Reunion Resort, offering an array of delights. Indulge in delectable dining experiences, take a dip in sparkling pools, savor refreshing drinks at poolside bars and grill. Embark on an extraordinary getaway that exceeds all expectations. Book your stay with us today!

Disney's Doorstep, 3 Bed 2 Bath, Waterslides!
Welcome to your dream vacation! This 3 bedroom, 2 bath, is right on Disney's doorstep, this amazing vacation rental has all the amenities you'd put on your dream list. Two water slides, a kids splash park, walk in pool, movie theater with wheelchair access, game room, fitness center, putting green, playground, shop for snacks, and more! This condo also comes fully furnished with a washer/dryer, WiFi, elevator for wheelchair access, and more. This is sure to be your relaxation destination.

Star Wars Condo in Windsor Hills 3 bdrm, 2 baths
Welcome to our Star Wars themed rental in Kissimmee, FL, just 3 miles from Disney World! Experience the ultimate vacation in a galaxy far, far away. Located in Windsor Hills Resort with a heated community pool and two water slides. The kids bedroom has Star Wars decor, twin bunk beds, and an electronic pinball machine. The condo is decorated with Star Wars artwork and a half-sized Darth Vader figure. The kitchen is fully equipped. Don't miss this chance to live out your Star Wars fantasies.

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!

Family, Disney, Windsor Hills, 11 am checkout.
Walk into your home away from home. Enjoy a relaxing stay. Located on 4th floor. Enjoy morning coffee on a screened-in balcony or a late snack. Pet-free home. Please NO Smoking. Children are always welcome. Come enjoy all of the accommodating facilities at Windsor Hills with a top-notched 24/7 gated security. FREE parking & leisure activities! Maximum of 3 cars allowed per reservation. This includes all guest that are visiting. All unregistered drivers will be denied access by HOA.

Oakwater Resort, Kissimmee , 1.5 Miles to Disney
Enjoy your vacation or business trip in this tastefully 1800 square feet, richly decorated 3 bedroom and 2 full and 1 half bathrooms.The condo located in gated community just 1.5 miles from the gates of Disney. Sleeping arrangements for 8 and more guests with bed linens and towels provided. Full equipped kitchen with pots, pans, and many more kitchen essentials. Washer and dryer There is a clubhouse a few steps from the condo with heated pool, fitness center, tennis court, playground.

Windsor Hills Resort - Disney Pool View Condo
Location, location, location! Windsor Hills pool view condo and only 2 miles to Disney World! This 3 bedroom pool view condo is in the beautiful Windsor Hills Resort gated community. The single level condo is located in the closest building to the pool, water park, clubhouse, hot tub, movie theater, and arcade. The condo has one of the best balcony views in the entire resort. Located on the third floor, the balcony looks directly over the resort pool and lake.

@Look@ ~ 3bed/2bath/1st floor! ~ Sleeps 7!
1ST FLOOR! 3 Bedroom/2 Bathroom Condo with 2 Master Suites! Main Master Suite has a King bed, TV and DVD player, walk in closet and a walk in shower. Second Master Suite has a King bed, TV and DVD player, and a door with direct access to the second bathroom. Guest Bedroom 3 has two Twin beds and a TV and DVD player. The living room features a TV over a beautiful electric fireplace and leather sofas - one is a sofa sleeper!

One in a Minion condo your kids will love +450Mbps
Enjoy of sophisticated and modern accommodations on your next visit to Orlando. This One in a Minion themed two bedroom condo boasts 1082 SQ FT of living space and it's fully equipped for 6 guests. Conveniently located on the ground floor and a short stroll to the clubhouse, pool and dueling water slides. It features a smart lock, High-speed WIFI Internet +450Mbps, cable TV, telephone line, linens & towels and washer/dryer.

Themed Resort Condo | Pool | Spa | Mins to Disney
The Magic Galaxy – an affordable 3 bedroom, 2 bath condo in the gated Windsor Palms resort, known for its cleanliness and thematic charm. The retreat features themes from Star Wars, Mickey Mouse, Jurassic World, and Harry Potter. Enjoy resort amenities like a pool, spa, splash pad, courts for basketball, tennis, and volleyball, a movie theater, game room, gym, Tiki bar and grill, and a sundry shop.

Lovely vacation condo close to Disney & Universal!
Family friendly 3 bedroom 2 bath condo on first level (handicap accessible) at Windsor Hills Resort. Gated access with private parking. Go straight to the condo with Lockbox access code. 7 minute drive to all Disney parks. As a guest you have access to the beautiful pool, hot tub, Water Park, gym, movie theater, Community Center at no extra cost. Everything is open and available.

Orlando Fun: Minutes to Disney and Margaritaville
A cozy, comfortable, and convenient 2-bedroom condominium with 2 full bathrooms, a fully-equipped kitchen (coffee and tea provided), a beautifully decorated living/ dining room, 2 walk-in closets (with plenty of shelves, drawers, and hangers), a washer, a dryer (with laundry detergent provided), an iron, AC (or heating in winter), cable TV, WiFi, and a screened-in balcony.
Popular amenities for Windsor Hills condo rentals
Weekly condo rentals

Poolside 3 Bed Vacation Retreat in Windsor Hills

Andy's Toy Chest at Windsor Hills, Next to Disney!

Renovated Luxury Condo in Windsor Hills Resort!

Lovely Place at Windsor Hills - Condo 2 bd / 2 bh

Sunny Condo Retreat ~ Clean. Cozy. Convenient.

Windsor Hills Condo Near Disney

#304 Resort 3BR/2BA Pool/Spa WindsorHill Disney

Mickey's Welcome Inn - Closest Resort to Disney
Pet-friendly condo rentals

9 miles from Disney - Bella Piazza spacious condo

Magical Champions Gate 3/2 Tuscan Penthouse

Penthouse Lakeview Minutes to Disney/ Universal

King Bed Small Studio Disney World Universal

Brand New AwardWinning Renovated Condo Near Disney

Pet Friendly in Orlando Area near Disney.

Bongo’s Pad~ Gated Resort~ 3 Miles to Disney!

*NEW* Adventureland Stay / Sleeps 6 / Near Disney
Condo rentals with a pool

BEAUTIFUL NEW APARTMENT A FEW MINUTES FROM DISNEY

Fully Themed Harry Potter Magical Experience!

Family Friendly II

Harry Potter 3BR | Windsor Hills - Close to Disney

House of Mouse, 2 bedroom condo

Your Sun, Fun and Everything Relaxation Retreat!

3 Bedrooms Condo Only Minutes From Disney!

WH1201 - NEW Listing - Windsor Hills
Quick stats about condo rentals in Windsor Hills

Total vacation rentals
Explore 60 vacation rentals in Windsor Hills

Nightly prices starting at
Windsor Hills vacation rentals start at $112 CAD per night before taxes and fees

Verified guest reviews
Over 60 verified reviews to help you choose

Family-friendly vacation rentals
50 properties offer extra space and kid-friendly amenities

Vacation rentals with a pool
60 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
60 of Windsor Hills vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Windsor Hills rentals

4.8 Average rating
Windsor Hills stays are highly rated by guests—averaging 4.8 out of 5!
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- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Universal's Volcano Bay
- SeaWorld Orlando
- Disney Springs
- Discovery Cove
- Old Town Kissimmee
- Disney's Animal Kingdom Theme Park
- Magic Kingdom Park
- Epcot
- ESPN Wide World of Sports
- Amway Center
- Reunion Resort Golf Courses - Palmer & Watson
- Walt Disney World Resort Golf
- Aquatica
- Island H2O Water Park
- Disney's Hollywood Studios
- ICON Park
- Southern Dunes Golf and Country Club
- Universal's Islands of Adventure
- Kissimmee Lakefront Park
- Ventura Country Club
- Shingle Creek Golf Club