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.

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Top guest favorite
A spacious pool area is featured, surrounded by palm trees and lounge chairs. The expansive waterpark includes vibrant waterslides, providing a lively atmosphere. A relaxing hot tub is also visible nearby, complemented by a well-maintained landscaping that enhances the resort's inviting ambiance.
Condo in Kissimmee
4.98 out of 5 average rating, 178 reviews

Poolside 3Br~Windsor Hills~Waterpark~2mi to Disney

Your Windsor Hills Getaway starts here! This top-rated condo overlooks the resort pool & waterpark and is just minutes from Disney World! New appliances and updated furnishings, this 3rd floor condo sleeps 8, with plenty of parking. The screened-in balcony can’t be beat, overlooking the pool, hot tub, and waterpark with waterslides! The clubhouse is just steps away, with a store, food, drinks, game room, and fitness center. No resort, parking, or hidden fees. Full access to all amenities!

Top guest favorite
Condo in Kissimmee
4.82 out of 5 average rating, 302 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 favorite
Condo in Kissimmee
4.98 out of 5 average rating, 110 reviews

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.

Top guest favorite
An inviting living space features a modern gray sofa centered around a round coffee table, set on a plush area rug adorned with a playful pattern. A wall-mounted fan circulates air beneath a vibrant Mickey Mouse artwork, while a dining table for four is positioned nearby.
Condo in Kissimmee
4.94 out of 5 average rating, 164 reviews

🏖 Resort Condo | 🎢 2mi -> Disney | 💦 Waterpark Fun

Welcome to Mickasita @ Windsor Hill's! Our condo is the ideal family vacation spot, conveniently located just minutes away from Disney World and all your desired attractions. During your stay, our whole-condo dehumidifier will maintain a comfortable and healthy level of humidity. Recently upgraded, our condo is sparkling clean and offers many resort amenities with the convenience of a home. You'll find new beds with fresh linens, flat-screen TVs, high-speed internet, a gym, and more.

Guest favorite
An aerial view showcases a resort-style pool surrounded by lounge chairs. A colorful water park with slides is located nearby, complemented by lush greenery and palm trees. Multiple buildings are visible in the background, offering a welcoming atmosphere for families.
Condo in Kissimmee
4.85 out of 5 average rating, 184 reviews

WH Condo. Pool/Waterpark and close to Disney!

Take an elevator to unit 302 and witness beautifully decorated Disney themed rooms. Directly outside is a lovely pool and kid-friendly waterpark. All amenities included in cost: game room, theater, exercise room, tennis courts, play grounds, sand volleyball, putting green, basketball court and a marketplace and grill. Located 15 minutes to all 4 Disney parks and Sea World! Looking for more space? Check out our townhome also located in Windsor Hills at 7668 Fitzclarence

Guest favorite
An aerial view captures the resort's inviting pool area, featuring a large, curvilinear swimming pool surrounded by lounge chairs. Adjacent, a water park offers colorful slides and play structures. The three-story condo is visible in the background, highlighted by lush landscaping.
Condo in Kissimmee
4.91 out of 5 average rating, 166 reviews

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.

Top guest favorite
A vibrant water park is featured with colorful slides and play structures, alongside a themed children's bedroom showcasing character decals. The king-sized bed is complemented by a bunk bed set. A stylish logo for Windsor Hills Resort emphasizes safety and fun.
Condo in Kissimmee
4.93 out of 5 average rating, 219 reviews

Andy's Toy Chest at Resort Minutes from Disney!

This fantastic 3 bedroom, 2 bathroom condo is located a few miles from Disney World in the highly coveted (and gated) Windsor Hills Resort. You will have access to all that Windsor Hills has to offer including A NEW WATER PARK, double Olympic sized pool, play grounds, clubhouse, gym, video arcade, marketplace and grill, tennis courts, and more! This condo features an amazing themed bedroom that will help your little ones feel the Disney magic!

Guest favorite
The living room features a comfortable sofa with colorful accent pillows, a coffee table, and a flat-screen TV mounted on the wall. A round dining table with chairs is visible in the background, along with artwork and decor that add a touch of elegance.
Condo in Kissimmee
4.86 out of 5 average rating, 214 reviews

@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!

Guest favorite
The aerial view showcases a spacious pool area surrounded by lush palm trees and lounge chairs. A bright water slide is visible in the background, leading to the pool. A serene lake serves as a picturesque backdrop, enhancing the resort's atmosphere.
Condo in Kissimmee
4.86 out of 5 average rating, 193 reviews

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.

Superhost
A vibrant water park area is visible, featuring various slides and water attractions surrounded by lush greenery. Brightly colored murals decorate nearby walls, showcasing popular animated characters. Comfortable seating is positioned throughout, inviting relaxation while enjoying the resort's amenities.
Condo in Kissimmee
4.8 out of 5 average rating, 142 reviews

Avenger's Retreat Near Disney

Step into the magic of Disney and make unforgettable memories at your very own Avengers Retreat - Luxurious 2-bed, 2-bath condo with themed rooms - Located 2.5 miles from Disney and steps to clubhouse - Free parking and no resort fees - Family-friendly with high chair, stroller, and Pack-N-Play - Access to outdoor pool, water park, fitness center, and more - Free Wifi with 400 Mbps speed

Top guest favorite
A spacious pool area is surrounded by palm trees and tropical landscaping. Sun loungers line the pool deck, and a water park with slides is visible nearby. The multi-level condo buildings create a vibrant backdrop, ensuring a family-friendly environment.
Condo in Kissimmee
4.79 out of 5 average rating, 144 reviews

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.

Top guest favorite
A vibrant children's room features a twin-over-full bunk bed with colorful bedding. The walls are painted in cheerful red and yellow tones, adorned with whimsical cloud and star decorations. A toy storage area holds stuffed animals and games, and a cozy seating area enhances the playful atmosphere.
Condo in View Park-Windsor Hills
5 out of 5 average rating, 180 reviews

Mickey's Imagination Condo at Windsor Hills Resort

Newly renovated 3BR/2BA first-floor condo just minutes from Disney! Family-friendly with Disney-themed rooms: Mickey’s Clubhouse kids’ room with toys & costumes, Animal Kingdom guest room with nursery, and Classic Mickey master with vintage Disney décor. Enjoy a fully stocked kitchen, baby gear, and resort amenities—perfect for families ready to experience the magic!

Popular amenities for Windsor Hills condo rentals

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 G$16,733 GYD 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 & kid-friendly amenities

  • Vacation rentals with a pool

    60 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Windsor Hills vacation rentals include wi-fi 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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