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Condo vacation rentals in Windsor Hills

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Top-rated condo rentals in Windsor Hills

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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, 188 reviews

Poolside 3Br Windsor Hills, Waterpark, Disney 2mi

Your Windsor Hills Getaway starts here! This immaculate 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!

Guest favorite
Condo in Kissimmee
4.92 out of 5 average rating, 158 reviews

New Luxury Condo near Disney

A passos da piscina e parque aquático. Covid-19 safe. Wi-fi de 500 megabytes! O apartamento possui localização privilegiada: está no condomínio fechado Windsor Hills, o mais próximo dos parques. A 10 minutos do Animal Kingdom, Epcot, Hollywood Studios e Magic Kingdom e a 25 minutos dos parques da Universal. Além disso, possui fácil acesso ao aeroporto (US 192, FL 417 e I-4), Downtown Orlando, Miami e a todos os atrativos da região da Central Flórida (Daytona Beach, Clearwater, St. Petersburg).

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
4.85 out of 5 average rating, 203 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. Slide and Water Park will not reopen until Wednesday, February 18th.

Top guest favorite
A vibrant outdoor water park is depicted, featuring two large water slides and a colorful kids' splash area. Surrounding palm trees provide shade, and a spacious pool area is visible in the background, inviting relaxation and fun.
Condo in Kissimmee
4.9 out of 5 average rating, 221 reviews

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.

Guest favorite
A modern bedroom features a spacious bed adorned with red and gray textiles. A large circular light installation highlights the textured wall behind. Two floor lamps provide soft illumination, while a desk with a chair is situated nearby. Floor-to-ceiling curtains frame the window.
Condo in Davenport
4.83 out of 5 average rating, 164 reviews

Intense Space-Themed Condo Near Disney

Make this newly renovated luxury condo your launching pad for your next intergalactic adventure! Enjoy custom lighting and artwork inspired by Galaxy's Edge, set in the midst of mature trees, lakes, and wildlife. Between ventures, relax at any of four pools, six hot tubs, and a beach with a fishing dock. Hit a few balls on the tennis and pickleball court or shoot some hoops, then cool off at the splash pad, dine at the Tradewinds restaurant, or rejuvenate at the Cenote spa, all on-site.

Guest favorite
Condo in Kissimmee
4.82 out of 5 average rating, 310 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
The community pool area features a winding pool surrounded by palm trees and lounge chairs. A colorful water slide is visible, along with shaded cabanas. The well-maintained grounds include lush greenery and pathways leading to residential buildings in the background.
Condo in Kissimmee
4.98 out of 5 average rating, 116 reviews

Family, Windsor Hills, Sleep In with 11AM 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
4.93 out of 5 average rating, 180 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, 186 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

Top guest favorite
The living area features a comfortable sofa facing a large smart TV mounted on the wall. Natural light enters through windows, enhancing the space. A round coffee table sits in the center, surrounded by potted plants, with a dining area and a modern kitchen visible in the background.
Condo in Kissimmee
4.93 out of 5 average rating, 214 reviews

Magical Stay Near Disney & ESPN

🏰 Make magical memories just minutes from Disney & ESPN! Bright 3BR, 2BA condo for up to 6 guests in a safe, gated community—perfect for families or friends! Why you’ll love it: Family-friendly & ideal for kids 🏡 Relax in comfort after a fun day at the parks 🍳 Fully equipped kitchen for easy meals 🛍️ Close to restaurants, shopping & entertainment 🎢 Only 1.5 miles from Disney World & ESPN Stress-free, unforgettable family vacation awaits!

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, 143 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

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, 151 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.

Popular amenities for Windsor Hills condo rentals

Quick stats about condo rentals in Windsor Hills

  • Total vacation rentals

    Explore 50 vacation rentals in Windsor Hills

  • Nightly prices starting at

    Windsor Hills vacation rentals start at G$23,012 GYD per night before taxes and fees

  • Verified guest reviews

    Over 60 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & kid-friendly amenities

  • Vacation rentals with a pool

    50 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    50 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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