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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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Guest favorite
Condo in Kissimmee
4.93 out of 5 average rating, 147 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).

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, 176 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
4.83 out of 5 average rating, 300 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
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
4.95 out of 5 average rating, 160 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 captures the sandy beach area lined with palm trees and shaded cabanas. Lounge chairs are arranged neatly in front of the beach, while a pool area with vibrant blue water is visible in the background surrounded by lush landscaping.
Condo in Davenport
4.85 out of 5 average rating, 185 reviews

Full-Service Gated Resort, Disney, Universal, MCO!

Minutes to Theme Parks, Full-Service Resort, Space for the Whole Family, Pools, Splash Pad & Much More! This 3-bedroom villa at Bahama Bay Resort & Spa is ideal for family or group vacations. Comfortable queen beds are standard in the main bedroom and first guest bedroom, while the second guest bedroom features two twin beds. The villa features two full bathrooms. All resort amenities are free and available to guests. 24/7 guard gate and front desk service.

Guest favorite
A modern dining area features a glass-top table surrounded by sleek white chairs. Elegant artwork adorns the brown accent wall, while natural light fills the space from sliding glass doors leading to a patio with a view of the golf course.
Condo in Four Corners
4.98 out of 5 average rating, 234 reviews

Luxury 3 Bedroom Home at ChampionsGate Golf Resort

This luxurious condo is located in one of the most exclusive golf communities in western Orlando, just 15 minutes from the Disney parks. The property has a direct view of the golf course, offering you the privacy that you deserve on your family vacation. Fully equipped for 10 guests with state-of-the-art furniture and appliances. The property is a two stories condo with private internal stairway that leads to the main social area and bedrooms.

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, 213 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 living area features a large leather sofa and wall art, creating an inviting space. The open-concept layout connects to the kitchen and dining area, while large windows allow natural light to fill the room. A vibrant resort-style pool area and water slides are visible outside.
Condo in Kissimmee
4.97 out of 5 average rating, 147 reviews

Disney Oasis

Enjoy Disney Oasis, our 3-bedroom, 2-bath condo, ideal for families! Nestled in a gated community with 24/7 security, we're just 3 miles from Walt Disney World® and close to other theme parks. Indulge in our resort-style amenities: a double Olympic-sized pool, thrilling waterslides, and a fun splash pad. Enjoy the convenience of nearby shopping, dining, and entertainment.

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, 178 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!

Top guest favorite
An aerial view captures a resort-style pool surrounded by lounge chairs and umbrellas, centered within the community. Nearby, tennis courts and a basketball court are visible, bordered by lush greenery. Ample parking spaces are noted in the surrounding area.
Condo in Kissimmee
4.97 out of 5 average rating, 130 reviews

Sol and Mar Resort Style Condo - NO RESORT FEES

This 3 bedroom, 2 bath condo has everything you could possibly need for the perfect vacation away from home. This is a gated community with 24 hour security. Located just a few miles from Walt Disney World and the Magic Kingdom, Margaritaville Resort, Epcot, Animal Kingdom, and Hollywood Studios theme parks.

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 $80 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!

Destinations to explore

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  3. Florida
  4. Osceola County
  5. Four Corners
  6. Windsor Hills
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