Available properties

Modern 5-bedroom, 4.5-bath home at Windsor Island Resort, perfect for families and groups. The property features a private heatable pool, contemporary décor, open-concept living spaces, and two themed kids’ bedrooms (Mickey and Ca...

Modern 5-bedroom, 4.5-bath home at Windsor Island Resort, perfect for families and groups. The property features a private heatable pool, contemporary décor, open-concept living spaces, and two themed kids’ bedrooms (Mickey and Cars). Guests enjoy full access to resort amenities including a resort-style pool, lazy river, water slides, and fitness center. Comfort, convenience, and fun just minutes from Orlando’s top attractions.

Welcome to a HoliStays home, where every stay feels seamless.

Managed by our local team specializing in Orlando-area vacation homes, we ensure spotless cleaning, responsive 24/7 support in multiple languages, concierge assistance at no extra cost, and the comfort of a resort-style experience from check-in to check-out.

This stylish 5-bedroom home is located at Windsor Island Resort, one of Orlando’s newest and most complete vacation communities. Featuring modern décor, spacious living areas, and a private pool, it’s ideal for families and groups seeking comfort, entertainment, and easy access to top attractions.

- Ground floor

• Open-concept living area with modern furnishings

• Fully equipped kitchen

• Dining area

• King master suite with ensuite bathroom

• Half bathroom near the pool area

- Second floor

• Cozy family lounge

• King suite with ensuite bathroom

• Queen suite with ensuite bathroom

• Mickey-themed bedroom with two twin beds

• Cars-themed bedroom with two twin beds

• Full shared bathroom for themed bedrooms

- Private outdoor space

• Private heatable pool

• Outdoor relaxation area

• Poolside half bathroom

• Pool heating available for an additional fee

• Barbecue use available for an additional fee

- Windsor Island Resort amenities

• Resort-style swimming pool

• Lazy river

• Water slides

• Kids splash pad

• Hot tub

• Fitness center

• Soccer field

• Basketball court

• Mini golf

• Fire pit area

• Clubhouse bar and dining

• 24/7 gated security

Every HoliStays home is inspected before each arrival to guarantee the quality and comfort you deserve.

From the first message to your final day, our team is available to help with anything you need — dining tips, park guidance, transportation or special requests.

Book your stay with confidence and let us take care of the rest.

Guests have exclusive access to the entire home, including all bedrooms, living areas, private pool, and all Windsor Island Resort amenities.

We provide a detailed digital guide with home and local information, and our team is available 24/7 to assist whenever needed.

Windsor Island Resort is a modern, secure, family-oriented community with easy access to Orlando’s top attractions, supermarkets, restaurants, and entertainment options.

The location offers quick access to major highways. A car is recommended, and free on-site parking is available.

Enjoy a premium vacation experience in this luxury 5-bedroom home at Windsor Island Resort, just minutes from Orlando’s top attractions. Featuring a private heatable pool, themed bedrooms, modern décor, and full access to resort a...

Enjoy a premium vacation experience in this luxury 5-bedroom home at Windsor Island Resort, just minutes from Orlando’s top attractions. Featuring a private heatable pool, themed bedrooms, modern décor, and full access to resort amenities including clubhouse, lazy river, and water slides, it’s ideal for families and groups of up to 11 guests seeking comfort, fun, and convenience in a secure resort setting.

Welcome to a HoliStays home, where every stay feels seamless.

Managed by our local team specializing in Disney-area vacation homes, we ensure spotless cleaning, responsive 24/7 support in multiple languages, concierge assistance at no extra cost, and the comfort of a resort-style experience from check-in to check-out.

This elegant 5-bedroom home at Windsor Island Resort blends modern design, comfort, and entertainment, making it ideal for families and groups. Featuring a private heatable pool, themed bedrooms inspired by iconic characters, and full access to one of Orlando’s most complete resorts, it offers a truly elevated vacation experience.

- Ground floor

• Bright open living area

• Dining area

• Fully equipped kitchen

• Queen bedroom

• Full bathroom

• Patio with private heatable pool

- Second floor

• Family lounge area

• King master suite

• Mickey Mouse themed bedroom with two twin beds

• Harry Potter themed bedroom with bunk bed (full + twin)

• Star Wars themed queen suite

- Additional amenities

• Laundry room with washer and dryer

• Free Wi-Fi

• Complimentary parking

• Starter bathroom and kitchen supplies

(Replenishment of supplies is the guest’s responsibility. Pool heating and barbecue grill are paid services.)

Every HoliStays home is inspected before each arrival to guarantee the quality and comfort you deserve.

From the first message to your final day, our team is available to help with anything you need — dining tips, park guidance, transportation or special requests.

Book your stay with confidence and let us take care of the rest.

Guests have exclusive access to the entire home, including the private pool, as well as all Windsor Island Resort amenities.

Our local team is available 24/7 to provide support, answer questions, and assist throughout your stay.

Windsor Island Resort is a modern, gated, and secure community in Orlando, close to supermarkets, restaurants, and major attractions.

The location provides easy access to Orlando’s main highways, making it simple to reach parks, outlets, and airports. Free on-site parking is available.

Located about 20 minutes from Disney, this 5-bedroom townhome at Champions Gate Resort delivers comfort, fun, and convenience in a true resort setting. Featuring a private pool, Star Wars and Princess themed bedrooms, fully equipp...

Located about 20 minutes from Disney, this 5-bedroom townhome at Champions Gate Resort delivers comfort, fun, and convenience in a true resort setting. Featuring a private pool, Star Wars and Princess themed bedrooms, fully equipped kitchen, and open living spaces, it comfortably accommodates up to 12 guests. Enjoy full access to the clubhouse, pools, lazy river, fitness center, sports courts, and nearby shopping and dining options.

Welcome to a HoliStays home, where every stay feels seamless.

Managed by our local team specializing in Disney-area vacation homes, we provide spotless cleaning, 24/7 multilingual support, complimentary concierge assistance, and a complete resort-style experience from check-in to check-out.

Located at Champions Gate Resort, this 5-bedroom, 4-bathroom townhome is thoughtfully designed to accommodate up to 12 guests. With spacious interiors and themed bedrooms, it’s ideal for families and groups seeking comfort and fun.

The outdoor area features a private pool, perfect for unwinding after park days. Pool heating and BBQ grill use are available for an additional fee.

Home layout

• Ground Floor

- Living room with games

- Dining area

- Fully equipped kitchen

- Queen bedroom

- Star Wars themed bedroom with two full beds

- Shared bathroom

• Second Floor

- Master suite with king bed and full bathroom

- King suite

- Princess themed bedroom with two twin beds and private bathroom

The home also includes washer and dryer, free Wi-Fi, on-site parking, and a starter welcome kit with basic bathroom and kitchen supplies. Replenishment is the guest’s responsibility.

Every HoliStays home is inspected prior to arrival to ensure the comfort and quality you expect.

Our team is available throughout your stay to assist with local recommendations, park tips, transportation, or special requests. Book with confidence and enjoy your vacation.

Guests have full exclusive access to the entire home, private pool, and all Champions Gate Resort amenities, including the clubhouse, pools, lazy river, fitness center, and sports courts.

Our team is available 24/7 via messaging to assist with support, local recommendations, and any needs during your stay.

Located in a secure gated resort community, Champions Gate offers top-tier amenities and easy access to Disney parks, supermarkets, outlets, restaurants, and major Orlando highways.

The home is conveniently located near major highways. A car is recommended, and free on-site parking is available.

High-end 5-bedroom, 5.5-bathroom home at Windsor at Westside Resort, just 10 minutes from Disney. Comfortably accommodating up to 10 guests, it features a private pool and spa, well-appointed bedrooms, TVs throughout the home, fas...

High-end 5-bedroom, 5.5-bathroom home at Windsor at Westside Resort, just 10 minutes from Disney. Comfortably accommodating up to 10 guests, it features a private pool and spa, well-appointed bedrooms, TVs throughout the home, fast Wi-Fi, and full access to resort amenities including clubhouse, lazy river, and kids’ water park. Ideal for families and groups seeking comfort, space, and a prime Orlando location.

Welcome to a HoliStays home, where every stay feels seamless.

Managed by our local team specializing in Disney-area vacation homes, we ensure spotless cleaning, responsive 24/7 support in multiple languages, concierge assistance at no extra cost, and the comfort of a resort-style experience from check-in to check-out.

This spacious 5-bedroom home at Windsor at Westside Resort is designed to deliver comfort, functionality, and a complete Orlando vacation experience. Offering 2,622 sq. ft., it accommodates up to 10 guests and features a west-facing private pool and spa, along with full access to one of the area’s top resort communities.

- Ground floor

• Open living area with 50” Smart TV

• Dining area

• Fully equipped kitchen

• Queen bedroom

• En-suite bathroom

• Half bathroom

• Access to private pool and spa area

- Second floor

• Family lounge with 50” Smart TV

• King master suite

• Second king suite

• Twin bedroom

• Full-size bed bedroom

• Full bathrooms

- Bed configuration

• 2 King beds

• 1 Queen bed

• 2 Twin beds

• 1 Full bed

- Amenities and details

• 43” Smart TVs in all bedrooms

• Spectrum Wi-Fi up to 100 Mbps

• Washer and dryer

• Garage available (manual opening)

• Baby items: Pack n’ Play and stroller

• Pet friendly (fees apply)

• Starter kitchen and bathroom supplies

- Pool & extra services

• Private pool and spa with optional heating

• Pool heat available at $35/day (3-day minimum)

• Grill rentals available upon request

• Extra and concierge services not included

- Important notes

• This is a self-catering home

• Supply replenishment is guest responsibility

• Pool enclosure doors remain locked for safety

• No mailbox available

• Florida wildlife may be present

Every HoliStays home is inspected before each arrival to guarantee the quality and comfort you deserve.

From the first message to your final day, our team is available to help with anything you need — dining tips, park guidance, transportation or special requests.

Book your stay with confidence and let us take care of the rest.

Guests have exclusive access to the entire home and all Windsor at Westside Resort amenities, including the clubhouse and leisure areas.

24/7 emergency support available by email throughout the stay.

Windsor at Westside is a modern, gated resort in Kissimmee offering full amenities and easy access to parks, shopping, and dining.

Strategically located with quick access to Highway 429, making it easy to reach Disney and Orlando’s top attractions.

Enjoy comfort, space, and fun in this 5-bedroom townhome at Champions Gate Resort, perfect for up to 10 guests. Featuring a private pool, themed bedrooms kids will love, and open living areas ideal for families and groups. The res...

Enjoy comfort, space, and fun in this 5-bedroom townhome at Champions Gate Resort, perfect for up to 10 guests. Featuring a private pool, themed bedrooms kids will love, and open living areas ideal for families and groups. The resort offers pools, a lazy river, fitness center, and sports courts, plus easy access to supermarkets, restaurants, and shops. Just 20 minutes from Disney, it’s the perfect home base for an unforgettable vacation.

Welcome to a HoliStays home, where every stay feels seamless.

Managed by our local team specializing in Disney-area vacation homes, we provide spotless cleaning, 24/7 multilingual support, complimentary concierge assistance, and a true resort-style experience from check-in to check-out.

Located at the prestigious Champions Gate Resort, this 5-bedroom, 4-bathroom townhome comfortably accommodates up to 10 guests. Perfect for families and groups, it offers spacious layouts, comfort, and access to one of Orlando’s top resort communities.

Enjoy your private pool, ideal for relaxing after park days. Pool heating.

Home layout

• Ground Floor

- Open-concept living and dining area

- Fully equipped kitchen

- Queen bedroom

- Themed kids bedroom with two twin beds

- Shared full bathroom

• Second Floor

- Master suite with king bed and private bathroom

- King bedroom with private bathroom

- Fifth bedroom with two full beds and private bathroom

The home also includes washer and dryer, free Wi-Fi, on-site parking, and a starter welcome kit with basic bathroom and kitchen supplies. Replenishment is the guest’s responsibility.

Every HoliStays home is inspected before arrival to ensure the comfort and quality you expect.

From your first message to check-out, our team is available to assist with recommendations, park tips, transportation, or special requests. Book with confidence and enjoy your stay.

Guests have full exclusive access to the entire home, private pool, and all Champions Gate Resort amenities, including the clubhouse, pools, lazy river, fitness center, and sports courts.

Our team is available 24/7 to provide support, guidance, and local recommendations throughout your stay.

Champions Gate Resort is a secure gated community located about 20 minutes from Disney, close to supermarkets, restaurants, outlets, and with easy access to Orlando’s main highways.

A car is recommended. Free on-site parking is available, with quick access to major roads and highways.