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.

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.

Recently renovated 4-bedroom townhome featuring modern design, wood flooring, and stylish decor throughout. Perfect for families, it offers a fully equipped kitchen, private patio, Wi-Fi, laundry, and a fun Lego-themed game room. ...

Recently renovated 4-bedroom townhome featuring modern design, wood flooring, and stylish decor throughout. Perfect for families, it offers a fully equipped kitchen, private patio, Wi-Fi, laundry, and a fun Lego-themed game room. Highlights include a Mickey-themed kids bedroom. Located in Kissimmee, just minutes from Disney and 2 minutes from Walmart, in a quiet community with a shared pool. Excellent value for a comfortable, well-located family vacation.

Welcome to a HoliStays home, where every stay is seamless and worry-free.

Managed by a local team specializing in Disney-area vacation homes, we provide spotless cleaning, responsive 24/7 support in multiple languages, complimentary concierge assistance, and the comfort of a resort-style experience from check-in to check-out.

This recently renovated 4-bedroom townhome combines modern design, comfort, and family-friendly details. Featuring wood floors, elegant decor, and bright, welcoming spaces, the home is ideal for relaxing after full days exploring Orlando, offering excellent value without compromising quality.

Home layout

• First floor

- Stylish and comfortable living area

- Fully equipped kitchen integrated with the social space

- Half bathroom

- Lego-themed game room, perfect for all ages

- Cozy private patio

• Second floor

- Elegant master suite with king-size bed and private bathroom

- Queen bedroom

- Mickey-themed kids bedroom with bunk bed (two full beds) and trundle

- Queen bedroom

- Spacious shared full bathroom

• Additional amenities

- High-speed Wi-Fi

- Washer and dryer

- Free parking

- Starter welcome kit

- Linens and individual towel set per guest


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

From your first message to your final day, our team is available to assist with anything you may need, including local recommendations and guidance.

Book with confidence and let HoliStays take care of the rest.

Guests have full access to the home and community amenities, including the gated entrance and shared swimming pool.

Our team is available 24/7, and guests receive a detailed digital guide with home instructions and local recommendations.

Summer Flowers is a quiet, family-friendly community in Kissimmee, just minutes from Disney, 2 minutes from Walmart, and close to restaurants, shopping, and main roads.

A car is recommended. The home offers easy access to major roads and attractions. Arrival instructions are sent by email after booking confirmation.

Just 6.5 miles from Disney, this fully themed 7-bedroom villa at Encore at Reunion blends fun, comfort, and prime location. Enjoy a private heatable pool, outdoor BBQ area, game room, five king suites, plus Harry Potter and Frozen...

Just 6.5 miles from Disney, this fully themed 7-bedroom villa at Encore at Reunion blends fun, comfort, and prime location. Enjoy a private heatable pool, outdoor BBQ area, game room, five king suites, plus Harry Potter and Frozen themed bedrooms. Perfect for families and groups seeking space, privacy, and a magical Orlando stay with everything needed for an unforgettable vacation experience.

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 a smooth experience from check-in to check-out.

Located in Encore at Reunion, just 6.5 miles from Disney, this fully themed 7-bedroom villa was professionally decorated to delight families and large groups. With a private heatable pool, game room, and five king suites, the home offers space, comfort, and entertainment in one of the most desirable communities in the area.

- Ground Floor

• Spacious open living area with sofa, loveseat, and Smart TV

• Direct access to the fully screened lanai and private pool area

• Outdoor charcoal grill (18") available upon request

• Dining table seating 8 guests

• Breakfast bar with seating for 4

• Fully equipped kitchen

• Guest bathroom

• King bedroom

• Master suite with King bed, Smart TV, and private bathroom with shower

- Second Floor

• Five additional bedrooms

• Laundry room with washer, dryer, iron, and ironing board

• Master Suite 1 with King bed, Smart TV, and private bathroom

• Master Suite 2 with King bed, Smart TV, and private bathroom

• King bedroom

• Harry Potter themed bedroom with bunk bed, Smart TV, and private bathroom

• Frozen themed bedroom with bunk bed, Smart TV, and private bathroom

• Smart TVs in all bedrooms

• Game room

• Free unlimited Wi-Fi

• 24-hour gated community

• Easy self check-in

Pool heating is available for an additional $40 per day (2-day minimum). Please request at least 48 hours prior to check-in.

Pet policy: $170 per pet. Only small dogs under 40 lbs allowed. Any damages or extra cleaning will be charged.

- Nearby distances:

• Walt Disney World – 6.5 miles

• SeaWorld – 17 miles

• Universal Studios – 20 miles

• Orlando International Airport – 29 miles

• Outlet shopping – 15 miles

• Supermarket – 1.5 miles

Important: This booking does not include access to the Encore clubhouse or water park. House use only.

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

From your first message to your final day, our team is available to assist with park guidance, dining tips, transportation, or special requests.

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

Guests have exclusive access to the entire home, including the private pool and driveway parking for up to 3 cars. Additional street and overflow parking are available nearby. There is no access to the Encore clubhouse or water park.

Our team is available 24/7 via message or phone to provide prompt support, local recommendations, and assistance throughout your stay.

Located in Encore at Reunion, a 24-hour gated community, the home is 6.5 miles from Disney, 20 miles from Universal, 17 miles from SeaWorld, and 29 miles from Orlando International Airport. Supermarkets, restaurants, and outlet malls are just a short drive away.

The home is conveniently located near major highways, allowing easy access to Orlando’s theme parks and attractions. A car is recommended for the best mobility during your stay.

Located in Windsor Cay Resort, this 7-bedroom, 5-bathroom home comfortably accommodates up to 20 guests with space and style. Featuring a private pool, spacious suites, and themed Mickey, Minions, and Star Wars bedrooms, it’s perf...

Located in Windsor Cay Resort, this 7-bedroom, 5-bathroom home comfortably accommodates up to 20 guests with space and style. Featuring a private pool, spacious suites, and themed Mickey, Minions, and Star Wars bedrooms, it’s perfect for large families and groups. Enjoy open living areas, full entertainment, and access to resort amenities just minutes from Orlando’s top attractions.

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.

Located in the sought-after Windsor Cay Resort, this home was designed to comfortably host large groups with space, functionality, and entertainment. With 7 bedrooms, 5 bathrooms, and accommodations for up to 20 guests, it’s ideal for extended families and group vacations looking to experience Orlando with comfort and privacy.

On the ground floor, you’ll find a spacious King master suite with a private bathroom and direct pool access. The open-concept living areas create the perfect space to gather and unwind after a full day at the parks.

- Ground Floor

• Open-concept living room

• Dining area

• Fully equipped kitchen

• Bedroom 1 – King master suite with private bathroom and pool access

- Second Floor

• Bedroom 2 – King suite

• Bedroom 3 – King suite

• Bedroom 4 – Mickey themed room with 2 Full beds

• Bedroom 5 – King bedroom

• Full hallway bathroom

• Bedroom 6 – Minions themed room with 2 Full beds

• Bedroom 7 – Star Wars themed room with 2 Full beds

• Full bathroom between themed rooms

The private outdoor pool area is perfect for relaxing under the Florida sun. Pool heating and BBQ grill service are available as optional add-ons to enhance your stay.

Windsor Cay Resort is one of the newest and most desirable communities in the Orlando area, offering modern amenities, entertainment, and security in one place.

• Resort-style swimming pool

• Lazy river

• Water slide

• Kids splash area

• Fully equipped fitness center

• Sports courts

• Playground

• Clubhouse

• Lounge and relaxation areas

• Gated community with security

- Extra Services (request at least 48h in advance)

• Pool heating: US$ 35 per night (minimum 3 nights)

• BBQ grill: US$ 95 per stay (includes propane and cleaning)

- House Rules

• No smoking indoors (US$ 300 fine)

• No pets allowed (US$ 300 fine)

• No parties or events

Check-in: 4:00 PM

Check-out: 10:00 AM

Pets are allowed. There is a $50 fee per pet.

Every HoliStays home is inspected before each arrival to guarantee the quality and comfort you deserve. From your first message to your final day, our team is available to assist with park guidance, dining tips, transportation, or special requests. Book with confidence and let us take care of the rest.

Guests have exclusive access to the entire home, including the private pool and garage. Full access to all Windsor Cay Resort amenities is also included during the stay.

Our local team provides 24/7 support via message or phone. We’re available to assist with guidance, recommendations, and additional service requests.

Windsor Cay Resort is a modern, gated community in the Orlando area with easy access to major highways, supermarkets, restaurants, and attractions. The location offers both tranquility and convenience for park visitors.

A car is recommended for convenience. The home offers on-site parking and quick access to major roads connecting to Disney, Universal, and local outlet malls.