Available properties

Discover a spacious 8‑bedroom home perfect for large groups and families, accommodating up to 18 guests at Windsor at Westside Resort, Kissimmee. Enjoy a private heatable pool, a large games area with pool table and foosball, and ...

Discover a spacious 8‑bedroom home perfect for large groups and families, accommodating up to 18 guests at Windsor at Westside Resort, Kissimmee. Enjoy a private heatable pool, a large games area with pool table and foosball, and inviting spaces to relax. Excellent location just minutes from Disney and Orlando’s top attractions. Includes Wi‑Fi, free parking, and an essential welcome kit to make your stay comfortable.

Welcome to a HoliStays home, where every stay feels seamless and memorable. Managed by our local team specializing in vacation homes in the Orlando area, we ensure spotless cleaning, 24/7 support, concierge assistance at no extra cost, and the comfort of a resort‑style experience from check‑in to check‑out.

This 8‑bedroom home at Windsor at Westside Resort offers space, comfort, and entertainment for up to 18 guests. With a private heatable pool and a fully equipped games room, this retreat is perfect for family and friends, just minutes from the magic of Disney and all of Orlando’s attractions.

- Ground Floor

• Spacious living room with dining area

• Fully equipped kitchen

• Queen bedroom with private bathroom

• Master king suite

- Second Floor

• Family room with pool table and foosball

• King suite

• Three rooms with two twin beds each (two Disney‑themed)

• One queen bedroom

• One room with two queen beds

• Four additional bathrooms

- Additional Amenities

• Laundry room with washer and dryer

• Complimentary Wi‑Fi

• Free parking

• Welcome kit with essential bathroom and kitchen supplies

• Pool heating and barbecue grill available for an additional fee

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 dining tips, park guidance, transportation, or special requests. Book your stay with confidence and let us take care of the rest.

Guests have full access to the entire home, including the private heated pool and all amenities at Windsor at Westside Resort, such as the clubhouse, community pool, lazy river, sports courts, gym, and more.

Our team is available 24/7 via message or phone to assist with anything you may need — from local tips to concierge requests.

Located in Windsor at Westside Resort in Kissimmee, this gated community offers a peaceful and secure environment with convenient access to Orlando’s top attractions. You're just minutes from Disney, outlet malls, restaurants, supermarkets, and more.

The home is close to major roads and highways, making it easy to reach Disney, Universal, SeaWorld, and shopping destinations. Free on-site parking is available for your convenience.

Experience the perfect escape for large groups and families in this spacious 7‑bedroom home at Champions Gate Resort, comfortably accommodating up to 15 guests. Relax by your private heatable pool or enjoy incredible resort amenit...

Experience the perfect escape for large groups and families in this spacious 7‑bedroom home at Champions Gate Resort, comfortably accommodating up to 15 guests. Relax by your private heatable pool or enjoy incredible resort amenities, including a water park, game room, tennis courts, golf and more. The open living and dining space with a fully equipped kitchen ensures memorable moments for everyone. Complimentary Wi‑Fi and free parking are included.

Welcome to a HoliStays home, where every stay feels seamless and memorable. Managed by our local team specializing in vacation homes in the Orlando area, we ensure spotless cleaning, 24/7 support, concierge assistance at no extra cost, and the comfort of a resort‑style experience from check‑in to check‑out.

This 7‑bedroom home at Champions Gate Resort offers space, comfort, and fun for up to 15 guests. With a private heatable pool, game room, and spacious open living areas, this home is perfect for families and groups looking to create unforgettable memories just minutes from Orlando’s theme parks and attractions.

- Ground Floor

• Open‑plan living room with dining area

• Fully equipped kitchen

• Bedroom with full bed and private bathroom

• Queen master suite

- Second Floor

• Family room with sofa bed

• King master suite

• King bedroom sharing a bathroom with a twin bedroom

• Queen bedroom sharing a bathroom with another twin bedroom

• Additional bathrooms

- Additional Amenities

• Laundry room with washer and dryer

• Complimentary Wi‑Fi

• Free parking

• Welcome kit with essential bathroom and kitchen supplies

• Pool heating and barbecue grill available for an additional fee

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 dining tips, park guidance, transportation, or special requests. Book your stay with confidence and let us take care of the rest.

Guests have full access to the entire home, including the private heated pool and all amenities at Champions Gate Resort, such as the water park, community pools, lazy river, sports courts, and fitness center.

Our team is available 24/7 via message or phone to assist with anything you may need — from activity recommendations to concierge requests.

Located in Champions Gate Resort, this community offers resort‑style living with top‑tier amenities and convenient access to Orlando’s major attractions. You’re approximately 20 minutes from Disney, with shopping, dining, supermarkets, and entertainment nearby.

The home is close to major roads and highways, making it easy to reach Disney, Universal, SeaWorld, and shopping destinations. Free on‑site parking is available for your convenience.

Experience comfort and modern design in this 7‑bedroom home for up to 15 guests at Windsor Cay Resort. Spacious living areas flow into a contemporary kitchen and large patio with a private heatable pool. Themed spaces include Mari...

Experience comfort and modern design in this 7‑bedroom home for up to 15 guests at Windsor Cay Resort. Spacious living areas flow into a contemporary kitchen and large patio with a private heatable pool. Themed spaces include Mario Bros, Mickey, Minions, Princess, and Toy Story rooms, and 3 elegant suites ensure privacy and style. Ideal for families and groups seeking a memorable Orlando vacation. Free Wi‑Fi, parking, and a welcome kit are included.

Welcome to a HoliStays home, where every stay feels seamless and memorable. Managed by our local team specializing in vacation homes in the Orlando area, we ensure spotless cleaning, 24/7 support, concierge assistance at no extra cost, and the comfort of a resort‑style experience from check‑in to check‑out.

Experience ultimate comfort and modern design in this beautifully decorated 7‑bedroom home at Windsor Cay Resort, ideal for up to 15 guests. With spacious living areas, a private heatable pool, and vibrant themed spaces, this home offers the perfect setting for an unforgettable family vacation near Orlando’s famous attractions.

- Ground Floor

• Open‑plan living room with dining area

• Fully equipped contemporary kitchen

• Large patio with private heatable pool and half bathroom

• Master king suite

- Second Floor

• Mario Bros themed family room

• King suite with ensuite bathroom

• Queen suite with ensuite bathroom

• Princess bedroom with two twins sharing a bathroom with Toy Story room (bunk beds)

• Mickey bedroom with queen sharing a bathroom with Minions room (double + single)

• Additional bathrooms

- Additional Amenities

• Laundry room with washer and dryer

• Complimentary Wi‑Fi

• Free parking (up to 4 cars)

• Welcome kit with essential supplies

• Pool heating and barbecue grill available for an additional fee

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 dining tips, park guidance, transportation, or special requests. Book your stay with confidence and let us take care of the rest.

Guests will enjoy full access to the entire property, including all bedrooms, living spaces, private heatable pool, and top‑tier amenities at Windsor Cay Resort, such as the resort‑style pool, lazy river, interactive splash pad, jacuzzi spa, fitness center, minigolf, and recreational areas. Free on‑site parking is available for up to 4 cars.

We provide a detailed digital guide with all the essential information you’ll need during your stay, including house details and local recommendations. Our team is available 24/7, so if you need any assistance or have questions at any time, we’re just a message away.

Welcome to Windsor Cay Resort Club, the perfect destination for family fun and relaxation. Ideally located just minutes from Orlando’s famous theme parks, shopping, and dining, this vibrant clubhouse offers everything you need for an unforgettable stay in a secure and lively environment.

The home is close to major roads and highways, making it easy to reach Disney, Universal, SeaWorld, and nearby shopping and dining destinations. Free on‑site parking is provided for your convenience.

Welcome to this family home with 6 bedrooms and 7 bathrooms in Bella Vida Resort, Kissimmee, perfect for family vacations or gatherings with friends. Sleeps up to 15 guests with a private pool and spa, fast Wi‑Fi, TVs in every bed...

Welcome to this family home with 6 bedrooms and 7 bathrooms in Bella Vida Resort, Kissimmee, perfect for family vacations or gatherings with friends. Sleeps up to 15 guests with a private pool and spa, fast Wi‑Fi, TVs in every bedroom, and full access to resort amenities. Just 15 minutes from Disney parks and close to dining and shopping. Dedicated support and easy check‑in ensure a comfortable stay.

Welcome to a HoliStays home, where every stay feels seamless. Our local team specializes in Orlando area vacation homes, ensuring spotless cleaning, responsive 24/7 support, concierge assistance at no extra cost, and comfort from check‑in to check‑out.

This spacious family home in Bella Vida Resort, Kissimmee, features 6 bedrooms, 7 bathrooms, and sleeps up to 15 guests comfortably. Enjoy a private pool with spa, high‑speed internet, and TVs throughout the main areas. Perfect for family vacations or group stays, offering relaxation and fun after a day at the parks.

- Layout & Rooms

• Ground Floor

• Open‑concept living room

• Fully equipped kitchen

• Bedroom with TV

• Guest bathroom

• Direct access to pool area

- Second Floor

• Master suite with King bed and TV

• Additional bedrooms with Queen, King, Twin beds and bunk with trundle

• Full bathrooms

Every HoliStays home is inspected before each arrival to guarantee quality and comfort. Our team is available to help with dining tips, park guidance, transportation, or special requests. Book with confidence and let us take care of the rest.

Guests have full access to the entire home, private pool, and all Bella Vida Resort amenities, including clubhouse, community pool, jacuzzi, game rooms, and leisure areas.

Our team is available 24/7 via messaging and phone to assist with local recommendations, concierge requests, and any questions throughout your stay.

Located in a gated community with 24‑hour security, Bella Vida Resort is about 15 minutes from Disney parks. The area offers easy access to restaurants, supermarkets, shops, and Orlando attractions.

The home is strategically close to major highways, making it easy to reach theme parks, outlets, and attractions. Free on‑site parking is available.

Experience the best of Orlando in this elegant 5-bedroom, 5-bathroom home in Reunion Resort, just 15 minutes from Disney. Sleeps up to 10 guests with a heatable private pool, open-concept layout, themed bedrooms (Princess, Mickey ...

Experience the best of Orlando in this elegant 5-bedroom, 5-bathroom home in Reunion Resort, just 15 minutes from Disney. Sleeps up to 10 guests with a heatable private pool, open-concept layout, themed bedrooms (Princess, Mickey & Toy Story), and modern décor. Perfect for families or groups seeking comfort and fun in one of the area’s most desirable communities. Book now and start making unforgettable memories.

HoliStays welcomes you to a home where comfort, style, and convenience come together. Our local team ensures spotless cleaning, multilingual 24/7 support, and complimentary concierge assistance — from check-in to check-out.

Located in the prestigious Reunion Resort, this elegant 5-bedroom, 5-bathroom home accommodates up to 10 guests comfortably. With magical themed rooms (Princess, Mickey, Toy Story), a private heatable pool, and chic décor, it strikes the perfect balance between luxury and family-friendly fun — all just 15 minutes from Disney.

- Layout & Rooms

• Ground Floor

• Open-concept living room

• Modern kitchen and dining area

• Princess-themed room (Queen bed + private bathroom)

• King suite with private bathroom

• Access to patio with private pool

• Half bath

- Second Floor

• Master King suite with private bathroom

• Mickey-themed room (2 twin beds + private bathroom)

• Toy Story-themed room (2 twin beds + private bathroom)

• Family lounge/media area

• Laundry room with washer and dryer

Every HoliStays property is carefully inspected before your arrival to ensure the highest standards. Our team is always available to assist with tips, bookings, or anything you need. Book with confidence — we’ll take care of the rest.

Guests have full access to the entire home, including all bedrooms, living spaces, private pool, and free on-site parking. Please note: Reunion Resort amenities are not available for guest use.

We provide a digital guide with all essential information about the house and area. Our team is available 24/7 via messaging for anything you may need during your stay.

Reunion Resort is one of Orlando’s most desirable areas, known for its beautiful surroundings, peaceful vibe, and prime location. Just 15 minutes from Disney with easy access to I‑4, shopping, dining, and entertainment are all nearby.

The home is close to major roads and highways, making it easy to get to parks and attractions. Free parking is available on-site.