Available properties

Just 15 minutes from Disney, this 5-bedroom home at Windsor at Westside features a private pool with jacuzzi, game room, and full access to a 5-star resort with lazy river, waterslide, restaurant, and gym. Perfect for up to 10 gue...

Just 15 minutes from Disney, this 5-bedroom home at Windsor at Westside features a private pool with jacuzzi, game room, and full access to a 5-star resort with lazy river, waterslide, restaurant, and gym. Perfect for up to 10 guests, it offers comfort, security, and fun in a gated community with 24-hour security and easy self check-in. Spacious and modern, ideal for families wanting convenience near the parks.

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 Windsor at Westside Resort, this elegant 5-bedroom, 4-bath home is just 15 minutes from Disney and close to Orlando’s top theme parks. Perfect for up to 10 guests, it combines comfort, functionality, and entertainment in one of the area’s most sought-after resorts.

- Main Living Area

• Open-concept living room with Smart TV

• Dining table for 8

• Fully equipped kitchen with stainless steel appliances

• Kitchen island with seating for 4

• Central air conditioning

• High-speed Wi-Fi

• Washer and dryer

- Bedrooms & Bathrooms

• Master Suite (Ground Floor)

• King bed

• Private ensuite bathroom

• Bedroom 2 (Ground Floor)

• Queen bed

• Full bathroom in hallway

• Bedroom 3 (Second Floor)

• Queen bed

• Bedroom 4 (Second Floor)

• Master Suite (Second Floor)

• King bed

• Private ensuite bathroom

• Two twin beds

• Full shared bathroom upstairs for Bedrooms 3 and 4

- Private Outdoor Area

• Private swimming pool

• Spillover jacuzzi

• Removable safety fence

• Furnished patio facing the garden

- Entertainment

• Garage game room with foosball, billiards, and ping pong

• Upstairs loft with TV and air hockey table

- As our guest, you will enjoy full access to Windsor at Westside Resort, featuring:

• 10,000 sq. ft. clubhouse

• Resort-style pool with waterslide

• Lazy river

• Kids splash area

• Restaurant, bar and lounge

• Fully equipped fitness center

• Sports courts

• Secure gated community with 24-hour security

- Additional options:

• Pool & jacuzzi heating: $40 per day (minimum 3 consecutive days)

• BBQ grill rental: $100 per stay

• Easy self check-in with personalized door code

• Welcome package with essential arrival items

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 assist with park guidance, dining recommendations, transportation tips, 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 jacuzzi. Full access to Windsor at Westside Resort amenities is included, such as the clubhouse, pools, lazy river, fitness center, and sports courts.

Our team is available 24/7 via message or phone. We provide full support throughout your stay, including complimentary concierge assistance.

Located in Kissimmee at Windsor at Westside Resort, the home is approximately 15 minutes from Disney, 25 minutes from Universal Studios, 30 minutes from Orlando International Airport, and close to supermarkets, outlets, and restaurants. Gated community with 24-hour security and a peaceful atmosphere.

Free parking is available in front of the home. Easy access to major highways makes reaching theme parks, outlets, and restaurants simple. A car is recommended for convenience during your stay.

Stylish 6-bedroom, 4.5-bath home at Windsor Island Resort, about 20 minutes from Disney. Accommodates up to 12 guests with Toy Story and Iron Man themed bedrooms, a game room with pool table and air hockey, open living spaces, and...

Stylish 6-bedroom, 4.5-bath home at Windsor Island Resort, about 20 minutes from Disney. Accommodates up to 12 guests with Toy Story and Iron Man themed bedrooms, a game room with pool table and air hockey, open living spaces, and a heatable private pool. Perfect for families and groups seeking comfort, fun, and full resort amenities including lazy river, water slides, and 24-hour security near Orlando’s top attractions.

Welcome to a HoliStays home, where every stay feels seamless and fully supported. Managed by our local team specializing in Disney-area vacation homes, we provide professional cleaning, 24/7 assistance, and full support throughout your stay so you can relax and enjoy every moment.

Located at Windsor Island Resort in Davenport, this 6-bedroom, 4.5-bathroom home accommodates up to 12 guests with style and personality. The décor blends modern elegance with playful Toy Story and Iron Man themed bedrooms, creating the perfect balance of sophistication and fun for all ages.

- Ground Floor

• Open-concept living room with comfortable sofas and TV

• Dining area with large table for group meals

• Fully equipped kitchen with appliances and cookware

• Master suite with King bed and private bathroom

• Half bathroom

• Private patio with outdoor dining and heatable pool

• Game room with pool table and air hockey

- Second Floor

• Second suite with King bed and private bathroom

• Toy Story themed bedroom with two twin beds

• Queen bedroom

• Shared full bathroom

• Iron Man themed bedroom with two twin beds

• Queen bedroom

• Shared full bathroom

• Family lounge with game table

- Additional amenities

• Complimentary high-speed Wi-Fi

• Laundry room with washer and dryer

• Free parking

• Starter kit of bathroom and kitchen essentials

- Windsor Island Resort offers outstanding amenities:

• Resort-style pool

• Lazy river

• Water slides

• Splash pad

• Fitness center

• Mini golf

• Basketball court

• Soccer field

• Outdoor bar and lounge area

• 24-hour manned security gate

Strategically located in Davenport, approximately 20 minutes from Disney, with easy access to restaurants, grocery stores, and outlets.

Important notes: bathroomand kitchen supplies are provided as a starter kit and must be replenished by guests. Pool heating is available for an additional fee. Use of the barbecue grill also incurs a separate charge.

Check-in: 4:00 PM

Check-out: 10:00 AM

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 recommendations and any needs during your stay. Book with confidence and enjoy a complete Orlando experience.

Guests have exclusive access to the entire home, including the private pool, all indoor areas, and full access to Windsor Island Resort amenities. Free on-site parking is available.

We provide a detailed digital guide with house instructions and local recommendations. Our team is available 24/7 via message for any assistance you may need.

Windsor Island Resort is located in Davenport, approximately 20 minutes from Disney, near Publix, Walmart, restaurants, pharmacies, and outlet shopping. The gated community offers 24-hour security and full resort-style amenities.

A car is recommended for convenience. The home is close to major highways providing easy access to Disney, Universal, and Orlando’s top attractions.

Brand new 5BR / 5BA home at Paradiso Grande Resort with an unbeatable International Drive location. Comfortably sleeps up to 16 guests and features spacious living areas, a fully equipped kitchen, and a fun game room perfect after...

Brand new 5BR / 5BA home at Paradiso Grande Resort with an unbeatable International Drive location. Comfortably sleeps up to 16 guests and features spacious living areas, a fully equipped kitchen, and a fun game room perfect after park days.

Just minutes from the Orange County Convention Center, SeaWorld, and about 10–12 minutes from Universal and Disney, this home is ideal for families or groups seeking space, comfort, and one of Orlando’s most strategic locations

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.

This brand new home at Paradiso Grande Resort was recently furnished and thoughtfully designed to host up to 18 guests with comfort and style. Located in the International Drive area, the home offers one of the most strategic locations in Orlando, just minutes from the Orange County Convention Center, SeaWorld, Universal Orlando Resort, and Walt Disney World. Spacious interiors, private leisure areas, and a smart layout make it perfect for large families and groups who want to enjoy the parks while still having their own relaxing retreat.

Paradiso Grande Resort is one of Orlando’s newest luxury resort communities, known for its prime location near International Drive and easy access to restaurants, outlets, entertainment, and the city’s main attractions.

- Ground Floor

• Open-concept living area with large sofa and Smart TV

• Dining area with table for group meals

• Fully equipped kitchen with modern appliances

• Direct access to the private pool area

• Queen Bedroom

• Bathroom

- Entertainment

• Game room for guests of all ages

- Outdoor Area

• Private swimming pool

• Outdoor seating space

• Perfect setting for family gatherings

- Second Floor

• Master suite with King bed and private bathroom

• Queen suite with private bathroom

• Suite with a triple bunk bed (twin over twin over twin), ideal for kids or teens

• Suite with a bunk bed (twin over twin) and private bathroom

Optional services available:

• Pool heating: $40 per day

• BBQ grill rental: $100 per stay

Please request these extras at least 48 hours before arrival so our team can prepare everything for you.

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 dining tips, park guidance, transportation, or special requests. B

ook with confidence and let us take care of the rest!

Guests have exclusive access to the entire home, including the private pool, game room, and all indoor areas.

Our team is available 24/7 via message or phone to assist with support, recommendations, or any needs during your stay.

Located in the Lake Buena Vista area of Orlando, the home offers easy access to Disney parks, restaurants, supermarkets, and major highways. It’s a prime location for convenience and proximity to attractions.

We recommend having a car for convenience. The home is close to major highways, making it easy to reach Disney, Universal, and nearby outlets.

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 Storey Lake Resort in Kissimmee, this 5-bedroom home combines space, comfort, and private leisure in one of the most sought-after gated communities near Disney. Positioned directly across from the clubhouse, it offers convenient access to resort amenities along with a private pool and spa for exclusive relaxation after a fun day at the parks.

Ground Floor

• Open living area with TV

• Dining area

• Fully equipped kitchen

• Direct access to the pool area

• Full bathroom

Outdoor Area

• Private swimming pool

• Integrated spa

• Outdoor dining area

• Relaxing space after park days

Bedrooms

• Bedroom 1: Queen bed

• Bedroom 2: King bed

• Bedroom 3: King bed

• Bedroom 4: 2 twin beds

• Bedroom 5: Queen bed

• 4 full bathrooms total

Comfort & Amenities

• Wi-Fi

• Ethernet connection

• Air conditioning

• Heating

• TVs in bedrooms

• Linens and extra blankets

• Free on-site parking

• Smoke detector

• Fire extinguisher

Storey Lake Resort is a gated community offering a resort-style clubhouse, community pool, fitness center, and shared leisure areas. Its prime location provides easy access to Disney, Universal, restaurants, supermarkets, and outlet malls.

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 dining tips, park guidance, 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 spa, plus access to Storey Lake Resort amenities such as the clubhouse, community pool, and fitness center.

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

Located in Storey Lake Resort in Kissimmee, the home is just minutes from Disney and close to supermarkets, restaurants, and outlet malls. The gated community offers security, leisure amenities, and an excellent base for exploring Orlando.

The home offers free on-site parking. Easy access to major highways makes it simple to reach Disney, Universal, SeaWorld, and other attractions. A car is recommended for convenience.

Experience a luxury stay in this brand-new 5-suite home at Windsor Cay Resort in Clermont, just minutes from Disney. Featuring a private pool, spacious modern interiors, two living areas, and a fully equipped kitchen, it offers co...

Experience a luxury stay in this brand-new 5-suite home at Windsor Cay Resort in Clermont, just minutes from Disney. Featuring a private pool, spacious modern interiors, two living areas, and a fully equipped kitchen, it offers comfort and privacy for families and groups. Enjoy access to the resort-style clubhouse with pools, fitness center, and leisure areas in a secure gated community.

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.

Discover this brand-new luxury 5-suite home at Windsor Cay Resort in Clermont. Designed for space, sophistication, and full privacy, the property features a private pool and access to exclusive resort amenities. It’s ideal for families and groups seeking comfort, security, and a prime location near the parks.

- 1st Floor

• Spacious living room

• Fully equipped kitchen

• Laundry area

• Master suite with King bed and private bathroom

• Guest bathroom

- 2nd Floor

• Second living room

• 3 King suites with private bathrooms

• 1 Queen suite with private bathroom

- Outdoor Area

• Private swimming pool

• Space to relax under the Florida sun

• Perfect setting for family time

- Comfort & Amenities

• Wi-Fi

• Air conditioning

• Fully equipped kitchen

• Linens and towels

• Parking for up to 3 vehicles

Windsor Cay Resort is a gated community offering a modern clubhouse with resort-style pools, fitness center, lounge areas, and shared amenities. Strategically located with easy access to Disney, restaurants, supermarkets, and major highways.

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 dining tips, park guidance, 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, as well as access to Windsor Cay Resort amenities such as the clubhouse, resort pools, and fitness center.

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

Located in Windsor Cay Resort in Clermont, the home is near Disney and Orlando’s top attractions. Quiet area, gated community, and easy access to supermarkets, restaurants, and highways.

Parking for up to 3 vehicles on-site. A car is recommended for convenient access to parks and nearby attractions.