Best Vacation Homes in Windsor Hills
19 Guests
6 Bedrooms
4 Bathrooms
Family Friendly
Villa
- Private Pool
- Fireplace/Heating
- Pool
R12,299/Night
For 7 Nights R86,101
1797.57 ft²
9 Guests
4 Bedrooms
4 Bathrooms
House
- Pool
- View
- Parking
R3,805/Night
For 7 Nights R26,631
1 Bedroom
1 Bathroom
Couples Retreat
Apartment
- Pool
- Parking
- Internet
R5,747/Night
For 7 Nights R40,225
8 Guests
1 Bedroom
3 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Pool
R9,139/Night
For 7 Nights R63,974
2303.48 ft²
12 Guests
5 Bedrooms
5 Bathrooms
Villa
- Oceanfront
- Hot Tub
- Spa
R6,093/Night
For 7 Nights R42,649
2812 ft²
12 Guests
6 Bedrooms
4 Bathrooms
Family Friendly
Villa
- Private Pool
- Hot Tub
- Fireplace/Heating
R7,690/Night
For 7 Nights R53,836
10 Guests
5 Bedrooms
5 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
R6,938/Night
For 7 Nights R48,562
8 Guests
1 Bedroom
3 Bathrooms
Family Friendly
House
- Kitchen
- Parking
- Air Conditioner
R6,928/Night
For 7 Nights R48,496
Windsor Hills Luxury Rentals
2497.23 ft²
12 Guests
5 Bedrooms
5 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
R35,869/Night
For 7 Nights R251,080
3000 ft²
15 Guests
6 Bedrooms
4 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
R29,998/Night
For 7 Nights R209,987
2766.32 ft²
14 Guests
6 Bedrooms
4 Bathrooms
Villa
- Oceanfront
- Fireplace/Heating
- Pool
R29,530/Night
For 7 Nights R206,711
1819.1 ft²
6 Guests
1 Bedroom
3 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- Air Conditioner
- Internet
R16,542/Night
For 7 Nights R115,795
2809.38 ft²
12 Guests
1 Bedroom
4 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- Air Conditioner
- Internet
R16,542/Night
For 7 Nights R115,795
11 Guests
5 Bedrooms
5 Bathrooms
House
- Parking
- Internet
- Child Friendly
R16,362/Night
For 7 Nights R114,534
1 Bedroom
1 Bathroom
Ocean View
House
- Ocean View
- Balcony/Terrace
- View
R15,910/Night
For 7 Nights R111,373
Windsor Hills Pet Friendly Vacation Rentals
9 Guests
1 Bedroom
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
R3,767/Night
For 7 Nights R26,369
1442.36 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Spa
R3,740/Night
For 7 Nights R26,189
1 Bedroom
1 Bathroom
Family Friendly
House
- Balcony/Terrace
- Pet Friendly
- Kitchen
R2,282/Night
For 7 Nights R15,969
3534 ft²
14 Guests
6 Bedrooms
4 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
R7,752/Night
For 7 Nights R54,261
2464.94 ft²
14 Guests
6 Bedrooms
4 Bathrooms
House
- Private Pool
- Oceanfront
- Pool
R6,159/Night
For 7 Nights R43,108
3500 ft²
16 Guests
6 Bedrooms
4 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
R10,631/Night
For 7 Nights R74,423
3500 ft²
16 Guests
6 Bedrooms
4 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
R10,826/Night
For 7 Nights R75,783
3032 ft²
12 Guests
6 Bedrooms
4 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
R5,321/Night
For 7 Nights R37,244
Windsor Hills Large Vacation Homes
12 Guests
5 Bedrooms
5 Bathrooms
Family Friendly
Villa
- Private Pool
- Hot Tub
- Fireplace/Heating
R6,214/Night
For 7 Nights R43,501
2809.38 ft²
14 Guests
6 Bedrooms
4 Bathrooms
Free Cancellation
House
- Spa
- Fireplace/Heating
- Pool
R4,100/Night
For 7 Nights R28,695
14 Guests
6 Bedrooms
4 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
R7,721/Night
For 7 Nights R54,049
8 Guests
1 Bedroom
3 Bathrooms
Family Friendly
Villa
- Fireplace/Heating
- Kitchen
- Parking
R3,325/Night
For 7 Nights R23,274
2809.38 ft²
12 Guests
6 Bedrooms
4 Bathrooms
Family Friendly
Villa
- Hot Tub
- Spa
- Fireplace/Heating
R12,497/Night
For 7 Nights R87,477
10 Guests
3 Bedrooms
2 Bathrooms
Group Friendly
Condo
- Fireplace/Heating
- Air Conditioner
- Internet
R3,145/Night
For 7 Nights R22,013
3500 ft²
12 Guests
6 Bedrooms
4 Bathrooms
Family Friendly
Villa
- Private Pool
- Hot Tub
- Fireplace/Heating
R6,666/Night
For 7 Nights R46,662
2500 ft²
11 Guests
5 Bedrooms
5 Bathrooms
Ocean View
Villa
- Private Pool
- Hot Tub
- Fireplace/Heating
R6,258/Night
For 7 Nights R43,812
Why Choose Rent By Owner for your Windsor Hills Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Popular Areas for Windsor Hills Vacation Rentals
Where are the best neighborhoods to stay in Windsor Hills?
Situated in the heart of Kissimmee, Windsor Hills offers an ideal neighborhood for your Florida getaway. When you choose to stay here, you'll enjoy easy access to local attractions while experiencing the comfort and convenience of well-maintained community amenities. This area is perfect for travelers seeking a relaxing retreat with the flexibility of nearby entertainment options, making it a top choice for vacation rentals in Kissimmee, Florida. Trust in a seamless booking process for your next trip to this vibrant neighborhood, where comfort and accessibility come together effortlessly.
West Kissimmee
This part of the region offers convenient access to popular attractions and a variety of spacious vacation rentals, making it an ideal choice for those seeking comfort and accessibility during their stay.
View 15721+ Rentals in West KissimmeeCrestwynd Bay
Here, you can enjoy tranquil surroundings with well-maintained vacation homes, creating a relaxing environment perfect for families and groups looking to unwind while exploring the area.
View 50+ Rentals in Crestwynd BayBest Times to Visit Windsor Hills
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit here can enhance your experience and help you make the most of your stay in this popular destination, ensuring you enjoy the best weather, amenities, and local events during your trip.
Peak Season Highlights
Summer (June to August)
During the summer months, this destination experiences its busiest period, making it ideal for travelers seeking lively atmospheres and extended daylight hours to explore the area’s attractions.
Average Temperature Daytime: high 80s°F to low 90s°F - Nighttime: mid 70s°F
Winter Holidays (December to February)
This time of year attracts visitors looking for a warm getaway amidst festive celebrations, with plenty of opportunities to enjoy the region's mild winter weather and holiday events.
Average Temperature Daytime: mid 70s°F - Nighttime: mid 50s°F to low 60s°F
Off-Season Highlights
Spring (March to May)
As the crowds thin out, you can enjoy more peaceful surroundings while experiencing the pleasant spring weather perfect for outdoor activities in this area.
Average Temperature Daytime: mid 70s°F to low 80s°F - Nighttime: mid 50s°F to mid 60s°F
Fall (September to November)
This season offers cooler temperatures and fewer visitors, providing a tranquil setting to relax and explore the scenic beauty of the region comfortably.
Average Temperature Daytime: mid 70s°F - Nighttime: mid 50s°F
Weekly Weather Forecast for Windsor Hills
How to Book Your Windsor Hills Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Windsor Hills
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Access to community swimming pools perfect for relaxing under the warm Florida sun
- Beautifully landscaped outdoor spaces with seating areas for enjoying the weather
- Playground facilities ideal for families traveling with children
- Nearby tennis courts to stay active during your visit
- Well-maintained walking and biking trails through the community
- Outdoor sports courts available for basketball or volleyball enthusiasts
- Picnic areas equipped with tables and grills for outdoor dining experiences
Top Attractions Around Windsor Hills
What attractions are nearby?
While staying in this area, you can enjoy a variety of nearby activities, including world-renowned theme parks, vibrant entertainment options, and outdoor recreational spots that make your visit to Kissimmee truly memorable.
Family Activities
- Windsor Hills Pool & Recreation Area: Relax and enjoy the community’s sparkling pools, splash pad, and playgrounds designed for family fun within the area.
- Disney World Resort: Take a short trip to one of the most iconic theme parks nearby, offering magical experiences for children and adults alike.
- Local Miniature Golf Courses: Spend quality time together at nearby miniature golf courses that provide entertaining challenges suitable for all ages.
- Kissimmee Lakefront Park: Discover outdoor adventures with scenic walking trails, playgrounds, and picnic spots along the beautiful lake in this central destination.
Adult Activities
- Golfing at Mystic Dunes Golf Club: Enjoy a leisurely round of golf at this renowned course nestled within the region, offering scenic views and challenging play for enthusiasts.
- Explore Local Dining Experiences: Indulge in a variety of restaurants nearby that showcase the area's diverse culinary scene, perfect for memorable evenings out.
- Visit Moments from Nature: Discover serene parks and nature preserves where you can unwind and enjoy the tranquility just minutes from your stay.
- Relax at Premier Spas: Pamper yourself with rejuvenating treatments at local spas designed to provide relaxation and wellness in the region’s convenient locations.
Windsor Hills Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Activities in Advance: Take advantage of the area's family-friendly attractions and entertainment options by scheduling your activities early to ensure a smooth and enjoyable stay.
- Explore Local Dining Options: Discover the region’s diverse cuisine offerings nearby, making dining out a delicious part of your vacation experience.
- Utilize On-Site Amenities: Make the most of your vacation rental’s amenities, from pools to game rooms, to relax and unwind without leaving the community.
- Stay Prepared for the Climate: Pack appropriate clothing and essentials to comfortably enjoy the warm weather typical here, whether you're lounging at your rental or exploring the area.
Transportation Options
- Rental Car Services: Conveniently explore the region with reputable rental car providers offering a range of vehicles suited for families and groups staying in Windsor Hills.
- Shuttle Services: Easily access nearby attractions and airports through reliable shuttle options tailored to visitors enjoying their stay here.
- Taxis and Rideshare: Flexible and on-demand transportation is available through taxis and rideshare apps, ensuring quick travel within the area and beyond.
- Public Transit: Local bus routes provide an economical way to navigate the surrounding region, connecting you to key destinations close to your vacation rental.
Local Customs Options
- Polite Greetings: Friendly and respectful greetings are a key part of local etiquette that you’ll notice in this welcoming community.
- Family-Oriented Celebrations: Participating in family-centered events and holidays showcases the region's emphasis on togetherness and community spirit.
- Respect for Nature: Environmental consciousness is reflected in the way locals care for public parks and natural spaces here, encouraging eco-friendly practices for visitors.
- Religious Respect: Observing local religious customs and traditions is appreciated when engaging with the diverse spiritual communities in this area.
Frequently Asked Questions About Windsor Hills?
1. What are the top vacation rentals in Windsor Hills?
There are a lot of options in Windsor Hills. If you plan on staying in the Windsor Hills area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Windsor Hills:
- Top-Rated Amazing Villa! Salt💧Pool, Game Room + Pool Heat, BBQ & Baby Gear
- Windsor Poolside Escape with Stunning Pool View-Perfect for Families!
- Our DisneyDreamVilla - minutes to DisneyWorld!
- Steps from Waterpark/Pool. Next to Disney w/Frozen, Aladdin, Beauty&Beast theme
- Villa Sonrisa - 5 Bedroom/5 Bath Luxury, Minutes To Disney In Windsor Hills
- Mickeys Magical Villa Disney Five Star Pool Villa Home at Windsor Hills
- Luxury for You, Fun for the Kids! 3BR/3BA 2 Miles from Disney
- Minutes Away from Theme Parks! 3-Bed Townhome, 6 minutes to Disney World!
- Wonderful Vacation Villa/Close to Disney, Epcot, Wide World of Sports and Golf
- Welcome to The Windsor Magic with Professional Arcade Room! Brand New 2024!
2. How many vacation rentals have private pools in Windsor Hills?
There are 1225 vacation rentals with private pools near Windsor Hills. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Windsor Hills are best for families?
If you are looking for a family-friendly vacation home in Windsor Hills, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Windsor Hills:
4. How many Rentbyowner vacation rentals are available in Windsor Hills?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 2350 in the Windsor Hills area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Windsor Hills.
5. What is the cancellation policy for vacation rentals in Windsor Hills, Kissimmee?
Cancellation policies vary depending on the specific property. To ensure you understand the terms, please review the listing details or contact the property owner directly before booking.
6. How do I confirm the availability of a rental property in this area?
Availability can change frequently; it’s best to check the current status directly through the listing or reach out to the host for real-time updates on your preferred dates.
7. Are there any house rules or restrictions I should be aware of when staying in these vacation rentals?
Each property may have its own set of house rules and restrictions. Be sure to read the listing carefully or ask the owner to confirm policies regarding noise, pets, or other specific guidelines.
8. What amenities are typically included in Windsor Hills vacation rentals near Orlando?
Most rentals offer a range of amenities such as private pools, fully equipped kitchens, Wi-Fi, and access to community facilities. Verify the included amenities by reviewing the individual listing details.
9. How do I ensure my stay in a rental property is secure and trustworthy?
Choosing listings with verified reviews and direct communication with the owner helps ensure a reliable and secure booking process. Always review the host’s profile and guest feedback before confirming your reservation.
Windsor Hills Top Rated Vacation Rentals
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Pool
- Balcony/Terrace
R3,855/Night
For 7 Nights R26,992
1245 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Condo
- Hot Tub
- Fireplace/Heating
- Pool
R4,264/Night
For 7 Nights R29,858
2966 ft²
10 Guests
5 Bedrooms
5 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
R5,675/Night
For 7 Nights R39,734
2000 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Villa
- Private Pool
- Hot Tub
- Fireplace/Heating
R4,361/Night
For 7 Nights R30,529
1440 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
R3,604/Night
For 7 Nights R25,223
1496 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
R3,838/Night
For 7 Nights R26,860
2700 ft²
10 Guests
5 Bedrooms
5 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
R4,852/Night
For 7 Nights R33,969
2800 ft²
12 Guests
5 Bedrooms
5 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
R9,053/Night
For 7 Nights R63,368
