Windsor vacation rentals

We found 202 vacation rentals — enter your dates for availability

Scroll through and select from vacation rentals in Windsor to find one that's perfect for your trip. Vacation homes provide the best amenities for you and your friends, family, or even pets, such as WiFi and a fireplace. At the end of the day, you'll find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.
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Find out more about Windsor

Find out more about Windsor

Why visit Windsor

  1. Scenic Outdoor Activities: Enjoy hiking, biking, and nature walks in the beautiful natural surroundings of Windsor.
  2. Family-Friendly Attractions: Engage in various family-oriented activities, perfect for creating lasting memories.
  3. Historical Exploration: Discover local history through nearby historic colleges and cultural sites.
  4. Charming Neighbourhoods: Explore welcoming communities like Windsor Hills, adding to the local charm.
  5. Diverse Accommodation Options: Choose from private vacation homes, cozy cottages, and modern condos for a comfortable stay.

Popular types of accommodation in Windsor

When exploring Windsor, you'll find a variety of vacation rentals to suit your needs, including houses, cozy cottages, and modern condos. Whether you're seeking a peaceful getaway at Windsor Island Resort or comfortable guest accommodations for your family, we have options that offer transparency, savings, and reassurance. Discover the perfect vacation home that aligns with your travel plans and enjoy all that Windsor has to offer!

  • Houses: The top choice for visitors to Windsor, offering spacious and comfortable spaces ideal for families and groups.
  • Condos: A popular option for those seeking modern amenities and a convenient location, perfect for both relaxation and exploration.
  • Cottages: These quaint and charming retreats provide a cozy atmosphere, ideal for a peaceful getaway.
  • Apartments: A versatile choice for solo travellers or couples looking for a home-like experience during their stay.
  • Cabins: A favourite among nature enthusiasts, offering a rustic experience amidst beautiful surroundings.**

Top attractions in Windsor

Windsor, Florida, offers an ideal setting for outdoor and family-oriented vacations, featuring attractions like national parks, historic colleges, and sports stadiums. Visitors can immerse themselves in the area's natural beauty while enjoying cultural experiences that cater to families and outdoor enthusiasts alike. Whether you're exploring the great outdoors or delving into local history, Windsor provides a variety of engaging activities for every type of traveller.

  1. University of Florida: A historic institution with rich cultural vibes, offering beautiful architecture and a vibrant campus life. You can explore its gardens and art exhibits, immersing yourself in the academic spirit.
  2. Ben Hill Griffin Stadium: Known as "The Swamp," this historic sports stadium is a hub of excitement and energy, especially during football season. Experience the passion of Gator fans and the thrill of live sports.
  3. Florida Museum of Natural History: A family-friendly attraction showcasing diverse exhibits about Florida's natural history. Engage with interactive displays and learn about the state's unique ecosystems.

Things to do recommended for couples

For a romantic getaway in Windsor, visit the Royal Manor Winery, located 32.2km away. Enjoy the enchanting atmosphere, sip on exquisite wines, and indulge in delightful entertainment, making it the perfect spot for couples to create lasting memories together.

Things to do recommended for families

During your family vacation in Windsor, Florida, explore Bivens Arm Nature Park for relaxation, enjoy outdoor fun at Haile Village Playground, and discover the serene Herzog Cave Preserve. Each destination offers unique experiences perfect for creating lasting family memories.

Things to do recommended for groups

Experience the thrill of races at Gainesville Raceway, only 14.5km from Windsor. Enjoy outdoor adventures at Kate's Fish Camp, just 6.4km away, or immerse yourself in culture and entertainment at the Hippodrome State Theatre, situated 12.9km from your base.

What do I need to keep in mind when booking a vacation in Windsor

If you're planning a trip with a group, family, or pets, or if you're considering an extended stay, be sure to prioritize your preferences when searching. Here are some helpful Vrbo booking tips for you.

  • Traveling to Windsor with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Windsor with young kids: Traveling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Windsor: For many families, a trip wouldn’t feel complete without their furry companions. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that all members of the family feel comfortable and at home.
  • Planning for a long term stay visiting Windsor: If you're in search of vacation rentals that offer discounts for month-long stays, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to consider adding features like parking, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay in Windsor

Windsor, Florida, offers an ideal vacation for outdoor enthusiasts and families alike. Nestled near vibrant cities like Orlando and charming neighborhoods such as Windsor Hills, visitors can immerse themselves in a welcoming atmosphere filled with luxury and family-friendly activities. Enjoy the perfect Florida getaway by exploring the scenic surroundings, engaging in outdoor adventures, and experiencing the local culture that makes this region truly special.

  • Rochelle: Located a mere 6.4km from Windsor, Rochelle is a quaint village that beckons outdoor enthusiasts and culture seekers alike. Visitors can immerse themselves in a variety of activities, from exploring the local parks to taking part in motor racing events. The area features charming historical landmarks, including a nearby historic college university and beautiful beaches, making it an ideal destination for those looking to combine adventure with educational experiences. Enjoy the thrill of nature and culture in this inviting locale.
  • Orange Heights: A short 9.7km from Windsor, Orange Heights is a picturesque village perfect for families and nature lovers. The vibrant public market is a highlight, offering fresh produce and local goods that reflect the community's spirit. With beautiful lakes and a nearby beach, visitors can enjoy a range of outdoor activities, including swimming and picnicking. Additionally, the proximity to a popular theme park adds an element of excitement for families looking to create lasting memories in this scenic area.
  • Hawthorne: Situated 11.3km away from Windsor, Hawthorne is a bustling city that boasts stunning natural scenery and adventure opportunities. The recreational areas invite visitors to enjoy activities such as hiking and fishing, while the nearby national state park offers breathtaking landscapes and diverse wildlife. With a focus on outdoor adventures, Hawthorne is a great place to explore lakes and rivers, providing a perfect backdrop for those seeking both relaxation and excitement in nature.

Best time to go to Windsor

If you're planning a trip to Windsor, it's a good idea to check both the weather and property rates. The warmest months are July and August. Peak season runs in January, March and July, while off-peak times, like June and October to November tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January55.8°F (13.2°C)Light RainMostly SunnySlightly HighSlightly Low
February60.1°F (15.6°C)Light RainMostly SunnyAverageSlightly Low
March64.2°F (17.9°C)Light RainMostly SunnySlightly HighSlightly Low
April70.2°F (21.2°C)Light RainMostly SunnyAverageAverage
May75.6°F (24.2°C)Light RainMostly SunnyAverageAverage
June80.1°F (26.7°C)Light RainMostly SunnySlightly LowAverage
July81.3°F (27.4°C)Light RainMostly SunnySlightly HighAverage
August81.3°F (27.4°C)Light RainMostly SunnyAverageAverage
September78.4°F (25.8°C)Light RainMostly SunnyAverageSlightly High
October72.0°F (22.2°C)Light RainMostly SunnySlightly LowSlightly High
November63.9°F (17.7°C)Light RainMostly SunnySlightly LowSlightly High
December59.7°F (15.4°C)Light RainMostly SunnyAverageAverage

Booking with Vrbo is simple

Are you aiming to save on your upcoming adventure? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, consider booking a longer stay to enjoy substantial savings. To discover a Vrbo property that aligns with your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway!

Vrbo Trips: Planning made easy

Vrbo’s Trip Board is designed to help you plan your journeys with ease. You can initiate new trips, refine your existing plans, or manage your bookings all in one place. Your saved or booked properties are conveniently categorized into Potential, Upcoming, or Current Trips for your convenience. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Choose a vacation rental for your Windsor getaway

Experience the unique character of Windsor with a stay in a vacation home rental. You'll find plenty to explore during your stay in the area. A vacation rental can help make your stay complete. Many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Windsor

Do you want to discover attractions to visit while you're in town? Venture out of your cozy vacation rental and experience everything that makes Windsor a one-of-a-kind vacation spot. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • Waldo Motorsports (11.4 mi / 18.4 km)
  • Ironwood Golf Course (7.2 mi / 11.7 km)

Exploring the natural features in Windsor

Whether you're an outdoor enthusiast or just want to take in the scenery, Windsor is a great place to get out in nature. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

  • Santa Fe Lake (9.3 mi / 14.9 km)
  • University of Florida Bat Houses (10.6 mi / 17.1 km)
  • Paynes Prairie Preserve State Park (11.1 mi / 17.8 km)
  • Kanapaha Botanical Gardens (13.6 mi / 21.9 km)
  • San Felasco Hammock Preserve State Park (17.1 mi / 27.5 km)
  • Kate's Fish Camp (4.5 mi / 7.2 km)

Traveling to and around Windsor

The nearest airport is in Gainesville Regional Airport (GNV), located 6.1 mi (9.8 km) from the city center.

Frequently asked questions

How much does it cost to rent a vacation rental in Windsor?
The average price for a vacation rental in Windsor is based on several factors, such as season, property type and length of stay. Whether you prefer a villa with space for extended family or a quaint cabin that's perfect for two, just enter your dates of travel to see stays with great value.
How much does it cost to rent a beach house in Windsor?
Prices for beach houses in Windsor can differ depending on the size and style of the property and when you plan to travel. Just enter your travel dates into Vrbo and the number of guests to view available options and prices. From there you can use our filters to narrow your search by amenities, nearby activities, ratings and more.
How old do you have to be to rent a vacation rental in Windsor?
You'll need to check with the Windsor vacation rental you're looking at on Vrbo as the age limit varies. However, generally it's 16, 18 or 21.
How long can I rent a vacation rental in Windsor for?
The length of time you can book a vacation rental in Windsor is down to the property. Simply enter your desired dates to look at a list of options offering extended stays. With a range of creature comforts such as laundries and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to discover somewhere just right to call your home away from home in Windsor.

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