Windsor holiday rentals

We found 248 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Windsor to find one that's perfect for your trip. Holiday homes offer the best amenities for you and your friends, family or even pets, such as Wi-Fi and a pool. No matter what you're looking for, you'll be sure to find a property to rent for everyone's needs, including accessible or non-smoking choices.

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  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Choose a holiday rental for your Windsor getaway

Learn about the unique charm of Windsor with a stay in a holiday home rental. This city has something for everyone. A holiday 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 in the area? Venture out of your cosy holiday rental and experience everything that makes Windsor a fun place to get away to. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Turkey Creek Golf Course (15.7 mi / 25.2 km)
  • Ironwood Golf Course (7.2 mi / 11.7 km)
  • Waldo Motorsports (11.4 mi / 18.4 km)

Exploring the natural features in Windsor

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Windsor is a great place to spend some time outside. Here are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Santa Fe Lake (9.2 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)
  • Kate's Fish Camp (4.5 mi / 7.2 km)
  • Crystal Lake (15.1 mi / 24.2 km)

Travelling to and around Windsor

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

Frequently asked questions

What is the best area to stay in Windsor when booking a holiday rental?
When considering a holiday rental in Windsor, Florida, the best area to stay is the charming neighbourhoods that surround the community. Windsor is known for its picturesque setting and serene atmosphere, making it an ideal retreat. One such area is the scenic waterfront, where you can find a delightful array of properties that offer stunning views and easy access to the calming waters.This region is not only tranquil but also conveniently located near several attractions. Just a short drive away, you can visit the captivating Indian River Lagoon, a superb spot for nature enthusiasts, where you might enjoy kayaking or birdwatching. Additionally, the vibrant local community often hosts events and activities that showcase the area's unique culture and charm.Another appealing option is to explore the serene residential enclaves that feature a mix of rental properties, providing a sense of seclusion while still being close to amenities. Staying here allows easy access to nearby attractions, such as the picturesque beaches along the Atlantic coast, where sunbathing and beachcombing await.
When is the best time to visit Windsor for a holiday rental?
January marks the start of the peak season in Windsor, Florida, drawing in visitors eager to enjoy the mild winter weather and vibrant local culture. This period, lasting until March, offers a delightful escape from colder climates, with temperatures typically ranging from 10 to 20 degrees Celsius. It's the superb time for outdoor activities, whether you're strolling through picturesque parks or exploring the scenic waterways nearby.During these months, you'll find a lively option, with plenty of opportunities to engage in local events and festivals that highlight Windsor's charm. The pleasant weather makes it an ideal time for sightseeing, whether you're visiting historic sites or enjoying nature walks.If you're looking for a more budget-friendly option, consider planning your visit in October. This month offers a quieter experience, allowing you to appreciate the natural beauty of Windsor without the hustle and bustle of peak season. The weather remains pleasant, making it a lovely time for outdoor activities like hiking or biking.Ultimately, the best time to visit Windsor depends on your preference for lively events and socializings versus a more tranquil getaway.
What are the top attractions in Windsor?
In Windsor, Florida, visitors can enjoy a tranquil escape surrounded by natural beauty and elegant architecture. The community is renowned for its stunning landscapes, with scenic trails for walking and biking that meander through lush greenery and along beautiful waterways. The nearby Windsor Lake offers opportunities for kayaking and fishing, making it a superb spot for outdoor enthusiasts.Additionally, the area features charming parks that provide picnic areas and playgrounds, ideal for families. While Windsor itself is primarily a residential community, it is conveniently located near the attractions of Vero Beach, where guests can explore pristine beaches, local shops, and art galleries.
Are all fees included in the Windsor holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Windsor holiday homes with parking?
Stayz offers a wide selection of holiday homes in Windsor with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Windsor holiday homes?
You can find great discounts on holiday homes in Windsor on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Windsor holiday home booking on Stayz?
To find Windsor holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Windsor?
A long-stay holiday home in Windsor is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Windsor holiday home?
Book your Windsor holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Windsor?
Prices for holiday homes in Windsor vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Windsor to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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