Middleburg holiday lettings

We found 117 holiday rentals — enter your dates for availability
Discover a selection of 22 homes and other holiday rentals in Middleburg that are perfect for your trip. Holiday rentals offer the best amenities for you and your friends, family or even pets, such as parking and a fireplace. You'll be able to choose a property to rent that has what everyone needs, including options that are accessible or non-smoking.

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  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Middleburg getaway

Enjoy the festivals and other features of Middleburg. This city's shopping, baseball games and restaurants draw many visitors. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in and around Middleburg

Are you looking for things to do while you're in the area? Venture out of your cosy holiday rental and experience everything that makes Middleburg a fun place to get away to. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Eagle Harbor Golf Club (8.4 mi / 13.6 km)
  • The Champions Club at Julington Creek (15.2 mi / 24.5 km)
  • St. John's Golf and Country Club (21.1 mi / 33.9 km)
  • The Golf Club At Fleming Island (8.6 mi / 13.9 km)
  • Magnolia Point Golf and Country Club (10.1 mi / 16.3 km)
  • Bent Creek Golf Course (12.2 mi / 19.6 km)

Exploring the natural landscape of Middleburg

Whether you're an adventurous traveller or just want to take in the scenery, Middleburg is a great place to get outside. These are some of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Clay County Fairgrounds (9.3 mi / 14.9 km)
  • Kingsley Lake (11 mi / 17.7 km)
  • Spring Park (12.1 mi / 19.5 km)
  • Mandarin Park (14.2 mi / 22.9 km)
  • Crystal Springs Park (16.4 mi / 26.3 km)
  • Pope Duval Park (16.7 mi / 26.8 km)

How to get to and around Middleburg

The nearest airport is in Jacksonville, FL (CRG-Jacksonville Executive at Craig), located 27.7 mi (44.5 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to Jacksonville International Airport (JAX), which is 31 mi (50 km) away.

Frequently asked questions

What is the best area to stay in Middleburg when booking a holiday rental?
When considering the best area to stay in Middleburg, Florida, it's worth exploring the charming neighbourhood of Oakleaf Plantation. This area is well-known for its family-friendly atmosphere and offers a variety of holiday rental properties, making it a popular choice for visitors. The community is home to numerous parks and recreational facilities, superb for those seeking outdoor activities.Another appealing neighbourhood is the historic district near downtown Middleburg. Here, you can enjoy a blend of local shops and restaurants, providing a delightful taste of the area's culture. One of the top attractions nearby is the Middleburg Historical Society, which offers insight into the town's rich heritage. Additionally, the proximity to the scenic Black Creek makes it a great spot for nature enthusiasts looking to engage in fishing or kayaking.
How much does it cost to rent a holiday home in Middleburg?
Prices for holiday rentals in Middleburg 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Middleburg to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Middleburg holiday house rentals?
You can find great discounts on house rentals in Middleburg on Vrbo, 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.
What is the most popular type of holiday rental accomodation in Middleburg?
In Middleburg, holiday houses are the predominant type of holiday rental, with around 54 available throughout the area. These homes often provide spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor areas for relaxation, making them ideal for families or larger groups. Additionally, there are several apartments, mobile homes, and condos that offer alternative options for travellers seeking a different experience. Most of these rentals are situated in tranquil neighbourhoods, providing a peaceful setting while still being conveniently located for exploring nearby attractions.
Are there any family house rentals in Middleburg?
In Middleburg, Florida, there are numerous family-friendly holiday rentals available—approximately 15 in total. The area is well-suited for families, offering spacious homes that often include amenities such as full kitchens, ample living spaces, and outdoor areas superb for children to play.Visitors can explore nearby attractions like the scenic Clarke House Park, which features picnic areas and walking trails, providing a lovely backdrop for family outings. Additionally, the local community is known for its friendly atmosphere, making it easy for families to settle in and enjoy their stay.
Can I rent a holiday home with a pool or hot tub in Middleburg?
In Middleburg, Florida, there are several holiday homes available for rent that feature pools or hot tubs, providing a refreshing way to enjoy the warm climate. This charming town, located just south of Jacksonville, offers a range of residential areas where these properties can be found, often surrounded by lush greenery and a peaceful atmosphere.Travellers can expect amenities such as private pools, hot tubs, spacious outdoor areas for relaxation, and fully equipped kitchens that make self-catering easy and enjoyable. Some homes may also offer additional features like patios for al fresco dining, barbecue facilities, and comfortable living spaces, ensuring a delightful stay for families or groups.
Can I find long-stay holiday rentals in Middleburg?
A long-stay holiday rental in Middleburg 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Middleburg?
In Middleburg, there are a variety of pet-friendly house rentals available, with around 20 options to choose from. These properties often feature spacious layouts, fully equipped kitchens, and outdoor areas where pets can enjoy the fresh air. Many rentals in the area come with amenities such as fenced yards, making it a safe environment for your furry companions.The neighbourhoods around Middleburg provide a serene atmosphere, ideal for families and pet owners. Close to the St. Johns River, there are opportunities for outdoor activities, whether it's a leisurely stroll along the riverbank or exploring nearby parks. The surrounding natural landscapes enhance the experience for both you and your pets, offering a peaceful retreat while still being conveniently located near essential amenities.
Are there any remote work holiday rentals in Middleburg?
In Middleburg, Florida, there are numerous options for remote work holiday rentals, with around 66 available to choose from. This charming town offers a peaceful environment ideal for those looking to balance work and leisure. Many properties come equipped with essential amenities such as high-speed internet and complimentary Wi-Fi, ensuring a reliable connection for remote work tasks.Travellers can expect a variety of accommodations, from cosy cottages to spacious homes, often featuring dedicated workspaces, comfortable living areas, and fully equipped kitchens for convenient meal preparation. The neighbourhood offers a serene setting, with nearby parks and nature trails for relaxation during breaks. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Middleburg holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Middleburg 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 on Vrbo 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.
What are popular rental amenities in Middleburg?
In Middleburg, popular rental amenities cater to a variety of traveller needs. Many holiday rentals permit pets, making them ideal for those who wish to bring their furry friends along. Most properties feature kitchens, allowing guests to prepare their own meals, while outdoor spaces such as decks or patios provide a pleasant area to relax and enjoy the surroundings. Additionally, amenities like coffee and tea makers are commonly included, ensuring that guests can enjoy a warm beverage at their convenience.
When is the best time to visit Middleburg for a holiday rental?
September is the most popular time to visit Middleburg, Florida, as the summer heat begins to ease, making outdoor activities more enjoyable. The peak season typically runs from July to September, when families and adventure seekers flock to the area to take advantage of the warm weather and engaging local events.During September, temperatures are pleasantly mild, averaging around 20 to 30 degrees Celsius, which is superb for exploring the scenic landscapes and engaging in outdoor pursuits like hiking and fishing. Visitors can also enjoy the charming community atmosphere, with various festivals and activities that showcase the area's rich culture.For those looking for a more budget-friendly option, consider planning your visit in October. This month offers a quieter experience, allowing you to fully appreciate Middleburg's natural beauty without the summer crowds. The weather remains agreeable, and it's a great time to enjoy leisurely walks or bike rides around the picturesque surroundings.Ultimately, the best time to book a holiday rental in Middleburg hinges on your preferences. If you thrive in a vibrant setting with plenty of activities, September is ideal. However, if you prefer a more relaxed pace with the beauty of autumn, October could be your superb choice.
How early should I book a Middleburg holiday rental?
Book your Middleburg holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price. *Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Middleburg home rental booking on Vrbo?
To find Middleburg holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo 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 Vrbo handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Middleburg holiday rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way. Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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