Photo by Cindy Simmonds

Middleburg Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Holiday Rentals in Middleburg

Relax in our cozy 3 BR home with a spacious master suite with soaking tub, large yard, pool, BBQ

10.0 out of 10, Exceptional, (23)
"Very responsive management and a great property for families."
Relax in our cozy 3 BR home with a spacious master suite with soaking tub, large yard, pool, BBQ

Hilton Vacation Club St. Augustine

3.5 star property
8.6 out of 10, Excellent, (283)
"Nice place !!"
The price is AU$360
includes taxes & fees
16 Oct - 17 Oct
Hilton Vacation Club St. Augustine

Kasa Southside Jacksonville

3.5 star property
9.0 out of 10, Wonderful, (29)
"Nice place to stay "
Kasa Southside Jacksonville

Landing Apartments Rolling Hills

3.0 star property
Landing Apartments Rolling Hills

The Van Zant House

3.5 star property
6.0 out of 10, (6)
"It was a great experience for my children and I bc this house was / used to be my family home…. My great grandparents home where my grandfather and other family members grew up and we had lots of family holidays!! It was wonderful to share that with my own children! Thank you!!"
The Van Zant House

Relaxing & charming home

9.4 out of 10, Exceptional, (45)
"Great place to stay! Luis was very helpful and responsive, thank you!"
Relaxing & charming home

Charming 3-bedroom House with AC and WiFi in lovely Jacksonville

2.0 star property
9.2 out of 10, Wonderful, (13)
"Traveling from Virginia to destin Florida. Place was a great pit stop in between road trip for some rest. I would definitely recommend "
The price is AU$330
includes taxes & fees
7 Oct - 8 Oct
Charming 3-bedroom House with AC and WiFi in lovely Jacksonville

Private Paradise in a Pristine Neighborhood - Fenced back yard, patio & firepit

9.6 out of 10, Exceptional, (39)
"Great place. Nice area. Very clean. "
The price is AU$369
includes taxes & fees
7 Oct - 8 Oct
Private Paradise in a Pristine Neighborhood - Fenced back yard, patio & firepit

Central 2BR Near Mayo Clinic with Fenced Yard and Patio!

2.0 star property
9.6 out of 10, Exceptional, (4)
"Location was perfect, house was exactly as advertised and was just right for our needs. Will definitely stay here again if we return to Jacksonville. "
The price is AU$363
includes taxes & fees
7 Oct - 8 Oct
Central 2BR Near Mayo Clinic with Fenced Yard and Patio!

Cozy Hideaway in Jacksonville

7.8 out of 10, Good, (21)
"It was nice and cozy"
The price is AU$161
includes taxes & fees
7 Oct - 8 Oct
Cozy Hideaway in Jacksonville

30 People Comfortably Gorgeous Home on Canal Boat Kayak access Two 85" & 75” TVs

9.4 out of 10, Exceptional, (21)
"The accommodations were wonderful! Exactly what we needed for our family to relax and enjoy for the wedding celebration at the Clay Theatre - thank you! "
The price is AU$2,727
includes taxes & fees
3 Oct - 4 Oct
30 People Comfortably Gorgeous Home on Canal Boat Kayak access Two 85" & 75” TVs

Boutique Home in Jax City

9.6 out of 10, Exceptional, (17)
"The property is extremely clean. The owner was extremely accessible, responsive, and accommodating. The property is centrally located near the river and multiple stadiums. Additionally, this property has massive TVs!"
The price is AU$260
includes taxes & fees
8 Oct - 9 Oct
Boutique Home in Jax City

Cozy Treetop Hideaway

10.0 out of 10, Exceptional, (82)
"Thank you for making my pet and I feel at home."
The price is AU$218
includes taxes & fees
7 Oct - 8 Oct
Cozy Treetop Hideaway

Westside home away from home-Live like local and chill in privacy. Super safe

9.8 out of 10, Exceptional, (21)
"Great stay!"
Westside home away from home-Live like local and chill in privacy. Super safe

Mi CASA es su CASA

10.0 out of 10, Exceptional, (86)
"Great stay with no issues. Great communication with host."
The price is AU$310
includes taxes & fees
8 Oct - 9 Oct
Mi CASA es su CASA

Luxurious Home w/ Spectacular Glass Room & Patios

9.8 out of 10, Exceptional, (160)
"Met all expectations "
The price is AU$618
includes taxes & fees
6 Oct - 7 Oct
Luxurious Home w/ Spectacular Glass Room & Patios

Charming Springfield Hideaway near downtown Jacksonville

2.0 star property
10.0 out of 10, Exceptional, (20)
"I stay here regularly and everything is always perfect, private and well put together. Highly recommended! "
Charming Springfield Hideaway near downtown Jacksonville

Unique Design Bungalow in Jax Riverside Area.

9.6 out of 10, Exceptional, (36)
"The property was clean and location was close to downtown."
The price is AU$385
includes taxes & fees
5 Oct - 6 Oct
Unique Design Bungalow in Jax Riverside Area.

Colorful Family Friendly, Pet Friendly Bungalow, Sleeps 6 - Jacksonville, FL

9.8 out of 10, Exceptional, (25)
"Relazing weekend, nice property!"
The price is AU$263
includes taxes & fees
5 Oct - 6 Oct
Colorful Family Friendly, Pet Friendly Bungalow, Sleeps 6 - Jacksonville, FL

4-bedroom house in lovely Saint Johns with enclosed 16’ X 32’ pool, WiFi, AC

9.0 out of 10, Wonderful, (2)
"This house was in an ideal location as we were visiting family nearby. Plus, we had a very large and clean backyard private pool!John, was over and above in accommodating our needs."
4-bedroom house in lovely Saint Johns with enclosed 16’ X 32’ pool, WiFi, AC
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Middleburg Hotel Reviews

Find out more about Middleburg

Find out more about Middleburg

Everything you need to know about Middleburg holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middleburg holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middleburg holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Middleburg holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middleburg. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middleburg holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middleburg holiday rentals we have selected for you start as low as AU$161 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Middleburg rentals

At Expedia, we put the best Middleburg holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Middleburg rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middleburg holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middleburg. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Middleburg?

Yes, there are holiday rentals close to the most popular sights in Middleburg, or you can select a more secluded option if you're looking for a relaxing stay. Middleburg is known for its shopping and baseball games. Make sure you have time to check out the restaurants and festivals during your trip.

What are some of the best holiday rentals that Middleburg has to offer?

Grande Villas at World Golf Village: This holiday home rental outside of Middleburg is located on a lake, and has an outdoor pool, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers an outdoor tennis court, a garden and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Middleburg?

Expedia has 18 holiday rentals for your stay in Middleburg.

What’s there to see and do in Middleburg?

While exploring the area, visit family-friendly sights like Ronnie Van Zant Park, or get outside and enjoy nature at Clay County Fairgrounds. In the wider area, you’ll find Jacksonville Naval Air Station and Eagle Harbor Golf Club.

What’s a holiday rental in Middleburg like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middleburg. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from public hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for a family trip or a small group gathering.