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Middleburg Vacation Rentals

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Vacation 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 !!"
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!!"
$245 nightly
The price is $266
Nov 2 - Nov 3
Total with taxes and fees
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 "
$193 nightly
The price is $216
Oct 7 - Oct 8
Total with taxes and fees
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. "
$216 nightly
The price is $242
Oct 7 - Oct 8
Total with taxes and fees
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. "
$212 nightly
The price is $238
Oct 7 - Oct 8
Total with taxes and fees
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"
$90 nightly
The price is $102
Oct 8 - Oct 9
Total with taxes and fees
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! "
$1,605 nightly
The price is $1,792
Oct 3 - Oct 4
Total with taxes and fees
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!"
$152 nightly
The price is $170
Oct 8 - Oct 9
Total with taxes and fees
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."
$128 nightly
The price is $142
Oct 7 - Oct 8
Total with taxes and fees
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."
$184 nightly
The price is $203
Oct 8 - Oct 9
Total with taxes and fees
Mi CASA es su CASA

Luxurious Home w/ Spectacular Glass Room & Patios

9.8 out of 10, Exceptional, (160)
"Met all expectations "
$364 nightly
The price is $404
Oct 6 - Oct 7
Total with taxes and fees
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."
$225 nightly
The price is $252
Oct 5 - Oct 6
Total with taxes and fees
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!"
$154 nightly
The price is $172
Oct 5 - Oct 6
Total with taxes and fees
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.
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Top Middleburg Hotel Reviews

Find out more about Middleburg

Find out more about Middleburg

Everything you need to know about Middleburg vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middleburg vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middleburg vacation 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 low season months. For more hustle and bustle, you may prefer to visit Middleburg in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $102 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middleburg rentals

At Expedia, we put the best Middleburg vacation 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 vacation.

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 vacation rentals in Middleburg?

Yes, you can find vacation rentals close to the most popular sights in Middleburg, or you can go with a secluded option if you're looking for relaxation. 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 vacation rentals in Middleburg?

Grande Villas at World Golf Village: This vacation home rental near Middleburg is located on a lake and has an outdoor pool, a terrace, and a barbecue grill 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 a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Middleburg?

Expedia has 18 vacation 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 larger area, you’ll find Jacksonville Naval Air Station and Eagle Harbor Golf Club.

What’s a vacation rental in Middleburg like?

A vacation rental is a private property you can stay in for a long or short time in Middleburg. Vacation rentals offer extras 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 a sanitized environment, vacation rentals can provide a sense of seclusion away from public hotel elevators and bustling concierge desks while still allowing you to travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for family trips.