Middleburg Vacation Rentals

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Our top choices for Middleburg vacation rentals

Baby it's Cold Outside Winter Promo on 4 - 6 night stays

Baby it's Cold Outside Winter Promo on 4 - 6 night stays
Middleburg
9.6 out of 10, Exceptional, (25)
"Very responsive management and a great property for families."
United States
Bob E.
Baby it's Cold Outside Winter Promo on 4 - 6 night stays

InTown Suites Extended Stay Jacksonville FL - St. Johns Bluff Rd

InTown Suites Extended Stay Jacksonville FL - St. Johns Bluff Rd
2.5 star property
Jacksonville
6.2 out of 10, (28)
"It was nice"
United States
Dhante
InTown Suites Extended Stay Jacksonville FL - St. Johns Bluff Rd

Landing Apartments Jacksonville - Windy Hill

Landing Apartments Jacksonville - Windy Hill
4.0 star property
Southside
Landing Apartments Jacksonville - Windy Hill

Cozy House close To Downtown

Cozy House close To Downtown
Northwest
8.6 out of 10, Excellent, (8)
"The house was nice, clean, and felt very homey. The host was wonderful. Had a big front and back yard for my dog. Can’t wait to book this home again. "
United States
Anonymous traveler
$180 nightly
The price is $202
Dec 12 - Dec 13
Total with taxes and fees
Cozy House close To Downtown

Remodeled house in San Marco steps from San Marco Square and Riverwalk

Remodeled house in San Marco steps from San Marco Square and Riverwalk
San Marco
9.4 out of 10, Exceptional, (22)
"The house was cute, comfortable, well stocked, and located within a short walking distance of fantastic restaurants and bars! Couldn't have asked for a better place to stay!"
United States
Kirkland L.
$212 nightly
The price is $238
Dec 11 - Dec 12
Total with taxes and fees
Remodeled house in San Marco steps from San Marco Square and Riverwalk

The Van Zant House

The Van Zant House
3.5 star property
Westside
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!!"
United States
Ashley
$249 nightly
The price is $271
Dec 11 - Dec 12
Total with taxes and fees
The Van Zant House

Cozy Timuquana Townhome Private Yard & Parking Family and Pet-friendly

Cozy Timuquana Townhome Private Yard & Parking Family and Pet-friendly
Westside
8.0 out of 10, Very Good, (3)
"Great place to stay "
United States
Timothy J.
Cozy Timuquana Townhome Private Yard & Parking Family and Pet-friendly

RelaxJax - a Private Paradise in a Pristine Neighborhood Fenced yard w/grill.

RelaxJax - a Private Paradise in a Pristine Neighborhood Fenced yard w/grill.
Avondale
9.6 out of 10, Exceptional, (45)
"This home was in a great and safe location. Planning on going back!"
United States
Heidi M.
$213 nightly
The price is $239
Dec 15 - Dec 16
Total with taxes and fees
RelaxJax - a Private Paradise in a Pristine Neighborhood Fenced yard w/grill.

Landing Apartments Rolling Hills

Landing Apartments Rolling Hills
3.0 star property
Northwest
10.0 out of 10, Exceptional, (1)
"The apartment was well appointed, so much so that I ordered a kitchen gadget for my own home that was in the apartment. There were plenty of towels, kitchen supplies (dishes, pots and pans, storage containers). A kitchen kit with dish soap, sponge and laundry detergent was provided. The area has everything that you would need. Very close to grocery stores and restaurants. Also close to freeway access. The bed was super comfortable and the rooms were spacious. The shower was HUGE. The...
United States
Michelle
Landing Apartments Rolling Hills

Cozy Hideaway in Jacksonville

Cozy Hideaway in Jacksonville
Arlington
7.6 out of 10, Good, (27)
"It was nice and cozy"
United States
Brandon G.
$94 nightly
The price is $107
Dec 11 - Dec 12
Total with taxes and fees
Cozy Hideaway in Jacksonville

Relaxing & charming home

Relaxing & charming home
Southside
9.4 out of 10, Exceptional, (51)
"Excellent; it was very clean, which made my short stay comfortable and enjoyable. It was in a great location, close to grocery stores and a shopping mall, making everything I needed easily accessible. I couldn’t have asked for a better place to stay while in Jacksonville.."
United States
Darryll C.
Relaxing & charming home

Kasa Southside Jacksonville

Kasa Southside Jacksonville
3.5 star property
Southside
9.2 out of 10, Wonderful, (32)
"Nice place to stay "
United States
Lovely Charles
Kasa Southside Jacksonville

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

Charming 3-bedroom House with AC and WiFi in lovely Jacksonville
2.0 star property
Northwest
9.0 out of 10, Wonderful, (14)
"This was such a cute quaint home that so cozy! Great location that was close to so many unique places and restaurants! It was surprisingly quiet for being so close to the interstate and train but overall a wonderful stay! "
United States
Courtney C.
$173 nightly
The price is $194
Jan 2 - Jan 3, 2026
Total with taxes and fees
Charming 3-bedroom House with AC and WiFi in lovely Jacksonville

Spacious 4-Bedroom Retreat Near Downtown & San Marco – Jacksonville Charm

Spacious 4-Bedroom Retreat Near Downtown & San Marco – Jacksonville Charm
2.0 star property
Spring Park
10.0 out of 10, Exceptional, (1)
"Very clean and great "
United States
Nahjai T.
$245 nightly
The price is $275
Dec 24 - Dec 25
Total with taxes and fees
Spacious 4-Bedroom Retreat Near Downtown & San Marco – Jacksonville Charm

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

30 People Comfortably Gorgeous Home on Canal Boat Kayak access Two 85" & 75” TVs
Fleming Island
9.2 out of 10, Wonderful, (23)
"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! "
United States
Kim M.
$1,692 nightly
The price is $1,879
Dec 11 - Dec 12
Total with taxes and fees
30 People Comfortably Gorgeous Home on Canal Boat Kayak access Two 85" & 75” TVs

Southern Charm w/Modern Comfort in peaceful Jacksonville

Southern Charm w/Modern Comfort in peaceful Jacksonville
Northwest
10.0 out of 10, Exceptional, (3)
"House was very clean and exactly as pictured. Communication was excellent, check in was easy and check out was the easiest I’ve ever experienced."
United States
Megan S.
$304 nightly
The price is $339
Jan 6 - Jan 7, 2026
Total with taxes and fees
Southern Charm w/Modern Comfort in peaceful Jacksonville

Newly remodeled house in San Marco few minutes walk to Square & Riverwalk

Newly remodeled house in San Marco few minutes walk to Square & Riverwalk
San Marco
9.8 out of 10, Exceptional, (11)
"Great location."
United States
Lori M.
$217 nightly
The price is $243
Dec 17 - Dec 18
Total with taxes and fees
Newly remodeled house in San Marco few minutes walk to Square & Riverwalk

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

Colorful Family Friendly, Pet Friendly Bungalow, Sleeps 6 - Jacksonville, FL
Northwest
9.8 out of 10, Exceptional, (31)
"Relazing weekend, nice property!"
United States
Michelle M.
$148 nightly
The price is $165
Dec 11 - Dec 12
Total with taxes and fees
Colorful Family Friendly, Pet Friendly Bungalow, Sleeps 6 - Jacksonville, FL

Cozy Treetop Hideaway

Cozy Treetop Hideaway
Northwest
10.0 out of 10, Exceptional, (84)
"Such a lovely little apartment. Very clean too. Daiv was a wonderful host. "
United States
S F.
$127 nightly
The price is $141
Dec 14 - Dec 15
Total with taxes and fees
Cozy Treetop Hideaway

The Peaceful Green - A Relaxing St. Augustine Getaway

The Peaceful Green - A Relaxing St. Augustine Getaway
St. Augustine
9.2 out of 10, Wonderful, (9)
"Nice place. Very easy to get in and out of."
United States
Phillip S.
The Peaceful Green - A Relaxing St. Augustine Getaway
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

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 $107 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?

Cozy Timuquana Townhome Private Yard & Parking Family and Pet-friendly: This vacation home rental near Middleburg offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Middleburg?

Expedia has 21 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 Latitude 30, or get outside and enjoy nature at Jennings State Forest. In the larger area, you’ll find Eagle Harbor Golf Club and Clay County Fairgrounds.

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.