A sunset over a calm lake with a dock and boats.

Middleburg Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Middleburg vacation rentals

Property grounds

1. Private Loft at a Working Show Barn ~ Pets Welcome!

Private Loft at a Working Show Barn ~ Pets Welcome!
Middleburg
9.6 out of 10, Exceptional, (27 reviews)
"Horses were great, stay was wonderful, very relaxing "
United States
Tina S.
$161 nightly
The price is $178
Sep 10 - Sep 11
Total with taxes and fees
Private Loft at a Working Show Barn ~ Pets Welcome!
Terrace/patio

2. NEW Waterfront Retreat "The Creek House" RENT JETSKIS POOL TABLE Sleep 10 KAYAKS

NEW Waterfront Retreat "The Creek House" RENT JETSKIS POOL TABLE Sleep 10 KAYAKS
Middleburg
$340 nightly
The price is $378
Sep 9 - Sep 10
Total with taxes and fees
NEW Waterfront Retreat "The Creek House" RENT JETSKIS POOL TABLE Sleep 10 KAYAKS
Interior

3. Country living at its best!

Country living at its best!
Middleburg
9.4 out of 10, Exceptional, (3 reviews)
"We had a wonderful stay at this quiet, country home. Spacious and renovated interior with a lovely side yard for relaxing in the evening. The host was fabulous and quick to respond to all our questions. We will definitely stay here again. "
United States
Amy M.
$294 nightly
The price is $327
Sep 7 - Sep 8
Total with taxes and fees
Country living at its best!
Terrace/patio

4. Pasture Bedtime Yurt

Pasture Bedtime Yurt
Middleburg
$279 nightly
The price is $309
Sep 7 - Sep 8
Total with taxes and fees
Pasture Bedtime Yurt
Room

5. Moo-Tel Yurt

Moo-Tel Yurt
Middleburg
$279 nightly
The price is $309
Sep 7 - Sep 8
Total with taxes and fees
Moo-Tel Yurt
View from property

6. StudioRes by Marriott Jacksonville Orange Park

StudioRes by Marriott Jacksonville Orange Park
3.0 star property
Westside
8.6 out of 10, Excellent, (46 reviews)
"Beautiful room... wish there was breakfast"
United States
Marquessa
$93 nightly
The price is $106
Sep 10 - Sep 11
Total with taxes and fees
StudioRes by Marriott Jacksonville Orange Park
Room

7. Cozy Private Entire Studio Suite Independent Guest Entrance

Cozy Private Entire Studio Suite Independent Guest Entrance
Westside
9.4 out of 10, Exceptional, (21 reviews)
"Nice and cozy!!Easy access, clean and comfortable!!Will book again "
United States
Shantrill G.
$126 nightly
The price is $140
Sep 7 - Sep 8
Total with taxes and fees
Cozy Private Entire Studio Suite Independent Guest Entrance
Pool

8. Suite Peace- New luxury apartment near NAS JAX and Orange park

Suite Peace- New luxury apartment near NAS JAX and Orange park
Westside
9.4 out of 10, Exceptional, (19 reviews)
"Convenient location. Very comfortable. "
United States
Aimee G.
$205 nightly
The price is $229
Sep 7 - Sep 8
Total with taxes and fees
Suite Peace- New luxury apartment near NAS JAX and Orange park
Apartment (0 Bedroom) | Interior

9. The Humming Bird Suite - Affordable Lakefront Fun

The Humming Bird Suite - Affordable Lakefront Fun
3.0 star property
Keystone Heights
$109 nightly
The price is $123
Sep 6 - Sep 7
Total with taxes and fees
The Humming Bird Suite - Affordable Lakefront Fun
Outdoor dining

10. Rustic Owl w/ 2Kings In Fleming Island

Rustic Owl w/ 2Kings In Fleming Island
Fleming Island
10.0 out of 10, Exceptional, (40 reviews)
"Great location. Property was well stocked, clean and comfortable."
United States
Joe T.
$386 nightly
The price is $429
Sep 7 - Sep 8
Total with taxes and fees
Rustic Owl w/ 2Kings In Fleming Island
Terrace/patio

11. Single house: 12guests,4bds/2baths,large backyard.

Single house: 12guests,4bds/2baths,large backyard.
Jacksonville
9.8 out of 10, Exceptional, (47 reviews)
"Great place for big families and small children. "
United States
Maria R.
$429 nightly
The price is $480
Sep 7 - Sep 8
Total with taxes and fees
Single house: 12guests,4bds/2baths,large backyard.
Interior

12. Charming Family Friendly, Pet Friendly Bungalow, Sleeps 6 - Jacksonville, FL

Charming Family Friendly, Pet Friendly Bungalow, Sleeps 6 - Jacksonville, FL
Northwest
10.0 out of 10, Exceptional, (46 reviews)
"Great place to stay"
United States
Summer I.
$144 nightly
The price is $161
Oct 5 - Oct 6
Total with taxes and fees
Charming Family Friendly, Pet Friendly Bungalow, Sleeps 6 - Jacksonville, FL
Signature Apartment | Living area

13. The Van Zant House

The Van Zant House
3.5 star property
Westside
6.4 out of 10, (7 reviews)
"Always a great time ! "
United States
Katherine
$253 nightly
The price is $275
Sep 7 - Sep 8
Total with taxes and fees
The Van Zant House
Outdoor dining

14. Magical Midsummer Night Glamping Loft w Bikes

Magical Midsummer Night Glamping Loft w Bikes
Northwest
10.0 out of 10, Exceptional, (9 reviews)
"It was Enchanting and the location perfect!"
United States
THC
$127 nightly
The price is $142
Sep 6 - Sep 7
Total with taxes and fees
Magical Midsummer Night Glamping Loft w Bikes
Room

15. Enchanted Forest: a Magical Luxury Studio

Enchanted Forest: a Magical Luxury Studio
Northwest
9.8 out of 10, Exceptional, (10 reviews)
"One of the best decorated and comfortable ihave stayed In in a great while. Tastefully decorated and old school Charm in a forest…."
United States
Richard
$142 nightly
The price is $159
Sep 6 - Sep 7
Total with taxes and fees
Enchanted Forest: a Magical Luxury Studio
Interior

16. Cozy Treetop Hideaway

Cozy Treetop Hideaway
Northwest
10.0 out of 10, Exceptional, (106 reviews)
"Good location, nice amenities"
United States
Sue
$138 nightly
The price is $154
Sep 8 - Sep 9
Total with taxes and fees
Cozy Treetop Hideaway
Living area

17. The Great Gatsby - Luxury Historic Riverside

The Great Gatsby - Luxury Historic Riverside
Northwest
9.8 out of 10, Exceptional, (10 reviews)
"So clean and a very cute property!!!!!"
United States
Julie
$142 nightly
The price is $159
Sep 6 - Sep 7
Total with taxes and fees
The Great Gatsby - Luxury Historic Riverside
Pool

18. Mi CASA es su CASA

Mi CASA es su CASA
St. Augustine
10.0 out of 10, Exceptional, (102 reviews)
"Great time and a very relaxing place to stay!"
United States
Debbie B.
$197 nightly
The price is $217
Sep 24 - Sep 25
Total with taxes and fees
Mi CASA es su CASA
Living area

19. Spacious Retreat: Projector & Pool Table

Spacious Retreat: Projector & Pool Table
Westside
9.8 out of 10, Exceptional, (7 reviews)
"We had a wonderful stay. No problems. Highly recommend. "
United Kingdom
Thomas K.
$304 nightly
The price is $340
Sep 7 - Sep 8
Total with taxes and fees
Spacious Retreat: Projector & Pool Table
Private kitchen

20. ⭐Stylish & Cozy⭐ 2BR/2BA w/King Bed, Pool & Gym Nr I295 & Downtown

⭐Stylish & Cozy⭐ 2BR/2BA w/King Bed, Pool & Gym Nr I295 & Downtown
Westside
9.4 out of 10, Exceptional, (28 reviews)
"The host was amazing and communicated through the entire stay"
United States
Ebony R.
$267 nightly
The price is $299
Sep 6 - Sep 7
Total with taxes and fees
⭐Stylish & Cozy⭐ 2BR/2BA w/King Bed, Pool & Gym Nr I295 & Downtown
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

Southbank Hotel by Marriott Jacksonville Riverwalk

Southbank Hotel by Marriott Jacksonville Riverwalk

10/10 Excellent
"We always stay here when in Jax. Clean, safe, super comfy and quiet rooms and very convenient to downtown. It has been beautifully redone too. And the bar is great. The price, exceptional value!"
Ginger 1-night trip
Posted less than an hour ago
Southbank Hotel by Marriott Jacksonville Riverwalk

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 $66 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.

Explore a world of travel with Expedia

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?

RelaxJax - a Private Paradise in a Pristine Neighborhood Fenced yard w/grill.: 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. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. 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 23 vacation rentals for your stay in Middleburg.

What’s there to see and do in Middleburg?

Doctors Lake and Jennings State Forest are a couple of lovely local spots to get outside and enjoy nature. 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.