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

Middleburg Vacation Rentals

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Our top choices for Middleburg vacation rentals

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, (28 reviews)
"Tracy was a great host I enjoyed talking with her. The loft was great the beds are comfortable very clean and has everything you need for a short or long stay I will definitely be back and this would be my first choice to stay at."
United States
Tina S.
The price is CA $136
CA $259 total
includes taxes & fees
Dec 3 - Dec 4
Private Loft at a Working Show Barn ~ Pets Welcome!

2. 1BR King Suite | Pool & Gym

1BR King Suite | Pool & Gym
Middleburg
10.0 out of 10, Exceptional, (1 review)
"Spotless, thoughtful, and stocked with everything we needed.We stayed two nights and couldn't have asked for more. The place was impeccably clean from the moment we walked in, and everything was well organized, so it was easy to find what we needed without hunting around. The kitchen and bathrooms were fully supplied, and great amenities, with thoughtful touches that made it feel like a home rather than a rental. Communication was easy and check-in was smooth. We'd happily stay again and...
United States
Vanessa S.
The price is CA $91
CA $333 total
includes taxes & fees
Nov 15 - Nov 16
1BR King Suite | Pool & Gym

3. 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
9.6 out of 10, Exceptional, (5 reviews)
"Absolutely gorgeous property!! House is very spacious and cozy! Back porch is screened in so no bugs can bother you. Grocery store and shopping are 5 minutes away. A great weekend getaway!"
United States
Vicki
The price is CA $220
CA $525 total
includes taxes & fees
Nov 16 - Nov 17
NEW Waterfront Retreat "The Creek House" RENT JETSKIS POOL TABLE Sleep 10 KAYAKS

4. Luxury 2BR Suite | Pool & Gym

Luxury 2BR Suite | Pool & Gym
Middleburg
The price is CA $107
CA $355 total
includes taxes & fees
Nov 16 - Nov 17
Luxury 2BR Suite | Pool & Gym

5. 2BR Family Suite | Pool & Gym

2BR Family Suite | Pool & Gym
Middleburg
2BR Family Suite | Pool & Gym

6. Pasture Bedtime Yurt

Pasture Bedtime Yurt
Middleburg
The price is CA $353
CA $429 total
includes taxes & fees
Nov 16 - Nov 17
Pasture Bedtime Yurt

7. Moo-Tel Yurt

Moo-Tel Yurt
Middleburg
The price is CA $353
CA $429 total
includes taxes & fees
Nov 15 - Nov 16
Moo-Tel Yurt

8. StudioRes by Marriott Jacksonville Orange Park

StudioRes by Marriott Jacksonville Orange Park
3.0 star property
Westside
8.6 out of 10, Excellent, (76 reviews)
"Super clean, everything is new, I loved this place!"
United States
Diana
The price is CA $114
CA $130 total
includes taxes & fees
Nov 19 - Nov 20
StudioRes by Marriott Jacksonville Orange Park

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

Single house: 12guests,4bds/2baths,large backyard.
Jacksonville
10.0 out of 10, Exceptional, (51 reviews)
"Great place for big families and small children. "
United States
Maria R.
The price is CA $230
CA $663 total
includes taxes & fees
Nov 20 - Nov 21
Single house: 12guests,4bds/2baths,large backyard.

10. Rustic Owl w/ 2Kings In Fleming Island

Rustic Owl w/ 2Kings In Fleming Island
Fleming Island
9.8 out of 10, Exceptional, (43 reviews)
"Great location. Property was well stocked, clean and comfortable."
United States
Joe T.
The price is CA $288
CA $592 total
includes taxes & fees
Nov 15 - Nov 16
Rustic Owl w/ 2Kings In Fleming Island

11. Cozy 1-bedroom Tiny Home on Peaceful Blueberry Farm.

Cozy 1-bedroom Tiny Home on Peaceful Blueberry Farm.
Jacksonville
8.0 out of 10, Very good, (1 review)
"The only issue we had was that the water had a terrible smell, but that has nothing to do with the owner of the property. Other than the water, it was a nice little tiny house that was perfect for our one-night stay in Jacksonville. It was as the listing described and the owner was very friendly when we messaged! I enjoyed how secluded it was and it was a quiet spot to rest. Would highly recommend if you are okay with things being a little tighter than average!"
United States
Emily F.
The price is CA $103
CA $149 total
includes taxes & fees
Nov 16 - Nov 17
Cozy 1-bedroom Tiny Home on Peaceful Blueberry Farm.

12. Tiny Farm: Charming Tiny House in the Country

Tiny Farm: Charming Tiny House in the Country
Green Cove Springs
The price is CA $116
CA $147 total
includes taxes & fees
Nov 16 - Nov 17
Tiny Farm: Charming Tiny House in the Country

13. 1 Full Bed | Premium,Micfridge

1 Full Bed | Premium,Micfridge
Westside
10.0 out of 10, Exceptional, (6 reviews)
The price is CA $85
CA $96 total
includes taxes & fees
Nov 17 - Nov 18
1 Full Bed | Premium,Micfridge

14. 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, (34 reviews)
"We had a great stay! The home was clean, comfortable, and exactly as described. Check-in was easy, communication with the host was excellent, and everything we needed was provided. We’d definitely stay here again and would recommend it to anyone visiting the area."
United States
Alex C.
The price is CA $802
CA $2,177 total
includes taxes & fees
Nov 20 - Nov 21
30 People Comfortably Gorgeous Home on Canal Boat Kayak access Two 85" & 75” TVs

15. Cozy Private Entire Studio Suite Independent Guest Entrance

Cozy Private Entire Studio Suite Independent Guest Entrance
Westside
9.4 out of 10, Exceptional, (22 reviews)
"Nice and cozy!!Easy access, clean and comfortable!!Will book again "
United States
Shantrill G.
The price is CA $94
CA $188 total
includes taxes & fees
Nov 16 - Nov 17
Cozy Private Entire Studio Suite Independent Guest Entrance

16. Sunset near the lake up to 12 guests,4bds,2baths

Sunset near the lake up to 12 guests,4bds,2baths
Westside
10.0 out of 10, Exceptional, (13 reviews)
"great for families "
United States
Dylan A.
The price is CA $282
CA $691 total
includes taxes & fees
Nov 24 - Nov 25
Sunset near the lake up to 12 guests,4bds,2baths

17. ⭐HOME OF THE JAGUARS⭐private patio, w/POOL Near Downtown, NAS & Shopping

⭐HOME OF THE JAGUARS⭐private patio, w/POOL Near Downtown, NAS & Shopping
Westside
9.4 out of 10, Exceptional, (16 reviews)
"We came here for work. Place was clean and comfortable. Similar price to a hotel but way more space and comfort. We’ll definitely stay here again if we come back to this area."
United States
Tia J.
The price is CA $137
CA $367 total
includes taxes & fees
Nov 29 - Nov 30
⭐HOME OF THE JAGUARS⭐private patio, w/POOL Near Downtown, NAS & Shopping

18. Ortega | Projector & Pool Table

Ortega | 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.
Ortega | Projector & Pool Table

19. 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, (48 reviews)
"Great place to stay"
United States
Summer I.
The price is CA $148
CA $241 total
includes taxes & fees
Nov 15 - Nov 16
Charming Family Friendly, Pet Friendly Bungalow, Sleeps 6 - Jacksonville, FL

20. 1 King Bed | Suite, Nsmk, Kitchen, Sofa-Bed

1 King Bed | Suite, Nsmk, Kitchen, Sofa-Bed
Southside
10.0 out of 10, Exceptional, (25 reviews)
"Wonderful staff"
United States
Anonymous traveller
The price is CA $76
CA $86 total
includes taxes & fees
Dec 1 - Dec 2
1 King Bed | Suite, Nsmk, Kitchen, Sofa-Bed
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Middleburg. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Lakefront Home with Outdoor Pool Table, Firepit, and Grill in Jacksonville: 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 4 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a pool table.

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.