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

Search Vacation Homes in Middleburg

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Middleburg vacation homes

A stable with horses, hay bales, and a wooden floor.

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 ￥13,536
￥28,191 total
includes taxes & fees
Oct 20 - Oct 21
Private Loft at a Working Show Barn ~ Pets Welcome!
A pool table with balls, a ceiling fan, a fireplace, and a seating area with a TV.

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
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful home, lots of space and plenty of places to hang out and lounge. Host communicated promptly and kindly. Highly recommend!"
United States
Brandon T.
The price is ￥24,364
￥60,299 total
includes taxes & fees
Oct 12 - Oct 13
NEW Waterfront Retreat "The Creek House" RENT JETSKIS POOL TABLE Sleep 10 KAYAKS
A house entrance with a red door, a welcome mat, and a doormat.

3. Luxurious Home w/ Spectacular Glass Room & Patios

Luxurious Home w/ Spectacular Glass Room & Patios
Lakeside
9.8 out of 10, Exceptional, (184 reviews)
"Nice property. The bunk bed mattresses were very uncomfortable and need replacing. The indoor patio was excellent for gathering. We enjoyed our stay"
United States
Cynthia J.
The price is ￥19,363
￥53,881 total
includes taxes & fees
Oct 14 - Oct 15
Luxurious Home w/ Spectacular Glass Room & Patios
A covered patio with a table and chairs, a window, and a door.

4. Rustic Owl w/ 2Kings In Fleming Island

Rustic Owl w/ 2Kings In Fleming Island
Fleming Island
10.0 out of 10, Exceptional, (41 reviews)
"Great location. Property was well stocked, clean and comfortable."
United States
Joe T.
The price is ￥31,979
￥67,876 total
includes taxes & fees
Oct 12 - Oct 13
Rustic Owl w/ 2Kings In Fleming Island
A conservatory with a glass roof, a potted plant, and a bench.

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

Single house: 12guests,4bds/2baths,large backyard.
Jacksonville
9.8 out of 10, Exceptional, (49 reviews)
"Great place for big families and small children. "
United States
Maria R.
The price is ￥28,496
￥76,036 total
includes taxes & fees
Oct 15 - Oct 16
Single house: 12guests,4bds/2baths,large backyard.
A modern living space with a dining area, sofa, kitchen, and a TV displaying a show.

6. Ocean view /HugePool/17/i295/NAS: Up to 12guest/4beds2baths

Ocean view /HugePool/17/i295/NAS: Up to 12guest/4beds2baths
Orange Park
9.4 out of 10, Exceptional, (3 reviews)
"It will be very difficult to convince mate other places to this beautiful rental. The pool was huge and clean the property had everything we needed. Would surely stay again!! The host was easily to access"
United States
BILLIE
The price is ￥52,638
￥115,459 total
includes taxes & fees
Oct 12 - Oct 13
Ocean view /HugePool/17/i295/NAS: Up to 12guest/4beds2baths
A gravel driveway leading to a wooden gate with a sign, surrounded by lush greenery and a clear sky.

7. Tiny Farm: Charming Tiny House in the Country

Tiny Farm: Charming Tiny House in the Country
Green Cove Springs
The price is ￥12,823
￥17,593 total
includes taxes & fees
Oct 19 - Oct 20
Tiny Farm: Charming Tiny House in the Country
A hotel room with a bed, a ceiling fan, a mirror, and a door leading to a bathroom.

8. The Trail & Tide House, Beaches, Trails, Hikes

The Trail & Tide House, Beaches, Trails, Hikes
Lakeside
The price is ￥22,440
￥50,675 total
includes taxes & fees
Oct 18 - Oct 19
The Trail & Tide House, Beaches, Trails, Hikes
A living room with a sofa, coffee table, TV, fireplace, and a dining area in the background.

9. 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 ￥28,496
￥76,195 total
includes taxes & fees
Oct 12 - Oct 13
Sunset near the lake up to 12 guests,4bds,2baths
A bedroom with a bed, a TV mounted on the wall, a bedside table, and a window with blinds.

10. Enjoyable 3-bedroom house with pool and AC in charming Jacksonville, Florida.

Enjoyable 3-bedroom house with pool and AC in charming Jacksonville, Florida.
Westside
6.0 out of 10, (2 reviews)
"My family and I loved the place very clean and comfortable and the host was excellent with getting back in touch with me when I reached out"
United States
Anonymous traveler
The price is ￥31,504
￥75,858 total
includes taxes & fees
Oct 12 - Oct 13
Enjoyable 3-bedroom house with pool and AC in charming Jacksonville, Florida.
A modern living room with a large flat-screen TV displaying a cityscape. There is a sofa, a coffee table, and a small side table.

11. Charming Retreat: Projector & Pool Table

Charming 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.
The price is ￥13,460
￥51,679 total
includes taxes & fees
Oct 12 - Oct 13
Charming Retreat: Projector & Pool Table
A modern kitchen with dark wood cabinets, a stainless steel refrigerator, and a built-in sink with a dish rack.

12. Ortega Duplex Unit w/ Theater, Kayaks & EV Charger

Ortega Duplex Unit w/ Theater, Kayaks & EV Charger
Westside
9.0 out of 10, Wonderful, (2 reviews)
"Property was very nice and clean. Tyler was a great help. Shower was the only kinda let down of our stay"
United States
Darrick S.
The price is ￥12,424
￥45,006 total
includes taxes & fees
Oct 12 - Oct 13
Ortega Duplex Unit w/ Theater, Kayaks & EV Charger
A bedroom with a bed, a ceiling fan, a nightstand, a lamp, and a view of the outdoors through a sliding glass door.

13. Spacious 3 BR Near NAS Jax l BBQ, WiFi, DirecTV

Spacious 3 BR Near NAS Jax l BBQ, WiFi, DirecTV
Westside
7.0 out of 10, Good, (2 reviews)
"The location was surprisingly amazing—we really enjoyed our time sitting out back. It was so quiet and peaceful, perfect for relaxing. I would definitely recommend this place to anyone looking for a calm and comfortable stay."
United States
Jennifer B.
The price is ￥16,456
￥43,926 total
includes taxes & fees
Oct 15 - Oct 16
Spacious 3 BR Near NAS Jax l BBQ, WiFi, DirecTV
A living room with floral-patterned sofas, a coffee table, a wooden console table with decorative items, and a framed picture on the wall.

14. Spacious 4-bedroom house in welcoming Jacksonville with AC, WiFi

Spacious 4-bedroom house in welcoming Jacksonville with AC, WiFi
Westside
10.0 out of 10, Exceptional, (3 reviews)
"Amazing stay, beautiful home!"
United States
Joel L.
The price is ￥25,013
￥62,308 total
includes taxes & fees
Nov 10 - Nov 11
Spacious 4-bedroom house in welcoming Jacksonville with AC, WiFi
A living room with a sectional sofa, a wooden coffee table, a bookshelf, and a painting on the wall.

15. Charming Animal-Themed Family Stay

Charming Animal-Themed Family Stay
Westside
10.0 out of 10, Exceptional, (2 reviews)
"This is a host who NEVER disappoints!! My family and I stayed at one of his other listings and it was amazing so I knew this was going to be the same experience! Located on the Westside of Jacksonville means you will be close to everything and more! The animal theme in the house was great, hot hot water for the shower and comfy bed! Not overly decorative but felt like home. I could go on forever but if you're looking for comfort, safety and relaxation this is your home! Thank you Geoff and Kat...
United States
Carla B.
The price is ￥16,781
￥43,774 total
includes taxes & fees
Oct 25 - Oct 26
Charming Animal-Themed Family Stay
A covered porch with red chairs and a table, brick pillars, and a view of the neighborhood.

16. Spacious Murray Hill Getaway for One or Two

Spacious Murray Hill Getaway for One or Two
Northwest
10.0 out of 10, Exceptional, (4 reviews)
"Loved the location to shops near by with plenty of options. Stay was cozy and the extra rags on top of the refrigerator was super helpful for cleanup. I would love to stay here again! My kid loved it too "
United States
dahlia t.
The price is ￥12,665
￥35,963 total
includes taxes & fees
Oct 12 - Oct 13
Spacious Murray Hill Getaway for One or Two
A modern kitchen with white cabinets, a stainless steel refrigerator, and a granite countertop.

17. Spacious 5BR Home • Sleeps 10 • Fenced Yard

Spacious 5BR Home • Sleeps 10 • Fenced Yard
Murray Hill
10.0 out of 10, Exceptional, (2 reviews)
"Loved everything about this place"
United States
Sha’niya A.
The price is ￥18,997
￥53,157 total
includes taxes & fees
Oct 13 - Oct 14
Spacious 5BR Home • Sleeps 10 • Fenced Yard
A modern living room with a sofa, coffee table, fireplace, and a large TV screen displaying a beach scene.

18. Mandarin Retreat - Entire Home

Mandarin Retreat - Entire Home
jacksonville
10.0 out of 10, Exceptional, (4 reviews)
"All around awesome place . Stayed for 4 nights. 10/10"
United States
Drew B.
The price is ￥25,567
￥54,093 total
includes taxes & fees
Oct 12 - Oct 13
Mandarin Retreat - Entire Home
A modern kitchen with white cabinets, a black and white tiled backsplash, stainless steel appliances, and a kitchen island with a sink and utensil holder.

19. Centrally located 3-Bedroom Large Lot Country Family home in sunny Jacksonville

Centrally located 3-Bedroom Large Lot Country Family home in sunny Jacksonville
Northwest
10.0 out of 10, Exceptional, (3 reviews)
"It was great I loved it!"
United States
Dblack P.
The price is ￥31,345
￥47,672 total
includes taxes & fees
Oct 14 - Oct 15
Centrally located 3-Bedroom Large Lot Country Family home in sunny Jacksonville
A narrow wooden pathway flanked by wooden fences, leading to a dark area beyond.

20. Stylish Bungalow Near Dining, Parks & Entertainment

Stylish Bungalow Near Dining, Parks & Entertainment
Avondale
10.0 out of 10, Exceptional, (17 reviews)
"great place and host! "
United States
Savannah F.
The price is ￥16,385
￥30,747 total
includes taxes & fees
Oct 12 - Oct 13
Stylish Bungalow Near Dining, Parks & Entertainment
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middleburg Hotel Reviews

Holiday Inn Express Jacksonville South Bartram Prk by IHG

Holiday Inn Express Jacksonville South Bartram Prk by IHG

8/10 Good
"Good"
Stephanie 3-night trip
Posted less than an hour ago
Holiday Inn Express Jacksonville South Bartram Prk by IHG

Find out more about Middleburg

Middleburg Vacation Homes information

Number of reviews
346
Accommodation
647 Vacation Homes
Lowest Price
￥17,593
Highest Price
￥115,459