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

Holiday Homes in Middleburg

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Middleburg holiday 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 €163
includes taxes & fees
28 Oct - 29 Oct
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, (3 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 €330
includes taxes & fees
26 Oct - 27 Oct
NEW Waterfront Retreat "The Creek House" RENT JETSKIS POOL TABLE Sleep 10 KAYAKS
A fenced outdoor area with a gravel path, a grassy field, and a building in the background.

3. Tiny Farm: Charming Tiny House in the Country

Tiny Farm: Charming Tiny House in the Country
Green Cove Springs
The price is €103
includes taxes & fees
23 Oct - 24 Oct
Tiny Farm: Charming Tiny House in the Country
A house entrance with a red door, a welcome mat, and a doormat.

4. Luxurious Home w/ Spectacular Glass Room & Patios

Luxurious Home w/ Spectacular Glass Room & Patios
Lakeside
9.8 out of 10, Exceptional, (186 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 €300
includes taxes & fees
25 Oct - 26 Oct
Luxurious Home w/ Spectacular Glass Room & Patios
A playground with a slide and climbing structures, surrounded by grass and trees.

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

The Trail & Tide House, Beaches, Trails, Hikes
Lakeside
10.0 out of 10, Exceptional, (1 review)
"The home was clean and spacious. There is not a lot of furniture but we only needed the bedrooms. The beds were comfortable and the linens were clean and high quality. The home is in a nice neighborhood and felt very secure."
United States
Brian K.
The Trail & Tide House, Beaches, Trails, Hikes
A conservatory with a glass roof, a potted plant, and a bench.

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

Single house: 12guests,4bds/2baths,large backyard.
Jacksonville
9.8 out of 10, Exceptional, (50 reviews)
"Great place for big families and small children. "
United States
Maria R.
The price is €448
includes taxes & fees
1 Nov - 2 Nov
Single house: 12guests,4bds/2baths,large backyard.
A covered patio with a table and chairs, a window, and a door.

7. 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 €377
includes taxes & fees
15 Nov - 16 Nov
Rustic Owl w/ 2Kings In Fleming Island
A modern kitchen with white cabinets, a wooden island, and a bar stool.

8. Coral Reef Retreat 30 min to Beach High Speed Wi-Fi

Coral Reef Retreat 30 min to Beach High Speed Wi-Fi
Westside
The price is €310
includes taxes & fees
25 Oct - 26 Oct
Coral Reef Retreat 30 min to Beach High Speed Wi-Fi
A modern living space with a dining area, sofa, kitchen, and a TV displaying a show.

9. 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 €653
includes taxes & fees
25 Oct - 26 Oct
Ocean view /HugePool/17/i295/NAS: Up to 12guest/4beds2baths
A bedroom with a bed, a ceiling fan, a nightstand, a lamp, and a view of the outdoors through a sliding glass door.

10. 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 €252
includes taxes & fees
28 Oct - 29 Oct
Spacious 3 BR Near NAS Jax l BBQ, WiFi, DirecTV
A residential house with a brick facade, a front door, and a small garden area with potted plants.

11. 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 traveller
The price is €414
includes taxes & fees
26 Oct - 27 Oct
Enjoyable 3-bedroom house with pool and AC in charming Jacksonville, Florida.
A modern kitchen with dark wood cabinets, a stainless steel refrigerator, and a built-in sink with a dish rack.

12. Home Theater, Kayaks & EV Charger in Ortega

Home Theater, Kayaks & EV Charger in Ortega
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 €253
includes taxes & fees
25 Oct - 26 Oct
Home Theater, Kayaks & EV Charger in Ortega
A wooden porch leading to a house with a front door, a lamp, and a doormat.

13. Gorgeous circa 1875 Plantation House (in city)

Gorgeous circa 1875 Plantation House (in city)
Orange Park
9.8 out of 10, Exceptional, (97 reviews)
"Our families enjoyed this lovely home. Everything is clean, the beds are comfy, plenty of towels and a well equipped kitchen. The grounds are lovely and well kept. Although it was a little too warm to sit outside, there were several inviting areas on the wrap around shaded porch. The host is very congenial and responsive. We would stay here again."
United States
Cheryl A.
The price is €460
includes taxes & fees
9 Nov - 10 Nov
Gorgeous circa 1875 Plantation House (in city)
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.

14. 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.
The price is €285
includes taxes & fees
25 Oct - 26 Oct
Spacious Retreat: Projector & Pool Table
A living room with a sofa, coffee table, TV, fireplace, and a dining area in the background.

15. 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 €454
includes taxes & fees
23 Oct - 24 Oct
Sunset near the lake up to 12 guests,4bds,2baths
A grand staircase with white balusters and wooden steps leading to an upper level.

16. 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)
"A beautifully decorated, comfortable, and spacious property.The back porch was our favorite place to gather for visiting and viewing the canal activities. It has a claw footed tub in the Jack and Jill bathroom. A large game room is on the second floor. Also many extra beds are available. The kitchen is well appointed with every possible need close at hand."
United States
Carol G.
The price is €1,393
includes taxes & fees
26 Oct - 27 Oct
30 People Comfortably Gorgeous Home on Canal Boat Kayak access Two 85" & 75” TVs
A living room with a sofa, armchairs, a coffee table, a fireplace, and a television.

17. Park Street Paradise 2BR Cottage

Park Street Paradise 2BR Cottage
Westside
The price is €293
includes taxes & fees
26 Oct - 27 Oct
Park Street Paradise 2BR Cottage
A living room with a sectional sofa, a wooden coffee table, a bookshelf, and a painting on the wall.

18. 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.
Charming Animal-Themed Family Stay
A covered porch with red chairs and a table, brick pillars, and a view of the neighborhood.

19. 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 €206
includes taxes & fees
4 Nov - 5 Nov
Spacious Murray Hill Getaway for One or Two
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

Marriott Jacksonville Downtown

Marriott Jacksonville Downtown

10/10 Excellent
"Nice clean accommodations. Great location. F=Courteous and helpful staff."
John 1-night trip
Posted 9 hours ago
Marriott Jacksonville Downtown

Find out more about Middleburg

Middleburg Holiday Homes information

Number of reviews
475
Accommodation
642 Holiday Homes
Lowest Price
€103
Highest Price
€1,393