House
9.8(12 Reviews)
2 Bedrooms
9 Guests
Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $115/Night
7 Nights - US $802
Middleburg Holiday Rentals
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Compare Villas, Resorts, & Rentals in Middleburg
9.8
House
10.0(1 Review)
1 Bedroom
7 Guests
Child Friendly
Barbecue/Outdoor Cooking
Sports/Activities
Security/Safety
US $206/Night
7 Nights - US $1,442
US $106/Night
7 Nights - US $741
House
9.6(29 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $277/Night
7 Nights - US $1,942
House
9.0(1 Review)
1 Bedroom
2 Guests
- Parking
- Air Conditioner
Internet
Pet Friendly
US $263/Night
7 Nights - US $1,841
House
9.6(27 Reviews)
1 Bedroom
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $178/Night
7 Nights - US $1,246
Apartment
9.6(14 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $210/Night
7 Nights - US $1,469
Apartment
9.6(9 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $175/Night
7 Nights - US $1,223
RV Rental
1 Bedroom
5 Guests
- Air Conditioner
- Internet
- Child Friendly
Bedding/Linens
US $347/Night
7 Nights - US $2,432
Luxury Holiday Rentals in Middleburg
Over 26+ Luxury Holiday Rentals in or Near Middleburg
House
9.8(41 Reviews)
4 Bedrooms
9 Guests
Hot Tub- Parking
Ocean View- Balcony/Terrace
US $393/Night
7 Nights - US $2,754
House
3 Bedrooms
8 Guests
- Air Conditioner
- Internet
- Child Friendly
Laundry
US $387/Night
7 Nights - US $2,706
US $385/Night
7 Nights - US $2,695
House
9.4(8 Reviews)
3 Bedrooms
8 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $382/Night
7 Nights - US $2,675
US $369/Night
7 Nights - US $2,583
House
9.8(31 Reviews)
3 Bedrooms
7 Guests
Private Pool- Parking
Pool- Ocean View
US $351/Night
7 Nights - US $2,454
US $344/Night
7 Nights - US $2,411
House
9.8(29 Reviews)
3 Bedrooms
8 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $343/Night
7 Nights - US $2,401
House
2 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
View
US $342/Night
7 Nights - US $2,397
Top-Rated Holiday Rentals with a Pool in Middleburg
Over 1+ The Best Private Villas and Holiday Rentals in Middleburg with a Pool
House
3 Bedrooms
6 Guests
- Private Pool
- Pool
- Kitchen
- Air Conditioner
US $145/Night
7 Nights - US $1,015
Pet-Friendly Holiday Rentals in Middleburg
Over 9+ Pet-Friendly Holiday Rentals in or Near Middleburg
House
9.8(16 Reviews)
3 Bedrooms
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $331/Night
7 Nights - US $2,317
US $329/Night
7 Nights - US $2,305
New
Apartment
The Escape at the Ravines |King Studio w/Daybed |Full Kitchen |Dogs Ok |Screened Porch |Wooded Views
9.4(13 Reviews)
1 Bedroom
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $193/Night
7 Nights - US $1,352
Apartment
1 Bedroom
2 Guests
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $192/Night
7 Nights - US $1,343
House
5.0(2 Reviews)
4 Bedrooms
8 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $469/Night
7 Nights - US $3,283
US $185/Night
7 Nights - US $1,297
Condo
5.0(1 Review)
1 Bedroom
3 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $109/Night
7 Nights - US $763
Apartment
1 Bedroom
2 Guests
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $200/Night
7 Nights - US $1,399
New
House
1 Bedroom
10 Guests
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $198/Night
7 Nights - US $1,386
Wheelchair Accessible Holiday Homes in Middleburg
Over 1+ Wheelchair Accessible Holiday Homes in or Near Middleburg
New
Hotel
8.5(2 Reviews)
EV Charge Station- Parking
- Air Conditioner
- Internet
US $113/Night
7 Nights - US $791
Middleburg Private Villas and Holiday Homes Under $200
Over 2+ Middleburg Private Villas and Holiday Homes Under $200
Cottage
9.6(11 Reviews)
1 Bedroom
2 Guests
- Air Conditioner
- Internet
- Child Friendly
- Barbecue/Outdoor Cooking
US $126/Night
7 Nights - US $885
Apartment
1 Bedroom
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $82/Night
7 Nights - US $574
Instantly Bookable Holiday Homes in Middleburg
Over 2+ Instantly Bookable Holiday Homes in or Near Middleburg
US $330/Night
7 Nights - US $2,307
House
10.0(13 Reviews)
3 Bedrooms
7 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $302/Night
7 Nights - US $2,112
Book a Last Minute Place to Stay in Middleburg
About Casai's Private Villas and Holiday Rentals in Middleburg
Discover more than 35 vacation rentals available in Middleburg. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Middleburg.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Middleburg, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Middleburg. On average, places to stay near Middleburg offer 903.44 ft², with nightly prices averaging US $258.
With Casai, finding and comparing holiday rentals in Middleburg is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
There are 35 Middleburg, FL Holiday Rentals
- Prices for a holiday home in Middleburg start at US $106
- Top rated vacation home in Middleburg is Fireside at the Creek
- Most popular short term in Middleburg is Creekfront 4BR Home | Hot Tub, Dock & Firepit | Sleeps 9 | No Pets
- Cheapest place to stay in Middleburg is Echo Suites Extended Stay by Wyndham Middleburg
- Most expensive holiday rental in Middleburg is Creekfront 4BR Home | Hot Tub, Dock & Firepit | Sleeps 9 | No Pets
Frequently Asked Questions About Middleburg?
What are the top holiday rentals in Middleburg?
With numerous options available in Middleburg, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Middleburg:
- Fireside at the Creek
- Creekfront 4BR Home | Hot Tub, Dock & Firepit | Sleeps 9 | No Pets
- 3BR Pool Home w/Yard + Dogs OK | Middleburg + Screened Porch
- Pool Home Retreat · Tesla EV Charger · Firepit · RV/Boat Access Near Ramp
- Waterfront 3BR Home | Private Boat Ramp & Firepit | 2 Small Dogs Welcome
- Clean 36’ 8” Travel Trailer on a small 5 acre farm. Bring the kids, room for 9!
- 1BR Rustic Treehouse on 30 Acres w/Black Creek Access, Firepit
- Private Loft at a Working Show Barn ~ Pets Welcome!
- Queen Studio | Full Kitchen, Screened Balcony | 1 Small Dog | Ravines
- King Studio | Full Kitchen, Screened Porch | 1 Small Dog | Ravines
Which holiday homes in Middleburg are best for families?
If you're searching for a family-friendly holiday home in Middleburg, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Middleburg:
How many Casai.com holiday rentals are available in Middleburg?
As of 2026, Casai boasts over 35 properties listed in the Middleburg area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Middleburg.
Nearby Neighborhood (1)
| Neighborhood | Property Count |
|---|---|
| OakLeaf Plantation Vacation Rentals in Jacksonville, Florida | 48 |
