
Holiday houses in Middleburg
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Top-rated holiday rentals in Middleburg
Guests agree: these stays are highly rated for location, cleanliness and more.
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Popular amenities for Middleburg holiday rentals
Other great holiday rentals in Middleburg

Home in Orange Park
4.75 out of 5 average rating, 4 reviewsRococo Entire Home- 1 king bed 1 bath/ Game room
JameaRating, 5 stars3 weeks ago
Me and my partner enjoyed our stay at Mezhon’s home! The home was spacious, clean, and we felt right at home. Looking forward to booking again!
Guest favourite

Apartment in Orange Park
4.95 out of 5 average rating, 21 reviewsYour, “Feels like home”.
KamiRating, 5 stars3 weeks ago
Beautiful home! Looks just like the pictures. Felt safe, it was peaceful! We will definitely come back!
Top Guest favourite

Home in Keystone Heights
5 out of 5 average rating, 8 reviewsThe Sweet Tea Cottage~Lakefront-Beach-Fire pit
LeeRating, 5 stars2 days ago
Wow! We absolutely loved spending the weekend at 'The Sweet Tea Cottage!' It was impeccably clean and organized! The view of the lake was fantastic from every room of the house! It had so many extra special little amenities that came in handy! The beds were very comfortable, the house was so nice & cool, & we had everything we needed to cook and grill out! We took the canoe out in the lake a few times and made a nice fire after sunset. We highly recommend the 'Sweet Tea Cottage!' We will be back the next time we are in the area! Natalie & Mike responded quickly and were very kind and helpful! It's the perfect place to chill on the lake.

Guesthouse in Middleburg
4.81 out of 5 average rating, 27 reviewsDock House
ShawnRating, 5 stars2 weeks ago
My wife and I wanted a small get away with something on the water that was peaceful and we couldn’t of asked for a more simple and beautiful place. We will definitely be back again!

Condo in Oakleaf Plantation
5 out of 5 average rating, 4 reviews3 Bedrooms Condos at Cottages Oakleaf
MaureenRating, 5 stars1 week ago
Very clean large house in quiet area right by lovely park with walks along water features. Good response time to questions and requests. We only used front bedroom- mattress was very good. Furnished mostly with tasteful new furniture. Good location right below large shopping / restaurant area. Convienent to route 23 for getting around Greater Jacksonville area. Suited our needs very well!
Guest favourite

Home in Middleburg
4.89 out of 5 average rating, 27 reviewsRetro Vibe - Modern Tech w/FAST Wi-Fi Quiet & Safe
RobRating, 5 stars5 months ago
This is an older, but well maintained and still very nice second floor apartment. It was clean and comfortable and well-stocked. The gated community was quiet and staff were pleasant. Marc was a great host, very responsive. I'm not familiar with gated communities, so I didn't know what to expect, but it wasn't a hassle at all. No fees or forms or signatures or keys or logins, just tell them the apartment number, your name, and show your ID. Easy.
Guest favourite

Campervan/RV in Middleburg
5 out of 5 average rating, 5 reviewsValhalla Estate Farm
JamesRating, 5 stars1 week ago
Amazing hospitality, the small farm allowed my youngest boys to roam and interact with the animals. Yvette was a great host and showed my kids a great time with looking at ducks/chickens/goats. Kept them off the electronics and outside. We all had a great time here.
Top Guest favourite

Private room in Southwest Jacksonville
4.99 out of 5 average rating, 543 reviewsCardinal's Cove- private bedroom/bath
AndreaRating, 5 stars2 weeks ago
💫 Miss Vicky is an exceptional host—warm, sweet, and incredibly hospitable. As a fellow world traveler, she’s thoughtful and understanding. I’m so grateful for her kindness and help during checkout. Her beautiful home made the stay even more special. Highly recommend! 🌟 🌟 🌟 🌟 🌟 5 Stars!!!
Quick stats about holiday rentals in Middleburg
Total rentals
30 properties
Nightly prices starting at
$83 NZD before taxes and fees
Total number of reviews
1.1K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Ponte Vedra Beach
- Summer Haven st. Augustine FL
- TIAA Bank Field
- Old A1A Beach
- Boneyard Beach
- Paynes Prairie Preserve State Park
- Kathryn Abbey Hanna Park
- Amelia Island State Park
- Butler Beach
- Crescent Beach
- Fountain of Youth Archaeological Park
- Guana Reserve Middle Beach
- North Beach Guana River Preserve
- Lightner Museum
- St. Augustine Alligator Farm Zoological Park
- Matanzas Beach
- Bent Creek Golf Course
- Eagle Landing Golf Club
- Driftwood Beach
- St. Marys Aquatic Center
- Florida Museum of Natural History
- Depot Park
- Ravine Gardens State Park
- Vilano Beach