Photo by Cindy Simmonds

Middleburg Holiday Rentals

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Holiday Rentals in Middleburg

3BR Home w/Private Pool |King En Suite w/Soaking Tub |Large Yard |Pet Friendly |Screened Patio |BBQ

10.0 out of 10, Exceptional, (17)
"Great home with pool. Smelled like moth balls the first 2 days…which made our bedding smell also. But Overall, we enjoyed the property and safe neighborhood to welcome the arrival of my new grandson . "
3BR Home w/Private Pool |King En Suite w/Soaking Tub |Large Yard |Pet Friendly |Screened Patio |BBQ

Bluegreen Vacations Grande Villas at World Golf Village

3.5 star property
8.6 out of 10, Excellent, (265)
"My family and I had a blast. It was beautiful. Did not need to travel far for some great food. Will definitely be back. Staff were so friendly, pool closed at 8:30p every night, that was the only disappointment, due to lighting or something. Overall great place! "
Bluegreen Vacations Grande Villas at World Golf Village

New Floating Luxury: Unique Houseboat Retreat

9.4 out of 10, Exceptional, (13)
"We have never been on a houseboat before and was really looking forward to our 3 night stay. The houseboat is really nice with all amenities. The lay out is a bit funky. Bedroom is upstairs with an outside entrance. Couch downstairs is second bed, didn’t sleep on it so don’t know how comfy that would be. We lost all water, through no fault of the owners and only got to stay one night. Owners graciously refunded 2 nights money. I would book again, very close to family. "
New Floating Luxury: Unique Houseboat Retreat

Mi CASA es su CASA

10.0 out of 10, Exceptional, (69)
"We went to visit our son, property was exactly as described. It was perfect for our needs. It was central to everything. Pool are was gorgeous. Check-in and check-out were easy. We would definitely go there again!!!"
The price is AU$334
includes taxes & fees
1 Dec - 2 Dec
Mi CASA es su CASA

Unique Design Bungalow in Jax Riverside Area.

10.0 out of 10, Exceptional, (22)
"The house was immaculate. The beds were comfortable and clean. Anything you could need was there for your use. Normally we eat out when in Jacksonville but the kitchen was so nice and well stocked with pots and dishes that we decided to cook. I can not say enough nice things."
The price is AU$442
includes taxes & fees
26 Nov - 27 Nov
Unique Design Bungalow in Jax Riverside Area.

Studio loft w/ pool, spa & gardens near downtown

9.2 out of 10, Wonderful, (28)
"The property was very nice, and the room was cozy. The only negative was not being able to utilize the hot tub when we wanted to, and the bed mattress needs to be replaced, it is very uncomfortable. "
Studio loft w/ pool, spa & gardens near downtown

Newly renovated condo close to St Augustine beaches and golf clubs

10.0 out of 10, Exceptional, (63)
""Our stay at World Gold Village was everything we hoped for. It was perfect for our family trip. The space was clean, comfortable, and had all the amenities we needed. The host “STEPHEN” was incredibly accommodating. I highly recommend this place to anyone looking for a place to stay as a family stay or a romantic retreat. This will definitely be my go-to place every time I visit St. Augustine. Thank you Stephen!"
Newly renovated condo close to St Augustine beaches and golf clubs

Coastal Retreat.

9.8 out of 10, Exceptional, (6)
"5/5 Stars We had an absolutely wonderful stay at Mariana's coastal retreat! We came to Jacksonville to see the Nicki Minaj concert. The space was perfectly suited for a nice getaway - spacious, comfortable, and beautifully appointed. Mariana was a fantastic host, promptly addressing a minor issue with the lock and ensuring our stay was seamless. The accommodations truly made our trip special. We can't wait to return and would highly recommend this lovely retreat to anyone looking for a relaxing...
Coastal Retreat.

Cheerful three bedroom home with a pool

10.0 out of 10, Exceptional, (22)
"Great place to stay!"
The price is AU$687
includes taxes & fees
3 Dec - 4 Dec
Cheerful three bedroom home with a pool

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

10.0 out of 10, Exceptional, (21)
"This home is beautiful, it has plenty of living space, two living room areas a large kitchen and plenty of space for dining! The beds are comfortable and there was plenty of room for our large party to stay. There are a ton of toys to keep the kids busy which was a plus! The kitchen is stocked with all cooking ware you need and the bathrooms are all stocked nicely. The host is great with communication and super nice! We enjoyed our stay here and will definitely stay again when we come back to...
The price is AU$581
includes taxes & fees
9 Dec - 10 Dec
Single house: 12guests,4bds/2baths,large backyard.

30 People Comfortably Gorgeous Home on Canal Boat Kayak access Two 85" & 75” TVs

9.6 out of 10, Exceptional, (16)
"Had 20 people do a golf trip. House worked out great for all of us. "
The price is AU$2,843
includes taxes & fees
26 Nov - 27 Nov
30 People Comfortably Gorgeous Home on Canal Boat Kayak access Two 85" & 75” TVs

Gorgeous circa 1875 Plantation House (in city)

9.8 out of 10, Exceptional, (63)
"This is such a beautiful home. Perfect place for family to gather and still have personal space for everyone. I highly recommend this property for anyone visiting Jacksonville. Lori was easy to work with. Excellent communication. "
Gorgeous circa 1875 Plantation House (in city)

Swim in Large Salt Water Pool, Ride Bikes, Relax On Deck, Enjoy Theater Room

9.6 out of 10, Exceptional, (134)
"Property is in a great location, not too far from anything. It was very accomodating. Pool waa nice even though we did not use it. It was Peaceful and relaxing. And the host was very helpful and at my assistance with the simplest thing."
Swim in Large Salt Water Pool, Ride Bikes, Relax On Deck, Enjoy Theater Room

Northeast Florida Retreat

8.8 out of 10, Excellent, (8)
"The house was musty smelling could use a dehumidifier. The shower drained slow and could use updating. Kitchen cabinet door would not close and the floor looks pretty rough. Would have been nice if the bedrooms had TV’s."
Northeast Florida Retreat

Cozy Treetop Hideaway

10.0 out of 10, Exceptional, (65)
"The property was beautiful the host THE BEST VRBO HOST EVER!! my husband and I enjoyed your weekend stay.. omg the bed is soooo comfortable. We will book again next year "
The price is AU$249
includes taxes & fees
1 Dec - 2 Dec
Cozy Treetop Hideaway

Large Pool🐬Billiards🎱Hammock & Grill 🔥Mural🦋Comfy Mattresses🔥Sleeps 10!

8.6 out of 10, Excellent, (11)
"We booked an extended weekend to visit my mom in her final days with terminal cancer. Just a couple days after booking, Hurricane Debby hit the east coast. We traveled in from Virginia, down the I-95 corridor, heading south on Thursday, the day Ole Debbie made the 2nd landfall in SC. Somehow we managed to avoid the worst of Debby and we were able to spend a few days with my mom. The little time we were able to spend at the house was great. We played a few games of billiards with the kids...
Large Pool🐬Billiards🎱Hammock & Grill 🔥Mural🦋Comfy Mattresses🔥Sleeps 10!

Downtown Jacksonville - La Casa De Blues

9.6 out of 10, Exceptional, (49)
"I recently stayed at this property in Jacksonville, and I couldn’t be more impressed! From the moment I walked in, I was greeted by a clean, well-kept space that felt like home. The location is perfect—close to all the main attractions yet peaceful and quiet enough for a relaxing getaway. The hosts were incredibly responsive and made sure we had everything we needed during our stay. The amenities provided exceeded expectations, and the comfortable beds made for a great night’s sleep after...
The price is AU$494
includes taxes & fees
9 Dec - 10 Dec
Downtown Jacksonville - La Casa De Blues

Seconds away from the fun in Historic Riverside!

10.0 out of 10, Exceptional, (102)
"The house, neighborhood, and host were all excellent. Highly recommend. "
Seconds away from the fun in Historic Riverside!

Modern 4 bedroom with Patio and Pool -- Sleeps 10

10.0 out of 10, Exceptional, (11)
"Just as advertised. Nice property in nice location. Absolutely no complaints or issues. Would recommend."
Modern 4 bedroom with Patio and Pool -- Sleeps 10

Downtown City View Loft

8.0 out of 10, Very good, (12)
"Couple of things wrong but overall good stay"
The price is AU$277
includes taxes & fees
26 Nov - 27 Nov
Downtown City View Loft
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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Other types of properties in Middleburg you may be interested in

Embassy Suites by Hilton Jacksonville Baymeadows

3.5 star property
8.4 out of 10, Very good, (1009)
"It’s always a pleasure to stay at any embassy suites by Hilton"
The price is AU$201
includes taxes & fees
22 Dec - 23 Dec
Embassy Suites by Hilton Jacksonville Baymeadows

Wyndham Garden Jacksonville

3.0 star property
7.2 out of 10, Good, (1505)
"The room was very nice. Only thing we didnt like is being directly next to the elevators."
The price is AU$131
includes taxes & fees
26 Nov - 27 Nov
Wyndham Garden Jacksonville

Hyatt Regency Jacksonville

4.0 star property
8.8 out of 10, Excellent, (1174)
"It seemed like it needs a refresh. I thought the hallways had a mild unpleasant smell that they tried to cover with scent. My bathroom had a chipped counter that had been repaired. When I called the front desk the first day to say I'm allergic to down pillows, I was first told to just feel the pillows for feathers and not use those! Didn't send any new pillows. That didn't work, and I woke up stuffed up. So I called again and they brought foam pillows and replaced the down comforter."
The price is AU$254
includes taxes & fees
27 Nov - 28 Nov
Hyatt Regency Jacksonville
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.
Beautiful view of the beach with palm trees

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Frequently asked questions

Are there holiday rentals in Middleburg?

Yes, there are holiday rentals close to the most popular sights in Middleburg, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Middleburg has to offer?

Bluegreen Vacations Grande Villas at World Golf Village: This holiday home rental outside of Middleburg is located on a lake, and has an outdoor pool, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers an outdoor tennis court, a garden and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Middleburg?

Expedia has 16 holiday rentals for your stay in Middleburg.

What’s there to see and do in Middleburg?

While exploring the area, visit family-friendly sights like Latitude 30, or get outside and enjoy nature at Clay County Fairgrounds. In the wider area, you’ll find Jacksonville Naval Air Station and Eagle Harbor Golf Club.

What’s a holiday rental in Middleburg like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middleburg. Holiday rentals feature amenities 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 cleanliness, holiday rentals can offer a sense of security away from public hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for a family trip or a small group gathering.