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

Modern Green Cove Springs 7 Bed Fence Beach 45 min
New Stylishly renovated home in Green Cove Springs just South of Fleming Island, Orange Park, Middleburg, West of Jacksonville Florida. Christmas 365! Farmhouse style with a touch of Christmas theme. 7 beds, Fenced yard, 65" LED TV, fast internet, front/back porches available up to 10 people. Beaches approx. 45 minutes. Camp Blanding 25min Close to restaurants, grocery stores, banks, gas stations, main hospital 8+miles). There are lakes and rivers locally to fish/boat, parks, and shopping:).

Casandra House - Peaceful / Salt Pool and Hot Tub
Welcome to Casandra House. A peaceful getaway in Orange Park, FL. Located in the vicinity of Doctor's Lake, this house sits on 3/4 of an acre surrounded with trees and vegetation. It provides just enough privacy to make you feel away from everything while minutes from shops and restaurants. Home includes a large backyard, patio screen enclosure, salt pool and hot tub. About 2 1/2 miles from the Orange Park Thrasher-Horne Center and 10 miles from NAS Jacksonville. Note: No direct lake access.

A Private Loft at Grand Landings Equestrian Center
Welcome to "The Loft" at Grand Landings LLC! Enjoy a taste of the country in our over-the-barn apartment, conveniently located on the outskirt of Jacksonville, Florida. Our recently renovated loft offers all the luxuries of home and comfortably sleeps 4 (with the option of a crib upon request). Enjoy a one-of-a-kind experience and go on a ride on our friendly horses, or venture out and enjoy easy access to nearby natural springs, beaches and restaurants. There's something here for everyone!

Haystays Farm-Cozy, Charming, Country, Modern Home
Welcome to our special farm house! The home sits on 1.5 acres that is perfectly located on the Orange Park and Fleming Island line. Our location is ideal to everyone! We have plenty of space that makes our farmhouse so AMAZING! You will experience the feel of country living with all the perks of great restaurants, shopping and convenience of being near everything Jacksonville has to offer. Our home is super clean with many amenities to make you feel at home. We love it here and so will you!

Tent 2-Relax,Retreat, Revive-boutique camping -A/C
-Experience nature with all the comforts of home-A/C keeps you cool! Heater keeps you warm! - Casper King size bed, deck,fire pit, coffee maker, -Private bathhouse - Located on Black Creek - Large above ground pool with deck - Grill - Less than 15 min from grocery stores/local restaurants - 40 min from downtown Jax - 50 min to St. Augustine If having difficulty booking your preferred date or you have a group, message us for more info on 1 additional tent and cabin on property .

Private, Modern And Cozy Guesthouse
Kick back and relax in this calm, stylish space. Enjoy the privacy of this recently renovated unit which includes a queen-sized bed, and a small living room with a sleeper sofa, so the place can comfortably accommodate up to three. Also included, a 50-inch smart TV, kitchenette, bathroom/shower, closet, and keypad lock for easy access in and out. Please note that we have an exterior security camera on the front to enhance your safety. Conveniently situated 1 mile off Highway 295.

Cozy Private Guest Room - Entire Studio Suite
This gorgeous and elegant Suite style room with a great Westside location. Very private, warm and Comfortable large Bedroom where you can have some privacy to work or just relax after a long day. Most of our guests are coming from all over the country for special events, or simply for a getaway as a couple. Brand new furniture’s, smart TV, WIFI, and Netflix. Electronic lock door and security measures, safety and friendly neighborhood You'll love this unique and romantic escape.

The Lazy Cow Yurt w/ Fluffy Cows, Sheep & Llamas!
Get ready for a cuteness overload at The Lazy Cow Yurt! Imagine an adorable, fluffy Highland cow, playful sheep, friendly ducks, and charming chickens all free-roaming around your uniquely designed yurt. You can also receive visits from adorable llamas! And the best part? You can cool off and float in your very own teal cowboy pool right from your deck, waving hello to your cute, fluffy cow friends! It's the perfect blend of relaxation and farm animal fun.

Guest Suite
Enjoy your stay at this vivid private space! This suite is a colorful paradise that is surrounded by nature on a 2 acre property. Guests will be surrounded by color and outdoorsy scenery. The designated parking area is to right at a colored bee post. As you walk up the steps that lead you to the patio, you will see the door that will lead you to your lively suite. Our Suite is attached to the main house, with everything private.

Secluded, Cozy Guest Suite on Black Creek
Come down the driveway and escape the world. Situated on the North Prong of Black Creek, this cute studio suite offers rural with benefits. There's something for all outdoor lovers- birdwatching, kayaking, fishing, paddle boarding, wildlife, and more. If you want to just listen to the birds and cicadas, that's ok, too. The apt has a microwave, Keurig, toaster, and small fridge. Wifi is fast for remote working.

Cute Cottage on 85-Acre Farm
Reconnect with nature and your loved ones when you spend a few days on our 85 acre hobby farm in a newly renovated 2 bedroom cottage! The kids will love our free range chickens, mini cows and horses and you are welcome to explore the pastures and surrounding woods, or bring your fishing poles to try for some catfish from our small pond.

Hip + Modern Florida Hideaway
Located in historic Murray Hill, our Florida hideaway is a fully renovated hip and stylish private guesthouse brimming with natural light and great vibes! Each room is keenly decorated with high-end modern furniture along with curated vintage art and decor. This space is packed with character and provides all the comforts of home.
Popular amenities for Middleburg holiday rentals
Other great holiday rentals in Middleburg

Creek House hideaway NEW HOT TUB !

The Canopy Cabin in Florahome, Florida

XL family home, Pool, Pool table, Private 1 acre.

K-Pop Apartment & Great Confort - Fast WiFi

Retro Vibe - Modern Tech w/FAST Wi-Fi Quiet & Safe

The Cheswick Escape I Team Joseph Ellen

Cardinal's Cove- private bedroom/bath

Updated Master Bedroom & Bath w/ Private Entrance
When is the best time to visit Middleburg?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £88 | £91 | £93 | £90 | £91 | £91 | £91 | £91 | £89 | £86 | £90 | £91 |
| Avg. temp | 13°C | 15°C | 17°C | 20°C | 24°C | 27°C | 28°C | 28°C | 26°C | 22°C | 17°C | 14°C |
Frequently Asked Questions
Do house rentals in Middleburg have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Middleburg. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Middleburg?
Middleburg has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Middleburg?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with free parking, over 10 homes with wifi, over 10 homes with a kitchen, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there pet-friendly vacation rentals in Middleburg?
Four-legged friends are welcome in Middleburg. Choose from more than 10 vacation rentals for guests traveling with pets.
Do house rentals in Middleburg have wifi?
Absolutely! We offer over 10 house rentals with wifi in Middleburg. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Middleburg?
Experience the best of Middleburg with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Middleburg have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Middleburg. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Middleburg?
Yes! Work meets play with ease at over 20 vacation rentals in Middleburg featuring dedicated workspaces. Stay connected and productive in your home away from home.
Quick stats about holiday rentals in Middleburg

Total holiday rentals
Explore 30 holiday rentals in Middleburg

Nightly prices starting at
Middleburg holiday rentals start at £37 per night before taxes and fees

Verified guest reviews
Over 1,270 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
20 of Middleburg holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Middleburg rentals

4.9 Average rating
Middleburg stays are highly rated by guests – averaging 4.9 out of 5!
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- EverBank Stadium
- Anastasia State Park
- University of Florida
- Summer Haven st. Augustine FL
- Whetstone Chocolates
- Paynes Prairie Preserve State Park
- Lightner Museum
- Fountain of Youth Archaeological Park
- Kathryn Abbey Hanna Park
- Depot Park
- Ravine Gardens State Park
- Adventure Landing Jacksonville Beach
- St. Augustine Alligator Farm Zoological Park
- St Augustine Amphitheatre
- Little Talbot
- Florida Museum of Natural History
- Fort Clinch State Park
- Autobahn Indoor Speedway & Events - Jacksonville, FL
- Memorial Park
- Saint Augustine Town Plan Historic District
- TPC Sawgrass
- Friendship Fountain
- San Sebastian Winery
- Museum of Science and History




