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.

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Guest favourite
A welcoming living area features a well-furnished gray sofa and a decorative coffee table. A beautifully decorated Christmas tree stands in the corner, adding a seasonal touch. An open kitchen with modern appliances is visible in the background, complemented by an inviting dining space.
Home in Green Cove Springs
4.96 out of 5 average rating, 118 reviews

Modern Green Cove Springs 6 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:).

Top guest favourite
A two-story house is set back on a spacious driveway, surrounded by lush trees and vegetation. A manicured lawn features well-maintained plant beds near the entrance, while the garage is visible on the left side of the structure under a clear blue sky.
Holiday home in Orange Park
4.92 out of 5 average rating, 103 reviews

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.

Guest favourite
Two horses are seen within a barn, each housed in individual stalls crafted from wood. A wooden storage chest is positioned on the ground, with various items visible in the background, including containers and a gated outdoor area.
Farm stay in Middleburg
4.89 out of 5 average rating, 259 reviews

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!

Top guest favourite
Farm stay in Middleburg
4.96 out of 5 average rating, 228 reviews

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!

Top guest favourite
A wooden dock extends over calm waters, reflecting the soft colors of a sunset. Cypress trees line the shore, offering shade. Nearby structures and boats can be seen along the river, which is highlighted by the warm glow of the evening sky.
Home in Jacksonville
4.97 out of 5 average rating, 205 reviews

Unwind. Cozy Creekside Cottage near Ortega/NAS

Enjoy this charming creekfront cottage in the heart of Jacksonville. Unwind as the sun sets over the water, relax under shady cypress trees while wildlife travel about the tidal creek, enjoy cocktails on the dock, engage in boating or try your luck fishing. A boat ramp is nearby for boat launching. (Plenty of room to park Boat/Trailer on the nearly 1 acre lot ) While this unique retreat provides a tranquil getaway, it is also centrally located making it convenient for you to get around.

Guest favourite
A light-colored tent is situated on a wooden deck surrounded by lush greenery. Two wooden chairs with armrests are positioned on either side of the entrance. Potted plants are placed near the tent, enhancing the natural setting.
Tent in Middleburg
4.94 out of 5 average rating, 155 reviews

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 .

Guest favourite
A well-lit bedroom features a spacious bed with soft linens, complemented by stylish lighting and neutral wall tones. The bathroom showcases a walk-in shower with clear glass doors, coupled with modern fixtures. The kitchenette is equipped with essential appliances and a small dining table, enhancing functionality.
Guest house in Jacksonville
4.96 out of 5 average rating, 188 reviews

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.

Guest favourite
A spacious bedroom features a king-size bed with white bedding and decorative pillows. A bright yellow throw blanket adds a pop of color. Two modern artworks are displayed above the bed, while a large mirror reflects the room's design, enhancing the sense of space.
Guest suite in Jacksonville
4.94 out of 5 average rating, 159 reviews

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.

Guest favourite
A cozy guest suite features a queen bed dressed in a blue quilt and accented with a striped throw pillow. Soft lighting is provided by a bedside lamp, and a comfortable chair is positioned in the corner. The room includes a private bathroom entrance visible in the background.
Guest house in Lakeshore
4.87 out of 5 average rating, 191 reviews

Quiet Private Entrance Backyard Guest Suite

Our small, clean, cozy, guest suite (about 220 sq ft) is located in our fenced backyard. It is detached from our house with a private entrance, in a quiet and safe residential neighborhood. It isn't fancy, but it's a good space for spending a few days while visiting Jax. We offer keyless check-in and free parking is in our driveway. A queen Sealy Posturepedic bed provides ultimate comfort. The suite has a mini-fridge and microwave for simple meals (no full kitchen).

Superhost
A fluffy Highland cow stands in the foreground, gazing curiously. In the background, a teal cowboy pool is surrounded by colorful floats and retro umbrellas, while cozy seating areas invite relaxation amidst the vibrant outdoor setting.
Yurt in Middleburg
4.87 out of 5 average rating, 53 reviews

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 favourite
A spacious sleeping area features a large bed adorned with a colorful coral-patterned quilt. Natural light floods the room through a window, highlighted by vibrant curtains. A small dining area with high chairs is visible, along with decorative accents like fresh flowers.
Guest suite in Orange Park
4.88 out of 5 average rating, 144 reviews

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.

Top guest favourite
A serene view of the North Prong of Black Creek is depicted, showcasing calm water reflecting lush greenery. Trees frame the scene, creating a peaceful atmosphere. Wooden docks are visible in the background, inviting moments of exploration and relaxation.
Guest suite in Middleburg
4.99 out of 5 average rating, 96 reviews

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.

Popular amenities for Middleburg holiday rentals

When is the best time to visit Middleburg?

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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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