Vacation rentals in Middleburg

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Top-rated vacation rentals in Middleburg

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favourite
An outdoor patio area features a wooden table and chairs, providing a relaxing space to enjoy views of the water. A flag flies in the distance, while a covered structure offers shade. Lush green grass surrounds the area, enhancing the natural setting.
Place to stay in Orange Park
4.93 out of 5 average rating, 112 reviews

Beautiful 3 bedroom 2 bathroom waterfront home

Welcome to Cedar house, located on Drs. lake in orange park Fl. Conveniently located to 295 and just 15 mins from N.A.S. Jax ,30 mins from down town Jax, and 30 mins from the shopping at St johns town center, our home has been recently remodeled in 2022 and is a cosy and relaxing escape. With brand new kitchen, bathrooms, and open floor plan and the new dock/ boat house its perfect for getting the boat on the water or relaxing with friends/family and enjoying the fishing under the Florida sun.

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, kayaks -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
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, 254 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
4.97 out of 5 average rating, 223 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
The kitchen features modern white cabinetry, sleek countertops, and stainless steel appliances. A dining area with vibrant red chairs is visible in the background. Black and white checkered mats line the floor, creating a functional and stylish space.
Home in Middleburg
4.95 out of 5 average rating, 117 reviews

Modern E. Orange Park Home 6 bed Fence Beach 45 Mn

New Stylishly renovated home just West of Fleming Island in Middleburg, South of Orange Park, West of Jacksonville Florida. Christmas 365! Farmhouse style, TV’s in all bedrooms, with a touch of Christmas theme. 6 beds, Fenced yard, 75" LED TV, front/back porches available up to 10 people. Beaches approx. 40 minutes The home is close to restaurants, grocery stores, banks, gas stations, main hospital(2+miles). There are lakes and rivers locally to fish/boat, parks, shopping, and trails:).

Guest favourite
The entryway is highlighted by double doors that open to a welcoming view of the front yard. Natural light floods the space through a large transom window above the doors, framing a picturesque scene of manicured grass and distant trees.
Home in Orange Park
4.9 out of 5 average rating, 243 reviews

Luxury Home w/ Glass Room & Patios

Spectacular Inside and Out This magnificent 2940 sq foot home is in a prestigious lakeside neighborhood. It offers a large open concept living area with an adjoining 400 sq foot climate controlled sun room with a pocketing glass interior wall; to bring the outside in and the inside out. The exterior of the sun room is constructed of glass doors which can also be opened and stacked to facilitate an open air porch. Owner lives in the neighborhood and is quick to respond to your needs.

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.
Guesthouse in Jacksonville
4.95 out of 5 average rating, 177 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, 153 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.

Top guest favourite
The rustic boathouse is positioned near a scenic wooden dock extending into the river. Sunlight reflects off the water while a peaceful horse stands nearby, surrounded by lush greenery. The weathered exterior of the boathouse complements the natural setting.
Guesthouse in East Palatka
4.93 out of 5 average rating, 103 reviews

Charming Rustic Boathouse

Come stay at our rustic boathouse along the serene river. Its weathered, wooden, exterior exudes charm, adorned with unique decor. The sunlight reflects the water, casting shimmering light against the boathouse. Surrounding it, is lush greenery and trees that create a picturesque backdrop. Inside, the boathouse is cozy and inviting, with simple furnishings and the gentle scent of wood. It's a haven where one can escape the bustle of everyday life and embrace the countryside.

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, 94 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.

Top guest favourite
Home in Interlachen
5 out of 5 average rating, 152 reviews

Lakefront Escape | Hot Tub + Kayaks & Paddleboards

Get ready for adventure and relaxation at this lakeside retreat! Paddleboard, kayak, or boat across a 400-acre lake, then unwind in the hot tub at sunset. Roast s’mores around the fire pit under the stars. Inside, enjoy lake views, modern comforts, and cozy spaces for everyone. Refresh in the spa-style shower and dive into another day of fun, sun, and unforgettable memories!

Top guest favourite
An open barn interior is illuminated by warm lighting, featuring a comfortable leather sofa paired with a modern armchair. A rustic coffee table sits in front, while a vintage truck and motorcycle add character to the space. Wood paneling enhances the cozy atmosphere.
Barn in Jacksonville
4.98 out of 5 average rating, 126 reviews

Studio styled barn on a Florida pecan farm.

Hosts live on-site, in the main house beside the barn. Located on a small pecan orchard, our barn was built to be a place of rest and creativity for our family and friends. One of our favorite things about where we live is being able to enjoy the open space of the country while being close to the vibrant city of Jacksonville and the beautiful beaches.

Popular amenities for Middleburg vacation 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 air conditioning, over 10 homes with a kitchen, over 10 homes with wifi, over 10 homes with free parking, 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 vacation rentals in Middleburg

  • Total vacation rentals

    Explore 30 vacation rentals in Middleburg

  • Nightly prices starting at

    Middleburg vacation rentals start at $69 CAD per night before taxes and fees

  • Verified guest reviews

    Over 1,200 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 of Middleburg vacation 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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