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
The two-story white house features a welcoming entrance with a central door flanked by large windows. Adjacent to the entrance, two armchairs are positioned around a small table on a circular patio, surrounded by lush green grass and decorative potted plants.
Home in Green Cove Springs
4.99 out of 5 average rating, 122 reviews

1920 Carriage House on Riverfront Estate

1920 Carriage House on lush private estate. Renovated and charming! Situated on secluded, majestic 6 acre riverfront property on the St. John’s River. Enjoy park like grounds filled with azaleas, ancient oak and hickory trees, dripping in Spanish moss. Sit back and watch and listen to hawks and bald eagles overhead! Wake up to a magical sunrise each day! See the manatees lazily grazing! Bass Pro Shop shot their Spring Catalogue here! Owners home is on the property and they are always available

Top guest favourite
The back patio features a cozy seating arrangement with a modern sofa and a small table. Twinkling string lights illuminate the area as evening approaches, providing a warm ambiance. A dining table for four is visible on the patterned outdoor rug, amidst a spacious fenced yard with trees.
Home in Fleming Island
4.96 out of 5 average rating, 188 reviews

The Flemingo- Game Room 3 Kings

Welcome to the Flemingo where can relax on the back patio with a glass of wine and twinkling string lights above. You'll watch the dogs and kids play in the large fenced yard while throwing a frisbee (provided). You'll love cooking a delicious meal in the spacious kitchen. You’ll have a blast in the garage game room! Battle it out on the air hockey table, foosball, darts or boxing bag. At night, the kids will hang out in the garage game room, in the living room playing board games or on

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, 120 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 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
4.95 out of 5 average rating, 124 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, 107 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, 261 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!

Guest favourite
Farm stay in Middleburg
4.97 out of 5 average rating, 230 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 spacious living area features a light-colored leather couch with yellow accent pillows. A dining table is in the background, and wooden cabinetry with dark countertops is visible in the adjoining kitchen. Soft lighting enhances the inviting atmosphere.
Home in Orange Park
4.93 out of 5 average rating, 107 reviews

Nature Cozy Home

Located in Orange Park FL , this rural, rustic, colorful getaway can be your home away from home! Guests can enjoy the forested and vintage scenery that reminds one of simpler times. The designated parking area is indicated by the, sign of three flowers at the left side of the driveway. Guests will also have their own seating area. Please note we have another Listings: Retreat Mobile Camper (back to house) and Guest Suite (attached to house)on the property! , with everything private Thanks

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, 160 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
4.95 out of 5 average rating, 194 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 wooden deck is illuminated by string lights, featuring a seating area with wicker furniture and a designated space for dancing. The tranquil river view and the sunset create a serene backdrop, with Spanish moss hanging from nearby oak trees.
Cabin in St. Augustine
4.87 out of 5 average rating, 181 reviews

ROMANTIC RIVERFRONT CABIN~ BRING BOAT ~ SLEEPS 2

Relax with your sweetheart while watching the fish jump from your own private deck. The cabin has been open for 3 years and has 92 reviews and has 4.89 STARS out of 5! "The View is absolutely beautiful, especially the sunsets! & You can see this amazing view right from the bed!" Alex April 2022/ We've replaced the microwave with an air fryer. Everything you need to have a wonderful vacation is right here! Including Breakfast foods!

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, 103 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

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

  • Do house rentals in Middleburg have free parking?

    Absolutely! We offer over 10 house rentals with free parking in Middleburg. Enjoy a tailored experience with all the comforts you desire.

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 £38 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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