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

Home

5 out of 5 average rating, 121 reviews

Rustic Owl in Fleming Island with 2 Kings

From our family to yours. Located in the heart of Fleming Island, Rustic Owl was designed and appointed with extended family in mind. We wanted a space for families to visit, relax and enjoy each other.... while being comfortable. This gem offers comfy beds, smart TVs, an open floor plan, laundry facilities, upgrades throughout and with inviting outdoor spaces that overlook a rustic nature preserve. Super clean, Super Fast Wifi and well appointed amenities. Level 2 EV Charger installed.

Guest favourite

Tipi

4.95 out of 5 average rating, 135 reviews

2-Relax- Retreat-Revive-boutique camping -A/C-Pool

- If having difficulty booking your preferred date or you have a group, message us for more info on 2 additional tents located on property . -Experience nature with all the comforts of home-A/C keeps you cool! see below for special bundle options - Casper King size bed, deck,fire pit, coffee maker, kayaks - 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

Guest favourite

Farm stay

4.9 out of 5 average rating, 209 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

4.97 out of 5 average rating, 197 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!

Guest favourite

Guest house

4.95 out of 5 average rating, 107 reviews

Private, Modern And Cozy Guesthouse

Kick back and relax in this calm, stylish space. Enjoy the privacy of this newly renovated unit complete with 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 security and safety. Conveniently situated 1 mile off Highway 295.

Guest favourite

Home

4.87 out of 5 average rating, 164 reviews

Cheerful three bedroom home with a pool

Relax with the whole family at this peaceful place to stay. Enjoy the pool or just lay out in the pool area with friends. Have a bbq and enjoy family. Spacious backyard with two hammocks and a tree swing. Front porch has a nice sitting area and tree swing. Connect to your favorite streaming platforms on the smart TV's, tv room has karaoke and free WiFi. Board games in hall closet to enjoy with family. 3 miles from Orange Park Mall, AMC movie theatre and many restaurants just minutes away

Guest favourite

Home

4.89 out of 5 average rating, 134 reviews

Lake house - Kayaks and Fishing Poles

Awesome sunsets - Silver Sands is one of the few area lakes that is full and natural spring fed. Water is crystal clear and soft yes soft. 2 private decks, laundry room, and 2 carports. Two kayaks, Lake front swimming and fishing - come relax. 5 minute drive to groceries and gas. New fast WiFi , interior paint and metal roof. Pets are welcome but don’t we do charge a fee. We also charge a late checkout fee. Fireplace is not in service. RV pad with electric and water at 100 night option .

Guest favourite

Home

5 out of 5 average rating, 115 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 colorful azaleas, ancient oak and hickory trees, dripping in Spanish moss. Sit back and watch and listen to incredible hawks and bald eagles overhead! Wake up to a magical sunrise each day! See the manatees lazily grazing! Owners home is on the property and they are always available.

Guest favourite

Guest house

4.98 out of 5 average rating, 106 reviews

Charming, Pet Friendly Retreat in Heart of NE FL

Welcome to Pop's Garage! Nestled in Jacksonville's vibrant Mandarin area, this beautifully renovated property blends modern comforts and rustic charm. As the perfect Northeast Florida retreat, Pop's Garage offers a cozy and convenient stay. The pet-friendly space includes a private and secure fenced-in area, allowing your canine to stretch out and explore. Discover the perfect balance of comfort and convenience at this one-of-a-kind vacation rental.

Guest favourite

Cottage

4.91 out of 5 average rating, 119 reviews

Charming lake front cottage

Keep it simple at this peaceful and centrally-located cottage on Little Lake Geneva. Clean and freshly updated interior with canoe and fishing gear for your outdoor enjoyment. This charmer is located near popular springs for diving as well as hiking and biking trails. Jacksonville and Gainesville are within easy driving distance. Come to “get away from it all” and enjoy the peaceful, quiet atmosphere that helps to unwind and recharge.

Guest favourite

Farm stay

4.99 out of 5 average rating, 123 reviews

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 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.