Holiday houses 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

Place to stay in Orange Park

4.92 out of 5 average rating, 102 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

Home in Green Cove Springs

4.97 out of 5 average rating, 102 reviews

Modern Green Cove Springs 7Beds Fence Beach 45min

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:).

Guest favourite

Farm stay in Middleburg

4.91 out of 5 average rating, 237 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, 216 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

Home in Orange Park

4.9 out of 5 average rating, 238 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.

Top Guest favourite

Home in Fleming Island

4.99 out of 5 average rating, 148 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.

Guest favourite

Home in Middleburg

4.95 out of 5 average rating, 56 reviews

Picturesque Middleburg Creek-view Vacation Home

Serene tranquil retreat with lovely panoramic water-front views, plus onsite water access from a 100 ft. long beach area. There is a boat dock, equipped with mooring connections - so you may bring your boat if you have one. A public boat ramp is located nearby. An elevated screened porch extends 2/3 of the way around the house and contains a fire-pit, lounge chairs, platform rockers, and an outside dining table for 6. Ideal for socializing, gazing at the water, or simply dreaming!

Top Guest favourite

Guesthouse in Southwest Jacksonville

4.96 out of 5 average rating, 160 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

Guest suite in Southwest Jacksonville

4.94 out of 5 average rating, 137 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

Tent in Middleburg

4.95 out of 5 average rating, 147 reviews

Tent 2-Relax,Retreat, Revive-boutique camping -A/C

- 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! Heater keeps you warm! - 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

Top Guest favourite

Home in Keystone Heights

4.9 out of 5 average rating, 165 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 50.00 flat fee. We also charge a late checkout fee. Fireplace is not in service.

Guest favourite

Cottage in Keystone Heights

4.88 out of 5 average rating, 156 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.