Vacation rentals in Middleburg

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

Charming Guest House on Riverfront Estate

Pretty Guest House situated on majestic 5 acre riverfront estate on the St. John’s River with 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! Bass Pro Shop did a photo shoot here for their Spring 2025 catalogue! Owners home is on the property and they are always available. 45 minutes to JAX Beaches. 35 min to St. Augustine.

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.

Modern Green Cove Springs 6 Bed 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:).

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.

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!

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!

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.

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 .

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.

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 socialising, gazing at the water, or simply dreaming!

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.