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 favorite
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, 195 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 favorite
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
4.94 out of 5 average rating, 125 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 favorite
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.
Vacation home in Orange Park
4.9 out of 5 average rating, 116 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 favorite
A modern living area features a spacious gray sofa and a festive Christmas tree adorned with decorations. Stockings hang from the fireplace, while a large TV is mounted on the wall. Natural light floods the space through nearby windows, enhancing the welcoming atmosphere.
Home in Green Cove Springs
4.95 out of 5 average rating, 127 reviews

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:)

Superhost
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, 264 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 favorite
Farm stay in Middleburg
4.97 out of 5 average rating, 231 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 favorite
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, 116 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 favorite
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, 252 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 favorite
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, 162 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 favorite
Home in Middleburg
4.95 out of 5 average rating, 65 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 socialising, gazing at the water, or simply dreaming!

Top guest favorite
A spacious outdoor deck features comfortable seating arrangements with plush cushions and a dining table. Lush greenery surrounds the area, with views of Lake Asbury in the background. Strands of lights hang above, creating a relaxed atmosphere perfect for enjoying the scenery.
Home in Green Cove Springs
4.91 out of 5 average rating, 56 reviews

Lakeside, Water View, Kayak, BBQ Grill, Fire Pit

Save my home, click the <3 in the upper corner! NO cleaning fee! No surprise fees! >Lakeside Wonderland - Lake Asbury >Pet friendly with fee and restrictions >2 miles from Old Ferry Boat Ramp >Backyard + patio with stunning lake views >Minutes from St. Johns River >Sleeps 6 >Kayaks + SUP with waiver >Drip Coffee Maker + Nespresso >Wood burning fire pit >Propane BBQ >Washer + Dryer >Nearby restaurants and shopping >3 days of supplies (TP, trash bags, pods, etc.)

Top guest favorite
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, 111 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 vacation rentals

When is the best time to visit Middleburg?

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Avg. priceG$23,642 GYDG$23,642 GYDG$23,642 GYDG$25,315 GYDG$25,525 GYDG$25,525 GYDG$25,525 GYDG$25,525 GYDG$25,106 GYDG$22,596 GYDG$22,805 GYDG$23,642 GYD
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Frequently Asked Questions

  • What are the best places to stay in Middleburg?

    Middleburg has vacation homes in quiet neighborhoods, properties with large yards, and accommodations near parks or wooded areas. Some stays highlight easy access to local trails, waterways, and family friendly amenities.

  • What are the best things to do in Middleburg with kids?

    Kids can explore the trails and creeks of Jennings State Forest, join educational programs in local libraries, or enjoy playgrounds in community parks. Occasionally, family-oriented events provide games, crafts, and outdoor fun.

  • What are some of the best things to do in Middleburg?

    Hike or paddle at Jennings State Forest, explore local markets, or visit the Black Creek Ravines Conservation Area for birdwatching. Many visitors also join community events or enjoy locally owned eateries.

  • How is the weather in Middleburg?

    Middleburg has mild winters around 45–65°F (7–18°C) and warm, humid summers reaching 91°F (33°C), with frequent rainfall from June through September. Bring lightweight clothing, rain protection, and sun gear, especially for summer visits.

  • When is the best time to visit Middleburg?

    Spring and fall are often recommended for visiting Middleburg, with mild temperatures near 65–79°F (18–26°C) and lower humidity. Many enjoy outdoor festivals and markets during these seasons.

  • What are the best places to visit in Middleburg?

    Jennings State Forest is frequently suggested for outdoor activities, while Black Creek Ravines Conservation Area invites wildlife watching and scenic walks. Downtown Middleburg has locally owned shops and eateries with a laid-back atmosphere.

  • What are some hiking trails in Middleburg?

    Explore natural trails in Jennings State Forest, which has wooded paths, water features, and opportunities to spot local wildlife. Black Creek Ravines Conservation Area is also frequently suggested for walking among pines and along scenic creek banks.

  • What are some family activities we can do in Middleburg?

    Families can enjoy hiking or picnicking at Jennings State Forest, fishing or paddling along Black Creek, or playing in local parks. Community festivals and farmers' markets sometimes include family-friendly activities and live music.

  • What are some of the best day trip ideas from Middleburg?

    Many choose to explore Jacksonville’s museums, coastal parks, or St. Augustine’s historic streets, both located near Middleburg. River tours, wildlife preserves, and farmers' markets in the surrounding region are often recommended.

  • Are there any pet friendly accommodations available in Middleburg?

    Many vacation rentals in Middleburg welcome pets, often providing fenced yards or easy access to outdoor spaces. Check individual listings for specific pet policies and nearby walking areas.

  • What are some local tips for visiting Middleburg?

    Bring sturdy shoes and sun protection for exploring outdoor spaces, and check for updates on local park conditions if planning a hike. Weekends at farmers’ markets or during seasonal fairs give a taste of Middleburg’s community traditions.

  • What is Middleburg known for?

    Middleburg is known for its rural charm, access to Jennings State Forest, and a community spirit shaped by agriculture and outdoor traditions. The area has locally rooted events and a network of waterways for recreation.

  • What are the best hidden gems to explore in Middleburg?

    Black Creek Ravines Conservation Area is a quiet spot for hiking and birdwatching, while Jennings State Forest has lesser-known trails through pine woods. Small cafés and historic sites around downtown provide glimpses of local history.

  • What are the best foods to try in Middleburg?

    Middleburg has Southern-inspired dishes, including smoked barbecue, fried catfish, and homestyle vegetables. Locally owned diners and grills often feature pies and classic comfort foods.

  • What should I bring for a trip to Middleburg?

    Pack comfortable shoes for hiking, lightweight clothing, and rain gear, especially in summer months. Sun protection, bug spray, and a reusable water bottle help make the most of outdoor adventures.

  • What is the nightlife in Middleburg like?

    Middleburg has a casual nightlife scene, with local grills, bars, and occasionally live music at community gathering spots. Many opt for relaxed evenings around fire pits or enjoying laid-back entertainment venues nearby.

  • What are the most popular events or festivals in Middleburg?

    Middleburg hosts seasonal community gatherings, such as fall fairs and holiday parades, which are often recommended for families. Nearby Clay County frequently suggests festivals centered on local heritage, crafts, and music throughout the year.

  • Are there family friendly vacation rentals in Middleburg?

    Middleburg has various family friendly vacation rentals, including single-family homes with spacious yards or properties near parks. Hosts often highlight features like kitchens, multiple bedrooms, and welcoming outdoor spaces.

Quick stats about vacation rentals in Middleburg

  • Total vacation rentals

    Explore 20 vacation rentals in Middleburg

  • Nightly prices starting at

    Middleburg vacation rentals start at G$10,461 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,350 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Middleburg vacation rentals include wi-fi 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!

  1. Airbnb
  2. United States
  3. Florida
  4. Clay County
  5. Middleburg