
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.

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

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

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.

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:)

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!

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

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 .

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!

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.)

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.

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, mini cows 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.
Popular amenities for Middleburg vacation rentals
Other great vacation rentals in Middleburg

Gator getaway! Lake house 20 min from UF

Luxury Pool - 5 bed House.

Waterfront Retreat-Dock, Fishing & More!

Updated Master Bedroom & Bath w/ Private Entrance

The Tiny Great Escape

Peaceful Lake View. The Butterfly Retreat

Cozy Jacksonville Retreat, family comfort.

Oakleaf 2BR Condo – Pool, Wi‑Fi, Walkable Shops
When is the best time to visit Middleburg?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $162 CAD | $168 CAD | $172 CAD | $166 CAD | $168 CAD | $168 CAD | $168 CAD | $168 CAD | $165 CAD | $149 CAD | $150 CAD | $155 CAD |
| Avg. temp | 13 °C | 15 °C | 17 °C | 20 °C | 24 °C | 27 °C | 28 °C | 28 °C | 26 °C | 22 °C | 17 °C | 14 °C |
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 vacation rentals in Middleburg

Total vacation rentals
Explore 30 vacation rentals in Middleburg

Nightly prices starting at
Middleburg vacation rentals start at $69 CAD per night before taxes and fees

Verified guest reviews
Over 1,270 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
20 of Middleburg vacation 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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