Holiday rentals in Fleming Island

5 out of 5 average rating, 70 reviews

Fleming Island 4/3 by River wifi&MILS! Beach45min

Newly renovated home in Fleming Island with Mother-In-Law Suite close to Orange Park, Middleburg, Green Cove and Jacksonville Florida. Farmhouse style with a touch of Christmas theme 365! 9 beds, (5)50+" LED 4K TV's in all rooms, fast internet, front/back porches available, A/C in Florida room. Home is next to St. Johns River on 1 acre, walk river street or enjoy the HUGE backyard. Beaches aprx 45 mins Close to restaurants, Publix, Walmart, Hospitals, Public boat ramp etc. All within 1-5 miles

Superhost

Home in Orange Park

4.91 out of 5 average rating, 161 reviews

Super Clean (Fantastic Pool) Home Near Everything

Your Home Away From Home Featuring A Fabulous Pool! You will say "Wow" as you walk in to your very private, very exclusive spacious 4 bedroom, 2 bathroom. Set in a quiet neighborhood thats still near everything. Grocery store, Orange Park Mall, 30 minutes from Downtown Jax, 30 miles from the beach. Sit back and enjoy one of 4 Tvs as you relax in the soothing ambiance. Want to cook? Perfect we have everything you need, and we have it twice! Fully equipped kitchen. Very Clean! BetterThan A Hotel.

4.93 out of 5 average rating, 42 reviews

Sunset River Retreat

Escape to this stunning 3-bedroom, family-friendly oasis nestled along Doctors Lake riverfront. With a sparkling pool and breathtaking sunset views every evening, this is the ultimate haven for relaxation and fun. Home has a pool, firepit, outdoor pool table, and direct access to the river, ideal for fishing or kayaking. 30 min to downtown Jacksonville, 10 min from NAS Jax Naval Base. 10 minutes to boat ramp. 2 story house, bedrooms on 2nd floor Inquire for Events ($500 Event Fee, Max 75 ppl).

4.95 out of 5 average rating, 162 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

4.97 out of 5 average rating, 214 reviews

Farm stay in Middleburg

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!

4.9 out of 5 average rating, 233 reviews

Home in Orange Park

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.

5 out of 5 average rating, 143 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.

Home in Green Cove Springs

5 out of 5 average rating, 118 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.

Home in Green Cove Springs

4.87 out of 5 average rating, 30 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.)

4.98 out of 5 average rating, 250 reviews

Guest house in Riverside

Enchanted Forest: a Magical Luxury Studio

Lost to time, at the end of a long forgotten forest path, where dappled sunlight outline trees, moss, and stone. Enjoy the luxurious richness of satin, velvet, chandeliers and candles. Looking to escape, we’d love to share the path to this hidden destination in Historical Riverside. Equipped for work travel, date night, solo escapes, or longer vacations, this enchanted forest destination is right for you.