Holiday rentals in Fleming Island

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Top-rated holiday rentals in Fleming Island

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A modern kitchen features white cabinetry and a sleek countertop, complete with essential appliances. Large windows allow natural light to fill the space, while a festive tree is visible through an adjacent dining area. A mixer and coffee maker are neatly arranged on the countertop.
Home in Fleming Island
5 out of 5 average rating, 86 reviews

Fleming Island 4/3 fence by river MILS Beach45min

Newly renovated home in Fleming Island with fully fenced yard, 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, walk river street or enjoy backyard. Beaches aprx 45 mins Close to restaurants, Publix, Walmart, Hospitals, Public boat ramp etc. All within 1-5 miles

Top guest favourite
A minimalist studio interior is displayed, featuring a warm wooden beam and a glass dividing wall. A comfortable orange couch is positioned near a window with natural light filtering through. Earthy tones create a calming atmosphere, complemented by a jute rug and layered textiles.
Flat in Riverside
4.89 out of 5 average rating, 122 reviews

Wabi-Sabi Inspired Studio w Bikes, Walk to River

Tucked away behind a historic building, is a wabi sabi inspired studio: a blend of natural charm & modernity. A minimalist interior features a warm wooden beam, glass dividing wall, and earthy tones. Modern comforts coexist with aged ceramics and jute rugs. Large windows invite natural light and provide a view of the backyard garden. The space embodies tranquility, celebrating simplicity & imperfection. This harmonious retreat offers a peaceful escape, where past & present beautifully converge.

Top guest favourite
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, 183 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 favourite
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
4.93 out of 5 average rating, 118 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 Fleming Island
5 out of 5 average rating, 5 reviews

Guest House by St. John's River

Unique, family friendly, tranquil getaway. Two bedroom Guest House, offering a breeze of St. John's river, a mile away from a plaza with multiple stores and restaurants, 40 minutes drive to St Augustine and the beaches. Easy access to Jacksonville as well local parks for hiking and biking. Upstairs Queen size bed, pull-out sofa plus large desk. Downstairs private bedroom has a single bed and full bathroom. Well equipped kitchen with large fridge and dining room table for 6 people plus 65” TV.

Guest favourite
A modern living area features a light-colored sofa adorned with dark cushions and a soft throw blanket. A glass coffee table is positioned on a textured area rug, complemented by a stylish floor lamp and a leafy plant beside it. A large abstract artwork adds a striking focal point.
Flat in Jacksonville
4.86 out of 5 average rating, 111 reviews

Lake View Escape to The Exchange

Give us your worries and we will give you an escape. Welcome to the Exchange! This Orange Park unit supports your work requirements and your playful desires. Multiple high volume healthcare facilities surround the area and the Naval Air Station is in the backyard. Luxury dinning and outdoor water activities abound. This new unit offers access to a resort style salt water pool, private garages, state of the art fitness center and wellness studio, dog park, clubhouse and lounge, and much more.

Guest favourite
Farm stay in Middleburg
4.96 out of 5 average rating, 228 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!

Top guest favourite
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, 102 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

Top guest favourite
An outdoor space features a stone patio with a circular arrangement of four black chairs surrounding a fire pit on gravel. Verdant landscaping and trees provide a natural backdrop, enhancing the tranquility of the area.
Home in Fleming Island
4.99 out of 5 average rating, 166 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
A charming tiny cottage sits surrounded by lush greenery, featuring a small porch with two black metal chairs and a matching table. The exterior displays a white wooden façade and a sloped roof, inviting guests into a serene natural setting.
Tiny home in Fleming Island
5 out of 5 average rating, 6 reviews

Chez Mimi - The Cottage

Discover the quiet nature that surrounds this tiny cottage. The flora and fauna of Florida surrounds this home, yet with the civilization of "new" Florida a stones throw away. This unique home has all the amenities of your own place in a small space. Day bed (twin size foam mattress and bolsters) Full bathroom with shower and instant hot water heater, kitchen has plenty of storage, full size sink - small fridge, microwave/convection oven/air fryer combo and a flat electric burner.

Guest favourite
A spacious bedroom features a king-size bed with white bedding and decorative pillows. A bright yellow throw blanket adds a pop of color. Two modern artworks are displayed above the bed, while a large mirror reflects the room's design, enhancing the sense of space.
Guest suite in Jacksonville
4.94 out of 5 average rating, 160 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.

Top guest favourite
A light-filled living area features a comfortable black sofa adorned with textured cushions. A round dining table with wooden chairs sits nearby. Natural elements are introduced through a potted plant and a woven light fixture, while a piece of artwork adds a touch of color to the wall.
Guest house in Springfield
4.99 out of 5 average rating, 157 reviews

Cozy Cottage in Springfield, Downtown Jax

🤍 We can't wait to host you! The Cottage on 4th is located in the eclectic Historic Springfield neighborhood in Jacksonville's urban core. Situated in close proximity to awesome restaurants, coffee shops, breweries, and entertainment venues. Located 1.5 miles or less from TIAA Bank Field, Daily’s Place, Vystar Veterans Memorial Arena, and 121 Financial Ballpark (Jacksonville Jumbo Shrimp stadium). 13 miles from JAX airport and 16 miles from the beach.

Popular amenities for Fleming Island holiday rentals

When is the best time to visit Fleming Island?

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Frequently Asked Questions

  • Do house rentals in Fleming Island have free parking?

    Absolutely! We offer over 20 house rentals with free parking in Fleming Island. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Fleming Island?

    Fleming Island has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there house rentals with a dedicated workspace in Fleming Island?

    Yes! Work meets play with ease at over 20 house rentals in Fleming Island featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Fleming Island have a kitchen?

    Absolutely! We offer over 20 house rentals with a kitchen in Fleming Island. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Fleming Island?

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with wifi, over 20 homes with free parking, over 20 homes with a kitchen, over 20 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do house rentals in Fleming Island have air conditioning?

    Absolutely! We offer over 20 house rentals with air conditioning in Fleming Island. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Fleming Island have wifi?

    Absolutely! We offer over 20 house rentals with wifi in Fleming Island. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly house rentals in Fleming Island?

    Four-legged friends are welcome in Fleming Island. Choose from more than 10 house rentals for guests traveling with pets.

Quick stats about holiday rentals in Fleming Island

  • Total holiday rentals

    Explore 40 holiday rentals in Fleming Island

  • Nightly prices starting at

    Fleming Island holiday rentals start at £22 per night before taxes and fees

  • Verified guest reviews

    Over 1,510 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    40 of Fleming Island holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Fleming Island rentals

  • 4.9 Average rating

    Fleming Island stays are highly rated by guests – averaging 4.9 out of 5!

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