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House holiday rentals in Fleming Island

Find and book unique houses on Airbnb

Top-rated house rentals in Fleming Island

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

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Guest favourite
The two-story white house features a welcoming entrance with a central door flanked by large windows. Adjacent to the entrance, two armchairs are positioned around a small table on a circular patio, surrounded by lush green grass and decorative potted plants.
Home in Green Cove Springs
4.99 out of 5 average rating, 122 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 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

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, 188 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

Guest favourite
A modern kitchen is showcased, featuring white cabinetry and a spacious countertop. Stainless steel appliances, including a refrigerator and oven, are visible. The tiled floor provides a practical surface, while a doorway leads to a dining area adorned with a decorative light fixture.
Home in Middleburg
4.95 out of 5 average rating, 133 reviews

Modern Orange Park Home w/6+Beds&Wash/Dryer Fence

Stylishly renovated home North of Middleburg and South of Orange Park Florida. 6+beds TV’s IN ALL ROOMS, available for use to accommodate up to 9 people. One King bed, 2 twin beds, double bed, a pull out queen sofa bed, and air mattress. Peace and quiet just minutes away from the city yet still comfortable. The home is close to many restaurants, grocery stores, banks, gas stations, and main hospital (1/2-2+miles). There are creeks and lakes locally to fish, parks. Beaches approx. 45 mins.

Guest favourite
The living room features a comfortable arrangement of light leather sofas and an armchair, complemented by wooden side tables. Natural light filters through vertical blinds, creating a bright and open atmosphere. A floral artwork adorns the wall, adding a touch of elegance to the space.
Home in Loretto
4.85 out of 5 average rating, 143 reviews

Mandarin Pearl. Close to everything.

Single family house in one of the best, quiet, safe, and beautiful neighborhoods in Jacksonville. walking distance of restaurants and supermarkets.3-bedroom ,1 bath, big front & back yard. Car port . Full kitchen, Netflix. Smart TV in the Master Bedroom that's has Netflix available. Also other apps like YouTube. Long term stay discount Smoking is not allowed inside the house only outside. $100.00 cleaning fee will be charged . Electric car charging available upon request for additional fee.

Guest favourite
An open-concept living area features light wood flooring and neutral-colored walls. A spacious sectional sofa faces a large television. The kitchen showcases wooden cabinets and modern appliances, with a breakfast bar that includes several stools. Natural light enters through multiple windows.
Home in Green Cove Springs
4.88 out of 5 average rating, 135 reviews

Cozy 3 bedroom house in town, bikes included!

Welcome to the Sunny Side Up Villa in charming Green Cove Springs! This private home is centrally located in historic downtown and includes bicycles for you to tour the city and visit all the sights. Spring Park and the St. John's River are just a mile down the road. The three bedroom home sleeps eight and features a brand new king bed in the master suite. The open concept living room and kitchen are great for entertaining and the backyard is completely fenced in for your four-legged pals.

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, 107 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
A nighttime view features a tranquil water fountain illuminated in soft turquoise, surrounded by lush palm trees. The setting includes reflected lights from nearby buildings, creating a peaceful ambiance by the water's edge.
Home in Jacksonville Beach
5 out of 5 average rating, 152 reviews

Seaspray Chalet: Just Steps to the Beach

Welcome to your beautiful, newly renovated spa-like home away from home just 4 houses from the warm sand and refreshing ocean. View the exotic birds at the park across the street & enjoy the playground, tennis & basketball courts. You'll have 1-3 private parking spots (depending on use if downstairs unit (Seabreeze Chalet) on site. Owners are nearby but will respect your privacy. We are leaving a buffer of at least a day between guests and are following Airbnb Enhanced Cleaning Protocol.

Guest favourite
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, 247 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.

Top guest favourite
A well-appointed bedroom features a spacious wooden sleigh bed with a light blue and white quilt. Natural light fills the room through windows with soft drapes, and a flat-screen TV is mounted on the wall opposite a matching wooden dresser and nightstand.
Home in Fruit Cove
4.99 out of 5 average rating, 111 reviews

King bed, Lake View, sleeps 8, 6 TVs, Public Pool

Escape to our cozy retreat! You'll unwind in style with up to 6 beds in our safe neighborhood, close to Publix and restaurants. You'll explore nearby beaches, parks and attractions or day trip to St. Augustine and Orlando. You'll enjoy serene lake views and backyard fishing. You'll love our top-notch amenities, including a recreational pool with slide, lap pool, basketball, fitness center and playground. You'll create unforgettable memories - book now! We look forward to hosting you.

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, 168 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
The living area features a modern design with custom wood paneling on one wall. A leather sofa is positioned in the foreground, while a decorative coffee table and a small workstation with a chair are visible. Soft lighting highlights a piece of scenic artwork above the table.
Home in St. Augustine
4.96 out of 5 average rating, 100 reviews

St Augustine Entire Home, King Bed, Pet Friendly

Casita Luxe Retreat Near Historic St. Augustine – Pet-Friendly Haven! Discover this luxurious 3-bedroom, 2-bath retreat! Designed with a modern luxe aesthetic, it features custom wood paneling, a fully equipped kitchen with a chic island, and a king-size plush mattress. Enjoy the large, fenced yard, fire pit, outdoor shower, and fun family games. Pet-friendly, with Wi-Fi, smart TVs, and parking included this home offers comfort and style in an up-and-coming neighborhood. Book now!

Guest favourite
The brick house features a welcoming façade with a front porch and large windows, surrounded by lush greenery. A small sitting area is set up to the right of the entrance. The driveway leads gently to the home, providing ample parking space.
Home in Green Cove Springs
4.93 out of 5 average rating, 110 reviews

Country Cove - 3 Bedroom Cottage on 2 Acres!

Awesome little brick house in the country close to downtown GCS, Clay County Fairgrounds and Green Cove Marine. House has been renovated with hardwood floors, GAS stove, dishwasher, ice maker with lots of counter space in kitchen! Farmhouse style decor with smart tv. Has Wifi. Has coin operated washer and dryer in a separate shared unfinished laundry room. Shared carport set up as a sitting area with a gas grill. House sits on over 2 acres! Other units on the property.

Popular amenities for house rentals in Fleming Island

When is the best time to visit Fleming Island?

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Quick stats about house rentals in Fleming Island

  • Total holiday rentals

    Explore 20 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 1,190 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

    20 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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