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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, 125 reviews

1920 Carriage House on Riverfront Estate- Weddings

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, 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 favourite
Home in St. Augustine
5 out of 5 average rating, 150 reviews

Private oasis, heated pool, exceeds expectations

Private retreat on 2 acres of gated land, just 20 minutes to historic downtown St. Augustine and 25 minutes to the beach. This fenced property offers a perfect blend of relaxation, fun, and comfort. Enjoy your private pool, or let the kids enjoy their own space in the pool house, featuring TV, games, and a cozy hangout area. Start your day with fresh eggs from our happy hens- an experience that feels both farm-fresh and uniquely memorable. This home is designed to make your stay unforgettable.

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, 139 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.

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, 121 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 favourite
The kitchen features modern white cabinetry, sleek countertops, and stainless steel appliances. A dining area with vibrant red chairs is visible in the background. Black and white checkered mats line the floor, creating a functional and stylish space.
Home in Middleburg
4.94 out of 5 average rating, 121 reviews

Modern E. Orange Park Home 6 bed Fence Beach 45 Mn

New Stylishly renovated home just West of Fleming Island in Middleburg, South of Orange Park, West of Jacksonville Florida. Christmas 365! Farmhouse style, TV’s in all bedrooms, with a touch of Christmas theme. 6 beds, Fenced yard, 75" LED TV, front/back porches available up to 10 people. Beaches approx. 40 minutes The home is close to restaurants, grocery stores, banks, gas stations, main hospital(2+miles). There are lakes and rivers locally to fish/boat, parks, shopping, and trails:)

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, 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.

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, 118 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, 171 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.

Top 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
4.97 out of 5 average rating, 115 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!

Top Guest favourite
The exterior of the home features a white brick facade with large windows and a black front door. A private driveway leads to a single-car garage, surrounded by a fenced yard with greenery. Outdoor seating is arranged on the patio, providing a welcoming entrance.
Home in Avondale
5 out of 5 average rating, 110 reviews

Industrial Van Value

Our 1,300 ft.² home was renovated in 2023 with new central heat and air, ceramic tile and hard wood flooring, kitchen appliances and cabinets, bathrooms, and electrical and plumbing. Due to owner allergies, we do not allow pets or companion animals. The home is a block away from 8 restaurants and many local shops. We allow a maximum of 6 overnight guests and 4 visitors on the property at one time.

Guest favourite
A spacious living area is furnished with two blue sofas and a rug, providing a comfortable setting. A ceiling fan is positioned above, and an open kitchen is visible in the background, featuring modern appliances and a dining table for six.
Home in Orange Park
4.9 out of 5 average rating, 112 reviews

Spacious 5/2 in Orange Park

The whole group will enjoy easy access to everything from this centrally located place. Fully remodeled with new flooring, modern kitchen, fresh paint and fast wifi. Large smart TV in living as well as in 4 bed rooms. Fully fenced backyard. Dog friendly. Close to tons of restaurants and shops. Great location right off 295 so you can get to anywhere in Jacksonville quick

Popular amenities for Fleming Island house rentals

When is the best time to visit Fleming Island?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$246 NZD$285 NZD$331 NZD$233 NZD$234 NZD$231 NZD$246 NZD$255 NZD$219 NZD$224 NZD$229 NZD$236 NZD
Avg. temp13°C15°C17°C20°C24°C27°C28°C28°C26°C22°C17°C14°C

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 $51 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,110 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Fleming Island holiday rentals include Wi-Fi 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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