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Holiday rentals in Fleming Island

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Fleming Island

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

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Guest favourite
The exterior of the house features a two-story design with light blue shutters, a grand entrance, and well-maintained landscaping. A lush green lawn surrounds the property, with colorful plantings adding vibrancy to the setting. Ample natural light reflects off the front windows.
Home in Orange Park
4.88 out of 5 average rating, 8 reviews

Rococo Entire Home- 1 king bed 1 bath/ Game room

Rococo offers plenty of room couples to enjoy a relaxing stay. The home features 1 king bed and 2 sleeper sofas accommodating up to 4 guests comfortably. The master bedroom located on the first floor includes a walk in shower perfect for unwinding. You'll appreciate our recently updated kitchen and the open, spacious living room that's ideal for gathering and relaxation. The property includes a private driveway with ample parking space for your convenience. The garage is not available for use.

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
4.95 out of 5 average rating, 177 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

Superhost
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, 101 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
A spacious bed is adorned with a navy and white coverlet, accompanied by decorative pillows, including a fluffy white one. Flanking the bed are two bedside tables with lamps, and a wall-mounted artwork features a city skyline, enhancing the serene ambiance.
Flat in Orange Park
4.82 out of 5 average rating, 33 reviews

My Dream Space

Located in a quiet residential area of ​​Orange Park close to St. Augustine and close to iconic locations such as BESTBET Racetrack and Spring Boil Park this modern apartment is the perfect refuge for couples or travelers looking for comfort, privacy and an excellent location, the apartment has a spacious room with air conditioning and heating, a fully equipped kitchen, an elegant bathroom and a work area ideal for those who need to combine rest with productivity. Welcome to my Dream Space.

Top guest favourite
Guest house in Springfield
5 out of 5 average rating, 21 reviews

La Casita Chiquita Near Events & Entertainment!

Welcome to "La Casita Chiquita" our unique little guest cottage - in the heart of Jacksonville! This 250 square foot cottage, with a loft bed and comfortable amenities is nestled in a garden setting, underneath majestic trees. You can be away from it all - and just blocks to sports, entertainment & convention venues, craft breweries, sports bars, unique eateries, and museums. Are you here for business? Downtown is 5 minutes away and major medical facilities less than 10 minutes away.

Top guest favourite
The kitchen area features modern white cabinetry and stainless steel appliances, including a dishwasher and sink. A colorful rug lies on the floor, enhancing the space. Bright natural light enters through the window, while a dining area with red chairs is visible in the background.
Home in Middleburg
4.95 out of 5 average rating, 113 reviews

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

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:)

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, 156 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.

Superhost
A peaceful lakeside scene captures a calm body of water bordered by lush greenery and trees draped in Spanish moss. A boat ramp is visible in the foreground, leading into the water, with docks located at the far side for boat access.
Campervan/Motorhome in Fleming Island
4.67 out of 5 average rating, 15 reviews

Camp in Paradise

Lakefront RV Paradise! Fully-equipped RV with 3 beds, master bedroom, & complete kitchen. Steps from the water with boat ramp and dock access included with your stay & complimentary kayak use. Enjoy WiFi, on-site laundry, & waterfront restaurant/bar featuring live bands, pool, darts & video gambling. Perfect for water lovers - bring your boat and toys for the ultimate lake getaway! Walking distance to dining, entertainment, and pristine waters. Your adventure awaits!

Top guest favourite
Flat in Middleburg
5 out of 5 average rating, 5 reviews

Escape to the Hidden Gem - a quiet country retreat

Start your adventure in a place where old-world charm meets quiet country luxury. Nestled in a serene gated community is your 1 bed/2 bath retreat, perfect for the seasoned traveler. Spend your days writing, reading, or listening to the sounds of nature. Explore the nearby trails, fish the local creeks or simply sip coffee on the porch. There’s a full kitchen for the culinary minded as well as the convenience of multiple restaurants and shops nearby.

Top guest favourite
Flat in Jacksonville
5 out of 5 average rating, 31 reviews

Lindo estudiojax

Charming Remodeled Studio with Patio Access & Free Parking Welcome to your cozy home away from home! This recently remodeled studio features a private bathroom and a convenient kitchenette, perfect for short or extended stays. Step outside to enjoy a peaceful patio space—ideal for your morning coffee or evening unwind. Located in a quiet neighborhood with free parking included, you'll have everything you need for a comfortable and relaxing stay.

Top guest favourite
A spacious sleeping area features a large bed adorned with a colorful coral-patterned quilt. Natural light floods the room through a window, highlighted by vibrant curtains. A small dining area with high chairs is visible, along with decorative accents like fresh flowers.
Guest suite in Orange Park
4.88 out of 5 average rating, 136 reviews

Guest Suite

Enjoy your stay at this vivid private space! This suite is a colorful paradise that is surrounded by nature on a 2 acre property. Guests will be surrounded by color and outdoorsy scenery. The designated parking area is to right at a colored bee post. As you walk up the steps that lead you to the patio, you will see the door that will lead you to your lively suite. Our Suite is attached to the main house, with everything private.

Popular amenities for Fleming Island holiday rentals

When is the best time to visit Fleming Island?

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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 £30 per night before taxes and fees

  • Verified guest reviews

    Over 1,280 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

    30 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!

  1. Airbnb
  2. United States
  3. Florida
  4. Clay County
  5. Fleming Island