Vacation rentals in Fleming Island

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Top-rated vacation rentals in Fleming Island

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

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Top guest favourite
The living area features a modern design with a large brick fireplace as a focal point. Comfortable seating options include a dark blue armchair, gray accent chairs, and a turquoise sofa. Natural light filters through multiple windows, illuminating a patterned area rug and coffee tables.
Home in Fleming Island
4.96 out of 5 average rating, 187 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
A studio guest suite features a queen bed with decorative pillows and a lightweight blanket. A work desk with a bar stool and a mounted TV are visible against the wall. Light wood flooring complements the soft blue wall, while a woven wall hanging adds texture to the space.
Guesthouse in Jacksonville
4.92 out of 5 average rating, 330 reviews

Studio Suite in Beautiful Central Neighborhood

Studio guest suite with queen bed and kitchenette in beautiful Miramar neighborhood, just 5 minutes from historic San Marco. Close to restaurants, grocery, MD Anderson Cancer Center and Wolfson Children's Hospital. Owners live in main house on site but suite has its own private entrance and parking. You will have access to an outdoor dining space and fenced in backyard. Dogs live on premises but will not interfere, although you may hear barking. Sofa bed available if needed, please inquire.

Top guest favourite
A serene backyard features a saltwater pool surrounded by landscaped areas. Vibrant pink flowering bushes add color to the scenery. A spacious patio includes a set of lounge chairs and an umbrella, offering a relaxing outdoor space, framed by lush greenery.
Vacation home in Orange Park
4.92 out of 5 average rating, 105 reviews

Casandra House - Peaceful / Salt Pool and Hot Tub

Welcome to Casandra House. A peaceful getaway in Orange Park, FL. Located in the vicinity of Doctor's Lake, this house sits on 3/4 of an acre surrounded with trees and vegetation. It provides just enough privacy to make you feel away from everything while minutes from shops and restaurants. Home includes a large backyard, patio screen enclosure, salt pool and hot tub. About 2 1/2 miles from the Orange Park Thrasher-Horne Center and 10 miles from NAS Jacksonville. Note: No direct lake access.

Guest favourite
Apartment in Jacksonville
4.87 out of 5 average rating, 113 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
4.97 out of 5 average rating, 229 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!

Guest favourite
Home in Orange Park
4.93 out of 5 average rating, 105 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 spacious living area is presented, featuring a comfortable gray sofa adorned with decorative pillows. A coffee table is centrally located, and a dining table is visible in the background. A Christmas tree and subtle holiday decorations complement the warm atmosphere. Light streams through the windows.
Home in Middleburg
4.95 out of 5 average rating, 117 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
The kitchen features white cabinetry with ample storage and a spacious countertop. Stainless steel appliances, including a double oven and dishwasher, are visible. A window allows natural light to illuminate the workspace, and a small area rug adds a touch of warmth.
Guesthouse in Jacksonville
4.98 out of 5 average rating, 392 reviews

Private Apartment

Unique private upstairs apartment near the beautiful Julington Creek very close to St. Johns, under majestic live oak trees offering a quiet and secluded setting, but close enough to everything you need for your next trip to Jacksonville. Short distance to great dining, beaches, shopping, St. Johns and St. Augustine! Guests will enjoy a one bedroom apartment with a fully equipped kitchen. Property access for our guests only. Complimentary beer, sodas, water and coffee! Adults only.

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
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 homes 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
Guesthouse in Riverside
4.97 out of 5 average rating, 230 reviews

Santorini A Mediterranean Studio Escape…Riverside

Escape to a tranquil Greek villa in the heart of Riverside, Jacksonville. Inspired by the cliff top town of Ioa on the island of Santorini, you will experience the allure of the Aegean Islands as you step into this whitewashed windswept studio. Immerse yourself in bleached white rock, stucco, and cobalt blue accents. Escape if you’d like or walk to local eateries and entertainment. Regardless, enjoy the magic of a Grecian villa hidden in the middle of Riverside Jacksonville!

Top guest favourite
Guesthouse in Springfield
4.99 out of 5 average rating, 161 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 vacation rentals

When is the best time to visit Fleming Island?

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Avg. price$198 CAD$186 CAD$187 CAD$186 CAD$187 CAD$205 CAD$201 CAD$212 CAD$182 CAD$182 CAD$213 CAD$196 CAD
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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 vacation rentals in Fleming Island

  • Total vacation rentals

    Explore 40 vacation rentals in Fleming Island

  • Nightly prices starting at

    Fleming Island vacation rentals start at $41 CAD per night before taxes and fees

  • Verified guest reviews

    Over 1,510 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    40 of Fleming Island vacation 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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