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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Guest favorite
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 favorite
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

Top guest favorite
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, 120 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 favorite
A spacious living area features a comfortable sectional sofa with decorative pillows, a coffee table, and a light rug. Natural light fills the room through a window, illuminating the adjacent dining area with a table and chairs. A ceiling fan provides ventilation.
Home in Orange Park
4.88 out of 5 average rating, 60 reviews

Dogwood Stay: Near the Lake

Comfy home perfectly located on a peaceful, dead-end street with public access to Doctor's Lake for kayaks, canoes and paddleboards. Master bedroom includes king-size bed, closet, dresser and private bathroom with shower. This room is a cozy hideway. 2nd bedroom is large with plenty of room to relax includes a king-size bed, dresser, closet and shares the main bathroom with tub/shower combo. 3rd bedroom is spacious and colorful with king-size bed, dresser, closet and shares the main bathroom.

Top guest favorite
A patio area is furnished with four white wooden chairs surrounding a small table. Lush greenery and palm trees are visible in the background, with a pathway leading toward the beach, where the ocean can be seen in the distance under a cloudy sky.
Condo in Ponte Vedra Beach
4.98 out of 5 average rating, 139 reviews

Oceanfront Surf Villa

This beachfront condo is perfect for your stay in Ponte Vedra Beach. Guests can enjoy the ocean and looking for endless sharks teeth and sea shells. This condo boasts (1) bedroom, (1) bathroom and an additional murphy bed for your guests. Music can be heard from the back patio on weekends, as well as the sounds of the sea. When back from soaking up the sun, enjoy our fully equipped kitchen, powerful shower and wifi. Our location is minutes away from Sawgrass TPC and nearby St. Augustine.

Top guest favorite
A two-story house is set back on a spacious driveway, surrounded by lush trees and vegetation. A manicured lawn features well-maintained plant beds near the entrance, while the garage is visible on the left side of the structure under a clear blue sky.
Vacation home in Orange Park
4.92 out of 5 average rating, 108 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.

Top guest favorite
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

Guest favorite
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 favorite
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.

Superhost
Home in Middleburg
5 out of 5 average rating, 3 reviews

Villa Marita B&B

Come as a guest and leave as a friend. This is a duplex house where only the right-hand (A) unit is available for rent. It includes a living room, dining room, kitchen, bathroom, and two bedrooms with queen beds, ideal for a family of four. Located between Orange Park and Middleburg, it's surrounded by nature and positive energy. We are close to nature parks, museums, St Johns River, beaches and historical sites. If you would like to explore the city check my guidebook.

Top guest favorite
A modern living area is furnished with a gray sofa and two light-colored armchairs. A textured rug covers the floor, while large windows allow natural light to illuminate the space. The kitchen can be partially seen in the background, featuring contemporary appliances.
Guesthouse in Fruit Cove
4.94 out of 5 average rating, 52 reviews

Luxury Cottage with River Access

Enjoy the peaceful ambiance of this brand new luxury cottage on Julington Creek in Saint Johns County. Centrally located -- we're just a 30 minute drive to the beach, downtown Jacksonville, and St. Augustine. Amenities include a king-sized bed, two TV's, and a fully-equipped kitchen. The cottage is located at the front of our 1-acre property. Our own home is situated just across the lawn from the cottage. Guests will walk through the backyard to access the river.

Superhost
The houseboat is anchored in a serene marina, featuring a modern design with large windows that provide ample natural light. Surrounding boats are docked neatly under solar panel canopies, reflecting a commitment to sustainability. The calm water enhances the tranquil atmosphere of the setting.
Houseboat in Fleming Island
4.9 out of 5 average rating, 107 reviews

New Floating Luxury: Unique Houseboat Retreat

Hit the "♡ Save" button to bookmark our unique property 》 Welcome to Home A Wave, a unique, fully furnished houseboat on the tranquil waterfront, promising an unforgettable stay. ★ Unbeatable Waterscape: Experience tranquility and adventure. ★ Top Deck Bedroom: Enjoy panoramic views and starry nights. ★ Water Activities: Swim, paddle, or fish directly off the deck. ★ Modern Amenities: Benefit from a well-equipped galley and in-house laundry.

Popular amenities for Fleming Island vacation rentals

When is the best time to visit Fleming Island?

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Avg. priceG$30,434 GYDG$28,545 GYDG$28,755 GYDG$28,545 GYDG$28,755 GYDG$31,483 GYDG$30,854 GYDG$32,533 GYDG$27,915 GYDG$27,915 GYDG$32,743 GYDG$30,014 GYD
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Frequently Asked Questions

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

    Fleming Island has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Fleming Island?

    Experience the best of Fleming Island with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

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

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

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

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

  • 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 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.

  • 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.

  • 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.

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 G$6,297 GYD 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 & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Fleming Island vacation 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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