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, 126 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

Guest favorite
A serene view of the riverfront at sunset is captured, showcasing vibrant colors across the sky. Silhouetted palm trees frame the scene, while a sparkling pool reflects the fading light. Lounge chairs are positioned nearby, inviting relaxation outdoors.
Home in Fleming Island
4.93 out of 5 average rating, 70 reviews

Sunset River Retreat

Escape to this stunning 3-bedroom, family-friendly oasis nestled along Doctors Lake riverfront. With a sparkling pool and breathtaking sunset views every evening, this is the ultimate haven for relaxation and fun. Home has a pool, firepit, outdoor pool table, and direct access to the river, ideal for fishing or kayaking. 30 min to downtown Jacksonville, 10 min from NAS Jax Naval Base. 10 minutes to boat ramp. 2 story house, bedrooms on 2nd floor Inquire for Events ($850 Event Fee, Max 50 ppl).

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, 197 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 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
4.94 out of 5 average rating, 127 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
4.89 out of 5 average rating, 65 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.

Guest favorite
A welcoming living area features a well-furnished gray sofa and a decorative coffee table. A beautifully decorated Christmas tree stands in the corner, adding a seasonal touch. An open kitchen with modern appliances is visible in the background, complemented by an inviting dining space.
Home in Green Cove Springs
4.95 out of 5 average rating, 132 reviews

Modern Green Cove Springs 6 Bed Fence Beach 45 min

New Stylishly renovated home in Green Cove Springs just South of Fleming Island, Orange Park, Middleburg, West of Jacksonville Florida. Christmas 365! Farmhouse style with a touch of Christmas theme. 7 beds, Fenced yard, 65" LED TV, fast internet, front/back porches available up to 10 people. Beaches approx. 45 minutes. Camp Blanding 25min Close to restaurants, grocery stores, banks, gas stations, main hospital 8+miles). There are lakes and rivers locally to fish/boat, parks, and shopping:).

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
4.89 out of 5 average rating, 118 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 favorite
Farm stay in Middleburg
4.97 out of 5 average rating, 233 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 favorite
Home in Fleming Island
4.9 out of 5 average rating, 31 reviews

Fleming Island Coastal Getaway

Located in Fleming Island Plantation; This gorgeous coastal-themed pool home has a spacious single-story layout with a massive primary bedroom. The backyard retreat features a beautiful sparkling pool for those who want to relax. Nearby is Fleming Island Town Center, which offers dining, entertainment, and shopping. This home is in close proximity to the Baptist Medical Center Clay. Those who enjoy an active lifestyle, Black Creek bike trail, the YMCA, golf course and recreational parks.

Top guest favorite
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 Southeast Jacksonville
4.98 out of 5 average rating, 401 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.

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, 254 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, 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.

Popular amenities for Fleming Island vacation rentals

When is the best time to visit Fleming Island?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 477ﺩ.ﺇ 595ﺩ.ﺇ 610ﺩ.ﺇ 499ﺩ.ﺇ 503ﺩ.ﺇ 551ﺩ.ﺇ 540ﺩ.ﺇ 569ﺩ.ﺇ 488ﺩ.ﺇ 488ﺩ.ﺇ 573ﺩ.ﺇ 525
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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 30 vacation rentals in Fleming Island

  • Nightly prices starting at

    Fleming Island vacation rentals start at ﺩ.ﺇ 110 per night before taxes and fees

  • Verified guest reviews

    Over 1,450 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

    30 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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