Holiday houses in Fleming Island

5 out of 5 average rating, 70 reviews

Fleming Island 4/3 by River wifi&MILS! Beach45min

Newly renovated home in Fleming Island with Mother-In-Law Suite close to Orange Park, Middleburg, Green Cove and Jacksonville Florida. Farmhouse style with a touch of Christmas theme 365! 9 beds, (5)50+" LED 4K TV's in all rooms, fast internet, front/back porches available, A/C in Florida room. Home is next to St. Johns River on 1 acre, walk river street or enjoy the HUGE backyard. Beaches aprx 45 mins Close to restaurants, Publix, Walmart, Hospitals, Public boat ramp etc. All within 1-5 miles

4.93 out of 5 average rating, 43 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 ($500 Event Fee, Max 75 ppl).

4.95 out of 5 average rating, 162 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

Place to stay in Orange Park

4.92 out of 5 average rating, 95 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.

4.97 out of 5 average rating, 214 reviews

Farm stay in Middleburg

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!

4.9 out of 5 average rating, 234 reviews

Home in Orange Park

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.

5 out of 5 average rating, 144 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.

Tiny home in Fleming Island

5 out of 5 average rating, 5 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.

Holiday home in Orange Park

4.91 out of 5 average rating, 92 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.

4.96 out of 5 average rating, 28 reviews

Boat in Orange Park

Houseboat - Boatiful Life

Island Life by It’s A Boatiful Life is a one of a kind getaway! A lovely space to unwind and allow your everyday worries to “float” away. This is truly water living at it’s best! Nestled in between the city and the country, the boat is perfect for a nice escape and home base for unique shops, excellent restaurants, community events and the Sunset Tiki Bar right on site. The island's location is ideal for small city outings to big city nightlife.

Houseboat in Fleming Island

4.91 out of 5 average rating, 81 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.

4.92 out of 5 average rating, 12 reviews

Welcome to the Weston House!

Discover serenity in our charming vacation home located in a tranquil neighborhood. Offering the perfect blend of comfort and relaxation with spacious interiors and a private patio, enjoy moments of peace and rejuvenation with your family. Escape the hustle and bustle and unwind in this idyllic retreat.

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Popular amenities for Fleming Island holiday rentals

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Other great holiday rentals in Fleming Island

Home in Orange Park

4.75 out of 5 average rating, 4 reviews

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

JameaRating, 5 stars2 weeks ago

Me and my partner enjoyed our stay at Mezhon’s home! The home was spacious, clean, and we felt right at home. Looking forward to booking again!

Campervan/RV in Fleming Island

4.88 out of 5 average rating, 8 reviews

Camp in Paradise

LottieRating, 5 stars3 weeks ago

my husband and son went fishing and didn't book anywhere to stay. called me and I found Michael's place on Airbnb. Michael and his wife met them there and showed them where to park the boat and got them in the camper. camper was very clean. There is also a boat ramp so they put in there this morning to fish. we will be back.

4.95 out of 5 average rating, 21 reviews

Apartment in Orange Park

Your, “Feels like home”.

KamiRating, 5 stars2 weeks ago

Beautiful home! Looks just like the pictures. Felt safe, it was peaceful! We will definitely come back!

Guesthouse in Middleburg

4.81 out of 5 average rating, 27 reviews

Dock House

ShawnRating, 5 stars1 week ago

My wife and I wanted a small get away with something on the water that was peaceful and we couldn’t of asked for a more simple and beautiful place. We will definitely be back again!

4.91 out of 5 average rating, 106 reviews

Home in Orange Park

*River Road Cottage* - Dock, Board Games, Wifi

ChristineRating, 5 stars2 months ago

This is the perfect place to get away without being isolated. Peaceful setting with great walking right out the door. Easy to get to anywhere you need to get to in Orange Park. Not far from the beaches. Loved sitting outside by the river. Such a refreshing way to start and end the day. The place is exactly as described.

Guesthouse in Orange Park

4.87 out of 5 average rating, 55 reviews

little dream

CherellRating, 5 stars3 days ago

I enjoyed my stay at little dream. It was perfect for my needs. I highly recommend, thank you Eugenia for sharing your space with us.

Guesthouse in Jacksonville

5 out of 5 average rating, 4 reviews

Luxury Cottage with River Access

JulieRating, 5 stars1 week ago

Sarah is an excellent hostess. She was very responsive to our needs and questions and provided a super clean, well designed and comfortable place for my daughter and I to stay while in the Julington Creek area of Jacksonville. The cottage was super clean, happy and bright, cool and comfortable. I would recommend this to anyone and hope to stay there again in the future! It is also super convenient to restaurants, grocery shopping, salons, parks, and there are public tennis courts close by, along with a public golf course near by.