
Holiday rentals in Fleming Island
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Top-rated holiday rentals in Fleming Island
Guests agree: these stays are highly rated for location, cleanliness and more.

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

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).

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

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.

Modern Green Cove Springs 6 Bed Fence Beach 45min
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:).

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.

Cozy 3 bedroom house in town, bikes included!
Welcome to the Sunny Side Up Villa in charming Green Cove Springs! This private home is centrally located in historic downtown and includes bicycles for you to tour the city and visit all the sights. Spring Park and the St. John's River are just a mile down the road. The three bedroom home sleeps eight and features a brand new king bed in the master suite. The open concept living room and kitchen are great for entertaining and the backyard is completely fenced in for your four-legged pals.

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

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.

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.

Secluded, Cozy Guest Suite on Black Creek
Come down the driveway and escape the world. Situated on the North Prong of Black Creek, this cute studio suite offers rural with benefits. There's something for all outdoor lovers- birdwatching, kayaking, fishing, paddle boarding, wildlife, and more. If you want to just listen to the birds and cicadas, that's ok, too. The apt has a microwave, Keurig, toaster, and small fridge. Wifi is fast for remote working.

Marsh Hawk Lane on Fleming Island
Conveniently located to Baptist Clay Hospital, shopping, dining and movies! Less than 10 mins to Doctors Lake Marina (best sunset view on island) and St. John’s River. Less than 10 mins to two golf courses: Fleming Island Plantation & Eagle Harbor. 45 mins from Jacksonville Airport. 1 hour to downtown Jacksonville for concerts and Jaguars Stadium.
Popular amenities for Fleming Island holiday rentals
Other great holiday rentals in Fleming Island

Spacious 5-Bedroom Family Retreat

Adorable studio with river access.

Cheerful three bedroom home with a pool

Zen Flamingo: Poolside Peace Near Beaches and TPC

Romantic Tiny Home Tubs Wellness Jungle Oasis New

Attached Updated In-Law-Suite

Orange Park Oasis 2bed/2bath

Family-Friendly Weston House with Fenced Backyard
When is the best time to visit Fleming Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £110 | £103 | £104 | £103 | £104 | £114 | £111 | £117 | £101 | £101 | £118 | £108 |
| Avg. temp | 13°C | 15°C | 17°C | 20°C | 24°C | 27°C | 28°C | 28°C | 26°C | 22°C | 17°C | 14°C |
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 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 £23 per night before taxes and fees

Verified guest reviews
Over 1,510 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
40 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!
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