A coastal highway bridge over a marshy area with a sunset in the background.

Fleming Island Holiday Rentals

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Our top choices for Fleming Island holiday rentals

1. Rustic Owl w/ 2Kings In Fleming Island

Rustic Owl w/ 2Kings In Fleming Island
Fleming Island
10.0 out of 10, Exceptional, (41 reviews)
"Great location. Property was well stocked, clean and comfortable."
United States
Joe T.
The price is NZ$752
includes taxes & fees
27 Sept - 28 Sept
Rustic Owl w/ 2Kings In Fleming Island

2. Luxurious Home w/ Spectacular Glass Room & Patios

Luxurious Home w/ Spectacular Glass Room & Patios
Lakeside
9.8 out of 10, Exceptional, (183 reviews)
"Nice property. The bunk bed mattresses were very uncomfortable and need replacing. The indoor patio was excellent for gathering. We enjoyed our stay"
United States
Cynthia J.
The price is NZ$592
includes taxes & fees
30 Sept - 1 Oct
Luxurious Home w/ Spectacular Glass Room & Patios

3. Suite Peace- New luxury apartment near NAS JAX and Orange park

Suite Peace- New luxury apartment near NAS JAX and Orange park
Westside
9.4 out of 10, Exceptional, (19 reviews)
"Convenient location. Very comfortable. "
United States
Aimee G.
The price is NZ$348
includes taxes & fees
28 Sept - 29 Sept
Suite Peace- New luxury apartment near NAS JAX and Orange park

4. StudioRes by Marriott Jacksonville Orange Park

StudioRes by Marriott Jacksonville Orange Park
3.0 star property
Westside
8.6 out of 10, Excellent, (47 reviews)
"Beautiful room... wish there was breakfast"
United States
Marquessa
The price is NZ$194
includes taxes & fees
30 Sept - 1 Oct
StudioRes by Marriott Jacksonville Orange Park

5. Gorgeous circa 1875 Plantation House (in city)

Gorgeous circa 1875 Plantation House (in city)
Orange Park
9.8 out of 10, Exceptional, (95 reviews)
"Great place to stay!"
United States
shannon d.
Gorgeous circa 1875 Plantation House (in city)

6. Cozy Private Tiny Guest House

Cozy Private Tiny Guest House
Westside
10.0 out of 10, Exceptional, (1 review)
"There's a gas station nearby. Have to drive a little for groceries and restaurants. The room was excellent in every way. "
United States
Theodore D.
The price is NZ$292
includes taxes & fees
27 Oct - 28 Oct
Cozy Private Tiny Guest House

7. Cozy Private Entire Studio Suite Independent Guest Entrance

Cozy Private Entire Studio Suite Independent Guest Entrance
Westside
9.4 out of 10, Exceptional, (21 reviews)
"Nice and cozy!!Easy access, clean and comfortable!!Will book again "
United States
Shantrill G.
The price is NZ$247
includes taxes & fees
27 Sept - 28 Sept
Cozy Private Entire Studio Suite Independent Guest Entrance

8. Private Loft at a Working Show Barn ~ Pets Welcome!

Private Loft at a Working Show Barn ~ Pets Welcome!
Middleburg
9.6 out of 10, Exceptional, (27 reviews)
"Horses were great, stay was wonderful, very relaxing "
United States
Tina S.
The price is NZ$315
includes taxes & fees
3 Oct - 4 Oct
Private Loft at a Working Show Barn ~ Pets Welcome!

9. AWESOME/LUXURY/PERFECT LOCATION/PVT HOME @SE/Mandarin

AWESOME/LUXURY/PERFECT LOCATION/PVT HOME @SE/Mandarin
Del Rio
10.0 out of 10, Exceptional, (55 reviews)
"Great property. Close to lots of things Clean, and very spacious."
United States
Jon C.
The price is NZ$539
includes taxes & fees
24 Oct - 25 Oct
AWESOME/LUXURY/PERFECT LOCATION/PVT HOME @SE/Mandarin

10. ⭐HOME OF THE JAGUARS⭐private patio, w/POOL Near Downtown, NAS & Shopping

⭐HOME OF THE JAGUARS⭐private patio, w/POOL Near Downtown, NAS & Shopping
Westside
9.4 out of 10, Exceptional, (16 reviews)
"We came here for work. Place was clean and comfortable. Similar price to a hotel but way more space and comfort. We’ll definitely stay here again if we come back to this area."
United States
Tia J.
The price is NZ$460
includes taxes & fees
8 Oct - 9 Oct
⭐HOME OF THE JAGUARS⭐private patio, w/POOL Near Downtown, NAS & Shopping

11. 30 People Comfortably Gorgeous Home on Canal Boat Kayak access Two 85" & 75” TVs

30 People Comfortably Gorgeous Home on Canal Boat Kayak access Two 85" & 75” TVs
Fleming Island
9.2 out of 10, Wonderful, (33 reviews)
"A beautifully decorated, comfortable, and spacious property.The back porch was our favorite place to gather for visiting and viewing the canal activities. It has a claw footed tub in the Jack and Jill bathroom. A large game room is on the second floor. Also many extra beds are available. The kitchen is well appointed with every possible need close at hand."
United States
Carol G.
The price is NZ$2,711
includes taxes & fees
28 Sept - 29 Sept
30 People Comfortably Gorgeous Home on Canal Boat Kayak access Two 85" & 75” TVs

12. Single house: 12guests,4bds/2baths,large backyard.

Single house: 12guests,4bds/2baths,large backyard.
Jacksonville
9.8 out of 10, Exceptional, (49 reviews)
"Great place for big families and small children. "
United States
Maria R.
The price is NZ$841
includes taxes & fees
7 Oct - 8 Oct
Single house: 12guests,4bds/2baths,large backyard.

13. Sunset near the lake up to 12 guests,4bds,2baths

Sunset near the lake up to 12 guests,4bds,2baths
Westside
10.0 out of 10, Exceptional, (13 reviews)
"great for families "
United States
Dylan A.
The price is NZ$848
includes taxes & fees
27 Sept - 28 Sept
Sunset near the lake up to 12 guests,4bds,2baths

14. NEW Waterfront Retreat "The Creek House" RENT JETSKIS POOL TABLE Sleep 10 KAYAKS

NEW Waterfront Retreat "The Creek House" RENT JETSKIS POOL TABLE Sleep 10 KAYAKS
Middleburg
10.0 out of 10, Exceptional, (1 review)
"Beautiful home with a beautiful creek view. We thoroughly enjoyed our stay. We had a group of ladies who finally got a chance to get away for a kid free weekend. It was so relaxing and such a wonderful environment. There were kayaks and fishing poles available for our use but we had so much fun catching up we forgot to use them. The location was close enough to Jacksonville we could go to a candy making class at Sweet Pete’s then go back and relax. The host was very pleasant and checked in a...
United States
Jamie L.
The price is NZ$671
includes taxes & fees
27 Oct - 28 Oct
NEW Waterfront Retreat "The Creek House" RENT JETSKIS POOL TABLE Sleep 10 KAYAKS

15. King bed, Water Views, sleeps 8, TVs in every room, public pool.

King bed, Water Views, sleeps 8, TVs in every room, public pool.
Fruit Cove
10.0 out of 10, Exceptional, (32 reviews)
"great place to stay"
United States
sione f.
King bed, Water Views, sleeps 8, TVs in every room, public pool.

16. Magical Midsummer Night Glamping Loft w Bikes

Magical Midsummer Night Glamping Loft w Bikes
Northwest
10.0 out of 10, Exceptional, (9 reviews)
"It was Enchanting and the location perfect!"
United States
THC
The price is NZ$250
includes taxes & fees
28 Sept - 29 Sept
Magical Midsummer Night Glamping Loft w Bikes

17. ⭐Stylish & Cozy⭐ 2BR/2BA w/King Bed, Pool & Gym Nr I295 & Downtown

⭐Stylish & Cozy⭐ 2BR/2BA w/King Bed, Pool & Gym Nr I295 & Downtown
Westside
9.4 out of 10, Exceptional, (30 reviews)
"The host was amazing and communicated through the entire stay"
United States
Ebony R.
The price is NZ$529
includes taxes & fees
27 Sept - 28 Sept
⭐Stylish & Cozy⭐ 2BR/2BA w/King Bed, Pool & Gym Nr I295 & Downtown

18. Cosmic Quarters, Whole House, Sleeps 6

Cosmic Quarters, Whole House, Sleeps 6
Westside
9.8 out of 10, Exceptional, (14 reviews)
"House great nice and clean ,family loved it thanks again."
United States
tony s.
The price is NZ$552
includes taxes & fees
27 Oct - 28 Oct
Cosmic Quarters, Whole House, Sleeps 6

19. 1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed

1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed
Southside
9.4 out of 10, Exceptional, (33 reviews)
"Cool place to stay"
United States
Anonymous traveller
The price is NZ$110
includes taxes & fees
4 Oct - 5 Oct
1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed

20. The Van Zant House

The Van Zant House
3.5 star property
Westside
6.4 out of 10, (7 reviews)
"Always a great time ! "
United States
Katherine
The price is NZ$483
includes taxes & fees
26 Oct - 27 Oct
The Van Zant House
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Fleming Island Hotel Reviews

Find out more about Fleming Island

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Fleming Island holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Fleming Island. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Fleming Island. Seeing all the best attractions is bound to make you fall in love with Fleming Island. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Fleming Island short-term rentals, that won’t be hard to do.

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Frequently asked questions

Can I find holiday rentals in Fleming Island?

Yes, there are holiday rentals close to the most popular sights in Fleming Island, or you can select a more secluded option if you're looking for a relaxing stay. The shops and restaurants are several reasons why visitors like Fleming Island. Make sure you have time to check out the entertainment choices and football games during your trip.

What are some of the best holiday rentals that Fleming Island has to offer?

Private home @ Pristine neighborhood: This holiday home rental outside of Fleming Island offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Fleming Island?

With 5 Expedia holiday rentals, you're guaranteed to find just the right place for your Fleming Island stay.

What’s there to see and do in Fleming Island?

Little Jessie Island and Doctors Lake are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Eagle Harbor Golf Club and The Golf Club At Fleming Island.

What’s a holiday rental in Fleming Island like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Fleming Island. Holiday rentals provide amenities like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from shared hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for a small group gathering.