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

Fleming Island Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Fleming Island holiday rentals

A covered patio with a table and chairs, a window, and a door.

1. Rustic Owl w/ 2Kings In Fleming Island

Rustic Owl w/ 2Kings In Fleming Island
Fleming Island
9.8 out of 10, Exceptional, (43 reviews)
"Great location. Property was well stocked, clean and comfortable."
United States
Joe T.
The price is AU$601
includes taxes & fees
25 Oct - 26 Oct
Rustic Owl w/ 2Kings In Fleming Island
A house entrance with a red door, a welcome mat, and a doormat.

2. Luxurious Home w/ Spectacular Glass Room & Patios

Luxurious Home w/ Spectacular Glass Room & Patios
Lakeside
9.8 out of 10, Exceptional, (186 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 AU$479
includes taxes & fees
25 Oct - 26 Oct
Luxurious Home w/ Spectacular Glass Room & Patios
A modern building with a storefront labeled "STUDIORES" and the number "8045".

3. StudioRes by Marriott Jacksonville Orange Park

StudioRes by Marriott Jacksonville Orange Park
3.0 star property
Westside
8.6 out of 10, Excellent, (61 reviews)
"Courteous staff, clean room, good parking"
United States
Marion
The price is AU$122
includes taxes & fees
8 Nov - 9 Nov
StudioRes by Marriott Jacksonville Orange Park
A swimming pool with lounge chairs, palm trees, and a building in the background.

4. 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, (20 reviews)
"Convenient location. Very comfortable. "
United States
Aimee G.
The price is AU$292
includes taxes & fees
22 Oct - 23 Oct
Suite Peace- New luxury apartment near NAS JAX and Orange park
A wooden porch leading to a house with a front door, a lamp, and a doormat.

5. Gorgeous circa 1875 Plantation House (in city)

Gorgeous circa 1875 Plantation House (in city)
Orange Park
9.8 out of 10, Exceptional, (97 reviews)
"Our families enjoyed this lovely home. Everything is clean, the beds are comfy, plenty of towels and a well equipped kitchen. The grounds are lovely and well kept. Although it was a little too warm to sit outside, there were several inviting areas on the wrap around shaded porch. The host is very congenial and responsive. We would stay here again."
United States
Cheryl A.
The price is AU$650
includes taxes & fees
22 Oct - 23 Oct
Gorgeous circa 1875 Plantation House (in city)
A modern kitchen with granite countertops, stainless steel appliances, and pendant lighting.

6. ⭐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 AU$369
includes taxes & fees
22 Oct - 23 Oct
⭐HOME OF THE JAGUARS⭐private patio, w/POOL Near Downtown, NAS & Shopping
A grand staircase with white balusters and wooden steps leading to an upper level.

7. 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, (34 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 AU$2,159
includes taxes & fees
26 Oct - 27 Oct
30 People Comfortably Gorgeous Home on Canal Boat Kayak access Two 85" & 75” TVs
A modern hotel room with two beds, white bedding, and a yellow throw blanket.

8. 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 AU$203
includes taxes & fees
25 Oct - 26 Oct
Cozy Private Entire Studio Suite Independent Guest Entrance
A hotel room with two beds, a blue armchair, a small round ottoman, a kitchenette, and a bathroom.

9. Cozy, private, small guesthouse

Cozy, private, small guesthouse
Westside
10.0 out of 10, Exceptional, (2 reviews)
"perfect clean space very peaceful and easy communication ..would def visit again ."
United States
Marlene A.
The price is AU$239
includes taxes & fees
23 Oct - 24 Oct
Cozy, private, small guesthouse
A rustic building with a wooden staircase leading to a deck, a covered area with a sign reading "GRAND LANDINGS," and outdoor seating.

10. 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, (28 reviews)
"Tracy was a great host I enjoyed talking with her. The loft was great the beds are comfortable very clean and has everything you need for a short or long stay I will definitely be back and this would be my first choice to stay at."
United States
Tina S.
The price is AU$257
includes taxes & fees
28 Oct - 29 Oct
Private Loft at a Working Show Barn ~ Pets Welcome!
A modern kitchen with white cabinets, a wooden island, and a bar stool.

11. Coral Reef Retreat 30 min to Beach High Speed Wi-Fi

Coral Reef Retreat 30 min to Beach High Speed Wi-Fi
Westside
The price is AU$478
includes taxes & fees
25 Oct - 26 Oct
Coral Reef Retreat 30 min to Beach High Speed Wi-Fi
A dirt road leading to a gated area with trees and a building in the distance.

12. Tiny Farm: Charming Tiny House in the Country

Tiny Farm: Charming Tiny House in the Country
Green Cove Springs
The price is AU$161
includes taxes & fees
23 Oct - 24 Oct
Tiny Farm: Charming Tiny House in the Country
A lobby with a sofa, armchair, and a table with a vase.

13. 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 AU$91
includes taxes & fees
29 Oct - 30 Oct
1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed
A nighttime view of a hotel with a swimming pool, palm trees, and outdoor seating areas.

14. Mi CASA es su CASA

Mi CASA es su CASA
St. Augustine
10.0 out of 10, Exceptional, (104 reviews)
"Great time and a very relaxing place to stay!"
United States
Debbie B.
The price is AU$313
includes taxes & fees
25 Oct - 26 Oct
Mi CASA es su CASA
A house with a small porch, a door, and a staircase leading to the main entrance.

15. Cozy Treetop Hideaway

Cozy Treetop Hideaway
Northwest
10.0 out of 10, Exceptional, (107 reviews)
"Good location, nice amenities"
United States
Sue
The price is AU$226
includes taxes & fees
22 Oct - 23 Oct
Cozy Treetop Hideaway
A tray with multiple cups and a bottle of water on a wooden surface.

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 AU$200
includes taxes & fees
22 Oct - 23 Oct
Magical Midsummer Night Glamping Loft w Bikes
A conservatory with a glass roof, a potted plant, and a bench.

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

Single house: 12guests,4bds/2baths,large backyard.
Jacksonville
9.8 out of 10, Exceptional, (50 reviews)
"Great place for big families and small children. "
United States
Maria R.
The price is AU$710
includes taxes & fees
22 Oct - 23 Oct
Single house: 12guests,4bds/2baths,large backyard.
A bedroom with a bed, a desk, a chair, a window with blue shutters, a painting of a coastal scene, and a round mirror on the wall.

18. A Santorini Escape w Bikes in Walkable Riverside

A Santorini Escape w Bikes in Walkable Riverside
Northwest
10.0 out of 10, Exceptional, (6 reviews)
"Fantastic stay! Very cute and well taken care of property. Hosts were extremely nice, attentive and all around awesome! Will absolutely recommend this to others and I will be planning to stay again in the future."
United States
Jared C.
The price is AU$232
includes taxes & fees
26 Oct - 27 Oct
A Santorini Escape w Bikes in Walkable Riverside
An indoor patio area with a tiled floor, a wrought iron gate, and a wall decorated with seashells.

19. Golf & Spa Resort Immaculate Paradise - St. Augustine w/ pools & hot tub

Golf & Spa Resort Immaculate Paradise - St. Augustine w/ pools & hot tub
St. Augustine
9.6 out of 10, Exceptional, (47 reviews)
"Great location and stay"
United States
David E.
The price is AU$281
includes taxes & fees
16 Nov - 17 Nov
Golf & Spa Resort Immaculate Paradise - St. Augustine w/ pools & hot tub
A living room with a dark grey sofa, a coffee table, a flat-screen TV, and a large window with blinds.

20. Spacious Retreat: Projector & Pool Table

Spacious Retreat: Projector & Pool Table
Westside
9.8 out of 10, Exceptional, (7 reviews)
"We had a wonderful stay. No problems. Highly recommend. "
United Kingdom
Thomas K.
The price is AU$464
includes taxes & fees
25 Oct - 26 Oct
Spacious Retreat: Projector & Pool Table
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

Hyatt Regency Jacksonville

Hyatt Regency Jacksonville

10/10 Excellent
"Hotel was clean and smelled pleasant! Beautiful views of downtown Jacksonville!"
Christa 1-night trip
Posted less than an hour ago
Hyatt Regency Jacksonville

Find out more about Fleming Island

Everything you need to know about Fleming Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Fleming Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Fleming Island holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Fleming Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Fleming Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Fleming Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Fleming Island holiday rentals we have selected for you start as low as AU$91 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Fleming Island rentals

At Expedia, we put the best Fleming Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Fleming Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Fleming Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Fleming Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Beautiful relaxing and Spacious 3 bedroom 2 bathhouse close to the beach,: This holiday home rental outside of Fleming Island has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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.