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
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

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 NZ$734
includes taxes & fees
1 Dec - 2 Dec
Rustic Owl w/ 2Kings In Fleming Island
A modern building with a storefront labeled "STUDIORES" and the number "8045".

2. StudioRes by Marriott Jacksonville Orange Park

StudioRes by Marriott Jacksonville Orange Park
3.0 star property
Westside
8.6 out of 10, Excellent, (75 reviews)
"Super clean, everything is new, I loved this place!"
United States
Diana
The price is NZ$161
includes taxes & fees
15 Nov - 16 Nov
StudioRes by Marriott Jacksonville Orange Park
A wooden porch leading to a house with a front door, a lamp, and a doormat.

3. Gorgeous circa 1875 Plantation House (in city)

Gorgeous circa 1875 Plantation House (in city)
Orange Park
9.8 out of 10, Exceptional, (97 reviews)
"Great for medium size family events."
United States
Davin O.
The price is NZ$791
includes taxes & fees
12 Nov - 13 Nov
Gorgeous circa 1875 Plantation House (in city)
A grand staircase with white balusters and wooden steps leading to an upper level.

4. 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)
"We had a great stay! The home was clean, comfortable, and exactly as described. Check-in was easy, communication with the host was excellent, and everything we needed was provided. We’d definitely stay here again and would recommend it to anyone visiting the area."
United States
Alex C.
The price is NZ$2,690
includes taxes & fees
15 Nov - 16 Nov
30 People Comfortably Gorgeous Home on Canal Boat Kayak access Two 85" & 75” TVs
A modern kitchen with granite countertops, stainless steel appliances, and pendant lighting.

5. ⭐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$451
includes taxes & fees
11 Nov - 12 Nov
⭐HOME OF THE JAGUARS⭐private patio, w/POOL Near Downtown, NAS & Shopping
A modern hotel room with two beds, white bedding, and a yellow throw blanket.

6. Cozy Private Entire Studio Suite Independent Guest Entrance

Cozy Private Entire Studio Suite Independent Guest Entrance
Westside
9.4 out of 10, Exceptional, (22 reviews)
"Nice and cozy!!Easy access, clean and comfortable!!Will book again "
United States
Shantrill G.
The price is NZ$234
includes taxes & fees
11 Nov - 12 Nov
Cozy Private Entire Studio Suite Independent Guest Entrance
A rustic building with a wooden staircase leading to a deck, a covered area with a sign reading "GRAND LANDINGS," and outdoor seating.

7. 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 NZ$304
includes taxes & fees
15 Nov - 16 Nov
Private Loft at a Working Show Barn ~ Pets Welcome!
A conservatory with a glass roof, a potted plant, and a bench.

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

Single house: 12guests,4bds/2baths,large backyard.
Jacksonville
10.0 out of 10, Exceptional, (51 reviews)
"Great place for big families and small children. "
United States
Maria R.
The price is NZ$859
includes taxes & fees
11 Nov - 12 Nov
Single house: 12guests,4bds/2baths,large backyard.
A living room with a brick fireplace, a blue armchair, a wooden cabinet, and a ceiling fan.

9. 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
7 Dec - 8 Dec
The Van Zant House
A hallway with a patterned rug, a console table with a vase, a mirror, and a door leading to another room.

10. Soul O Studio - Walkable Riverside w Bikes

Soul O Studio - Walkable Riverside w Bikes
Northwest
9.6 out of 10, Exceptional, (11 reviews)
"Our stay was wonderful. It was welcoming, comfortable, convenient, and had everything we needed. We will definitely stay there again!"
United States
Karen W.
The price is NZ$269
includes taxes & fees
12 Nov - 13 Nov
Soul O Studio - Walkable Riverside w Bikes
A lobby with a sofa, armchair, and a table with a vase.

11. 1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed

1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed
Southside
9.0 out of 10, Wonderful, (36 reviews)
"Cool place to stay"
United States
Anonymous traveller
The price is NZ$107
includes taxes & fees
2 Dec - 3 Dec
1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed
A house with a small porch, a door, and a staircase leading to the main entrance.

12. Cozy Treetop Hideaway

Cozy Treetop Hideaway
Northwest
10.0 out of 10, Exceptional, (107 reviews)
"Our host has been amazing and the until had everything we needed and more and was extremely clean. Would definitely recommend."
United States
Melissa P.
The price is NZ$264
includes taxes & fees
11 Nov - 12 Nov
Cozy Treetop Hideaway
A living room with a dark grey sofa, a coffee table, a flat-screen TV, and a large window with blinds.

13. Ortega | Projector & Pool Table

Ortega | 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 NZ$642
includes taxes & fees
9 Dec - 10 Dec
Ortega | Projector & Pool Table
A cozy interior with a wooden ceiling, a brown leather sofa, a world map on the wall, and a sliding glass door.

14. Tiny Farm: Charming Tiny House in the Country

Tiny Farm: Charming Tiny House in the Country
Green Cove Springs
The price is NZ$183
includes taxes & fees
11 Nov - 12 Nov
Tiny Farm: Charming Tiny House in the Country
A covered patio with a glass table and chairs, overlooking a landscaped garden with a pond and palm trees.

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.
The price is NZ$1,183
includes taxes & fees
23 Nov - 24 Nov
King bed, Water Views, sleeps 8, TVs in every room, public pool.
A living room with a sofa, coffee table, TV, fireplace, and a dining area in the background.

16. 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.
Sunset near the lake up to 12 guests,4bds,2baths
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

17. Vibrant Stay Near Museums and Beaches

Vibrant Stay Near Museums and Beaches
Southside
The price is NZ$556
includes taxes & fees
11 Nov - 12 Nov
Vibrant Stay Near Museums and Beaches
A cozy room with a green artificial grass floor, a round table, and wicker chairs. There is a television on the left and a white cabinet on the right.

18. Magical Midsummer Night Glamping Loft w Bikes

Magical Midsummer Night Glamping Loft w Bikes
Northwest
10.0 out of 10, Exceptional, (10 reviews)
"It was Enchanting and the location perfect!"
United States
THC
The price is NZ$249
includes taxes & fees
11 Nov - 12 Nov
Magical Midsummer Night Glamping Loft w Bikes
A compact kitchen with a sliding barn door, a coffee maker, a microwave, and a small trash bin.

19. Cozy 1-bedroom Tiny Home on Peaceful Blueberry Farm.

Cozy 1-bedroom Tiny Home on Peaceful Blueberry Farm.
Jacksonville
8.0 out of 10, Very good, (1 review)
"The only issue we had was that the water had a terrible smell, but that has nothing to do with the owner of the property. Other than the water, it was a nice little tiny house that was perfect for our one-night stay in Jacksonville. It was as the listing described and the owner was very friendly when we messaged! I enjoyed how secluded it was and it was a quiet spot to rest. Would highly recommend if you are okay with things being a little tighter than average!"
United States
Emily F.
The price is NZ$185
includes taxes & fees
1 Dec - 2 Dec
Cozy 1-bedroom Tiny Home on Peaceful Blueberry Farm.
A modern kitchen with white cabinetry, a large island, stainless steel appliances, and pendant lighting.

20. 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
9.6 out of 10, Exceptional, (5 reviews)
"Absolutely gorgeous property!! House is very spacious and cozy! Back porch is screened in so no bugs can bother you. Grocery store and shopping are 5 minutes away. A great weekend getaway!"
United States
Vicki
The price is NZ$795
includes taxes & fees
23 Nov - 24 Nov
NEW Waterfront Retreat "The Creek House" RENT JETSKIS POOL TABLE Sleep 10 KAYAKS
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

La Quinta Inn & Suites by Wyndham Jacksonville Butler Blvd

La Quinta Inn & Suites by Wyndham Jacksonville Butler Blvd

10/10 Excellent
"Staff was extremely friendly and helpful, breakfast was excellent had a great stay."
Rondell 3-night trip
Posted 2 hours ago
La Quinta Inn & Suites by Wyndham Jacksonville Butler Blvd

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 favorite 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 depends 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 NZ$109 per night. Entering your travel dates in the search wizard you might find 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. 

Explore a world of travel with Expedia

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.