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

Fleming Island Vacation Rentals

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Check prices for these dates

In two weeks
4 Sep - 6 Sep
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Fleming Island vacation rentals

Outdoor dining

1. Rustic Owl w/ 2Kings In Fleming Island

Rustic Owl w/ 2Kings In Fleming Island
Fleming Island
10.0 out of 10, Exceptional, (40 reviews)
"The property and location and all amenities met our needs. "
United States
Karen Y.
The price is AED 742
AED 1,593 total
includes taxes & fees
24 Aug - 25 Aug
Rustic Owl w/ 2Kings In Fleming Island
Interior

2. 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, (32 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 AED 1,735
AED 5,458 total
includes taxes & fees
24 Aug - 25 Aug
30 People Comfortably Gorgeous Home on Canal Boat Kayak access Two 85" & 75” TVs
Exterior detail

3. Luxurious Home w/ Spectacular Glass Room & Patios

Luxurious Home w/ Spectacular Glass Room & Patios
Lakeside
9.8 out of 10, Exceptional, (182 reviews)
"Very nicely decorated … beds were comfortable, kitchen well equipped, beautiful neighborhood and very quiet. Well worth the cost … and host was wonderful."
United States
Trudie Ann M.
The price is AED 547
AED 1,393 total
includes taxes & fees
24 Aug - 25 Aug
Luxurious Home w/ Spectacular Glass Room & Patios
View from property

4. StudioRes by Marriott Jacksonville Orange Park

StudioRes by Marriott Jacksonville Orange Park
3.0 star property
Westside
8.6 out of 10, Excellent, (46 reviews)
"Beautiful room... wish there was breakfast"
United States
Marquessa
The price is AED 342
AED 388 total
includes taxes & fees
30 Aug - 31 Aug
StudioRes by Marriott Jacksonville Orange Park
Interior

5. Gorgeous circa 1875 Plantation House (in city)

Gorgeous circa 1875 Plantation House (in city)
Orange Park
9.8 out of 10, Exceptional, (93 reviews)
"Beautiful home"
United States
Barbara M.
The price is AED 657
AED 1,882 total
includes taxes & fees
24 Aug - 25 Aug
Gorgeous circa 1875 Plantation House (in city)
Smart TV

6. Ocean view /HugePool/17/i295/NAS: Up to 12guest/4beds2baths

Ocean view /HugePool/17/i295/NAS: Up to 12guest/4beds2baths
Orange Park
9.4 out of 10, Exceptional, (3 reviews)
"It will be very difficult to convince mate other places to this beautiful rental. The pool was huge and clean the property had everything we needed. Would surely stay again!! The host was easily to access"
United States
BILLIE
The price is AED 820
AED 2,205 total
includes taxes & fees
25 Aug - 26 Aug
Ocean view /HugePool/17/i295/NAS: Up to 12guest/4beds2baths
Coffee/tea maker, fridge, microwave, oven

7. ⭐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, (28 reviews)
"The host was amazing and communicated through the entire stay"
United States
Ebony R.
The price is AED 411
AED 1,112 total
includes taxes & fees
28 Aug - 29 Aug
⭐Stylish & Cozy⭐ 2BR/2BA w/King Bed, Pool & Gym Nr I295 & Downtown
Pool

8. 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.
Suite Peace- New luxury apartment near NAS JAX and Orange park
Terrace/patio

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

Single house: 12guests,4bds/2baths,large backyard.
Jacksonville
9.8 out of 10, Exceptional, (47 reviews)
"Great place for big families and small children. "
United States
Maria R.
The price is AED 579
AED 1,678 total
includes taxes & fees
24 Aug - 25 Aug
Single house: 12guests,4bds/2baths,large backyard.
1 bedroom, iron/ironing board, WiFi, bed sheets

10. 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 AED 268
AED 545 total
includes taxes & fees
23 Sep - 24 Sep
Cozy Private Entire Studio Suite Independent Guest Entrance
Smart TV, fireplace

11. 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 AED 479
AED 1,550 total
includes taxes & fees
25 Aug - 26 Aug
Sunset near the lake up to 12 guests,4bds,2baths
Property grounds

12. 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 AED 314
AED 654 total
includes taxes & fees
24 Aug - 25 Aug
Private Loft at a Working Show Barn ~ Pets Welcome!
Smart TV, fireplace

13. Spacious 4-bedroom house in welcoming Jacksonville with AC, WiFi

Spacious 4-bedroom house in welcoming Jacksonville with AC, WiFi
Westside
10.0 out of 10, Exceptional, (3 reviews)
"Amazing stay, beautiful home!"
United States
Joel L.
Spacious 4-bedroom house in welcoming Jacksonville with AC, WiFi
Coffee/tea maker, fridge, microwave, oven

14. Retreat the Marco - Heated Pool+Arcade Games Close to everything

Retreat the Marco - Heated Pool+Arcade Games Close to everything
Southside
10.0 out of 10, Exceptional, (16 reviews)
"It was a beautiful place to have your family with the pool and the games"
United States
Richard P.
The price is AED 1,451
AED 2,887 total
includes taxes & fees
23 Sep - 24 Sep
Retreat the Marco - Heated Pool+Arcade Games Close to everything
Interior

15. Pet friendly Comfortable 2 bedroom with huge yard and EV charging lvl1

Pet friendly Comfortable 2 bedroom with huge yard and EV charging lvl1
Westside
10.0 out of 10, Exceptional, (8 reviews)
"A modest but very comfortable and nicely equipped place in a quiet neighborhood. Communication with the host(s) was excellent, they were very helpful and proactive."
United States
Keith W.
The price is AED 404
AED 1,056 total
includes taxes & fees
24 Aug - 25 Aug
Pet friendly Comfortable 2 bedroom with huge yard and EV charging lvl1
Cookware/dishes/utensils

16. Vibrant Stay Near Museums and Beaches

Vibrant Stay Near Museums and Beaches
Southside
Vibrant Stay Near Museums and Beaches
Coffee/tea maker, fridge, microwave, oven

17. ⭐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 AED 336
AED 971 total
includes taxes & fees
2 Sep - 3 Sep
⭐HOME OF THE JAGUARS⭐private patio, w/POOL Near Downtown, NAS & Shopping
Interior

18. Cozy Treetop Hideaway

Cozy Treetop Hideaway
Northwest
10.0 out of 10, Exceptional, (106 reviews)
"Good location, nice amenities"
United States
Sue
The price is AED 298
AED 557 total
includes taxes & fees
24 Aug - 25 Aug
Cozy Treetop Hideaway
Smart TV

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
9.4 out of 10, Exceptional, (45 reviews)
"Great location and stay"
United States
David E.
The price is AED 393
AED 721 total
includes taxes & fees
24 Aug - 25 Aug
Golf & Spa Resort Immaculate Paradise - St. Augustine w/ pools & hot tub
3 bedrooms, WiFi, bed sheets

20. Cosmic Quarters, Whole House, Sleeps 6

Cosmic Quarters, Whole House, Sleeps 6
Westside
9.8 out of 10, Exceptional, (12 reviews)
"House great nice and clean ,family loved it thanks again."
United States
tony s.
The price is AED 423
AED 1,031 total
includes taxes & fees
24 Aug - 25 Aug
Cosmic Quarters, Whole House, Sleeps 6
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
"The room was nice and clean. The staff was amazing!"
Chelsea 1-night trip
Posted less than an hour ago
Hyatt Regency Jacksonville

Frequently asked questions

Can I find vacation rentals in Fleming Island?

Yes, we give you a choice of vacation rentals near popular local attractions in Fleming Island, or you can select a secluded option if you'd like a relaxing place to 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 vacation home rentals in Fleming Island?

Cozy Timuquana Townhome Private Yard & Parking Family and Pet-friendly: Visitors like this Fleming Island vacation home rental. It offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Fleming Island?

With 7 Expedia vacation rentals, you're sure to find just the right place for your Fleming Island stay.

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

Doctors Lake and Little Jessie Island 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 vacation rental in Fleming Island like?

A vacation rental is a private property you can book for a few weeks or just a few days in Fleming Island. Vacation rentals feature extras like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from shared hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for a family trip or a small group gathering.