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
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Fleming Island vacation 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 ￥31,827
￥65,033 total
includes taxes & fees
Nov 23 - Nov 24
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)
"Thank you for a wonderful stay!"
United States
Katherine B.
The price is ￥19,399
￥51,722 total
includes taxes & fees
Nov 16 - Nov 17
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, (73 reviews)
"Super clean, everything is new, I loved this place!"
United States
Diana
The price is ￥12,000
￥13,620 total
includes taxes & fees
Nov 8 - Nov 9
StudioRes by Marriott Jacksonville Orange Park
A wooden porch leading to a house with a front door, a lamp, and a doormat.

4. 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 ￥22,845
￥70,310 total
includes taxes & fees
Nov 9 - Nov 10
Gorgeous circa 1875 Plantation House (in city)
A grand staircase with white balusters and wooden steps leading to an upper level.

5. 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 ￥88,628
￥239,069 total
includes taxes & fees
Nov 4 - Nov 5
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.

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 ￥15,078
￥40,514 total
includes taxes & fees
Nov 9 - Nov 10
⭐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.

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 ￥10,352
￥20,794 total
includes taxes & fees
Nov 9 - Nov 10
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.

8. 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 ￥13,077
￥24,781 total
includes taxes & fees
Nov 4 - Nov 5
Cozy, private, small guesthouse
A stable with horses, hay bales, and a wooden floor.

9. 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 ￥13,500
￥26,853 total
includes taxes & fees
Nov 4 - Nov 5
Private Loft at a Working Show Barn ~ Pets Welcome!
A hotel with a modern design, featuring a large glass facade, palm trees, and a well-maintained lawn.

10. 1 Queen Bed | Non-Smoking, Kitchen

1 Queen Bed | Non-Smoking, Kitchen
Southside
10.0 out of 10, Exceptional, (6 reviews)
The price is ￥8,419
￥9,907 total
includes taxes & fees
Nov 8 - Nov 9
1 Queen Bed | Non-Smoking, Kitchen
A reception desk with a staff member, a guest, and a child.

11. 1 Queen Bed | Smoking, Kitchen

1 Queen Bed | Smoking, Kitchen
Jacksonville
10.0 out of 10, Exceptional, (6 reviews)
The price is ￥7,501
￥8,865 total
includes taxes & fees
Nov 9 - Nov 10
1 Queen Bed | Smoking, Kitchen
A compact kitchen with a wooden ceiling, a television mounted above the counter, and a dining area with a table and chairs.

12. Tiny Farm: Charming Tiny House in the Country

Tiny Farm: Charming Tiny House in the Country
Green Cove Springs
The price is ￥12,762
￥16,249 total
includes taxes & fees
Nov 10 - Nov 11
Tiny Farm: Charming Tiny House in the Country
A living room with a brick fireplace, a blue armchair, a wooden cabinet, and a ceiling fan.

13. 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 ￥10,001
￥42,929 total
includes taxes & fees
Dec 1 - Dec 2
The Van Zant House
A lobby with a sofa, armchair, and a table with a vase.

14. 1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed

1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed
Southside
9.0 out of 10, Wonderful, (35 reviews)
"Cool place to stay"
United States
Anonymous traveler
The price is ￥8,466
￥9,609 total
includes taxes & fees
Nov 5 - Nov 6
1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed
A compact kitchen with a sliding barn door, a coffee maker, a microwave, and a small trash bin.

15. 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 ￥11,344
￥16,425 total
includes taxes & fees
Nov 9 - Nov 10
Cozy 1-bedroom Tiny Home on Peaceful Blueberry Farm.
A nighttime view of a hotel with a swimming pool, palm trees, and outdoor seating areas.

16. 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 ￥11,817
￥30,157 total
includes taxes & fees
Nov 5 - Nov 6
Mi CASA es su CASA
A dining table set with a vase of blue flowers, plates, and cutlery.

17. 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 ￥13,471
￥23,440 total
includes taxes & fees
Nov 4 - Nov 5
Cozy Treetop Hideaway
An indoor patio area with a tiled floor, a wrought iron gate, and a wall decorated with seashells.

18. 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, (48 reviews)
"Great location and stay"
United States
David E.
The price is ￥16,875
￥29,492 total
includes taxes & fees
Nov 5 - Nov 6
Golf & Spa Resort Immaculate Paradise - St. Augustine w/ pools & hot tub
An aerial view of a resort with a large swimming pool, surrounded by palm trees and a small lake.

19. 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 ￥46,795
￥104,629 total
includes taxes & fees
Nov 4 - Nov 5
King bed, Water Views, sleeps 8, TVs in every room, public pool.
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.

20. 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 ￥10,504
￥21,882 total
includes taxes & fees
Nov 4 - Nov 5
Magical Midsummer Night Glamping Loft w Bikes
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
"Excellent visit, everything was great!"
jeromie 2-night trip
Posted 12 hours ago
Hyatt Regency Jacksonville

Find out more about Fleming Island

Search for holiday rentals in Fleming Island on Expedia! You can easily find your home rentals, villas, holiday apartments in Fleming Island using one of the methods below:

  • View our selection of featured holiday rentals in Fleming Island
  • Use the map to find apartments and other holiday homes in the Fleming Island neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Fleming Island while they last

Look no further and take a look at our great range of rental properties in Fleming Island!

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?

Beautiful relaxing and Spacious 3 bedroom 2 bathhouse close to the beach,: Visitors like this Fleming Island vacation home rental. It has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many vacation rentals are there in Fleming Island?

With 5 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?

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 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.