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

Holiday Homes in Fleming Island

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Fleming Island holiday homes

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
10.0 out of 10, Exceptional, (40 reviews)
"Great location. Property was well stocked, clean and comfortable."
United States
Joe T.
The price is NZ$731
includes taxes & fees
8 Sept - 9 Sept
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, (182 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$626
includes taxes & fees
8 Sept - 9 Sept
Luxurious Home w/ Spectacular Glass Room & Patios
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, (94 reviews)
"Beautiful home"
United States
Barbara M.
The price is NZ$863
includes taxes & fees
9 Sept - 10 Sept
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, (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 NZ$2,638
includes taxes & fees
21 Sept - 22 Sept
30 People Comfortably Gorgeous Home on Canal Boat Kayak access Two 85" & 75” TVs
A stable with horses, hay bales, and a wooden floor.

5. 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$303
includes taxes & fees
10 Sept - 11 Sept
Private Loft at a Working Show Barn ~ Pets Welcome!
A living room with two black leather sofas, a glass coffee table, and a beige armchair. There is a red and beige rug on the floor.

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

AWESOME/LUXURY/PERFECT LOCATION/PVT HOME @SE/Mandarin
Del Rio
10.0 out of 10, Exceptional, (53 reviews)
"Great property. Close to lots of things Clean, and very spacious."
United States
Jon C.
The price is NZ$565
includes taxes & fees
8 Oct - 9 Oct
AWESOME/LUXURY/PERFECT LOCATION/PVT HOME @SE/Mandarin
A living room with a sofa, coffee table, TV, fireplace, and a dining area in the background.

7. 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$823
includes taxes & fees
12 Sept - 13 Sept
Sunset near the lake up to 12 guests,4bds,2baths
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
9.8 out of 10, Exceptional, (48 reviews)
"Great place for big families and small children. "
United States
Maria R.
The price is NZ$823
includes taxes & fees
8 Sept - 9 Sept
Single house: 12guests,4bds/2baths,large backyard.
A modern kitchen with dark wood cabinets, a stainless steel refrigerator, and a built-in sink with a dish rack.

9. Ortega Duplex Unit w/ Kayaks & EV Charger

Ortega Duplex Unit w/ Kayaks & EV Charger
Westside
9.0 out of 10, Wonderful, (2 reviews)
"Property was very nice and clean. Tyler was a great help. Shower was the only kinda let down of our stay"
United States
Darrick S.
Ortega Duplex Unit w/ Kayaks & EV Charger
A modern living room with a large flat-screen TV displaying a cityscape. There is a sofa, a coffee table, and a small side table.

10. 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 NZ$603
includes taxes & fees
6 Oct - 7 Oct
Spacious Retreat: Projector & Pool Table
An aerial view of a resort with a large swimming pool, surrounded by palm trees and a small lake.

11. 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.
A dining area with a wooden table and chairs, a decorative heart sculpture, and a view of the outdoors.

12. 2Bedroom-Special @Graceful House

2Bedroom-Special @Graceful House
Westside
The price is NZ$565
includes taxes & fees
14 Sept - 15 Sept
2Bedroom-Special @Graceful House
A modern kitchen with wooden flooring, a built-in oven, and a refrigerator.

13. 2-bedroom townhome in Bartram Park, full remote work set up.

2-bedroom townhome in Bartram Park, full remote work set up.
Jacksonville
8.4 out of 10, Very good, (6 reviews)
"Was a convenient stop for our stay in town."
United States
Jeni M.
The price is NZ$454
includes taxes & fees
14 Sept - 15 Sept
2-bedroom townhome in Bartram Park, full remote work set up.
A modern living room with a sofa, a dining area with a table and chairs, a kitchen with white cabinets, and a TV in the background.

14. 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 NZ$1,242
includes taxes & fees
13 Sept - 14 Sept
Ocean view /HugePool/17/i295/NAS: Up to 12guest/4beds2baths
A modern living room with a sofa, coffee table, fireplace, and a large TV screen displaying a beach scene.

15. Mandarin Retreat - Entire Home

Mandarin Retreat - Entire Home
jacksonville
10.0 out of 10, Exceptional, (4 reviews)
"All around awesome place . Stayed for 4 nights. 10/10"
United States
Drew B.
The price is NZ$574
includes taxes & fees
8 Sept - 9 Sept
Mandarin Retreat - Entire Home
A covered outdoor area with a wooden deck, wicker furniture, and a table with chairs.

16. 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
The price is NZ$649
includes taxes & fees
14 Sept - 15 Sept
NEW Waterfront Retreat "The Creek House" RENT JETSKIS POOL TABLE Sleep 10 KAYAKS
A modern kitchen with a central island, dark cabinetry, and stainless steel appliances.

17. Fantastic 5-bedroom house near Oakleaf Shopping center

Fantastic 5-bedroom house near Oakleaf Shopping center
Middleburg
The price is NZ$709
includes taxes & fees
8 Sept - 9 Sept
Fantastic 5-bedroom house near Oakleaf Shopping center
A corner with a wooden table and chairs, a potted plant, and a view of a residential area through a glass door.

18. Lakefront |Long Term Friendly |Pets|Cozy Fireplace

Lakefront |Long Term Friendly |Pets|Cozy Fireplace
Southside
The price is NZ$448
includes taxes & fees
9 Sept - 10 Sept
Lakefront |Long Term Friendly |Pets|Cozy Fireplace
A modern kitchen with grey cabinets, a stainless steel refrigerator, a microwave, and a coffee maker.

19. La Casita by Amarelys and lazaro

La Casita by Amarelys and lazaro
Southside
10.0 out of 10, Exceptional, (9 reviews)
"Was very clean and comfortable "
United States
Natasha M.
La Casita by Amarelys and lazaro
A spacious living room with a white sofa, wooden flooring, and a dining area with chairs and a table.

20. Central Avenues Central Cozy 3BR@ Water

Central Avenues Central Cozy 3BR@ Water
Jacksonville
9.4 out of 10, Exceptional, (3 reviews)
"Great space, we only stayed 1 night but it was comfy! Hosts communicate great! "
United States
Carolyne H.
Central Avenues Central Cozy 3BR@ Water
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 staff from valet, check in, room service were just very friendly and kind."
Aaron 3-night trip
Posted 1 hour ago
Hyatt Regency Jacksonville

Find out more about Fleming Island

Fleming Island Holiday Homes information

Number of reviews
499
Accommodation
772 Holiday Homes
Lowest Price
NZ$303
Highest Price
NZ$2,610