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Fleming Island Vacation Rentals

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Our top choices for Fleming Island vacation rentals

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 CA $280
CA $598 total
includes taxes & fees
Aug 24 - Aug 25
Rustic Owl w/ 2Kings In Fleming Island

2. StudioRes by Marriott Jacksonville Orange Park

StudioRes by Marriott Jacksonville Orange Park
3.0 star property
Westside
8.6 out of 10, Excellent, (44 reviews)
"Great place!"
United States
Leslie
The price is CA $122
CA $139 total
includes taxes & fees
Aug 20 - Aug 21
StudioRes by Marriott Jacksonville Orange Park

3. Luxurious Home w/ Spectacular Glass Room & Patios

Luxurious Home w/ Spectacular Glass Room & Patios
Lakeside
9.8 out of 10, Exceptional, (181 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 CA $207
CA $524 total
includes taxes & fees
Aug 23 - Aug 24
Luxurious Home w/ Spectacular Glass Room & Patios

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, (19 reviews)
"Convenient location. Very comfortable. "
United States
Aimee G.
The price is CA $81
CA $254 total
includes taxes & fees
Aug 24 - Aug 25
Suite Peace- New luxury apartment near NAS JAX and Orange park

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 CA $248
CA $704 total
includes taxes & fees
Aug 18 - Aug 19
Gorgeous circa 1875 Plantation House (in city)

6. 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)
"Quiet and very clean. We had a very relaxing stay."
United States
Terry M.
The price is CA $91
CA $194 total
includes taxes & fees
Aug 18 - Aug 19
Cozy Private Entire Studio Suite Independent Guest Entrance

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 CA $162
CA $427 total
includes taxes & fees
Aug 18 - Aug 19
⭐Stylish & Cozy⭐ 2BR/2BA w/King Bed, Pool & Gym Nr I295 & Downtown

8. 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 CA $119
CA $247 total
includes taxes & fees
Aug 18 - Aug 19
Private Loft at a Working Show Barn ~ Pets Welcome!

9. 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 CA $613
CA $1,968 total
includes taxes & fees
Aug 19 - Aug 20
30 People Comfortably Gorgeous Home on Canal Boat Kayak access Two 85" & 75” TVs

10. 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)
"Nice, quiet residential area close to St. Joseph’s Church. Home is very clean and spacious. The backyard is beautiful. The living room has plenty of comfortable seating, which we loved. Close to everything. Host was great! Check in and check out very easy! Thank you!"
United States
Toni R.
AWESOME/LUXURY/PERFECT LOCATION/PVT HOME @SE/Mandarin

11. 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 CA $310
CA $829 total
includes taxes & fees
Aug 18 - Aug 19
Ocean view /HugePool/17/i295/NAS: Up to 12guest/4beds2baths

12. 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 CA $181
CA $584 total
includes taxes & fees
Aug 18 - Aug 19
Sunset near the lake up to 12 guests,4bds,2baths

13. 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 CA $219
CA $631 total
includes taxes & fees
Aug 18 - Aug 19
Single house: 12guests,4bds/2baths,large backyard.

14. 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 CA $224
CA $477 total
includes taxes & fees
Aug 18 - Aug 19
Mandarin Retreat - Entire Home

15. ⭐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)
"The apartment was exactly what we needed for our weekend stay in Jacksonville. We didn't do any cooking but it had all the necessary cookware and dishes should we have decided to eat in. It was clean and very comfortable."
United States
Danielle L.
The price is CA $127
CA $365 total
includes taxes & fees
Sep 2 - Sep 3
⭐HOME OF THE JAGUARS⭐private patio, w/POOL Near Downtown, NAS & Shopping

16. Ortega Farms Duplex: Projector & Pool Table

Ortega Farms Duplex: 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 CA $144
CA $485 total
includes taxes & fees
Sep 15 - Sep 16
Ortega Farms Duplex: Projector & Pool Table

17. 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 CA $99
CA $390 total
includes taxes & fees
Aug 18 - Aug 19
The Van Zant House

18. 1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed

1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed
Southside
9.8 out of 10, Exceptional, (30 reviews)
"Cool place to stay"
United States
Anonymous traveller
The price is CA $77
CA $88 total
includes taxes & fees
Aug 18 - Aug 19
1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed

19. 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 CA $140
CA $380 total
includes taxes & fees
Aug 18 - Aug 19
Pet friendly Comfortable 2 bedroom with huge yard and EV charging lvl1

20. 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 CA $149
CA $271 total
includes taxes & fees
Aug 18 - Aug 19
Golf & Spa Resort Immaculate Paradise - St. Augustine w/ pools & hot tub
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

Find out more about Fleming Island

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Fleming Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.