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.
$360 nightly
The price is $403
Nov 15 - Nov 16
Total with taxes and fees
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
$89 nightly
The price is $101
Nov 8 - Nov 9
Total with taxes and fees
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)
"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.
$389 nightly
The price is $435
Nov 9 - Nov 10
Total with taxes and fees
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.
$1,322 nightly
The price is $1,479
Nov 8 - Nov 9
Total with taxes and fees
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.
$223 nightly
The price is $251
Nov 9 - Nov 10
Total with taxes and fees
⭐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, (21 reviews)
"Nice and cozy!!Easy access, clean and comfortable!!Will book again "
United States
Shantrill G.
$115 nightly
The price is $129
Nov 9 - Nov 10
Total with taxes and fees
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.
$149 nightly
The price is $166
Nov 15 - Nov 16
Total with taxes and fees
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.
$422 nightly
The price is $476
Nov 9 - Nov 10
Total with taxes and fees
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
$255 nightly
The price is $277
Nov 8 - Nov 9
Total with taxes and fees
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.
$130 nightly
The price is $146
Nov 8 - Nov 9
Total with taxes and fees
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 traveler
$52 nightly
The price is $59
Nov 26 - Nov 27
Total with taxes and fees
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.
$125 nightly
The price is $141
Nov 8 - Nov 9
Total with taxes and fees
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 Pool Table and Projector

Ortega Pool Table and Projector
Westside
9.8 out of 10, Exceptional, (7 reviews)
"We had a wonderful stay. No problems. Highly recommend. "
United Kingdom
Thomas K.
$289 nightly
The price is $326
Nov 9 - Nov 10
Total with taxes and fees
Ortega Pool Table and Projector
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
$91 nightly
The price is $101
Nov 10 - Nov 11
Total with taxes and fees
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.
$623 nightly
The price is $691
Nov 23 - Nov 24
Total with taxes and fees
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.
$419 nightly
The price is $473
Nov 11 - Nov 12
Total with taxes and fees
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
$301 nightly
The price is $301
Nov 8 - Nov 9
Total with taxes and fees
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
$124 nightly
The price is $139
Nov 9 - Nov 10
Total with taxes and fees
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.
$92 nightly
The price is $102
Nov 8 - Nov 9
Total with taxes and fees
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
10.0 out of 10, Exceptional, (4 reviews)
"Great place! Highly recommend"
United States
Nyle K.
$319 nightly
The price is $357
Nov 16 - Nov 17
Total with taxes and fees
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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Find vacation rentals that suit your style

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Top Fleming Island Hotel Reviews

A hotel lobby with a reception desk, seating area, and a television.
Holiday Inn Express & Suites Fleming Island by IHG

Holiday Inn Express & Suites Fleming Island by IHG

Holiday Inn Express & Suites Fleming Island by IHG
Fleming Island

10/10 Excellent

Excellent place to stay
United States
Ernesto Antonio
Reviewed December 2, 2024
Holiday Inn Express & Suites Fleming Island by IHG

Find out more about Fleming Island

Everything you need to know about Fleming Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Fleming Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Fleming Island vacation 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 low season months. For more hustle and bustle, you may prefer to visit Fleming Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $101 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Fleming Island rentals

At Expedia, we put the best Fleming Island vacation 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 vacation.

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.

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.

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