Fleming Island Holiday Rentals

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Our top choices for Fleming Island holiday rentals

New Floating Luxury: Unique Houseboat Retreat

New Floating Luxury: Unique Houseboat Retreat
Orange Park
9.4 out of 10, Exceptional, (31 reviews)
"Very clean, peaceful, beautiful view"
United States
Anonymous traveller
The price is NZ$784
includes taxes & fees
17 May - 18 May
New Floating Luxury: Unique Houseboat Retreat

Rustic Owl w/ 2Kings In Fleming Island

Rustic Owl w/ 2Kings In Fleming Island
Fleming Island
10.0 out of 10, Exceptional, (36 reviews)
"Great communication with host, quiet neighborhood, nicely decorated, great outdoor space with fire pit. Bonus: Host left all materials needed for s’mores! "
United States
Denise S.
Rustic Owl w/ 2Kings In Fleming Island

Charming Family Friendly, Pet Friendly Bungalow, Sleeps 6 - Jacksonville, FL

Charming Family Friendly, Pet Friendly Bungalow, Sleeps 6 - Jacksonville, FL
Northwest
9.8 out of 10, Exceptional, (37 reviews)
"Just a perfect comfortable stay"
United States
Jim F.
The price is NZ$288
includes taxes & fees
21 May - 22 May
Charming Family Friendly, Pet Friendly Bungalow, Sleeps 6 - Jacksonville, FL

*The Murray Hill Bungalow*-Arcade games/Patio

*The Murray Hill Bungalow*-Arcade games/Patio
Murray Hill
10.0 out of 10, Exceptional, (7 reviews)
"House and property were cute, in a quiet neighborhood. We had a great time exploring the local scene. "
United States
Jeffrey & Christine M.
The price is NZ$468
includes taxes & fees
18 May - 19 May
*The Murray Hill Bungalow*-Arcade games/Patio

Cozy spacious 2 bedrooms 2 bathrooms near beach

Cozy spacious 2 bedrooms 2 bathrooms near beach
Sandalwood
8.8 out of 10, Excellent, (43 reviews)
"Everything was as described. Clean and easy location for getting around town. Enough seating for watching shows on the big screen in the evenings. Neighborhood was quiet. "
United States
carrie b.
The price is NZ$464
includes taxes & fees
21 May - 22 May
Cozy spacious 2 bedrooms 2 bathrooms near beach

Mi CASA es su CASA

Mi CASA es su CASA
St. Augustine
10.0 out of 10, Exceptional, (97 reviews)
"The property was clean, beautiful and safe. The hit tub and pool was very beautiful and so was the condo. "
United States
Ryan
The price is NZ$344
includes taxes & fees
14 May - 15 May
Mi CASA es su CASA

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, (24 reviews)
"Horses were great, stay was wonderful, very relaxing "
United States
Tina S.
The price is NZ$298
includes taxes & fees
25 May - 26 May
Private Loft at a Working Show Barn ~ Pets Welcome!

Cozy Treetop Hideaway

Cozy Treetop Hideaway
Northwest
10.0 out of 10, Exceptional, (99 reviews)
"Great stay "
United States
Antonio J.
The price is NZ$246
includes taxes & fees
14 May - 15 May
Cozy Treetop Hideaway

Private 2BR Home • 10 min to airport & downtown •WiFi • Patio •Comfortable stay

Private 2BR Home • 10 min to airport & downtown •WiFi • Patio •Comfortable stay
Northwest
The price is NZ$525
includes taxes & fees
17 May - 18 May
Private 2BR Home • 10 min to airport & downtown •WiFi • Patio •Comfortable stay

Cozy Private Entire Studio Suite Independent Guest Entrance

Cozy Private Entire Studio Suite Independent Guest Entrance
Westside
9.4 out of 10, Exceptional, (20 reviews)
"Nice place to chill out before you go on vacation cruise. "
United States
Christopher W.
The price is NZ$235
includes taxes & fees
18 May - 19 May
Cozy Private Entire Studio Suite Independent Guest Entrance

La Casita by Amarelys and lazaro

La Casita by Amarelys and lazaro
Southside
10.0 out of 10, Exceptional, (9 reviews)
"Very clean and neat place, the host is also very responsive. In General it was very good place to stay at."
United States
Hanna S.
The price is NZ$471
includes taxes & fees
1 June - 2 June
La Casita by Amarelys and lazaro

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

1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed
Southside
10.0 out of 10, Exceptional, (29 reviews)
"Cool place to stay"
United States
Anonymous traveller
The price is NZ$127
includes taxes & fees
26 May - 27 May
1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed

Beautiful relaxing and Spacious 3 bedroom 2 bathhouse close to the beach,

Beautiful relaxing and Spacious 3 bedroom 2 bathhouse close to the beach,
Sandalwood
10.0 out of 10, Exceptional, (16 reviews)
"Definitely the best rental property I’ve ever stayed at…very clean and very clean…quiet neighborhood as well…very safe as well…"
United States
Robert M.
The price is NZ$583
includes taxes & fees
17 May - 18 May
Beautiful relaxing and Spacious 3 bedroom 2 bathhouse close to the beach,

Private Studio Entry

Private Studio Entry
Palm Valley
10.0 out of 10, Exceptional, (95 reviews)
"Quiet, clean space. Great communication with hosts. Will likely stay there again!"
United States
Judith O.
The price is NZ$390
includes taxes & fees
21 May - 22 May
Private Studio Entry

Guest Favorite! 8th Floor Luxe King Suite PetOK

Guest Favorite! 8th Floor Luxe King Suite PetOK
Downtown Jacksonville
The price is NZ$522
includes taxes & fees
21 May - 22 May
Guest Favorite! 8th Floor Luxe King Suite PetOK

Magical Midsummer Night Glamping Loft w Bikes

Magical Midsummer Night Glamping Loft w Bikes
Northwest
10.0 out of 10, Exceptional, (9 reviews)
"It was Enchanting and the location perfect!"
United States
THC
The price is NZ$250
includes taxes & fees
24 May - 25 May
Magical Midsummer Night Glamping Loft w Bikes

Modern, Cozy and Private Studio

Modern, Cozy and Private Studio
Arlington
9.8 out of 10, Exceptional, (6 reviews)
"Excellent place, extra clean, modern, safe, quiet and prívate. Gustavo is a great host, always available. A pleasure stay here. "
United States
Marcela R.
The price is NZ$205
includes taxes & fees
20 May - 21 May
Modern, Cozy and Private Studio

Luxurious Home w/ Spectacular Glass Room & Patios

Luxurious Home w/ Spectacular Glass Room & Patios
Lakeside
9.8 out of 10, Exceptional, (176 reviews)
"The house, host & neighborhood were all very nice. Plenty of room and lots of comfortable seating. "
United States
Dawn S.
The price is NZ$694
includes taxes & fees
28 May - 29 May
Luxurious Home w/ Spectacular Glass Room & Patios

Lakefront Home with Outdoor Pool Table, Firepit, and Grill in Jacksonville

Lakefront Home with Outdoor Pool Table, Firepit, and Grill in Jacksonville
Southside Estates
10.0 out of 10, Exceptional, (4 reviews)
"Great house! Had everything we needed and was perfect! Would definitely recommend this place!!"
United States
Hope B.
The price is NZ$504
includes taxes & fees
20 May - 21 May
Lakefront Home with Outdoor Pool Table, Firepit, and Grill in Jacksonville

Chill Retreat with Private Yard · Near Downtown

Chill Retreat with Private Yard · Near Downtown
Downtown Jacksonville
9.8 out of 10, Exceptional, (30 reviews)
"Everything was very clean and great communication with the host, would stay here again"
United States
Nikole R.
The price is NZ$291
includes taxes & fees
17 May - 18 May
Chill Retreat with Private Yard · Near Downtown
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

Everything you need to know about Fleming Island holiday rentals

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

Fleming Island holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Fleming Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Fleming Island holiday rentals we have selected for you start as low as NZ$160 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Fleming Island rentals

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

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 holiday rentals in Fleming Island?

Yes, there are holiday rentals close to the most popular sights in Fleming Island, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Fleming Island has to offer?

RelaxJax - a Private Paradise in a Pristine Neighborhood Fenced yard w/grill.: This holiday home rental outside of Fleming Island offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Fleming Island?

With 6 Expedia holiday rentals, you're guaranteed to find just the right place for your Fleming Island stay.

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

Enjoy the area's cultural attractions such as Mandarin Museum, or get outdoors into nature at a spot like Little Jessie Island. Other places in town to visit include Eagle Harbor Golf Club and The Golf Club At Fleming Island.

What’s a holiday rental in Fleming Island like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Fleming Island. Holiday rentals provide amenities like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from shared hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for a small group gathering.