Fleming Island Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Fleming Island holiday rentals

Outdoor dining

Rustic Owl w/ 2Kings In Fleming Island

Rustic Owl w/ 2Kings In Fleming Island
Fleming Island
10.0 out of 10, Exceptional, (35 reviews)
"The property and location and all amenities met our needs. "
United States
Karen Y.
The price is HK$1,576
HK$3,251 total
includes taxes & fees
18 Jan - 19 Jan
Rustic Owl w/ 2Kings In Fleming Island
1 bedroom, WiFi

Quaint 1-bedroom cabin with AC in Jacksonville

Quaint 1-bedroom cabin with AC in Jacksonville
2.0 star property
Arlington
The price is HK$362
HK$1,010 total
includes taxes & fees
20 Jan - 21 Jan
Quaint 1-bedroom cabin with AC in Jacksonville
Fridge, microwave, stovetop, coffee/tea maker

La Casita by Amarelys and lazaro

La Casita by Amarelys and lazaro
Southside
10.0 out of 10, Exceptional, (6 reviews)
"Great location, easy access to route 95. Nice neighborhood ."
United States
herman c.
The price is HK$632
HK$2,204 total
includes taxes & fees
9 Feb - 10 Feb
La Casita by Amarelys and lazaro
Outdoor dining

Sunshine Haven: 2BR w/Pool, Theater, Gym, Tennis

Sunshine Haven: 2BR w/Pool, Theater, Gym, Tennis
Jacksonville
9.8 out of 10, Exceptional, (6 reviews)
"Our host (Luke) was VERY responsive when we had questions prior to & during our stay. The rooms were a good size and each had their own bathroom, which was nice. The location was good for us in relation to where our daughter moved, but also to the beach, shopping, restaurants and just a short drive to St. Augustine. We wouldn’t hesitate to stay here again."
United States
Nicholas B.
The price is HK$546
HK$2,822 total
includes taxes & fees
18 Jan - 19 Jan
Sunshine Haven: 2BR w/Pool, Theater, Gym, Tennis
Exterior

Heart of San Marco • Porch • BBQ • Bikes

Heart of San Marco • Porch • BBQ • Bikes
2.0 star property
San Marco
10.0 out of 10, Exceptional, (4 reviews)
"Good location. Nice property."
United States
Steve H.
The price is HK$681
HK$1,822 total
includes taxes & fees
19 Jan - 20 Jan
Heart of San Marco • Porch • BBQ • Bikes
1 bedroom, desk, iron/ironing board, WiFi

Magical Midsummer Night Glamping Loft w Bikes

Magical Midsummer Night Glamping Loft w Bikes
2.0 star property
Northwest
10.0 out of 10, Exceptional, (5 reviews)
"The property was great & in a good location. It was very nicely decorated and was in excellent condition. It was updated completely & very well taken care of by owners. The garden was very nice. The only problem I had was the stairs - I’m almost 70 & had a little trouble. I wouldn’t recommend for elderly & handicap persons. "
United States
Frances
The price is HK$530
HK$1,090 total
includes taxes & fees
20 Jan - 21 Jan
Magical Midsummer Night Glamping Loft w Bikes
Interior

Soul O Studio - Walkable Riverside w Bikes

Soul O Studio - Walkable Riverside w Bikes
2.0 star property
Northwest
10.0 out of 10, Exceptional, (1 review)
"A lovely place to stay! Small but never felt that way with the furnishings and smart storage design. We loved the area, walking distance to 3 different sections with dining and stores. Perfect location if you need to be at St Vincent’s. Laundry was convenient and street parking was always available. Highly recommend!"
United States
Michelle S.
The price is HK$562
HK$1,124 total
includes taxes & fees
19 Jan - 20 Jan
Soul O Studio - Walkable Riverside w Bikes
Fridge, microwave, oven, stovetop

Gorgeous Florida Pool and Spa Home

Gorgeous Florida Pool and Spa Home
2.0 star property
Arlington
9.6 out of 10, Exceptional, (15 reviews)
"Beautiful home and pool. 5 star stay. "
United States
Jason C.
The price is HK$737
HK$2,724 total
includes taxes & fees
18 Jan - 19 Jan
Gorgeous Florida Pool and Spa Home
Beach nearby

Private Studio Entry

Private Studio Entry
Palm Valley
10.0 out of 10, Exceptional, (88 reviews)
"Lovely and private!"
United States
Allison P.
The price is HK$772
HK$1,583 total
includes taxes & fees
21 Jan - 22 Jan
Private Studio Entry
Smart TV

Cozy spacious 2 bedrooms 2 bathrooms near beach

Cozy spacious 2 bedrooms 2 bathrooms near beach
Sandalwood
8.6 out of 10, Excellent, (34 reviews)
"Had a great weekend staying here! Host was responsive and very kind. Would highly recommend!"
United States
Maegan C.
The price is HK$858
HK$2,255 total
includes taxes & fees
30 Jan - 31 Jan
Cozy spacious 2 bedrooms 2 bathrooms near beach
Exterior detail

Charming 1-bedroom queen bed cottage in tranquil Jacksonville with AC

Charming 1-bedroom queen bed cottage in tranquil Jacksonville with AC
2.0 star property
Arlington
The price is HK$564
HK$884 total
includes taxes & fees
20 Jan - 21 Jan
Charming 1-bedroom queen bed cottage in tranquil Jacksonville with AC
Property grounds

Riverfront House With Breathtaking Views, Grill, King Bed, Near Jaguars Stadium!

Riverfront House With Breathtaking Views, Grill, King Bed, Near Jaguars Stadium!
Northwest
10.0 out of 10, Exceptional, (11 reviews)
"Great location "
United States
Robert L.
The price is HK$577
HK$1,954 total
includes taxes & fees
25 Jan - 26 Jan
Riverfront House With Breathtaking Views, Grill, King Bed, Near Jaguars Stadium!
TV

2B1BA Central - Airport, Riverside, Zoo, Beach

2B1BA Central - Airport, Riverside, Zoo, Beach
2.0 star property
Northwest
8.4 out of 10, Very good, (10 reviews)
"Quiet, and very nice home to enjoy a getaway. Will stay here again"
United States
Mc H.
The price is HK$653
HK$1,605 total
includes taxes & fees
19 Jan - 20 Jan
2B1BA Central - Airport, Riverside, Zoo, Beach
Interior

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

Colorful Family Friendly, Pet Friendly Bungalow, Sleeps 6 - Jacksonville, FL
Northwest
9.8 out of 10, Exceptional, (34 reviews)
"Relazing weekend, nice property!"
United States
Michelle M.
Colorful Family Friendly, Pet Friendly Bungalow, Sleeps 6 - Jacksonville, FL
1 bedroom, iron/ironing board, WiFi, bed sheets

Cozy Private Entire Studio Suite Independent Guest Entrance

Cozy Private Entire Studio Suite Independent Guest Entrance
Westside
9.8 out of 10, Exceptional, (17 reviews)
"Nice place to chill out before you go on vacation cruise. "
United States
Christopher W.
The price is HK$569
HK$1,157 total
includes taxes & fees
1 Feb - 2 Feb
Cozy Private Entire Studio Suite Independent Guest Entrance
1 bedroom, desk, iron/ironing board, free WiFi

San Marco/Downtown Modern Suite

San Marco/Downtown Modern Suite
2.0 star property
San Marco
9.8 out of 10, Exceptional, (9 reviews)
"Great place, great location! "
United States
Meghan C.
The price is HK$555
HK$1,397 total
includes taxes & fees
19 Jan - 20 Jan
San Marco/Downtown Modern Suite
Dining

Cozy House close To Downtown

Cozy House close To Downtown
Northwest
8.8 out of 10, Excellent, (11 reviews)
"The house was nice, clean, and felt very homey. The host was wonderful. Had a big front and back yard for my dog. Can’t wait to book this home again. "
United States
Anonymous traveller
The price is HK$456
HK$1,559 total
includes taxes & fees
19 Jan - 20 Jan
Cozy House close To Downtown
Exterior detail

Charming 3-bedroom House with AC and WiFi in lovely Jacksonville

Charming 3-bedroom House with AC and WiFi in lovely Jacksonville
2.0 star property
Northwest
9.0 out of 10, Wonderful, (14 reviews)
"This was such a cute quaint home that so cozy! Great location that was close to so many unique places and restaurants! It was surprisingly quiet for being so close to the interstate and train but overall a wonderful stay! "
United States
Courtney C.
The price is HK$562
HK$1,502 total
includes taxes & fees
19 Jan - 20 Jan
Charming 3-bedroom House with AC and WiFi in lovely Jacksonville
1 bedroom, WiFi, bed sheets

Cozy Private Tiny Guest House

Cozy Private Tiny Guest House
Westside
The price is HK$648
HK$1,289 total
includes taxes & fees
16 Jan - 17 Jan
Cozy Private Tiny Guest House
Fridge, microwave, oven, stovetop

2-bedroom house with/huge yard near Mayo

2-bedroom house with/huge yard near Mayo
2.0 star property
Southside
2-bedroom house with/huge yard near Mayo
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Fleming Island Hotel Reviews

Wyndham Garden Jacksonville

Wyndham Garden Jacksonville

10/10 Excellent
"They did a wonderful job. "
Janice 3-night trip
Posted 14 hours ago
Wyndham Garden 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 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 7 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.