Photo by Ash Feky

Holiday Rentals in Fleming Island

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Fleming Island

New Floating Luxury: Unique Houseboat Retreat

9.4 out of 10, Exceptional, (13)
"We have never been on a houseboat before and was really looking forward to our 3 night stay. The houseboat is really nice with all amenities. The lay out is a bit funky. Bedroom is upstairs with an outside entrance. Couch downstairs is second bed, didn’t sleep on it so don’t know how comfy that would be. We lost all water, through no fault of the owners and only got to stay one night. Owners graciously refunded 2 nights money. I would book again, very close to family. "
New Floating Luxury: Unique Houseboat Retreat

Watch the magnificent sunsets from Island Life!

10.0 out of 10, Exceptional, (8)
"The houseboat is wonderful!"
Watch the magnificent sunsets from Island Life!

Bluegreen Vacations Grande Villas at World Golf Village

3.5 star property
8.6 out of 10, Excellent, (268)
"A little old and very basic no thrills, towels where a little on rough side, nothing fancy here, photos look better than what it actually is, not bad and clean. Chairs in living room where worn. Beds were comfy enough. 3 stars is about right. "
Bluegreen Vacations Grande Villas at World Golf Village

Downtown Jacksonville - La Casa De Blues

9.6 out of 10, Exceptional, (50)
"Great house and location. "
The price is €308
includes taxes & fees
14 Jan - 15 Jan
Downtown Jacksonville - La Casa De Blues

Fancy private pool home in Jax beach

9.8 out of 10, Exceptional, (15)
"We came in for a Jags game. House was a great place for us to meet up with friends. Would def stay again. "
The price is €503
includes taxes & fees
5 Jan - 6 Jan
Fancy private pool home in Jax beach

Single house: 12guests,4bds/2baths,large backyard.

10.0 out of 10, Exceptional, (23)
"This home is beautiful, it has plenty of living space, two living room areas a large kitchen and plenty of space for dining! The beds are comfortable and there was plenty of room for our large party to stay. There are a ton of toys to keep the kids busy which was a plus! The kitchen is stocked with all cooking ware you need and the bathrooms are all stocked nicely. The host is great with communication and super nice! We enjoyed our stay here and will definitely stay again when we come back to...
The price is €378
includes taxes & fees
9 Jan - 10 Jan
Single house: 12guests,4bds/2baths,large backyard.

Studio loft w/ pool, spa & gardens near downtown

9.2 out of 10, Wonderful, (28)
"The property was very nice, and the room was cozy. The only negative was not being able to utilize the hot tub when we wanted to, and the bed mattress needs to be replaced, it is very uncomfortable. "
Studio loft w/ pool, spa & gardens near downtown

2 BDRM in RIVERSIDE! historic walkable. Close to restaurants, bars, stadium!

9.6 out of 10, Exceptional, (54)
"The apartment was great. The listing was accurate and specific which was very helpful. The price was right- it is an older home with older home quirks, but it was clean and comfortable which was all we hoped for. If we come back to Jacksonville, I’d absolutely stay here again. "
2 BDRM in RIVERSIDE! historic walkable. Close to restaurants, bars, stadium!

Mi CASA es su CASA

10.0 out of 10, Exceptional, (74)
"We had a great time exploring the city, which was very busy, but then back to quiet and serene surroundings."
Mi CASA es su CASA

Unique Design Bungalow in Jax Riverside Area.

9.8 out of 10, Exceptional, (26)
"The house is very clean with all the amenities, the backyard area is very nice, we enjoyed our stay."
The price is €277
includes taxes & fees
5 Jan - 6 Jan
Unique Design Bungalow in Jax Riverside Area.

Cozy Treetop Hideaway

10.0 out of 10, Exceptional, (68)
"An awesome spot with easy access to Jax center. Utmost privacy for rest, reading, and relaxation. "
The price is €152
includes taxes & fees
19 Jan - 20 Jan
Cozy Treetop Hideaway

Spend the Holidays at Sugar Magnolia House. An extraordinarily historic home.

10.0 out of 10, Exceptional, (28)
"I cannot express how totally wonderful our experience was... From our wonderful host, to the atmosphere of this stunning house, our dreams came to life! "
Spend the Holidays at Sugar Magnolia House. An extraordinarily historic home.

Northeast Florida Retreat

8.8 out of 10, Excellent, (8)
"The house was musty smelling could use a dehumidifier. The shower drained slow and could use updating. Kitchen cabinet door would not close and the floor looks pretty rough. Would have been nice if the bedrooms had TV’s."
Northeast Florida Retreat

Historic Green Cove Springs Home - Walk to Coast!

9.8 out of 10, Exceptional, (41)
"Classic old home with lots of character! Have never been in a VRBO that was so well stocked. You don't need to bring anything but your clothes. Comfy beds. Would love to see a taller toilet upstairs like the one on the main level. Need to get the yard in shape, looked pretty rough. Close to the St. Johns river, Friday nite food truck and live entertainment. Would stay again!"
Historic Green Cove Springs Home - Walk to Coast!

Luxurious Home w/ Spectacular Glass Room & Patios

9.8 out of 10, Exceptional, (148)
"Great house and great neighborhood! "
Luxurious Home w/ Spectacular Glass Room & Patios

Relaxing two bedroom waterfront home near beaches

10.0 out of 10, Exceptional, (24)
"We love the location and house! We've stayed two times now visiting family and will continue to use this place in the future."
The price is €449
includes taxes & fees
9 Jan - 10 Jan
Relaxing two bedroom waterfront home near beaches

Coastal Retreat.

8.8 out of 10, Excellent, (8)
"The apartment was in a quiet gated community, nearby many places. It was uber clean and comfy. Had everything needed for a stay."
Coastal Retreat.

Private Pool |1/2 Acre Wooded Lot |Feels Like an Authentic English Cottage |Fenced |Dogs Ok |3 Bikes

9.4 out of 10, Exceptional, (50)
" Just like in the description. You'll enjoy it"
Private Pool |1/2 Acre Wooded Lot |Feels Like an Authentic English Cottage |Fenced |Dogs Ok |3 Bikes

Bettys Place a Cozy Modern 3BR/2BA SFH w/ Fenced Yard, Inside W/D, Gig WiFi

10.0 out of 10, Exceptional, (14)
"Great property, great hosts. I wish I hadn’t scheduled up all our time in Jacksonville. Could easily have enjoyed a great trip without ever leaving the house. It’s that good. "
Bettys Place a Cozy Modern 3BR/2BA SFH w/ Fenced Yard, Inside W/D, Gig WiFi

Northeast Florida Retreat

9.6 out of 10, Exceptional, (22)
"The location for us was perfect because we were there for a medical appointment and it was only 5 minutes away. The yard was great for our little dogs. It’s an older home, but clean and decorated very nicely."
Northeast Florida Retreat
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.
Don't see what you're looking for?
See all available properties in Fleming Island
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Fleming Island you may be interested in

Holiday Inn Express & Suites Fleming Island, an IHG Hotel

2.5 star property
9.0 out of 10, Wonderful, (1002)
"Front Desk took care of us"
The price is €117
includes taxes & fees
26 Jan - 27 Jan
Holiday Inn Express & Suites Fleming Island, an IHG Hotel

New Floating Luxury: Unique Houseboat Retreat

9.4 out of 10, Exceptional, (13)
"We have never been on a houseboat before and was really looking forward to our 3 night stay. The houseboat is really nice with all amenities. The lay out is a bit funky. Bedroom is upstairs with an outside entrance. Couch downstairs is second bed, didn’t sleep on it so don’t know how comfy that would be. We lost all water, through no fault of the owners and only got to stay one night. Owners graciously refunded 2 nights money. I would book again, very close to family. "
New Floating Luxury: Unique Houseboat Retreat

Embassy Suites by Hilton Jacksonville Baymeadows

3.5 star property
8.4 out of 10, Very good, (1009)
"The property looked a little older but was a good experience with kids. Enjoyed the breakfast. Be sure to get down early because of long lines. Enjoyed the complimentary drink tickets."
The price is €135
includes taxes & fees
9 Jan - 10 Jan
Embassy Suites by Hilton Jacksonville Baymeadows
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.

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?

Bluegreen Vacations Grande Villas at World Golf Village: This holiday home rental outside of Fleming Island is located on a lake, and has an outdoor pool, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers an outdoor tennis court, a garden and 1 hot tub so that you can immerse yourself in your holiday.

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.