Photo by Ash Feky

Fleming Island Vacation Rentals

  • 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

Vacation 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, (7)
"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, (265)
"My family and I had a blast. It was beautiful. Did not need to travel far for some great food. Will definitely be back. Staff were so friendly, pool closed at 8:30p every night, that was the only disappointment, due to lighting or something. Overall great place! "
Bluegreen Vacations Grande Villas at World Golf Village
Mi CASA es su CASA
10.0 out of 10, Exceptional, (69)
"The property is in a large gated community. The grounds and surrounding homes are beautiful. It is very peaceful and quiet. The amenities are great and there is a lot to do within a 10-30 minute drive. The property owner communicated with us very well and our stay couldn’t have gone better. It was an awesome place to stay & a great experience for my family and Me."
The price is CA $124
CA $299 total
includes taxes & fees
Nov 24 - Nov 25
Mi CASA es su CASA
Fancy private pool home in Jax beach
9.8 out of 10, Exceptional, (14)
"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 CA $391
CA $768 total
includes taxes & fees
Nov 24 - Nov 25
Fancy private pool home in Jax beach
Unique Design Bungalow in Jax Riverside Area.
10.0 out of 10, Exceptional, (22)
"The house was immaculate. The beds were comfortable and clean. Anything you could need was there for your use. Normally we eat out when in Jacksonville but the kitchen was so nice and well stocked with pots and dishes that we decided to cook. I can not say enough nice things."
The price is CA $175
CA $397 total
includes taxes & fees
Nov 25 - Nov 26
Unique Design Bungalow in Jax Riverside Area.
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
Newly renovated condo close to St Augustine beaches and golf clubs
10.0 out of 10, Exceptional, (63)
""Our stay at World Gold Village was everything we hoped for. It was perfect for our family trip. The space was clean, comfortable, and had all the amenities we needed. The host “STEPHEN” was incredibly accommodating. I highly recommend this place to anyone looking for a place to stay as a family stay or a romantic retreat. This will definitely be my go-to place every time I visit St. Augustine. Thank you Stephen!"
Newly renovated condo close to St Augustine beaches and golf clubs
Centrally located, Cozy Family Friendly Home.
9.0 out of 10, Wonderful, (45)
"This place aas beautiful. The back yard was a nice touch to have with kids. Conviently located close to everything. We enjoyed it very much"
Centrally located, Cozy Family Friendly Home.
Coastal Retreat.
9.8 out of 10, Exceptional, (6)
"5/5 Stars We had an absolutely wonderful stay at Mariana's coastal retreat! We came to Jacksonville to see the Nicki Minaj concert. The space was perfectly suited for a nice getaway - spacious, comfortable, and beautifully appointed. Mariana was a fantastic host, promptly addressing a minor issue with the lock and ensuring our stay was seamless. The accommodations truly made our trip special. We can't wait to return and would highly recommend this lovely retreat to anyone looking for a relaxing...
Coastal Retreat.
Cheerful three bedroom home with a pool
10.0 out of 10, Exceptional, (22)
"Great place to stay!"
The price is CA $279
CA $617 total
includes taxes & fees
Dec 3 - Dec 4
Cheerful three bedroom home with a pool
New luxury country house, near St Augustine & World golf Village.
10.0 out of 10, Exceptional, (52)
"The house was beautiful, new, clean, and stylishly decorated. Although off of a main 2 lane road, you couldn't hear the road noise when out by the pool or BBQ area. Our group was large (15) and we fit comfortably in the house and common areas. My only critique would be the master bed was extremely hard. We felt the other beds and they all seemed much more comfortable. The master bed is the only reason I would hesitate staying here again. Our host was great, very responsive. The pool was...
New luxury country house, near St Augustine & World golf Village.
Single house: 12guests,4bds/2baths,large backyard.
10.0 out of 10, Exceptional, (21)
"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 CA $177
CA $528 total
includes taxes & fees
Dec 5 - Dec 6
Single house: 12guests,4bds/2baths,large backyard.
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."
Relaxing two bedroom waterfront home near beaches
30 People Comfortably Gorgeous Home on Canal Boat Kayak access Two 85" & 75” TVs
9.6 out of 10, Exceptional, (16)
"Had 20 people do a golf trip. House worked out great for all of us. "
The price is CA $1,116
CA $2,561 total
includes taxes & fees
Nov 26 - Nov 27
30 People Comfortably Gorgeous Home on Canal Boat Kayak access Two 85" & 75” TVs
Gorgeous circa 1875 Plantation House (in city)
9.8 out of 10, Exceptional, (63)
"Property was clean and comfortable. Close to grocery stores and restaurants . There were 7 of us staying there and we had plenty of room. There was a problem with the hot water and we messaged the owner they responded back very quickly . "
Gorgeous circa 1875 Plantation House (in city)
Swim in Large Salt Water Pool, Ride Bikes, Relax On Deck, Enjoy Theater Room
9.6 out of 10, Exceptional, (134)
"Property is in a great location, not too far from anything. It was very accomodating. Pool waa nice even though we did not use it. It was Peaceful and relaxing. And the host was very helpful and at my assistance with the simplest thing."
Swim in Large Salt Water Pool, Ride Bikes, Relax On Deck, Enjoy Theater Room
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
Cozy Treetop Hideaway
10.0 out of 10, Exceptional, (65)
"The property was beautiful the host THE BEST VRBO HOST EVER!! my husband and I enjoyed your weekend stay.. omg the bed is soooo comfortable. We will book again next year "
The price is CA $130
CA $223 total
includes taxes & fees
Dec 15 - Dec 16
Cozy Treetop Hideaway
Large Pool🐬Billiards🎱Hammock & Grill 🔥Mural🦋Comfy Mattresses🔥Sleeps 10!
8.6 out of 10, Excellent, (11)
"We booked an extended weekend to visit my mom in her final days with terminal cancer. Just a couple days after booking, Hurricane Debby hit the east coast. We traveled in from Virginia, down the I-95 corridor, heading south on Thursday, the day Ole Debbie made the 2nd landfall in SC. Somehow we managed to avoid the worst of Debby and we were able to spend a few days with my mom. The little time we were able to spend at the house was great. We played a few games of billiards with the kids...
Large Pool🐬Billiards🎱Hammock & Grill 🔥Mural🦋Comfy Mattresses🔥Sleeps 10!
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, (987)
"Staff was extremely helpful the entire stay"
The price is CA $155
CA $175 total
includes taxes & fees
Dec 8 - Dec 9
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, (1006)
"The pool is indoor hot tub didn't bubble that much. Breakfast is good has 4 elevevators. We had a suite shower was outdated. Had two events the same night so when we came back there was no parking. It was quit even tho it was indoor they were always cleaning had an area with chairs an tabels for smoking. Overall a good experience would stay again"
The price is CA $161
CA $183 total
includes taxes & fees
Dec 22 - Dec 23
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until December 4 with our Black Friday deals. Stay by December 15, 2025.

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?

Bluegreen Vacations Grande Villas at World Golf Village: Visitors like this Fleming Island vacation home rental. It is located on a lake and has an outdoor pool, a terrace, and a barbecue grill 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 a spa tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Fleming Island?

With 8 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?

Enjoy the area's cultural attractions such as Mandarin Museum, or get outdoors into nature at a spot like Little Jessie Island. Jacksonville Naval Air Station and St. Johns Town Center are other popular places to visit in the area.

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.