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Fleming Island Holiday Rentals

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Holiday Rentals in Fleming Island

New Floating Luxury: Unique Houseboat Retreat
9.4 out of 10, Exceptional, (12)
"My husband and I stayed here for 4 nights to celebrate our 30th wedding anniversary & had a great time. The boat is amazingly spacious, and the views (particularly the gorgeous sunsets) are lovely. Having the tiki bar nearby was a nice plus. We look forward to coming back!"
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, (259)
"The resort is well laid out but is showing signs of wear and tear. The hot tub didn’t work until the last day of our week there. They have played Jenna with other features. They used to have a high end coffee and hot drink machine. That has been replaced with a cheaper and more basic one, with fewer options. Less staff available and the main building closed overnight. The World Golf Hall of Fame is no longer in the adjacent facility and the whole space feels like a ghost town. The people...
Bluegreen Vacations Grande Villas at World Golf Village
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Fancy private pool home in Jax beach
9.8 out of 10, Exceptional, (8)
"It was very comfortable and cozy felt like home."
The price is NZ$1,192
per night
16 Jun - 17 Jun
Fancy private pool home in Jax beach
Swim in Large Salt Water Pool, Ride Bikes, Relax On Deck, Enjoy Theater Room
9.6 out of 10, Exceptional, (120)
"Peaceful relaxing and quiet."
Swim in Large Salt Water Pool, Ride Bikes, Relax On Deck, Enjoy Theater Room
Mi CASA es su CASA
10.0 out of 10, Exceptional, (64)
"It was a beautiful property with exceptional grounds. The pool and hot tub were wonderful! We really enjoyed the stay. If we could change or add anything, it would be safety bars in the tub, a map of the facility telling us if we had access to any of the other areas and much more time to enjoy it! Thanks so much!"
The price is NZ$372
per night
9 Jun - 10 Jun
Mi CASA es su CASA
Experience Jacksonville's Rich Culture & Nature in Style! Pets Allowed, Kitchen!
9.2 out of 10, Wonderful, (7)
"Room was small. They never cleaned the room when we were there. Roaches were found in our room alive. The elevator was out of service and I am handicapped and both persons are over 70. The price was extremely high for the accommodation ."
The price is NZ$181
per night
9 Jun - 10 Jun
Experience Jacksonville's Rich Culture & Nature in Style! Pets Allowed, Kitchen!
Newly renovated condo close to St Augustine beaches and golf clubs
10.0 out of 10, Exceptional, (53)
"This is our go-to place when staying in St. Augustine. The owner now feels like family."
The price is NZ$458
per night
24 Jun - 25 Jun
Newly renovated condo close to St Augustine beaches and golf clubs
Water View Tropical Retreat at Gated Golf Community
9.0 out of 10, Wonderful, (6)
"The location of this condo was beautiful! The building itself was very nice. The fountains, pool and hot tub was wonderful! The walk to the room could use some work. Maybe new carpet or hardwood floors would be better as it had that musty smell. The inside of the condo was surprisingly spacious. It fit my family of 4 comfortably. The kitchen and bathroom was updated. It had all good working appliances. The main room could just some TLC. There were things from previous renters that were left...
Water View Tropical Retreat at Gated Golf Community
Romantic Sugar Magnolia House in Historic Springfield neighborhood near downtown
10.0 out of 10, Exceptional, (16)
"We absolutely loved the place! The kids didn’t want to leave, they had so many rooms to explore and enjoyed just lounging around and relaxing. The house is beautiful, huge and was very clean! We were provided plenty of towels and soap. The kitchen also provided everything we needed to cook a meal. We would definitely love to stay again in the near future!"
Romantic Sugar Magnolia House in Historic Springfield neighborhood near downtown
Studio loft w/ pool, spa & gardens near downtown
9.8 out of 10, Exceptional, (19)
"We loved this property. It had a fun vibe and the outside area was just beautiful. Highly recommend!"
Studio loft w/ pool, spa & gardens near downtown
Relaxing two bedroom waterfront home near beaches
10.0 out of 10, Exceptional, (19)
"Lovely property, great neighborhood. Glad we chose this property while we were in the area."
The price is NZ$752
per night
13 Jun - 14 Jun
Relaxing two bedroom waterfront home near beaches
Private Pool |1/2 Acre Wooded Lot |Feels Like an Authentic English Cottage |Fenced |Dogs Ok |3 Bikes
9.4 out of 10, Exceptional, (39)
"Beautiful older home with all the charm of an older home. Very comfortable and we had everything we needed. Thank you."
Private Pool |1/2 Acre Wooded Lot |Feels Like an Authentic English Cottage |Fenced |Dogs Ok |3 Bikes
Beautiful Home! Private pool! Close to the beach
8.2 out of 10, Very good, (10)
"Kids enjoyed , loved the house. Overall everything was great !"
Beautiful Home! Private pool! Close to the beach
Unique Design Bungalow in Jax Riverside Area.
9.8 out of 10, Exceptional, (11)
"My wife needed to visit the Mayo Clinic for testing, and we wanted to bring our dogs and this place was perfect for them. Fenced in back yard and very nice interior. I would recommend this place for sure."
The price is NZ$469
per night
13 Jun - 14 Jun
Unique Design Bungalow in Jax Riverside Area.
Cozy house on the river, enjoy the view or fish right off the river bank
10.0 out of 10, Exceptional, (75)
"Very clean and well priced!"
Cozy house on the river, enjoy the view or fish right off the river bank
Modern 4 bedroom with Patio and Pool -- Sleeps 10
10.0 out of 10, Exceptional, (2)
"Beautiful stay for our quick family getaway. House layout is perfect for a family. Plenty of room, open spaces, great beds, linens, etc. Pool area was perfect and very safe with kids age 5+."
Modern 4 bedroom with Patio and Pool -- Sleeps 10
Cheerful three bedroom home with a pool
9.8 out of 10, Exceptional, (16)
"This was a nice home for our family and friend group. My husband and I were in town to see George Strait in Jacksonville. Our childcare plans had to change and we brought our daughter and had a friend meet us with her family to watch her. The host was accommodating and understood the situation. The place was clean and had plenty of space for our last minute addition. The pool was BIG hit with the kids. Getting them out almost made us late for checkout!!! Much nicer than any hotel I have stayed...
The price is NZ$723
per night
9 Jun - 10 Jun
Cheerful three bedroom home with a pool
Cozy spacious 2 bedrooms 2 bathrooms near beach
8.8 out of 10, Excellent, (8)
"We were pleasantly surprised with this property! The owner was amazing in responding to any questions we had. I would highly recommend this property!!"
The price is NZ$438
per night
12 Jun - 13 Jun
Cozy spacious 2 bedrooms 2 bathrooms near beach
Cozy Treetop Hideaway
10.0 out of 10, Exceptional, (62)
"As a frequent user of VRBO properties this is the first house that I’ve been to that I felt right at home!! The owners absolutely thought of everything from shaving cream to fingernail polish remover. From the cleanliness to the decor, this property sets the standard very high and other property owners should take note. The very cute and cozy hideaway is a must!!! Next time I’m in Jacksonville I will check to see if this property is available. Thank you gentlemen for your southern hospitality!"
The price is NZ$262
per night
9 Jun - 10 Jun
Cozy Treetop Hideaway
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See all available properties in Fleming Island
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.

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, (900)
"Staff was excellent. Room was clean and attractive. More road signage would be nice, as sits back off road. "
The price is NZ$210
per night
7 Jul - 8 Jul
Holiday Inn Express & Suites Fleming Island, an IHG Hotel
New Floating Luxury: Unique Houseboat Retreat
9.4 out of 10, Exceptional, (12)
"My husband and I stayed here for 4 nights to celebrate our 30th wedding anniversary & had a great time. The boat is amazingly spacious, and the views (particularly the gorgeous sunsets) are lovely. Having the tiki bar nearby was a nice plus. We look forward to coming back!"
New Floating Luxury: Unique Houseboat Retreat
Embassy Suites by Hilton Jacksonville Baymeadows
3.5 star property
8.2 out of 10, Very good, (1012)
"First time staying in embassy and had a great experience with staff and the property very friendly "
The price is NZ$208
per night
1 Jul - 2 Jul
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Fleming Island holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Fleming Island. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Fleming Island. Seeing all the best attractions is bound to make you fall in love with Fleming Island. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Fleming Island short-term rentals, that won’t be hard to do.

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 8 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. Jacksonville Naval Air Station and St. Johns Town Center are other popular places to visit in the area.

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.

Recent reviews of Fleming Island properties
Expedia verified reviews