Photo by Ash Feky

Search Vacation Homes in Fleming Island

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 833 Vacation Homes in Fleming Island with updated reviews, rates, and availability.

Grande Villas at World Golf Village
Outdoor pool

Grande Villas at World Golf Village

3.5 star property
8.6 out of 10, Excellent, (273)
"Room and service waa great. Would benefit from having a pool bar and restaurant on property."
Grande Villas at World Golf Village
Coziest House In JAX | 3BR, 7 Minutes To Downtown
Interior

Coziest House In JAX | 3BR, 7 Minutes To Downtown

8.0 out of 10, Very Good, (22)
"Host was very gracious and easy to work with. Eduard....Thank you a million for providing such a beautiful accommodation for my employees to stay in while working out of town. "
The price is AED 184
AED 574 total
includes taxes & fees
13 May - 14 May
Coziest House In JAX | 3BR, 7 Minutes To Downtown
Fancy private pool home in Jax beach
Smart TV

Fancy private pool home in Jax beach

9.8 out of 10, Exceptional, (17)
"Had a wonderful stay and the hosts were very helpful! "
The price is AED 1,028
AED 1,995 total
includes taxes & fees
12 May - 13 May
Fancy private pool home in Jax beach
New luxury country house, near St Augustine & World golf Village.
Outdoor pool, a heated pool

New luxury country house, near St Augustine & World golf Village.

10.0 out of 10, Exceptional, (65)
"Wonderful place to stay"
New luxury country house, near St Augustine & World golf Village.
Riversides Relaxing Retreat
Private kitchen

Riversides Relaxing Retreat

10.0 out of 10, Exceptional, (18)
"We needed a place close to hospital while family member was having surgery. This place was perfect! Very close, great neighborhood. Lovely little apartment. "
Riversides Relaxing Retreat
Swim in Large Salt Water Pool, Ride Bikes, Relax On Deck, Enjoy Theater Room
Outdoor pool

Swim in Large Salt Water Pool, Ride Bikes, Relax On Deck, Enjoy Theater Room

9.6 out of 10, Exceptional, (142)
"We spent Christmas at this home and we had a great time. The property is clean and spacious, it was like being back home. Plenty of rooms and a nice theater room. Ideal location to stores and restaurants. "
Swim in Large Salt Water Pool, Ride Bikes, Relax On Deck, Enjoy Theater Room
Ponte Vedra Wilderness Oasis minutes from TPC and the beach
Exterior

Ponte Vedra Wilderness Oasis minutes from TPC and the beach

9.8 out of 10, Exceptional, (30)
"Loved the property!"
Ponte Vedra Wilderness Oasis minutes from TPC and the beach
Modern 4 bedroom with Patio and Pool -- Sleeps 10
Outdoor pool

Modern 4 bedroom with Patio and Pool -- Sleeps 10

9.8 out of 10, Exceptional, (16)
"If you’re looking for a clean, cozy stay this is the place fore you"
Modern 4 bedroom with Patio and Pool -- Sleeps 10
Private Loft at a Working Show Barn ~ Pets Welcome!
Exterior

Private Loft at a Working Show Barn ~ Pets Welcome!

9.4 out of 10, Exceptional, (20)
"All around great experience with a fantastic atmosphere. 10/10 would recommend to everyone. "
The price is AED 349
AED 693 total
includes taxes & fees
13 May - 14 May
Private Loft at a Working Show Barn ~ Pets Welcome!
Mandarin Pearl close to everything
Smart TV, books

Mandarin Pearl close to everything

9.2 out of 10, Wonderful, (24)
"Mandarin Pearl was clean, quiet, well located, and cozy. My husband and I stayed for one week and our host, Richard, answered all our questions quickly. The house was well stocked and comfortable. We would book again!"
Mandarin Pearl close to everything
Spring has Sprung - 15% off 3 night stays thru end of May!
Pool

Spring has Sprung - 15% off 3 night stays thru end of May!

9.4 out of 10, Exceptional, (58)
"Very nice place with plenty of room to visit with Kids and take in the a few of the sights of Jacksonville. "
Spring has Sprung - 15% off 3 night stays thru end of May!
Private Paradise in a Pristine Neighborhood - Fenced back yard, patio & firepit
Property grounds

Private Paradise in a Pristine Neighborhood - Fenced back yard, patio & firepit

9.8 out of 10, Exceptional, (33)
"We really enjoyed the games and outdoor area! "
The price is AED 441
AED 924 total
includes taxes & fees
12 May - 13 May
Private Paradise in a Pristine Neighborhood - Fenced back yard, patio & firepit
2 Cozy bedroom house W/ huge patio!
Outdoor dining

2 Cozy bedroom house W/ huge patio!

9.4 out of 10, Exceptional, (15)
"Great place, great neighborhood very quiet "
The price is AED 320
AED 853 total
includes taxes & fees
13 May - 14 May
2 Cozy bedroom house W/ huge patio!
South Hampton 75” TV Golf Club Saint Augustine Golf Course View!
Beach nearby

South Hampton 75” TV Golf Club Saint Augustine Golf Course View!

9.0 out of 10, Wonderful, (36)
"In town for a golf trip and the homes were great for location and comfort"
South Hampton 75” TV Golf Club Saint Augustine Golf Course View!
Charming 2-bedroom house in welcoming Jacksonville with WiFi, Laundry, Sunroom
Fridge, microwave, oven, stovetop

Charming 2-bedroom house in welcoming Jacksonville with WiFi, Laundry, Sunroom

9.0 out of 10, Wonderful, (7)
The price is AED 312
AED 636 total
includes taxes & fees
14 May - 15 May
Charming 2-bedroom house in welcoming Jacksonville with WiFi, Laundry, Sunroom
3-bedroom bungalow in fabulous downtown Springfield area in JAX FL- WiFi, AC
Interior

3-bedroom bungalow in fabulous downtown Springfield area in JAX FL- WiFi, AC

4.0 out of 10, (1)
"The pictures of this property make it look a lot better than it is. There were holes in the walls, a huge gap in the side door, and other defects such as a sink faucet that was barely attached. There was no soap/shampoo, no internet and the remotes for the TV did not work. The host was kind and check in was good, but this place could use some serious TLC. Also, please be cautious when booking this place because the surrounding neighborhood is suspect. There were people sifting through trash and...
The price is AED 180
AED 611 total
includes taxes & fees
12 May - 13 May
3-bedroom bungalow in fabulous downtown Springfield area in JAX FL- WiFi, AC
Nocatee Family Retreat – Private Yard & Lanai
Fridge, microwave, oven, stovetop

Nocatee Family Retreat – Private Yard & Lanai

10.0 out of 10, Exceptional, (6)
"My wife and I visited with our 3 year old and 1 year old. This place is nice and spacious, and the outdoor area was great for kids. "
Nocatee Family Retreat – Private Yard & Lanai
Historic Green Cove Springs Home - Walk to Coast!

Historic Green Cove Springs Home - Walk to Coast!

9.8 out of 10, Exceptional, (47)
"We had a short weekend stay for a wedding, and this house was very nice. It had plenty of space for parking, and the interior was well kept. Would stay again "
Historic Green Cove Springs Home - Walk to Coast!
Turquoise Oasis I Family & Dog Friendly I Saltwater Pool I Firepits
Interior

Turquoise Oasis I Family & Dog Friendly I Saltwater Pool I Firepits

10.0 out of 10, Exceptional, (1)
"Great little house near the Mayo Clinic. "
Turquoise Oasis I Family & Dog Friendly I Saltwater Pool I Firepits
Spring has Sprung - 15% off 3 night stays thru end of May!
Pool

Spring has Sprung - 15% off 3 night stays thru end of May!

9.2 out of 10, Wonderful, (28)
"We booked this VRBO because of the proximity to the surgery center where my husband was having a procedure done. This home also offered a recliner which was a must have and this was the only VRBO we found that had one."
Spring has Sprung - 15% off 3 night stays thru end of May!
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
Sign in
Sign up, it's free

Other property types in Fleming Island

New Floating Luxury: Unique Houseboat Retreat
Interior

New Floating Luxury: Unique Houseboat Retreat

9.4 out of 10, Exceptional, (15)
"Tony & I and CoCo Chanel enjoyed looking out over the lake.....and the birds! Location was nice and easy to get to Great restaurants and shops and stores. Went to St. Augustine and enjoyed all day there! Went to Jacksonville Beach and had lunch! Nice realxing Christmas celebration for just the three of us! I want to go back in the Summer and rent a jet ski!"
New Floating Luxury: Unique Houseboat Retreat
Grande Villas at World Golf Village
Outdoor pool

Grande Villas at World Golf Village

3.5 star property
8.6 out of 10, Excellent, (273)
"Room and service waa great. Would benefit from having a pool bar and restaurant on property."
Grande Villas at World Golf Village
2 Cozy bedroom house W/ huge patio!
Outdoor dining

2 Cozy bedroom house W/ huge patio!

9.4 out of 10, Exceptional, (15)
"Great place, great neighborhood very quiet "
The price is AED 320
AED 853 total
includes taxes & fees
13 May - 14 May
2 Cozy bedroom house W/ huge patio!
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.