Book Holiday Homes in Fleming Island

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Featured Holiday Homes in Fleming Island

Bluegreen Vacations Grande Villas at World Golf Village

Bluegreen Vacations Grande Villas at World Golf Village

3.5 out of 5
100 Front Nine Dr, St. Augustine, FL
Located in St. Augustine, Bluegreen Vacations Grande Villas at World Golf Village is on a lake, a 2-minute drive from King and Bear Golf Course and 10 minutes ...
Bluegreen Vacations Grande Villas at World Golf Village
Coziest House In JAX | 3BR, 7 Minutes To Downtown

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

Jacksonville
The price is AU$299 per night from 15 Apr to 16 Apr
AU$299
includes taxes & fees
15 Apr - 16 Apr
With a stay at this vacation home in Jacksonville (Northside), you'll be within a 10-minute drive of VyStar Veterans Memorial Arena and Jacksonville Zoo and ...
Coziest House In JAX | 3BR, 7 Minutes To Downtown
Fancy private pool home in Jax beach

Fancy private pool home in Jax beach

Jacksonville
The price is AU$879 per night from 15 Apr to 16 Apr
AU$879
includes taxes & fees
15 Apr - 16 Apr
With a stay at this vacation home in Jacksonville Beach (Southside), you'll be a 4-minute drive from Mayo Clinic Florida and 8 minutes from Jacksonville Beach ...
Fancy private pool home in Jax beach
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New luxury country house, near St Augustine & World golf Village.

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

St. Augustine
With a stay at this vacation home in St. Augustine, you'll be within a 10-minute drive of World Golf Village and St. Augustine Premium Outlets.
New luxury country house, near St Augustine & World golf Village.
Riversides Relaxing Retreat

Riversides Relaxing Retreat

Jacksonville
With a stay at this vacation home in Jacksonville (Northwest), you'll be within a 10-minute drive of VyStar Veterans Memorial Arena and EverBank Stadium.
Riversides Relaxing Retreat
Swim in Large Salt Water Pool, Ride Bikes, Relax On Deck, Enjoy Theater Room

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

Jacksonville
With a stay at this vacation home in Jacksonville (Northwest), you'll be within a 15-minute drive of VyStar Veterans Memorial Arena and Gateway Shopping ...
Swim in Large Salt Water Pool, Ride Bikes, Relax On Deck, Enjoy Theater Room
Ponte Vedra Wilderness Oasis minutes from TPC and the beach

Ponte Vedra Wilderness Oasis minutes from TPC and the beach

Ponte Vedra Beach
With a stay at this vacation home in Ponte Vedra Beach (Palm Valley), you'll be within a 15-minute drive of TPC Sawgrass and Sawgrass Village.
Ponte Vedra Wilderness Oasis minutes from TPC and the beach
Modern 4 bedroom with Patio and Pool -- Sleeps 10

Modern 4 bedroom with Patio and Pool -- Sleeps 10

Jacksonville
With a stay at this vacation home in Jacksonville (Arlington), you'll be a 5-minute drive from University of North Florida and 7 minutes from St. Johns Town ...
Modern 4 bedroom with Patio and Pool -- Sleeps 10
Private Loft at a Working Show Barn ~ Pets Welcome!

Private Loft at a Working Show Barn ~ Pets Welcome!

Middleburg
With a stay at this vacation home in Middleburg, you'll be within a 15-minute drive of Poochie's Park and Camp Blanding Museum and Memorial Park.
Private Loft at a Working Show Barn ~ Pets Welcome!
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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.

Fleming Island Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Fleming Island vacation homes are the perfect way for you to wing it.

Holiday houses in Fleming Island let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Fleming Island in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Fleming Island adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Fleming Island with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Fleming Island vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Fleming Island Holiday Homes essential information

Accommodation
841 Holiday Homes
Lowest Price
AU$142
Highest Price
AU$879
Popular accommodation
Bluegreen Vacations Grande Villas at World Golf Village, Coziest House In JAX | 3BR, 7 Minutes To Downtown, Fancy private pool home in Jax beach, New luxury country house, near St Augustine & World golf Village., Riversides Relaxing Retreat, Swim in Large Salt Water Pool, Ride Bikes, Relax On Deck, Enjoy Theater Room, Ponte Vedra Wilderness Oasis minutes from TPC and the beach, Modern 4 bedroom with Patio and Pool -- Sleeps 10 , Private Loft at a Working Show Barn ~ Pets Welcome!

Top trending hotels in Fleming Island

Holiday Inn Express & Suites Fleming Island by IHG

Holiday Inn Express & Suites Fleming Island by IHG

2.5 out of 5
1815 East West Pkwy., Fleming Island, FL
The price is AU$236 per night from 20 Apr to 21 Apr
AU$236
includes taxes & fees
20 Apr - 21 Apr
With a stay at Holiday Inn Express & Suites Fleming Island by IHG, you'll be centrally located in Fleming Island, within a 15-minute drive of Jacksonville Naval ...
Holiday Inn Express & Suites Fleming Island by IHG
Embassy Suites by Hilton Jacksonville Baymeadows

Embassy Suites by Hilton Jacksonville Baymeadows

3.5 out of 5
9300 Baymeadows Road, Jacksonville, FL
Fully refundableReserve now, pay when you stay
The price is AU$230 per night from 13 Apr to 14 Apr
AU$230
includes taxes & fees
13 Apr - 14 Apr
Located in Jacksonville (Southside), Embassy Suites by Hilton Jacksonville Baymeadows is within a 10-minute drive of St. Johns Town Center and University of ...
Embassy Suites by Hilton Jacksonville Baymeadows
Wyndham Garden Jacksonville

Wyndham Garden Jacksonville

3 out of 5
4660 Salisbury Road, I-95 Exit 344 (Butler Boulevard), Jacksonville, FL
Fully refundableReserve now, pay when you stay
The price is AU$142 per night from 13 Apr to 14 Apr
AU$142
includes taxes & fees
13 Apr - 14 Apr
Located in Jacksonville (Southside), Wyndham Garden Jacksonville is within a 10-minute drive of St. Johns Town Center and University of North Florida.
Wyndham Garden Jacksonville
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Hyatt Regency Jacksonville

Hyatt Regency Jacksonville

4 out of 5
225 E Coastline Dr, Jacksonville, FL
Fully refundableReserve now, pay when you stay
The price is AU$295 per night from 17 Apr to 18 Apr
AU$295
includes taxes & fees
17 Apr - 18 Apr
Hyatt Regency Jacksonville is centrally located in Jacksonville, a 4-minute walk from Florida Theatre and 8 minutes by foot from Times-Union Center for the Performing ...
Hyatt Regency Jacksonville
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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.

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^Subject to availability and chosen travel dates.