Fleming Island vacation rentals

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Best Fleming Island vacation rentals

Most recommended vacation rentals in Fleming Island

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My Relaxing Place - Fleming Island - Pool
My Relaxing Place
Fleming Island, FL
8.9Very good(7)
Pool
$494+
Check availability
Rustic Owl w/ 2Kings In Fleming Island - Fleming Island - Balcony
Rustic Owl w/ 2Kings In Fleming Island
Fleming Island, FL
9.8Wonderful(24)
Free Wi-Fi
Pet friendly
$336+
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The Retreat On Florida St - Fleming Island - Bedroom
The Retreat On Florida St
Fleming Island, FL
Free Wi-Fi
Pet friendly
$337+
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Fleming Island, Orange Park Florida Home 3/2 With Private Pool, and Hot Tub - Fleming Island - Dining room
Fleming Island, Orange Park Florida Home 3/2 With Private Pool, and Hot Tub
Fleming Island, FL
Free Wi-Fi
Pool
$440+
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Bermuda Drive Abode - Fleming Island - Living room
Bermuda Drive Abode
Fleming Island, FL
Free Wi-Fi
Pet friendly
$305+
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Cozy Fruit Cove Cottage on Hobby Farm with Wildlife! - Fleming Island - Bedroom
Cozy Fruit Cove Cottage on Hobby Farm with Wildlife!
Fleming Island, FL
Free Wi-Fi
Pet friendly
$260+
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Honey Bee Hideaway - Fleming Island - Beach
Honey Bee Hideaway
Fleming Island, FL
Free Wi-Fi
Pet friendly
$351+
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Fruit Cove Home with Hot Tub and Lake View! - Fleming Island - Living room
Fruit Cove Home with Hot Tub and Lake View!
Fleming Island, FL
9.0Wonderful(5)
Free Wi-Fi
Pet friendly
$297+
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New Floating Luxury: Unique Houseboat Retreat - Fleming Island - Living room
New Floating Luxury: Unique Houseboat Retreat
Fleming Island, FL
8.7Very good(7)
Parking
Free Wi-Fi
Pet friendly
$369+
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30 People Comfortably Gorgeous Home on Canal Boat Kayak access Two 85\' & 75” TVs - Fleming Island - Living room
30 People Comfortably Gorgeous Home on Canal Boat Kayak access Two 85\' & 75” TVs
Fleming Island, FL
$1,219+
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The W in Green Cove Springs - Fleming Island - Living room
The W in Green Cove Springs
Fleming Island, FL
Free Wi-Fi
$1,063+
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Lake Retreat on golf course, sleeps 8 + amenities - Fleming Island
Lake Retreat on golf course, sleeps 8 + amenities
Fleming Island, FL
$355+
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Absolutely Gorgeous home walking distance to Dr's Lake on Fleming Island! - Fleming Island
Absolutely Gorgeous home walking distance to Dr's Lake on Fleming Island!
Fleming Island, FL
Pool
Pet friendly
$626+
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Island Life By Home A Wave - Water Living At It’s Best - Fleming Island
Island Life By Home A Wave - Water Living At It’s Best
Fleming Island, FL
Pet friendly
$369+
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Luxury Waterfront Fishing And Golf Vacation Rental - Fleming Island
Luxury Waterfront Fishing And Golf Vacation Rental
Fleming Island, FL
Pet friendly
Spa
$567+
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$260 - $500$500 - $740$740 - $980$980 - $1,219$1,219+ per night

Property Types

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Free cancellationFree breakfastFree parkingFree internet
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Good to know

Low season

November

High season

May

Average price (weeknight)

$221

Average price (weekend night)

$287
Cheapest month to stay with an average 42% drop in price.
Most expensive month to stay with an average 79% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Fleming Island vacation rental deals

  • The best vacation rental properties in Fleming Island are The Retreat On Florida St (9.9, 21 reviews), Rustic Owl w/ 2Kings In Fleming Island (9.8, 24), and Honey Bee Hideaway (9.6, 21), based on ratings and reviews from real travelers.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Fleming Island for 3 days.

FAQs when booking a vacation home in Fleming Island

  • What types of vacation rentals are available in Fleming Island?

    There are loads of different property types that you can make your vacation home in Fleming Island. You’ll find boats and houses.

  • Are there any pet-friendly vacation rentals in Fleming Island?

    If you’re wanting to bring your furry-friend along you’re in luck. Around 67% of Fleming Island vacation rentals are dog and pet-friendly.

  • How can I find vacation rentals near me in Fleming Island?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Fleming Island?

Our map will help you find the perfect place to stay in Fleming Island by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Fleming Island

Fleming Island vacation rental deals. Search for vacation homes, apartments, condos, cabins, cottages, villas and more in Fleming Island. Find cheap vacation homes to rent in Fleming Island. KAYAK searches hundreds of travel sites to help you find and book a vacation rental in Fleming Island that suits you best.

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