Vacation rentals in Fleming Island

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Top-rated vacation rentals in Fleming Island

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Guest favorite

Home in Fleming Island

5.0 out of 5 average rating, 33 reviews

Fleming Island 4/3 by River wifi&MILS! Beach45min

Newly renovated home in Fleming Island with Mother-In-Law Suite close to Orange Park, Middleburg, Green Cove and Jacksonville Florida. Farmhouse style with a touch of Christmas theme 365! 9 beds, (5)50+" LED 4K TV's in all rooms, fast internet, front/back porches available, A/C in Florida room. Home is next to St. Johns River on 1 acre, walk river street or enjoy the HUGE backyard. Beaches aprx 45 mins Close to restaurants, Publix, Walmart, Hospitals, Public boat ramp etc. All within 1-5 miles

Jun 17 – 24

G$39,273 GYD per night

Guest favorite

Home in Fleming Island

4.93 out of 5 average rating, 116 reviews

Game Room+3 Kings+Fast Wi-Fi+Close to river

Welcome to the Flemingo where can relax on the back patio with a glass of wine and twinkling string lights above. You'll watch the dogs and kids play in the large fenced yard while throwing a frisbee (provided). You'll love cooking a delicious meal in the spacious kitchen. You’ll have a blast in the garage game room! Battle it out on the air hockey table, foosball, darts or boxing bag. At night, the kids will hang out in the garage game room, in the living room playing board games or on

Nov 14 – 21

G$55,263 GYD per night

Guest favorite

Farm stay in Middleburg

4.93 out of 5 average rating, 177 reviews

A Private Loft at Grand Landings Equestrian Center

Welcome to "The Loft" at Grand Landings LLC! Enjoy a taste of the country in our over-the-barn apartment, conveniently located on the outskirt of Jacksonville, Florida. Our recently renovated loft offers all the luxuries of home and comfortably sleeps 4 (with the option of a crib upon request). Enjoy a one-of-a-kind experience and go on a ride on our friendly horses, or venture out and enjoy easy access to nearby natural springs, beaches and restaurants. There's something here for everyone!

Jun 30 – Jul 7

G$27,938 GYD per night

Guest favorite

Tent in Middleburg

4.97 out of 5 average rating, 112 reviews

2-Relax- Retreat-Revive-boutique camping -A/C-Pool

- If having difficulty booking your preferred date or you have a group, message us for more info on 2 additional tents located on property . -Experience nature with all the comforts of home-A/C keeps you cool! see below for special bundle options - Casper King size bed, deck,fire pit, coffee maker, kayaks - Located on Black Creek - Large above ground pool with deck - Grill - Less than 15 min from grocery stores/local restaurants - 40 min from downtown Jax - 50 min to St. Augustine

Nov 7 – 14

G$21,184 GYD per night

Guest favorite

Home in Orange Park

4.89 out of 5 average rating, 129 reviews

Cheerful three bedroom home with a pool

Relax with the whole family at this peaceful place to stay. Have a pool party or just lay out in the pool area with friends. Have a bbq and enjoy family. Spacious backyard with two hammocks and a tree swing. Front porch has a nice sitting area and tree swing. Connect to your favorite streaming platforms on the smart TV's, tv room has karaoke and free WiFi. Board games in hall closet to enjoy with family. 3 miles from Orange Park Mall, AMC movie theatre and many restaurants just minutes away.

Mar 29 – Apr 5

G$36,559 GYD per night

Guest favorite

Farm stay in Middleburg

4.97 out of 5 average rating, 174 reviews

Haystays Farm-Cozy, Charming, Country, Modern Home

Welcome to our special farm house! The home sits on 1.5 acres that is perfectly located on the Orange Park and Fleming Island line. Our location is ideal to everyone! We have plenty of space that makes our farmhouse so AMAZING! You will experience the feel of country living with all the perks of great restaurants, shopping and convenience of being near everything Jacksonville has to offer. Our home is super clean with many amenities to make you feel at home. We love it here and so will you!

Aug 6 – 13

G$26,350 GYD per night

Guest favorite

Guest suite in Middleburg

4.93 out of 5 average rating, 44 reviews

No cleaning fees, No chores! Just relax and enjoy!

Remember when AirBnb offered a fun alternative to hotels, with no chores or cleaning fees? Those days are back at beautiful North Fork Suites! Relax and enjoy historic Middleburg in our 2 room Guest Suite offering a private entrance, separate living and bedroom areas, a comfortable king size bed, and a private bathroom in our rural home. See horses across the street, but still be within 3 miles of many shops and restaurants, all with friendly hosts normally on site. Welcome home!

Aug 29 – Sep 5

G$16,826 GYD per night

Superhost

Condo in St. Augustine

4.78 out of 5 average rating, 147 reviews

Luxury 1 Bedroom World Golf Studio with Pool

Welcome to St. Augustine!! Wonderfully located in the Laterra Condos this Luxury 1-bedroom, 1-bathroom vacation rental offers resort amenities you’ll love coming home to after exploring downtown’s Castillo de San Marcos, the Fountain of Youth or St. Augustine Beach! Located in the King and Bear Golf Course. Explore the resort amenities including access to world class golf courses, multiple pools, a full service spa, tennis courts, hot tub, and state of the art fitness center

Sep 24 – Oct 1

G$17,739 GYD per night

Guest favorite

Home in Green Cove Springs

5.0 out of 5 average rating, 108 reviews

1920 Carriage House on Riverfront Estate

1920 Carriage House on lush private estate. Renovated and charming! Situated on secluded, majestic 6 acre riverfront property on the St. John’s River. Enjoy park like grounds filled with colorful azaleas, ancient oak and hickory trees, dripping in Spanish moss. Sit back and watch and listen to incredible hawks and bald eagles overhead! Wake up to a magical sunrise each day! See the manatees lazily grazing! Owners home is on the property and they are always available.

Jan 5 – 12

G$84,065 GYD per night

Guest favorite

Home in Fleming Island

5.0 out of 5 average rating, 94 reviews

Rustic Owl in Fleming Island with 2 Kings

From our family to yours. Located in the heart of Fleming Island, Rustic Owl was designed and appointed with extended family in mind. We wanted a space for families to visit, relax and enjoy each other.... while being comfortable. This gem offers comfy beds, smart TVs, an open floor plan, laundry facilities, upgrades throughout and with inviting outdoor spaces that overlook a rustic nature preserve. Super clean, Super Fast Wifi and well appointed amenities.

Feb 11 – 18

G$48,690 GYD per night

Guest favorite

Guesthouse in Saint Johns

4.98 out of 5 average rating, 207 reviews

Entire Cottage in St Johns, FL with a Water View

We are an easy 35-minute drive to downtown Jacksonville and 45 minutes to historic St. Augustine. Our property is nestled in a serene, tree-lined neighborhood on a canal that flows into the St. Johns River. The cottage is thoroughly cleaned and sanitized before your arrival with a minimum of 24 hours between bookings. The nightly rate INCLUDES St Johns County's bed tax, but Florida sales tax will be added to your booking fees by Airbnb.

Jun 26 – Jul 3

G$24,778 GYD per night

Guest favorite

Guest suite in Saint Johns

4.92 out of 5 average rating, 170 reviews

Adorable studio with river access.

Relax with your friend or with family at this peaceful place with direct Saint John's river access. You can watch the beautiful sunset on the river. Bring your kayaks and fishing accessories. The river at the property is more than two and a half miles wide. You may fish or do a BBQ at the river. Motor home or RV parking is OK.

Mar 18 – 25

G$23,901 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Fleming Island vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Fleming Island's top sights

Whitey's Fish Camp31 locals recommend

AMC Fleming Island 126 locals recommend

V Pizza & Tap Garden - Fleming Island5 locals recommend

Other great vacation rentals in Fleming Island

Guest favorite

Guest suite in Saint Johns

5.0 out of 5 average rating, 23 reviews

Spanish Style Guest Suite-River Oasis Retreat

Nov 25 – Dec 2

G$27,567 GYD per night

Guest favorite

Camper/RV in Green Cove Springs

4.95 out of 5 average rating, 43 reviews

Green Cove Getaway

May 10 – 17

G$12,488 GYD per night

Guest favorite

Home in Green Cove Springs

4.92 out of 5 average rating, 60 reviews

CozyHome Near Jacksonville&St.Augustine

Dec 3 – 10

G$22,278 GYD per night

Guest favorite

Home in Fleming Island

5.0 out of 5 average rating, 31 reviews

The Gathering Place

Aug 12 – 19

G$47,461 GYD per night

Guest favorite

Guesthouse in Jacksonville

4.97 out of 5 average rating, 76 reviews

Charming, Pet Friendly Retreat in Heart of NE FL

Nov 11 – 18

G$30,187 GYD per night

Guest favorite

Home in Green Cove Springs

5.0 out of 5 average rating, 10 reviews

Arthurs Lake House

Nov 28 – Dec 5

G$122,723 GYD per night

Guest favorite

Guest suite in Middleburg

5.0 out of 5 average rating, 40 reviews

Secluded, Cozy Guest Suite on Black Creek

May 18 – 25

G$17,984 GYD per night

Guest favorite

Guesthouse in Orange Park

4.93 out of 5 average rating, 27 reviews

little dream

Nov 23 – 30

G$17,903 GYD per night

Show all

Quick stats about vacation rentals in Fleming Island

Total rentals
10 properties
Local attractions
Whitey's Fish Camp, Fleming Island Golf Club, and AMC Fleming Island 12
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
10 properties include access to wifi
Total number of reviews
220 reviews
Nightly prices starting at
G$6,267 GYD before taxes and fees

Vacation rentals in Fleming Island

Top-rated vacation rentals in Fleming Island

Home in Fleming Island

Home in Fleming Island

Farm stay in Middleburg

Tent in Middleburg

Home in Orange Park

Farm stay in Middleburg

Guest suite in Middleburg

Condo in St. Augustine

Home in Green Cove Springs

Home in Fleming Island

Guesthouse in Saint Johns

Guest suite in Saint Johns

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Fleming Island vacation rentals

Stay near Fleming Island's top sights

Other great vacation rentals in Fleming Island

Guest suite in Saint Johns

Camper/RV in Green Cove Springs

Home in Green Cove Springs

Home in Fleming Island

Guesthouse in Jacksonville

Home in Green Cove Springs

Guest suite in Middleburg

Guesthouse in Orange Park

Quick stats about vacation rentals in Fleming Island

Total rentals

Local attractions

Popular amenities

Wifi availability

Total number of reviews

Nightly prices starting at

Destinations to explore