Vacation rentals in Fleming Island

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Top-rated vacation rentals in Fleming Island

Guests agree: these stays are highly rated for location, cleanliness, and more.

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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

Oct 6 – 13

$230 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!

Aug 2 – 9

$94 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

Oct 4 – 11

$99 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.

Dec 15 – 22

$151 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!

Sep 15 – 22

$120 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!

Sep 29 – Oct 6

$71 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

Oct 23 – 30

$73 per night

Guest favorite

Guest suite in Saint Johns

5.0 out of 5 average rating, 23 reviews

Spanish Style Guest Suite-River Oasis Retreat

Welcome! Our river home offers a private large space, a bird and butterfly sanctuary, watching fish jumping, and viewing manatees. Includes a living room, bedroom, full bath, spacious dining, and kitchenette area. A calm oasis with full access to a beautiful backyard garden, pool, and kayaking experience. In the backyard is a seasonal refuge for manatees and many tropical birds. Experience Kayaking the beautiful St. Johns River and sunsets at Alpine Grove Park, a must-see!

Nov 25 – Dec 2

$115 per night

Guest favorite