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

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

Guest favorite

Guest suite in St. Augustine

Entire guest suite short walk to beach.

Enjoy exploring beautiful, historical St. Augustine then kick back and take it easy at this private, quiet beach retreat within a short walk to the beach. Separate keyless entry allows for self check-in. Queen size bed, fully furnished, with amenities including a Keurig coffee maker, iron, hair dryer, beach cruiser bicycles, beach chairs, towels, umbrella and gas grill for cooking out. Flat screen TVs in both the living room and bedroom with Netflix and Amazon Prime included and Free WiFi

Guest favorite

Farm stay in Middleburg

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!

Guest favorite

Tipi in Middleburg

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

Guest favorite

Condo in St. Augustine

Luxury World Golf Village 1 Bed 1 Bath Condo

Escape to St. Augustine and enjoy a luxury one bedroom condo with new renovations and upgrades! Located within the private gates of the World Golf Village in the Laterra resort, home of the King and Bear Golf Course. Explore the resort amenities including access to golf, multiple pools, a full service spa, lighted tennis courts, hot tub, and fitness center. Minutes away from restaurants, shopping and the Golf Hall of Fame. Travel to Historic St. Augustine and beaches in less than 30 minutes!

Guest favorite

Farm stay in Middleburg

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!

Guest favorite

Home in Southwest Jacksonville

Unwind. Cozy Creekside Cottage near Ortega/NAS

Enjoy this charming creekfront cottage in the heart of Jacksonville. Unwind as the sun sets over the water, relax under shady cypress trees while wildlife travel about the tidal creek, enjoy cocktails on the dock, engage in boating or try your luck fishing. A boat ramp is nearby for boat launching. (Plenty of room to park Boat/Trailer on the nearly 1 acre lot ) While this unique retreat provides a tranquil getaway, it is also centrally located making it convenient for you to get around.

Guest favorite

Guesthouse in Murray Hill

Large 1 bedroom Cottage with full kitchen

This is a full size one bedroom house with full brand new kitchen and private entrance. The entire place was renovated late 2021. A luxurious king size bed awaits you and a twin sized sofa bed for one adult or two kids. The kitchen has a full sized brand new oven, stove, microwave, dishwasher and fridge and is stocked with utensils etc so you can easily make full meals or stay for an extended time. There's one free off-street parking spot available and plentiful free street parking.

Guest favorite

Guesthouse in Saint Johns

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.

Guest favorite

Home in Keystone Heights

Lake house - Kayaks and Fishing Poles

Awesome sunsets - Silver Sands is one of the few area lakes that is full and natural spring fed. Water is crystal clear and soft yes soft. 2 private decks, laundry room, and 2 carports. Two kayaks, Lake front swimming and fishing - come relax. 5 minute drive to groceries and gas. New fast WiFi , interior paint and metal roof. Pets are welcome but don’t we do charge a fee. We also charge a late checkout fee.

Guest favorite

Guesthouse in Riverside

Enchanted Forest: a Magical Luxury Studio

Lost to time, at the end of a long forgotten forest path, where dappled sunlight outline trees, moss, and stone. Enjoy the luxurious richness of satin, velvet, chandeliers and candles. Looking to escape, we’d love to share the path to this hidden destination in Historical Riverside. Equipped for work travel, date night, solo escapes, or longer vacations, this enchanted forest destination is right for you.

Guest favorite

Condo in St. Augustine

My HOME is their HOME

Inspired by the Spanish architecture St. Augustine is known for, you can enjoy old world feel with modern perks in this fully furnished one bedroom one bath resort-like condo. There is a full service spa/salon on site. A short 5 min walk is a fitness center, tennis courts, playground etc. offering so much more than a regular hotel for the money!

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

Camp Chowenwaw Park4 locals recommend

Other great vacation rentals in Fleming Island

Guest favorite

Home in Green Cove Springs

Cozy 3 bedroom house in town, bikes included!

Guest favorite

Home in Fleming Island

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

Guest favorite

Guesthouse in Mandarin

Charming, Pet Friendly Retreat in Heart of NE FL

Guest favorite

Guesthouse in Fruit Cove

Cozy Cottage

Guest favorite

Home in Fleming Island

Rustic Owl in Fleming Island with 2 Kings

Guest favorite

Rental unit in Southwest Jacksonville

Tranquil Blue

Guest favorite

Home in Orange Park

Dogwood Stay: Near the Lake

Guest favorite

Home in Southeast Jacksonville

Quiet townhouse Backyard. Pet friendly. I-95.

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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
$30 before taxes and fees

Vacation rentals in Fleming Island

Top-rated vacation rentals in Fleming Island

Home in Fleming Island

Guest suite in St. Augustine

Farm stay in Middleburg

Tipi in Middleburg

Condo in St. Augustine

Farm stay in Middleburg

Home in Southwest Jacksonville

Guesthouse in Murray Hill

Guesthouse in Saint Johns

Home in Keystone Heights

Guesthouse in Riverside

Condo in St. Augustine

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

Home in Green Cove Springs

Home in Fleming Island

Guesthouse in Mandarin

Guesthouse in Fruit Cove

Home in Fleming Island

Rental unit in Southwest Jacksonville

Home in Orange Park

Home in Southeast Jacksonville

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