Family-friendly holiday rentals in Fleming Island

The Flemingo- Game Room 3 Kings

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

Kitchen · Indoor spaces · Check-in

Beautiful 3 bedroom 2 bathroom waterfront home

Welcome to Cedar house, located on Drs. lake in orange park Fl. Conveniently located to 295 and just 15 mins from N.A.S. Jax ,30 mins from down town Jax, and 30 mins from the shopping at St johns town center, our home has been recently remodeled in 2022 and is a cosy and relaxing escape. With brand new kitchen, bathrooms, and open floor plan and the new dock/ boat house its perfect for getting the boat on the water or relaxing with friends/family and enjoying the fishing under the Florida sun.

Family · Kitchen · Barbecue

Guest House-Enchanted Oaks Estate-Weddings-Dock

Pretty Guest House situated on majestic 5 acre riverfront estate on the St. John’s River with 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! Bass Pro Shop did a photo shoot here for their Spring 2025 catalogue! Owners home is on the property and they are always available. 45 minutes to JAX Beaches. 35 min to St. Augustine.

Kitchen · Indoor spaces · Parking

Private oasis, heated pool, exceeds expectations

Private retreat on 2 acres of gated land, just 20 minutes to historic downtown St. Augustine and 25 minutes to the beach. This fenced property offers a perfect blend of relaxation, fun, and comfort. Enjoy your private pool, or let the kids enjoy their own space in the pool house, featuring TV, games, and a cozy hangout area. Start your day with fresh eggs from our happy hens- an experience that feels both farm-fresh and uniquely memorable. This home is designed to make your stay unforgettable.

Indoor spaces · Family · Beach

Casandra House - Peaceful / Salt Pool and Hot Tub

Welcome to Casandra House. A peaceful getaway in Orange Park, FL. Located in the vicinity of Doctor's Lake, this house sits on 3/4 of an acre surrounded with trees and vegetation. It provides just enough privacy to make you feel away from everything while minutes from shops and restaurants. Home includes a large backyard, patio screen enclosure, salt pool and hot tub. About 2 1/2 miles from the Orange Park Thrasher-Horne Center and 10 miles from NAS Jacksonville. Note: No direct lake access.

Kitchen · Family · Wi-Fi

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!

Kitchen · Family · Condition

Cozy 3 bedroom house in town, bikes included!

Welcome to the Sunny Side Up Villa in charming Green Cove Springs! This private home is centrally located in historic downtown and includes bicycles for you to tour the city and visit all the sights. Spring Park and the St. John's River are just a mile down the road. The three bedroom home sleeps eight and features a brand new king bed in the master suite. The open concept living room and kitchen are great for entertaining and the backyard is completely fenced in for your four-legged pals.

Indoor spaces · Kitchen · Barbecue

Modern E. Orange Park Home 6 bed Fence Beach 45Mn

New Stylishly renovated home just West of Fleming Island in Middleburg, South of Orange Park, West of Jacksonville Florida. Christmas 365! Farmhouse style, TV’s in all bedrooms, with a touch of Christmas theme. 6 beds, Fenced yard, 75" LED TV, front/back porches available up to 10 people. Beaches approx. 40 minutes The home is close to restaurants, grocery stores, banks, gas stations, main hospital(2+miles). There are lakes and rivers locally to fish/boat, parks, shopping, and trails:).

Indoor spaces · Kitchen · Layout

Luxury Home w/ Glass Room & Patios

Spectacular Inside and Out This magnificent 2940 sq foot home is in a prestigious lakeside neighborhood. It offers a large open concept living area with an adjoining 400 sq foot climate controlled sun room with a pocketing glass interior wall; to bring the outside in and the inside out. The exterior of the sun room is constructed of glass doors which can also be opened and stacked to facilitate an open air porch. Owner lives in the neighborhood and is quick to respond to your needs.

Kitchen · Family · Parking

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. Level 2 EV Charger.

Kitchen · Family · Hospitality

Cheerful three bedroom home with a pool

Relax with the whole family at this peaceful place to stay. Enjoy the pool 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. 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

Family · Kitchen · Laundry

4 Queen bed 3bds/2 ba, playroom 295, 17. Townhouse

The townhouse has a ground floor which is very suitable for seniors and those with special needs because it has a room with two Queen beds/full bathroom/kitchen/living room/dining area/an exit to a playroom,a small backyard,a laundry room. The second floor has 2 rooms+full bathroom+crib+TV. One of them is a walk-through room and has no window. Wide parking (4 cars). Good location in orange park. Quiet area.

Family · Indoor spaces · Value