Family-friendly holiday rentals in Fleming Island

4.96 out of 5 average rating, 205 reviews

The back patio features a cozy seating arrangement with a modern sofa and a small table. Twinkling string lights illuminate the area as evening approaches, providing a warm ambiance. A dining table for four is visible on the patterned outdoor rug, amidst a spacious fenced yard with trees.

Home 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

KitchenIndoor spacesPets

Place to stay in Orange Park

An outdoor patio area features a wooden table and chairs, providing a relaxing space to enjoy views of the water. A flag flies in the distance, while a covered structure offers shade. Lush green grass surrounds the area, enhancing the natural setting.

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.

KitchenFamilyAmenities

4.94 out of 5 average rating, 136 reviews

Cottage in Green Cove Springs

Two charming guest houses are surrounded by well-maintained landscaping filled with colorful azaleas. Mature trees provide shade, and sunlight filters through, creating a serene outdoor space. The residences feature distinct architectural styles, showcasing a harmonious blend with the lush surroundings.

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.

KitchenFamilyCheckout

4.98 out of 5 average rating, 157 reviews

5.0 out of 5 average rating, 156 reviews

Home in St. Augustine

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 spacesFamilyPool

Holiday home in Orange Park

A two-story house is set back on a spacious driveway, surrounded by lush trees and vegetation. A manicured lawn features well-maintained plant beds near the entrance, while the garage is visible on the left side of the structure under a clear blue sky.

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.

Indoor spacesFamilyDecor

4.85 out of 5 average rating, 123 reviews

4.97 out of 5 average rating, 240 reviews

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!

Indoor spacesFamilyComfort

4.93 out of 5 average rating, 123 reviews

A spacious living area features a light-colored leather couch with yellow accent pillows. A dining table is in the background, and wooden cabinetry with dark countertops is visible in the adjoining kitchen. Soft lighting enhances the inviting atmosphere.

Home in Orange Park

Nature Cozy Home

Located in Orange Park FL , this rural, rustic, colorful getaway can be your home away from home! Guests can enjoy the forested and vintage scenery that reminds one of simpler times. The designated parking area is indicated by the, sign of three flowers at the left side of the driveway. Guests will also have their own seating area. Please note we have another Listings: Retreat Mobile Camper (back to house) and Guest Suite (attached to house)on the property! , with everything private Thanks

Indoor spacesFamilyLocation

4.94 out of 5 average rating, 127 reviews

The kitchen area features modern white cabinetry and stainless steel appliances, including a dishwasher and sink. A colorful rug lies on the floor, enhancing the space. Bright natural light enters through the window, while a dining area with red chairs is visible in the background.

Home in Middleburg

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:).

KitchenIndoor spacesLaundry

4.85 out of 5 average rating, 240 reviews

Home in Orange Park

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 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

Indoor spacesFamilyNearby

4.99 out of 5 average rating, 173 reviews

An outdoor space features a stone patio with a circular arrangement of four black chairs surrounding a fire pit on gravel. Verdant landscaping and trees provide a natural backdrop, enhancing the tranquility of the area.

Home in Fleming Island

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.

KitchenIndoor spacesPets

Home in Southwest Jacksonville

A welcoming living area is depicted, featuring a spacious sofa with decorative cushions and a rectangular glass coffee table. A large TV stands on a media console, and a ceiling fan provides airflow. The open layout connects to the dining area in the background.

Sunset near the Lake/12guests/4bdrs/2baths

Welcome to our beautifully remodeled vacation home on a safe, quiet street. Enjoy a stylish full kitchen, cozy living and dining areas, and direct lake access for fishing. Conveniently located near downtown Jacksonville, with easy access to Walmart, restaurants, beaches, Blue Springs, historic sites, NAS Jax, the airport, seaport, and local colleges. We look forward to hosting you and making your stay comfortable and memorable!

KitchenFamilyNearby

4.94 out of 5 average rating, 266 reviews

Townhouse in Southwest Jacksonville

A spacious living area is revealed, featuring a comfortable dark sofa and light-colored accents. A round coffee table sits on a textured rug, while a large television is mounted on the wall. Natural light enters through the windows, illuminating the open layout.

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.

KitchenIndoor spacesTV

4.98 out of 5 average rating, 603 reviews

Popular amenities for Fleming Island family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A clear swimming pool is depicted, showcasing calm water with scattered floating toys. Sunlight reflects off the surface, creating a serene atmosphere. Surrounding the pool are several black lounge chairs, providing space for relaxation.

4.88 out of 5 average rating, 246 reviews

Private FL Home with Pool, Hot tub & Luxury Master

KitchenIndoor spacesLocation

4.87 out of 5 average rating, 344 reviews

A well-maintained outdoor pool area is framed by palm trees and lush green landscaping. The sparkling blue pool features a central fountain and is surrounded by loungers, creating a serene environment for relaxation.

Condo in St. Augustine

Full Condo in St. Augustine’s World Golf Village

FamilyKitchenAccuracy

4.85 out of 5 average rating, 111 reviews

A spacious pool area is surrounded by lush greenery, featuring a large, sparkling blue pool and a jetted hot tub. Lounge chairs are placed along the poolside, complemented by a shaded area for relaxation. A clear sky is visible above, enhancing the outdoor atmosphere.

Home in Jacksonville

Gorgeous Florida Pool and Spa Home

FamilyIndoor spacesHospitality

4.81 out of 5 average rating, 151 reviews

~Billiard Abode_Sleeps 12_Heated Pool & Spa~

FamilyIndoor spacesHospitality

Home in Jacksonville Beach

An outdoor space features a rectangular saltwater pool surrounded by lounge chairs. Green foliage and a wooden fence provide privacy, while a shaded area includes a seating structure. The clear water of the pool reflects sunlight, inviting relaxation.

Pool & Hot Tub Home w/ Game Room! 1 Mile to Beach!

FamilyIndoor spacesHot tub

4.88 out of 5 average rating, 121 reviews

4.87 out of 5 average rating, 107 reviews

Home in Palm Valley

Seaside Paradise - Pool! Spa! Game Room! 12 Beds!

KitchenFamilyNearby

Apartment in St. Augustine

Condo near Downtown St Augustine/beach/golf

Indoor spacesFamilyAccess

4.96 out of 5 average rating, 134 reviews

Guesthouse in Ponte Vedra

Guesthouse/TPC/Guana Views/Walk Beach/Hot Tub

FamilyKitchenQuiet

4.92 out of 5 average rating, 181 reviews

Family- and pet-friendly home rentals

Home in Green Cove Springs

An open-concept living area features light wood flooring and neutral-colored walls. A spacious sectional sofa faces a large television. The kitchen showcases wooden cabinets and modern appliances, with a breakfast bar that includes several stools. Natural light enters through multiple windows.

Cozy 3 bedroom house in town, bikes included!

FamilyKitchenLayout

4.86 out of 5 average rating, 146 reviews

A tranquil outdoor area features a swimming pool surrounded by a sun deck with lounge chairs. A table set for dining stands nearby, complemented by trees and blue sky above. The home in the background blends with the natural surroundings.

4.88 out of 5 average rating, 102 reviews

Posh Pool and Pond Landing

FamilyIndoor spacesQuiet

A modern kitchen is equipped with sleek white cabinets and a spacious countertop. A stainless steel refrigerator and high-end appliances are visible, along with an induction cooktop seamlessly integrated into the surface. Soft lighting illuminates the area, creating a functional cooking space.

4.91 out of 5 average rating, 128 reviews

Cozy house in a heart of Mandarin

KitchenFamilyCondition

4.81 out of 5 average rating, 135 reviews

Putt Putt Pool Home - Mini Golf,Grill,Ping Pong

Indoor spacesKitchenBathroom

Apartment in Southwest Jacksonville

A resort-style swimming pool is surrounded by lush palm trees and lounge chairs. The pool features a clear blue surface reflecting the evening sky with subtle hues of purple and orange. Nearby, a shaded seating area is visible, offering additional relaxation options.

Luxury Apartment w/Great pool 3 Miles from NAS JAX

KitchenIndoor spacesHospitality

4.9 out of 5 average rating, 106 reviews

4.98 out of 5 average rating, 157 reviews

Guesthouse in Mandarin

Pet Friendly Studio w/ Private Fenced Yard

KitchenIndoor spacesCleanliness

4.85 out of 5 average rating, 196 reviews

Mandarin. Modern and Cozy!

KitchenIndoor spacesAccess

4.99 out of 5 average rating, 137 reviews

A serene night scene features a heated pool illuminated in vibrant purple tones. Comfortable lounge chairs sit at the water's edge, surrounded by lush greenery and softly glowing string lights strung overhead, creating a cozy outdoor setting.

Home in Vilano Beach

Walk to Beach | Heated Pool | Game Room

FamilyIndoor spacesCleanliness

Family-friendly home rentals with a pool

4.98 out of 5 average rating, 126 reviews

A well-appointed bedroom features a spacious wooden sleigh bed with a light blue and white quilt. Natural light fills the room through windows with soft drapes, and a flat-screen TV is mounted on the wall opposite a matching wooden dresser and nightstand.

Home in Fruit Cove

King bed, Lake View, sleeps 8, 6 TVs, Public Pool

KitchenIndoor spacesCheck-in

Home in Southwest Jacksonville

The pool area is enclosed by a protective screen, illuminated by soft lighting, creating a serene atmosphere. The turquoise water reflects a tranquil ambiance, while the surrounding space is designed for relaxation and recreation.

Cozy Home with Heated Private Pool and Patio

FamilyKitchenOutdoor spaces

4.92 out of 5 average rating, 169 reviews

Apartment in Southwest Jacksonville

SuperHost Special! 1BR/1BA Luxe Stay in Jax

FamilyIndoor spacesWi-Fi

4.89 out of 5 average rating, 118 reviews

4.94 out of 5 average rating, 101 reviews

A serene community swimming pool is surrounded by lush greenery, with lounge chairs positioned nearby for relaxation. The clear water reflects the blue sky, while palm trees add to the tranquil atmosphere. Access to the pool is complimentary for guests.

Home in Fruit Cove

*Gorgeous Home! Safe, very peaceful*

Indoor spacesKitchenValue

Apartment in Southwest Jacksonville

A seating area contains two black leather couches and a coffee table with decorative items. A large mural depicting a sports-themed scene is displayed above the couches. Natural light enters through glass doors, which provide access to the outdoor space, framed by dark curtains.

Jaguars Suite | King • Sleeps 6 • Pool • Pets

FamilyKitchenHeating

4.87 out of 5 average rating, 163 reviews

Home in Southwest Jacksonville

Retreat on the river

Indoor spacesKitchenBathroom

4.89 out of 5 average rating, 403 reviews

A spacious backyard features a clear blue pool surrounded by a concrete deck. A large inflatable unicorn floats in the water, while a sun lounger and two patio chairs are positioned nearby. Lush greenery and trees frame the area, enhancing the serene setting.

4.87 out of 5 average rating, 118 reviews

Elegant & Stylish Pool House with Arcade!

FamilyKitchenCondition