Family-friendly vacation rentals in Lakeside

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Lakeside

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Jacksonville

4.85 out of 5 average rating, 158 reviews

Mandarin. Modern and Cozy!

Single family house in Mandarin, one of the best, quiet, safe, and beautiful neighborhoods in Jacksonville. 3-bedroom & 2-bathroom (one with Jacuzzi Tub), front and back yard. The Backyard has a paved area. Driveway capacity 4 cars. Full kitchen, Netflix in the living room , Florida Room, Internet: 75 Mbps . offer Long term stay discount LICENSE NUMBER: DWE2613929 **Smoking is not allow inside the premises, additional $100.00 cleaning fee will be charged if smoking is detected inside the home*

Apr 16 – 23

G$31,001 GYD per night

Guest favorite

Home in Jacksonville

4.99 out of 5 average rating, 164 reviews

Seconds away from the fun in Historic Riverside!

Stay on the scene in this adorable 1940s duplex suite in Historic Riverside! Ranked #6 as the most desirable neighborhood for millennials in the country! Located next door to the King Street District, enjoy walking to the restaurants, bars, cafes, and shoppes nearby. Business professionals and medical interns will be pleased with the very close proximity to the downtown offices and several hospitals. Trip for pleasure? Anything you'd want or need is either a very short walk, bike, or drive away!

Jun 8 – 15

G$25,400 GYD per night

Guest favorite

Guesthouse in Jacksonville

4.98 out of 5 average rating, 129 reviews

The Funk House-A Retreat

If you are requesting to book, make sure that your AIRBNB profile is complete with a current profile pic and a description telling me a little bit about your self. This is a private home, not just a rental, the connections I make through Airbnb are part of the whole experience for me. The Retreat is separate from the main house (The Funk House) it is located in the back, on the top floor garage apartment. It has been completely renovated and furnished into a comfortable place to "Retreat".

Nov 22 – 29

G$16,658 GYD per night

Guest favorite

Home in Jacksonville

4.9 out of 5 average rating, 407 reviews

Cozy Riverside Home. Walking Distance To 5-Points!

This home is located in the heart of Riverside. Cozy and aesthetic! You are centrally located in the center of 5-points. Park your car and leave it!! You are within walking distance to everything. We also have fun bikes located on the property. This home is perfect for couples, business travelers, or if you are traveling alone. - Due to Coronavirus, we’re taking extra care to disinfect frequently touched surfaces between all reservations. • Parking is available on the STREET ONLY

Jul 10 – 17

G$28,580 GYD per night

Guest favorite

Cottage in Green Cove Springs

4.98 out of 5 average rating, 139 reviews

Charming Guest House on Riverfront Estate

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! Enjoy a stroll around the entire estate with owners permission. Owners home is on the property and they are always available. 45 minutes to JAX Beaches. 35 min to St. Augustine.

Jan 17 – 24

G$83,918 GYD per night

Guest favorite

Home in Jacksonville

4.98 out of 5 average rating, 567 reviews

The 1910 General Store - residence

This historic country general store, listed on the National Register of Historic Places, is within easy walking distance to art galleries and cultural events, restaurants, bars, night life, and family-friendly activities. This residence is good for couples, solo adventurers, business travelers, families, and furry friends (pets, max. of 2). We are unable to allow guests to host gatherings and house parties. Off street parking available. "Historic hospitality with a southern accent!"

Feb 2 – 9

G$37,795 GYD per night

Guest favorite

Home in Orange Park

4.89 out of 5 average rating, 211 reviews

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.

Dec 22 – 29

G$45,606 GYD per night

Guest favorite

Guesthouse in Jacksonville

4.98 out of 5 average rating, 350 reviews

Private Apartment

Unique private upstairs apartment near the beautiful Julington Creek very close to St. Johns, under majestic live oak trees offering a quiet and secluded setting, but close enough to everything you need for your next trip to Jacksonville. Short distance to great dining, beaches, shopping, St. Johns and St. Augustine! Guests will enjoy a one bedroom apartment with a fully equipped kitchen. Property access for our guests only. Complimentary beer, sodas, water and coffee! Adults only.

Apr 5 – 12

G$25,817 GYD per night

Guest favorite

Home in Jacksonville

4.84 out of 5 average rating, 170 reviews

Private FL Home with Pool, Hot tub & Luxury Master

This is a lovely family home in the Mandarin area of Jacksonville which has undergone many renovations and upgrades. The master boasts its own, ensuite, tv, fireplace and sitting area, as well as a private entrance from the pool and hot tub area. The house itself has newer furnishings, flooring, modern decor, a large fenced in backyard, pickle ball court and firepit. Located safe South East Suburb of Jacksonville, not far from shopping, beaches and many other Florida attractions.

Apr 19 – 26

G$40,024 GYD per night

Guest favorite

Bungalow in Jacksonville

4.81 out of 5 average rating, 247 reviews

San Marco Area Bungalow * Cozy Screened Porch*

Welcome to Stylish Historic San Marco charming bungalow with cozy front porch, the perfect retreat for your next Airbnb getaway! Nestled in a peaceful neighborhood, this adorable bungalow offers a cozy and inviting atmosphere that will make you feel right at home. Centrally located making it convenient to downtown, medical facilities, beaches and more. *There are other cottages next door, perfect for groups or families that want to stay in the same location.

Jul 5 – 12

G$27,239 GYD per night

Guest favorite

Home in Jacksonville

4.93 out of 5 average rating, 350 reviews

* The Cowford House *

Stay at our cute, 910 square foot home built in 1944. Situated in the established neighborhood of Lake Shore on a safe, quiet street. It's kid-friendly with a fenced in yard and an enjoyable neighborhood for evening walks. Close proximity to local produce, groceries, a mall, coffee, restaurants, etc, anything you could need. Nestled between State Road 21 (Blanding Blvd) & U.S. Route 17 (Roosevelt Blvd) we are just minutes from I-10, I-95 & I-295 Interstates.

Jun 15 – 22

G$26,016 GYD per night

Guest favorite

Apartment in Jacksonville Beach

5.0 out of 5 average rating, 199 reviews

"Sweet Water" Waterfront Studio Apartment

Experience inter-coastal living in a well-appointed waterfront, upstairs studio guest house. Furnished with a queen bed, full-size sleeper sofa & many amenities. Only minutes from the beaches, Mayo Clinic, restaurants, nightlife, Players Championship Golf Course, shopping & more. Conveniently located near lots of activities, but not too close to interfere with your rest & relaxation. Whether on vacation or business, it's the ideal location!

Aug 15 – 22

G$26,923 GYD per night