Family-friendly vacation rentals in Lakeside

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Lakeside family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
A balcony view showcases the tranquil ocean during sunrise, with two adirondack chairs placed on either side of a small table. Coffee cups are positioned on the table, surrounded by lush greenery and the gentle waves in the distance.
Home in St. Augustine
4.8 out of 5 average rating, 5 reviews

Beachfront Getaway Directly on St. Augustine Beach

DaphneRating, 5 stars5 months ago
All was wonderful, easy drive to condo, easy to get in, good restaurants around us, easy drive to town... beach was awesome! I love coming to FL this time of the year in November we have had great luck with the weather and temperature of water and best of all less crowds. Appreciated the beach towels not having to bring them was a lifesaver, we were limited in space in the vehicle. The garage was well stocked, we loved having the ability to bike ride, body surf (I will buy one for myself HA), tennis rackets, just great.
Guest favorite
The exterior of a two-story home is presented, showcasing a blend of light and dark siding. Large windows provide a view of the front entryway, flanked by greenery. A separate structure is visible to the left, adding to the overall spaciousness of the property.
Home in St. Augustine
4.93 out of 5 average rating, 164 reviews

5*Pool Oversized Home*Beach*Walk to all

TomRating, 5 stars4 months ago
We loved staying here. Beautiful home, extremely comfortable and very convenient to the old town. A nice surprise that Nancy decorated for Christmas with a tree, lights, etc. and set the mood for our Thanksgiving week with the town’s lights.
Guest favorite
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.
Home in Southeast Jacksonville
4.85 out of 5 average rating, 201 reviews

Private FL Home with Pool, Hot tub & Luxury Master

CarmelRating, 5 stars4 weeks ago
Amazing spaces indoor and out. The Airbnb pictures don’t do it justice. 3 bedroom, 3 bath, pullout couch. Sleeps 8 adults (willing to share beds) and 4 children (pullout couch and blow up mattress). Plenty of room for cooking, dining, well-equipped kitchen w/ air fryer, 2 coffee makers, crock pot and more. Great location 20 minutes from anything. Walked to stores (1.5 miles each way). Games and puzzles. Great master suite. Takes a few minutes to get hot water to back bathrooms, but be patient, it’s worth it. This could be a repeat for us!
Top guest favorite
A well-organized closet features shelving and storage solutions, showcasing a variety of items including beach chairs, towels, and sports equipment. Hangers are used for clothing, while rolling carts and containers add functionality, creating an efficient space for guests' needs.
Condo in Beaches
4.96 out of 5 average rating, 26 reviews

Breathtaking Oceanfront Views!

AlmaRating, 5 stars6 months ago
Great condo all the amenities you could want - nice wide balcony with a beautiful view. We spent lots of time there from early morning to late at night - we did not cook at night but if you wanted the kitchen was equipped with everything you might need. Convenient to beach restaurants. Pool was nice. Other condo guests were friendly. Highly recommended
Guest favorite
Guesthouse in St. Augustine
4.91 out of 5 average rating, 569 reviews

Captain's Quarters Tiny House

JenniferRating, 5 stars5 days ago
I would like to say first and foremost this was THE MOST COMFORTABLE BED we’ve slept in an air bnb and the place would be a top choice just for that alone. We had access to the hot tub that was much needed after sight seeing. We enjoyed the outdoor showering area as well. We had everything we needed for the few days we were there visiting. We will be back !
Guest favorite
A compact bathroom features a circular mirror above a white sink with storage cabinets. A toilet is positioned nearby, and a glass shower with a frosted door is visible. Natural light enhances the neutral-toned walls, creating a clean and functional space.
Condo in St. Augustine Beach
4.94 out of 5 average rating, 355 reviews

~Hot Tub~Just Steps to the Beach~King Bed~2 Pools

Chanda & TomRating, 5 stars5 days ago
Absolutely a great place to stay for families, singles or couples. So convenient to the beach. The condo felt like home. Everything has been thought of that you could need for a comfortable and convenient stay. Super responsive and friendly host! Will definitely be back!
Home in Beaches
4.74 out of 5 average rating, 88 reviews

Artist's Beach Retreat under Oaks - Hot Tub, Mayo

ChelseaRating, 5 stars7 months ago
We had an amazing time at David’s home. Everything was conveniently labeled and clean. The home is beautiful and located very close to downtown and the beach. David was responsive with any questions or concerns we had and was extremely nice. We would definitely stay here again.
Guest favorite
The bathroom features a clean, light-toned design with a tub and shower combination. Decorative seashell curtains add a coastal touch, while a spacious vanity with a white countertop and multiple fixtures creates a functional area. Towels and toiletries are organized for convenience.
Apartment in St. Augustine Beach
4.8 out of 5 average rating, 79 reviews

Top Floor (Elevator Building) Ocean View Condo!

StefRating, 5 stars5 days ago
The place was lovely with a wonderful view of the beach. It was easy to access and perfectly located. Marty was very responsive and patient with my over tired mom brain questions. I loved the proximity to not only the beach but hot tubs and pools. With a short drive to some wonderful restaurants and downtown!

Family- and pet-friendly home rentals

Guest favorite
A living room features a black leather sofa and a glass coffee table. A wall-mounted television displays the Netflix logo. Decorative items are arranged on a console table. Natural light filters through double French doors, leading to an outdoor area.
Home in Southeast Jacksonville
4.85 out of 5 average rating, 178 reviews

Mandarin. Modern and Cozy!

RogerRating, 5 stars1 month ago
Great location and neighborhood. Good amenities. Host is very responsive and helpful.
Top guest favorite
A private pool area is surrounded by a wooden fence and tropical landscaping. A ladder leads into the clear blue water, inviting relaxation. Sunlight filters through the trees, creating a serene atmosphere. A sign indicating 'Beach Access' is prominently displayed.
Home in St. Augustine
4.94 out of 5 average rating, 131 reviews

The Lazy Anchor-Pool-Walk to Beach-Dog Friendly

MelissaRating, 5 stars4 months ago
Absolutely beautiful stay, super close to beach access, short drive to the historic district of St. Augustine. A thoughtful and well stocked home, great for folks that are looking to cook + have meals with their families. Dalerie’s a clear communicator and responsive host. We hope to be back one day!
Top guest favorite
A bright bedroom features a double bed covered with a yellow patterned blanket. Natural light enters through two windows, framed with sheer curtains. A small nightstand holds decorative items, and a ceiling fan adds a functional element to the space.
Apartment in St. Augustine Beach
4.88 out of 5 average rating, 274 reviews

Low Tide - Beach Bungalow

MandyRating, 5 stars4 months ago
We love Low Tide and look forward to our beach trip every year! It's the absolute best pet friendly place to stay, my dogs always have the best time going for walks on the beach and hanging out in the beautiful backyard. Inside is cozy and comfortable too. The best part is being only steps away from the beach, and many great food options also within walking distance. My favorites are Burrito Works, Beachcomber, and Cone Heads for ice cream (and pup cups!) Low Tide has just about everything you could possibly need, and Laurie is always making improvements to her beautiful place. We're always sad when it's time to leave!
Superhost
A historic two-story craftsman bungalow is showcased under a clear blue sky. The structure features a welcoming front porch with white railings and brick supports, surrounded by lush greenery and old growth trees. The vibrant green siding contrasts with the natural landscape.
Apartment in Riverside
4.78 out of 5 average rating, 237 reviews

* Best Location * Walk to Everything * 1st Floor *

MikeRating, 5 stars15 months ago
Tyson and his place were awesome ! Tyson was easy to communicate with and the unit was huge (it was only my wife and me). The neighborhood is very safe and walkable and there were many, many bars and restaurants a short distance away. We recommend Tyson’s property and will surely try to stay there again the next time we are in town.
Top guest favorite
Home in St. Augustine
4.99 out of 5 average rating, 403 reviews

Your Home Away From Home

AshleyRating, 5 stars1 week ago
I cant say enough good things about Fred and Lynn's home away from home. I've stayed at a few locations in St Augustine, but they deserve more than 5 stars. My family enjoyed every second of their peaceful surroundings. The home was gorgeous, pool felt amazing, and hosts and fur babies were super friendly. We are definitely planning on returning now that we have found this hidden gem. Close enough to great restaurants, but so private that deer felt safe enough to lay in their yard. Fred met us as soon as we arrived with Ellie and they gave us the grand tour, checked in during our stay to make sure we were comfortable, and Lynn came out to have conversation and offered my daughter a pool float. Even making sure she had sun screen. It was the little moments like that that made this place so special!! I said several times "reminds me of grandma's house as a kid." Thank you again Fred, Lynn, Ellie, and Boo. We miss yall already!
Guest favorite
A heated pool is surrounded by palm trees and vibrant greenery, featuring a tiled patio with six blue lounge chairs positioned along one side. The pool area offers a tranquil space for relaxation and outdoor enjoyment.
Home in St. Augustine
4.88 out of 5 average rating, 331 reviews

Pure Relaxation: heated pool, beach, cabana & more

KaceyRating, 5 stars2 weeks ago
This home is probably one of my favorite stays thus far! Walking distance to the beautiful caps on the water restaurant and walking distance to the beach. The house was nice and clean with plenty of space. The pool was clean as well and overall a great experience!
Superhost
An open living space includes a dining table surrounded by chairs, with a cozy seating area featuring light-colored sofas. Shelving displays decorative items, and a well-equipped kitchen is visible in the background. Natural light illuminates the space through multiple windows.
Home in St. Augustine
4.91 out of 5 average rating, 216 reviews

The Anastasia House Close to Downtown and beaches

TammyRating, 5 stars11 months ago
Great place to stay close to the historic area and lots of places to eat. close to beaches. The place was cute and clean great enclosed patio should def rebook next time we are in St Augustine
Top guest favorite
An open concept studio features a spacious bed adorned with ocean-themed bedding. A comfortable blue chair sits near a wooden storage chest. Two bedside lamps provide soft lighting, while a wall-mounted TV and decorative wall art add to the inviting space.
Vacation home in St. Augustine
4.98 out of 5 average rating, 124 reviews

1st Street Retreat, Dog Friendly Updated Apartment

BradRating, 5 stars1 week ago
First time staying here, but we've always had a great experience staying at Lisa's properties in St. Augustine, always clean with thoughtful amenities, and very close to the beach. Lisa is an amazing hostess, and we're so lucky that she loves dogs!

Family-friendly home rentals with a pool

Superhost
A clear view of a swimming pool is seen, with steps leading in. Palm trees are visible beside the pool, and the ocean can be seen in the background, revealing waves meeting the shore.
Condo in Beaches
4.85 out of 5 average rating, 65 reviews

D&G Beach House

KatieRating, 5 stars1 month ago
this place was perfect for our group of four! walkable to everything and right on the beach. The space was clean and private and exactly what the pictures showed. We couldn't have been happier. Staley was also super nice and responsive and had great recommendations for places to eat in her welcome book. We definitely will stay here again!
Superhost
A modern bathroom is displayed with a sleek dark vanity topped by a light-colored countertop. A mirror framed in gold hangs above, and various toiletries are arranged neatly nearby. A shower curtain partially obscures the shower area, while a clean, white toilet is positioned discreetly.
Home in Orange Park
4.8 out of 5 average rating, 83 reviews

Cozy House mins from NAS JAX & Orange Park Mall

MaggiRating, 5 stars3 weeks ago
John was friendly. He responded quickly to any issue we had, and wee had very few. The water pressure was low. I was unhappy with the neighborhood, which was on its way to becoming a slum. But John was the BEST host ever. He always responded almost immediately. It was too cool to use the pool. We were close to our friends and Church. I would rent from him again.
Guest favorite
Apartment in St. Augustine Beach
4.94 out of 5 average rating, 182 reviews

Modern & Comfy Beach Gem: Pool ~ Ocean Views ~ Pkg

LoriRating, 5 stars3 weeks ago
Mark and Melanie have a GEM at St Augustine Beach! The kitchen is so well stocked there is nothing missing. The seaside decor sets the tone for a very comfortable and relaxing getaway! The unit is clean, bright, well designed and the walkout patio directly to the beautiful Pool is a highlight ! The condo complex is securely gated. And extremely well maintained. And they’ve thought of everything , all The beach chairs, toys and towels are included which makes packing for a beach vacay a breeze. Melanie was very responsive and prompt with checkin instructions and local Recommendations. The beach is our favorite with white sugar sand , rolling surf, shells and it Is perfect for daily walks. We’ve stayed at many condos in St Augustine and this is by far the favorite ! We’ve reserved for a return trip next year and look forward to the sun, ocean, and relaxing here again !
Superhost
Home in St. Augustine
4.68 out of 5 average rating, 244 reviews

Beach Side 4/2 home steps from the Ocean and Pool

SusanRating, 5 stars6 days ago
The condo was well equipped and conveniently located. We had everything we needed and the furniture was nice, beds comfy, and the outside deck was a nice place to gather.
Guest favorite
An open living area features comfortable seating options, including a patterned couch and a light-colored armchair. A small round table is set for dining, while natural light enters through large windows adorned with colorful curtains. A flat-screen television is situated against a wall.
Cottage in St. Augustine
4.71 out of 5 average rating, 206 reviews

Cozy Retreat, Cottage w/Pool | Near Yoga & Brewery

JohnRating, 5 stars3 weeks ago
Quiet and private side street with a friendly neighborhood. Walking distance to downtown and local bar/brewpub. Renee and Aloe were always available and responsive to my texts but they just let us relax and enjoy the space without any interfering. We treated the house as if it were our own (per their friendly advice) and respected the property throughout our stay. If we were to stay in St Augustine again I would definitely contact Renee and Aloe first. Totally enjoyed our stay.
Top guest favorite
The image displays a well-maintained pool area surrounded by lounge chairs and umbrellas. Lush greenery and palm trees create a serene backdrop. The pool's depth is marked at 6 feet 7 inches, ensuring clear visibility of its dimensions and inviting atmosphere.
Condo in Ponte Vedra Beach
4.99 out of 5 average rating, 154 reviews

Gated Sawgrass Beach Club - WALK to BEACH!

StefanieRating, 5 stars1 week ago
Vanessa's place was perfect for our long weekend. It is across the street from the beach, had all the things we might need for the beach or for cooking and it was very clean! Vanessa was also very helpful with advice or answering questions. The space is small but perfect for 2. Highly recommend!
Top guest favorite
Condo in St. Augustine
4.94 out of 5 average rating, 291 reviews

Gorgeous Sea Place Ocean View Condo

CynthiaRating, 5 stars3 weeks ago
Elaine's condo is beautifully decorated and she goes above and beyond with all the extra touches to make you feel welcome and right at home. The kitchen is well stocked with anything you need and it is nice quality. The condo was spotlessly clean with nice towels and linens to make your stay enjoyable and peaceful. This host was very accommodating and quick to respond with any questions we had about our stay. We will definitely keep this condo on our list to stay again when we are in St. Augustine.
Top guest favorite
A view from the balcony showcases a well-maintained landscape with lush green grass and palm trees. The image features a swimming pool surrounded by lounge chairs and elegantly designed buildings in the background, all while the ocean is visible beyond the manicured grounds.
Condo in St. Augustine
4.95 out of 5 average rating, 106 reviews

Sea Place Ocean View

DianaRating, 5 stars1 month ago
This condo is perfect. It met our needs and is located in beautiful St. Augustine. Great location. Ocean views. Peaceful.

Quick stats about vacation rentals that are family-friendly in Lakeside

  • Total rentals

    30 properties

  • Nightly prices starting at

    ﺩ.ﺇ220 before taxes and fees

  • Total number of reviews

    2K reviews

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with a pool

    10 properties have a pool

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore