Family-friendly holiday 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

Guest favourite
Home in St. Augustine
4.93 out of 5 average rating, 165 reviews

5*Pool Oversized Home*Beach*Walk to all

TomRating, 5 stars6 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.
Top guest favourite
Home in Southeast Jacksonville
4.86 out of 5 average rating, 207 reviews

Private FL Home with Pool, Hot tub & Luxury Master

JoanRating, 5 stars2 weeks ago
Sandra was a terrific host. her place was as described even better. beds were comfortable,lots of bathrooms, lots of outdoor seating, and pool toys and indoor and outdoor toys/games. perfect for us as we had a family wedding in the area. neighborhood was nice, quiet nearby to stores and restaurants.
Top guest favourite
Home in Southeast Jacksonville
4.95 out of 5 average rating, 190 reviews

The confetti house - 1 mile from the Mayo clinic!

MohammadRating, 5 stars2 days ago
We had a chance meeting Frank and Pat and it was fantastic! The house was spotless, location was perfect, we are thankful that host welcomed us with our favorite brand chocolate a bottle of red wine and vanilla ice cream. Special appreciation should be given for hot tub, koi pond in lanai, putting green and nice fenced yard. Both of our huskies loved it. Outstanding host, always quick to respond, helpful with recommendations. We tend to go new places and visit new things but future stays here are anticipated.
Top guest favourite
Apartment in St. Augustine Beach
4.9 out of 5 average rating, 333 reviews

Beach side condo

DiannRating, 5 stars1 week ago
Doug and Lori's place was great! Enough room for our family of 4. Having 2 beds in the second bedroom is nice, the beds were very comfortable. It was easy to walk to the beach, and this beach is wide and not crowded- a big plus. Kitchen had everything you needed. Supplied beach towels which is nice so you don't have to pack them. Only down side, we didn't stay long enough! It's a great area!
Guest favourite
Flat in St. Augustine
4.93 out of 5 average rating, 170 reviews

Ocean View 3br Condo! Indoor pool, steps to beach

AngelaRating, 5 stars2 weeks ago
This is THE PLACE for families. Tons of families with kids we're staying at this condo association, so our children easily found playmates. There's food trucks that come on site during the day and a large field between the pool and the condo buildings where kids congregate after dinner to play games, watch movies, and play music. The pool, field, and playground are all viewable from the balcony. Easy boardwalk to the beach. The condo was perfect for a beach stay- large covered balcony, and master bed was very comfortable.
Guest favourite
Home in Beaches
4.88 out of 5 average rating, 170 reviews

Renovated Beach Escape HTD Pool, Spa, Putt Putt

RobinRating, 5 stars1 month ago
We enjoyed the home and pool! The house was exactly like the photos. It was extremely clean and the kitchen was well equipped! There were plenty of linens, including pool towels. The host was always quick to reply and always polite. We would stay here again!
Guest favourite
Home in St. Augustine
4.93 out of 5 average rating, 134 reviews

Hawaiian Island Escape ~ Heated Pool/Spa/Beach

GilbertRating, 5 stars2 weeks ago
I can’t say enough about this place! From the beautiful house with all the needed amenities to the gorgeous private pool and hot tub area. The decor was absolutely beautiful and the beds were so comfortable! The location is quiet and private but still close to all the history and beauty of St. Augustine. Abrina was very helpful in recommending a close beach access which is very easy to get to and walkable or just a 2 minute ride if you prefer. She was very responsive to any questions and made things so smooth! I would definitely stay here again without a second thought!
Superhost
Home in St. Augustine
4.86 out of 5 average rating, 235 reviews

1st street, Cedar Beach House Retreat

JohnRating, 5 stars1 month ago
An excellent place where I'd happily stay again. It is a just a block from the main road that runs along the beach. The neighborhood was quiet and very conveniently located. We were pleasantly surprised at the near miraculous cleanliness of the location when we arrived. The small items makes this host an A+ choice. MANY towels available for beach and house use. A great blender available in the kitchen.l and more than enough plates and silverware so you didn't have to worry about running out. If you are vacationing do not miss the alligator farm (where the roosting birds may have been more fascinating then the alligators), going on a kayak eco tour, and Mojo Tacos.

Family- and pet-friendly home rentals

Top guest favourite
Home in St. Augustine
4.94 out of 5 average rating, 133 reviews

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

SandraRating, 5 stars2 weeks ago
We ended up booking Dalerie’s place at the last minute due to a rental that did not meet our needs due to a recent surgery. Dalerie was quick to respond to our request and the place was perfect for our family. We had an 11 month old along so the availability of a highchair and the large space for us to move around was a huge win. Her house was stocked appropriately for things for the beach as well as the kitchen. The pool was a must as we have a four year-old granddaughter who loves to swim. It was the perfect opportunity in the afternoon to burn off some more energy after the beach before we went to one of many yummy places nearby for dinner. The screen porch is lovely! And her location in Vilano Beach is terrific. If you want to walk to the beach it is easily accessible down the street. We prefer Porpoise Point beach in order to drive with all our stuff and it is 5 minutes down the road. I highly recommend this rental!
Top guest favourite
Home in St. Augustine
4.99 out of 5 average rating, 412 reviews

Your Home Away From Home

ArleneRating, 5 stars5 days ago
This was our second visit to Fred and Lynn's home and it didn't disappoint. When visiting other home I have always taken my own pots and pans as I always encounter cheap thrift store cookware, but not here. I left my kitchen home this trip and it was great! We love how secluded and private it is. You would never know you are only 5 minutes away from shopping and grocery stores. Especially when the local deer herd visits in the early mornings and late afternoons. We plan on returning next summer! 😊
Top guest favourite
Home in Beaches
4.94 out of 5 average rating, 110 reviews

The Wave Beach House 602 A

DeanRating, 5 stars3 months ago
Great time Thanks we will be back
Guest favourite
Flat in St. Augustine
4.95 out of 5 average rating, 284 reviews

FREE BIKES Dog-friendly apt in the heart of St A

KimRating, 5 stars1 week ago
My husband and I came for a week to celebrate our anniversary and we couldn’t have been more satisfied with our stay at Villa Mulvey!!! Benoit and Lindsey were very responsive and their place was charming, cozy and super clean! The back yard was perfect for our dogs (they loved it!). The location was close enough to walk to downtown, restaurants and the fort but far enough away to be peaceful! Our next trip to St Augustine will be planned around the availability of this Airbnb!!! Loved it!!
Guest favourite
Home in St. Augustine
4.88 out of 5 average rating, 337 reviews

Pure Relaxation: heated pool, beach, cabana & more

TanyaRating, 5 stars2 days ago
My family and I had a wonderful stay at this property. The kids loved the pool. Pool was beautiful and heated. Lovely places to sit. Loved the porch and pool house.
Guest favourite
Guest suite in Beaches
4.86 out of 5 average rating, 522 reviews

Beach Cottage Style Studio Apt.

BrooklynRating, 5 stars2 months ago
This place was a perfect place to stay by Jax beach. We were able to walk to restaurants and they even offered us bikes. They were super friendly and made sure we had a great stay. I would definitely stay here again. Very nice neighborhood. We had a very nice weekend getaway.
Superhost
Home in St. Augustine
4.92 out of 5 average rating, 238 reviews

DOWNTOWN ~ Victorian Home ~ ABOVE CUPCAKE SHOP!

CarolynRating, 5 stars3 days ago
This is a great little hideaway! We would stay here again, you could walk anywhere you needed to go, and you could actually go downstairs and get your breakfast from the cupcake shop. Friendly and responsive host!
Guest favourite
Guest suite in St. Augustine
4.88 out of 5 average rating, 724 reviews

Beach and Serenity

SummerRating, 5 stars2 weeks ago
We enjoyed our beach getaway! It was a very comfortable stay. The location was great & the beach and local coffee shop was just a short walk away.

Family-friendly home rentals with a pool

Guest favourite
Apartment in St. Augustine
4.93 out of 5 average rating, 104 reviews

Lovely 2BR/2BA Oceanview Condo, St Augustine Beach

LindaRating, 5 stars3 weeks ago
Jeremy’s place was everything we wanted! Incredibly clean, had everything we needed (even had snacks and a bottle of wine waiting for us after our 10 hour road trip). Incredibly easy access to a peaceful beach and tons of cards games and board games for downtime at the condo. He was responsive and very friendly to any and all questions we had. Definitely recommend and would stay again!
Top guest favourite
Apartment in St. Augustine Beach
4.94 out of 5 average rating, 193 reviews

The Beach Retreat!

SheridanRating, 5 stars1 month ago
We had a great time! Being so close to the beach, pier and restaurants was perfect.
Guest favourite
Flat in St. Augustine Beach
4.94 out of 5 average rating, 186 reviews

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

BarbaraRating, 5 stars4 days ago
The location on the beach of Saint Augustine was heavenly. Angela Melanie responded to all of our questions promptly. The pictures do not do it justice. You are on the beach, walking in sand almost immediately after you exit your condo. Weekly price was great and well worth it with everything included in the condo and on the grounds. Love this place and the host and will definitely visit again.
Guest favourite
Apartment in Beaches
4.92 out of 5 average rating, 102 reviews

Beachfront Luxurious Charming 2BR Condo

CathyRating, 5 stars3 weeks ago
Our entire week was perfect! Shastri was kind to us as our schedule changed and I had to move my date staying at his place. The instructions that were sent are clear and they give you everything that you need to know! The view from his place was amazing! Needed a peaceful getaway with family and this was the right spot! I would not hesitate going back again. Great host, great spot and beautiful location!
Guest favourite
Flat in Lincolnville
4.95 out of 5 average rating, 111 reviews

F2 Downtown, POOL, beaches, free parking!

AlaneRating, 5 stars1 month ago
Kirsten is a great host, very friendly and helpful. The home is in a quiet neighborhood, walkable to restaurants, historical sites and the bay front. Definitely a place I would stay at in the future.
Top guest favourite
Home in St. Augustine
5 out of 5 average rating, 141 reviews

Southern Charmer w/Pool - Walk to Everything!

TiffanyRating, 5 stars2 months ago
Came for a wedding. The home was exactly as the pics showed and it was pristine inside with all the necessities including beach chairs, umbrellas and towels. Perfect location, walkable quaint little area, lots of great recommendations too. Great space, amazing host, Pauline always responded quickly and went above and beyond to accommodate us. We thoroughly enjoyed our time there, just needed another day or two to enjoy the town. Highly recommend.
Superhost
Flat in St. Augustine
4.94 out of 5 average rating, 179 reviews

Updated and clean, private beach access condo

KerriRating, 5 stars2 months ago
We really enjoyed our week stay and hope to return next year. Susan was a very responsive host and condo was comfy and nicely decorated with coastal decor. We especially loved the beautiful, private beach…well worth the walk!
Superhost
Apartment in St. Augustine
4.91 out of 5 average rating, 149 reviews

"Captain Jacks" First Floor 2BR/2Bath Condo

SherriRating, 5 stars3 weeks ago
Staying at this AirBnB is quickly becoming a yearly family tradition for us! The condo has everything we need as a family of 4, the private beach access is delightful, and St. Augustine never disappoints. The owner is very responsive and addresses any needs as soon as possible, doing everything he can to make our stay as comfortable as possible. Highly recommend!

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

  • Total rentals

    30 properties

  • Nightly prices starting at

    ₹5,160 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