
Family-friendly vacation rentals in Lakeside
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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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Popular amenities for Lakeside family-friendly rentals
Family-friendly home rentals with a hot tub

Beachfront Getaway Directly on St. Augustine Beach
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.

5*Pool Oversized Home*Beach*Walk to all
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.

Private FL Home with Pool, Hot tub & Luxury Master
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!

Breathtaking Oceanfront Views!
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

Captain's Quarters Tiny House
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 !

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

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

Top Floor (Elevator Building) Ocean View Condo!
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

Mandarin. Modern and Cozy!
Great location and neighborhood. Good amenities. Host is very responsive and helpful.

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

Low Tide - Beach Bungalow
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!

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

Your Home Away From Home
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!

Pure Relaxation: heated pool, beach, cabana & more
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!

The Anastasia House Close to Downtown and beaches
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

1st Street Retreat, Dog Friendly Updated Apartment
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

D&G Beach House
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!

Cozy House mins from NAS JAX & Orange Park Mall
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.

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

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

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

Gated Sawgrass Beach Club - WALK to BEACH!
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!

Gorgeous Sea Place Ocean View Condo
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.

Sea Place Ocean View
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
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- Ponte Vedra Beach
- Driftwood Beach
- Old A1A Beach
- Pablo Creek Club
- Kathryn Abbey Hanna Park
- Boneyard Beach
- Matanzas Beach
- Eagle Landing Golf Club
- St. Augustine Alligator Farm Zoological Park
- TIAA Bank Field
- Florida Museum of Natural History
- Vilano Beach
- Fountain of Youth Archaeological Park
- Guana Reserve Middle Beach
- Amelia Island Lugar Lindo
- St. Marys Aquatic Center
- Lightner Museum
- Depot Park
- Fort Mose Historic State Park
- North Beach Guana River Preserve
- Bent Creek Golf Course
- Adventure Landing Jacksonville Beach
- Crescent Beach
- Butler Beach