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

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.

St Augustine Villa | Pools, Hot Tub & Beach Access
This place was perfect for our anniversary weekend! The location is perfect- you can walk to the pool or beach in minutes, but it is also a close drive to downtown St. Augustine. The beach felt like your own private beach- not crowded at all! I loved that the condo was away from the main building so it was very quiet. They had snacks and coffee available for us as well! We will definitely be back!

The confetti house - 1 mile from the Mayo clinic!
This house had everything! W e watched the Koi fish, fine tuned our putting game, and enjoyed the wonderful screen porch while watching TV at night. Very clean and lots of extra amenities for the family+

Beach side condo
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!

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

Renovated Beach Escape HTD Pool, Spa, Putt Putt
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!

Hawaiian Island Escape ~ Heated Pool/Spa/Beach
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!

1st street, Cedar Beach House Retreat
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

Elegant, FREE BIKES dog-friendly downtown apart.
Location was in a quiet neighborhood. Historic building with so much charm. Enjoyed riding the provided bikes and grilling out back. Being close to downtown was very convenient. Thank you for a lovely stay and the last minute requested change.

Avery s Ocean Breeze - Family and Pet Friendly !
Great place to stay with family. Easy access to the ocean and beaches. Location is spot on, only 20 mins to almost anything you may need.

Beachfront Luxurious Charming 2BR Condo
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!

1st Street Retreat, Dog Friendly Updated Apartment
I cannot say enough good things about our stay at Lisa’s in St. Augustine! The location was unbeatable - barely a five minute walk to the beach, with a taco stand and brewery at each corner and lots of amazing walkable places nearby (Kookaburra Coffee and Island Donuts to name a few)! It was barely fifteen minutes to downtown St. Augustine as well. The Airbnb itself was easy to find and had a parking spot. The space was clean, cozy, and comfortable, with an outdoor shower and dog run - it took all the stress out of traveling with dogs! We truly had the best time; my only regret is that I wish we had gotten enough time off work to stay longer! Lisa even allowed us a complimentary late checkout to enjoy more time at the beach. If you are traveling with dogs and looking for a simple, cozy, convenient place to escape to the ocean and historic St. Augustine, this is the place! We can’t wait to come back!

Paradise Retreat*Vilano Beach*Sand & Ocean Breeze
Given the need for an immediate relocation, Inga was very helpful and her home was just what we needed to enjoy the rest of our vacation. You could tell her home was cleaned very well and we felt right at home.

Crescent Moon: soft sand beach, pets welcome
What a gem! Perfectly positioned one block from the beach, this bungalow is just adorable. Fun decor, comfortable bed, more than enough room for my two teens and I to spread out. Shopping and dining are mere minutes away. The beach is a VERY short walk and beach itself is clean and beautiful. Martie was very accommodating and easy to work with. Five stars all the way! We’d love to come back!

Crescent Beach House
I am so very thankful for my stay at this beautiful home. Everything we needed and then some! Absolutely, gorgeous. Made a nice meal in the kitchen as well. The deck is super nice. Chris and Evelyn are excellent host. I loved the bible verse in the sun room too! Felt very comforted by that. Thank you again very much. You made this an amazing weekend for graduation. Thank you ☺️

5 walking minutes to the beach
had a wonderful stay at Sonja's place for my birthday weekend!! exactly as pictured, very quiet and peaceful, super easy and walkable to the beach. not too far from downtown st augustine either :)
Family-friendly home rentals with a pool

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

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

The Beach Retreat!
We had a great time! Being so close to the beach, pier and restaurants was perfect.

Pure Relaxation: heated pool, beach, cabana & more
This is the second time we stayed at this amazing property. It’s quiet and close to so many things. Pet friendly in most areas. Our puppy was super happy to be so close to the beach. The hosts responded almost immediately every time and honestly are so sweet. This is now our go to place for a quick weekend trip! Thank you so much!!!!

Direct Oceanfront ~ Fantastic Views!
Beautiful view of the beach and right next to the pool. We had a short stay but so glad we chose to stay here. Also highly recommend Commanders Outpost restaurant (3 minute drive down the street) for a great dinner

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

F2 Downtown, POOL, beaches, free parking!
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.

Southern Charmer w/Pool - Walk to Everything!
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.
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
- Summer Haven st. Augustine FL
- TIAA Bank Field
- Old A1A Beach
- Boneyard Beach
- Kathryn Abbey Hanna Park
- Amelia Island State Park
- Butler Beach
- Crescent Beach
- Fountain of Youth Archaeological Park
- North Beach Guana River Preserve
- Guana Reserve Middle Beach
- Lightner Museum
- Dungeness Beach
- St. Augustine Alligator Farm Zoological Park
- MalaCompra Park
- Matanzas Beach
- Eagle Landing Golf Club
- Bent Creek Golf Course
- Driftwood Beach
- St. Marys Aquatic Center
- Florida Museum of Natural History
- Depot Park
- Ravine Gardens State Park