
Family-friendly holiday rentals in Historic District, St. Augustine
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Top-rated family-friendly rentals in Historic District, St. Augustine
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Popular amenities for Historic District, St. Augustine 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.

Luxury Condo at the Beach
The place was perfect and the host was quick and responsive. I recommend big tile for an awesome stay.

Hidden Gem... 101 Palm Harbor unit307A
My wife and I enjoyed it so much that it is highly likely we will stay longer next time! Loved it all! The European Village was so cute! Loved the weekend farmers market and all the kiosks! Saturday night music in the courtyard was awesome!

~Hot Tub~Just Steps to the Beach~King Bed~2 Pools
It’s a nice cozy place within walkable distance to the beach. We had a great stay! I would definitely recommend this place.

#1 Most Wish-Listed Airbnb in Flagler County!
We spent a week here and can’t wait to return! We loved waking up and seeing all the bunnies from the balcony each morning! The kids loved the bunk room and the big bathtub! We had everything we needed and the property is just perfect for families! Everything was wonderful.

Beach side condo
Very clean and welcoming. Lots of fun stuff around the place to look at. Easy check in and a short walk to the beach.

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.

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!
Family- and pet-friendly home rentals

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!

Your Home Away From Home
Fred & Linda’s place felt like we were right home. The place was very serene and tranquil right in the middle of St. Augustine. Anything we needed, it was there. The hosts also let us know that if we needed anything, to let them know. Their salt water pool felt great on hot afternoons and evenings. The kids loved the place. Even their little dog Ellie came to play ball with the kids. Would recommend staying here.

Waterfront Cottage on Private Island in Preserve
This home is a peaceful and scenic retreat, perfect for relaxation and reconnecting with nature. With stunning marsh views and plenty of space, my family felt completely at home. Though it’s about a 25-minute drive to downtown St. Augustine and the beaches, the tranquil surroundings make it well worth the trip—especially for those who love fishing, boating, or outdoor adventures. From paddleboarding and swinging on the swing to gathering around the fire pit and playing tag in the beautiful Florida weather, this place truly feels magical. Patricia is a wonderful host—always responsive and ensuring a comfortable stay. The cozy beds and well-equipped space exceeded our expectations, making it hard to say goodbye. We created unforgettable family memories here and can’t wait to return. Thank you, Patricia, for making our family reunion truly special!

OWLS LOFT West King Historic District & Beaches
This was a last minute stay. It was close to get to most things. I would say it was very basic, no frills like a cabin vibe. There wasnt a coffee maker so you might want to keep that in mind . The bed I slept on was very firm. I was there for Easter weekend so the town was alive and plenty to do.

The Anastasia House Close to Downtown and beaches
We really enjoyed our stay! The house was super clean, cozy, and just as cute as the photos. It’s located in a safe, quiet neighborhood which made us feel right at home. Definitely recommend to anyone looking for a comfortable and charming place to stay!

Beach and Serenity
This place was really nice, cute and worth every penny. The location is great. We had access to bikes and beach chairs.

DOWNTOWN ~ Victorian Home ~ ABOVE CUPCAKE SHOP!
My Wife and I stayed here for a few nights to explore Saint Augustine on foot and really enjoyed the place! its right in the heart of the downtown area so we were able to hit up all of the main attractions including the fort with a short walk without the need to drive and find parking elsewhere, which is quite expensive in the tourist areas. The place was exactly as described and was very clean and homey. Definitely recommend to anyone looking to check out Saint Augustine! The cupcake shop downstairs is great too for anyone looking for sweets or breakfast food. Our host was very flexible with us and made the stay easy and convenient.

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!
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.

Poolside Ocean Living for the Family
Erin’s place was immaculate, featuring a fully equipped kitchen that made it feel just like home. She thought of everything, providing thoughtful extras that enhanced our stay and created a truly stress-free and enjoyable retreat. We appreciated the abundance of extra blankets and pillows, several beach towels, and pantry essentials like condiments, cooking oil, sugar, coffee, tea, and spices. Erin also supplied paper towels, toilet paper, shampoo, conditioner, and plenty of cleaning products. We loved the use of cotton napkins to reduce waste and enjoyed the vibrant Fiesta dinnerware. Situated in a quiet neighborhood, the landscaping offered us privacy to fully enjoy the lanai and pool. Erin was responsive to all my questions, making our stay even more pleasant. I highly recommend staying here for a relaxing getaway!

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!!!!

Modern & Comfy Beach Gem: Pool ~ Ocean Views ~ Pkg
Exactly what we needed. Quiet, comfortable and so close to the ocean.

Oceanside/pool view-Surf Crest Village-Pets welcom
We booked Jody’s place two years in a row for a family vacation. Pet friendly, which is a must. Our four legged family go with us on every vacation. Excellent place and wonderful year round neighbors, I couldn’t as for much more.

"Captain Jacks" First Floor 2BR/2Bath Condo
Matthew's condo, located in Butler Beach, on Anastasia Island was a short drive to some great locations including St. Augustine Old Town, a great place to spend time, beautiful Anastasia Island State Park and much more. We took a sunset cruise in the bay, toured St Augustine, played mini golf and had plenty of beach time. Comfortable accommodations, had most everything we needed. Must have a car to enjoy the area. Great stay ll in all. Glad we came down in April, wasn't terribly crowded.
Quick stats about holiday rentals that are family-friendly in Historic District, St. Augustine
Total rentals
200 properties
Nightly prices starting at
$101 NZD before taxes and fees
Total number of reviews
15K reviews
Pet-friendly rentals
100 properties allow pets
Rentals with a pool
30 properties have a pool
Rentals with dedicated workspaces
110 properties have a dedicated workspace
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- House rentals Historic District
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- Ponte Vedra Beach
- Summer Haven st. Augustine FL
- TIAA Bank Field
- Old A1A Beach
- Boneyard Beach
- Daytona Lagoon
- Daytona Beach Boardwalk and Pier
- Kathryn Abbey Hanna Park
- Amelia Island State Park
- Butler Beach
- Crescent Beach
- Fountain of Youth Archaeological Park
- Guana Reserve Middle Beach
- North Beach Guana River Preserve
- Lightner Museum
- Palm Harbor Golf Club
- St. Augustine Alligator Farm Zoological Park
- MalaCompra Park
- Matanzas Beach
- Eagle Landing Golf Club
- Bent Creek Golf Course
- Driftwood Beach
- Neptune Approach
- Vilano Beach