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Family-friendly holiday rentals in Anastasia Island

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Anastasia Island family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Apartment in Palm Coast
4.79 out of 5 average rating, 121 reviews

Luxury Condo at the Beach

RachelRating, 5 stars2 days ago
Allen’s place was very spacious and clean. It is exactly as described. He responded right away when we had a question. We enjoyed our time here and the beach was an easy 2 min walk. He had beach chairs, umbrella and sand toys, which was a total plus for us!!! If we were to visit Palm Coast again, this is where we would stay!!!
Guest favourite
Flat in Palm Coast
4.84 out of 5 average rating, 378 reviews

Hidden Gem... 101 Palm Harbor unit307A

AlanRating, 5 stars2 weeks ago
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!
Top guest favourite
Apartment in Palm Coast
4.99 out of 5 average rating, 269 reviews

#1 Most Wish-Listed Airbnb in Flagler County!

LaurenRating, 5 stars1 week ago
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.
Top guest favourite
Apartment in St. Augustine Beach
4.9 out of 5 average rating, 333 reviews

Beach side condo

DiannRating, 5 stars4 days 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 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.
Guest favourite
Home in St. Augustine
4.87 out of 5 average rating, 336 reviews

Direct Ocean & Beach View Home

HollyRating, 5 stars2 days ago
Not only was this location perfect, with a beautiful view of the beach from the house and a private/peaceful backyard, but the host David was an absolute gem! He was very accommodating, extremely helpful, and overall such a nice person. Will definitely book again!

Family- and pet-friendly home rentals

Top guest favourite
Home in St. Augustine
4.99 out of 5 average rating, 412 reviews

Your Home Away From Home

ArleneRating, 5 stars2 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! 😊
Guest favourite
Flat in St. Augustine
4.92 out of 5 average rating, 211 reviews

Elegant, FREE BIKES dog-friendly downtown apart.

SandyRating, 5 starstoday
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.
Guest favourite
Home in St. Augustine
4.91 out of 5 average rating, 105 reviews

Waterfront Cottage on Private Island in Preserve

ErrolRating, 5 stars3 weeks ago
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!
Guest favourite
Townhouse in St. Augustine
4.9 out of 5 average rating, 128 reviews

Avery s Ocean Breeze - Family and Pet Friendly !

KyleRating, 5 stars1 week ago
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.
Top guest favourite
Holiday home in St. Augustine
4.98 out of 5 average rating, 128 reviews

1st Street Retreat, Dog Friendly Updated Apartment

LeslieRating, 5 stars6 days ago
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!
Guest favourite
Tiny home in St. Augustine
4.8 out of 5 average rating, 741 reviews

The St Augustine Tiny House - park and walk 2 town

AmberRating, 5 stars2 weeks ago
My husband and I thoroughly enjoyed our stay at the St. Augustine tiny house. We had a very cozy and intimate stay just a few steps away from dining and drinks. We especially liked the proximity to restaurants and things to do while also enjoying the privacy offered. We loved this location and can’t wait to come back! The home has absolutely everything you could possibly need and is organized so well. You can tell the space was very carefully thought out and it truly doesn’t feel like a ‘tiny’ home. The memorable touch of the Polaroid to create memories was the cherry on top. Thank you for hosting us!
Guest favourite
Home in St. Augustine
4.97 out of 5 average rating, 149 reviews

Charming Downtown Cottage with Private Pool!

DesaRaeRating, 5 stars11 months ago
This was mine and my family’s second time staying at this location and we will continue to return. My children enjoyed the pool and lizard hunting around the vegetation. We took advantage of the grill one night for dinner, and walked to waterway to fish at the end of the street. This is an extremely walkable area and feels safe doing so. Can’t wait to return.
Superhost
Home in St. Augustine
4.88 out of 5 average rating, 187 reviews

Crescent Beach House

DianeRating, 5 stars3 weeks ago
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 ☺️

Family-friendly home rentals with a pool

Superhost
Home in St. Augustine
4.88 out of 5 average rating, 8 reviews

Beachfront Getaway Directly on St. Augustine Beach

MillieRating, 5 stars2 weeks ago
We love it here! It’s a great place with plenty of room for everyone to have their own space. Can’t wait to go back next summer!
Superhost
Apartment in St. Augustine
4.72 out of 5 average rating, 74 reviews

Direct Oceanfront-Private Balcony-Kitchen-Pool

NoraidaRating, 5 stars2 months ago
Would definitely recommend, lovely, private, spacious. I felt at home, can’t wait to come back!! Very friendly and informative host. Thank you for opening up your home to us.
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!
Guest favourite
Villa in St. Augustine
4.88 out of 5 average rating, 94 reviews

St Augustine Villa | Pools, Hot Tub & Beach Access

MonicaRating, 5 stars2 weeks ago
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!
Superhost
Apartment in St. Augustine
4.74 out of 5 average rating, 72 reviews

Saint Augustine Beach, Oceanside - Book Now!

LeslieRating, 5 stars1 week ago
This is a spacious first-floor condo that was well equipped with beach/kitchen/bathroom items. The beds were comfortable and all appliances worked well except, we found the dryer was slow to dry clothes, likely made more difficult by the humidity due to it being the heat of the summer. The beach was very close and the complex pool was in good shape. The other guests at the complex were mostly vacationers as well, and were very friendly. Lots of other kids around for my kid to splash around at the pool with. We enjoyed local restaurants like the Purple Olive that was a few miles up A1A. All in all, great place to stay and we'd stay here again.
Guest favourite
Home in St. Augustine
4.87 out of 5 average rating, 334 reviews

Pure Relaxation: heated pool, beach, cabana & more

KarenRating, 5 stars4 weeks ago
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!!!!
Superhost
Home in St. Augustine
4.77 out of 5 average rating, 126 reviews

Oceanside/pool view-Surf Crest Village-Pets welcom

JudyRating, 5 stars11 months ago
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.
Guest favourite
Apartment in St. Augustine Beach
4.93 out of 5 average rating, 84 reviews

The Sandy Anchor - Best Location on SA Beach

KaraRating, 5 stars1 week ago
This was a wonderful condo for a Saint Augustine Beach stay. It felt much larger than it looked in pictures. With 6 adults and a baby we were very comfortable with the space. The location is ideal. At the northern end of the beach there are several dining/coffee/food options within easy walking distance. We enjoyed a morning stroll to Kookaburra or to pick up donuts from Island Donuts. A quick drive landed us at Parlour donuts for an amazing treat. It was easy to end the day with a treat from Rita’s or Mayday Ice Cream. Historic downtown was an easy drive. The kitchen is well equipped for a short term rental. There were plenty of towels/linens. Seating at the pool was plentiful. Great stay!

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