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Family-friendly vacation 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

Guest favorite
The exterior of a two-story home is presented, showcasing a blend of light and dark siding. Large windows provide a view of the front entryway, flanked by greenery. A separate structure is visible to the left, adding to the overall spaciousness of the property.
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.
Superhost
A spacious living area is highlighted by a large sectional sofa in a deep green fabric, complemented by pink throw pillows. A round coffee table with a marble top and gold base occupies the center. Soft natural light filters in through multiple windows adorned with simple white blinds.
Condo in Palm Coast
4.79 out of 5 average rating, 121 reviews

Luxury Condo at the Beach

RachelRating, 5 stars3 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 favorite
A comfortable living area showcases a dark gray sectional sofa accented with decorative pillows. A wooden coffee table is centered on a light rug, while a small dining table with a floral centerpiece is visible. Natural light filters through the window, illuminating the space.
Apartment in Palm Coast
4.84 out of 5 average rating, 378 reviews

Hidden Gem... 101 Palm Harbor unit307A

AlanRating, 5 stars3 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 favorite
A resort-style pool area features a large swimming pool with a gradual entry. Surrounded by tropical palm trees, lounge chairs line the deck, providing ample space for relaxation. The clubhouse, visible in the background, complements the inviting atmosphere.
Condo 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 favorite
A distant view showcases the ocean with gentle waves rolling onto the sandy shore. A wooden walkway leads to the beach, framed by lush greenery and palm trees. The sky is bright with a few scattered clouds, creating a serene coastal atmosphere.
Condo in St. Augustine Beach
4.9 out of 5 average rating, 333 reviews

Beach side condo

DiannRating, 5 stars5 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 favorite
A scenic view from the balcony shows a large pool surrounded by lounge chairs, with the ocean and sandy beach visible in the background. Lush green landscaping enhances the outdoor area, offering a serene atmosphere for relaxation under a clear blue sky.
Apartment 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 favorite
The backyard is illuminated by soft lighting, showcasing a private heated pool surrounded by a screened enclosure. Lush palm trees and well-maintained landscaping enhance the tranquil atmosphere. The two-story home is visible in the background, adding to the serene nighttime setting.
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
The living area features a light blue wall, a large flat-screen television mounted above a dark wooden console, and a comfortable seating arrangement. One brown leather armchair complements a dark sofa, with natural light filtering through a doorway leading to another space.
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 favorite
The exterior of a single-story house is displayed, featuring a sloped roof and an inviting entryway. Green grass surrounds the home, complemented by mature trees and landscaped bushes. A concrete driveway leads up to the entrance, providing accessible access.
Home in St. Augustine
4.99 out of 5 average rating, 412 reviews

Your Home Away From Home

ArleneRating, 5 stars3 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 favorite
The exterior of the house displays a charming design with multiple gabled roofs. A spacious brick terrace is surrounded by lush green yard, featuring several seating areas and decorative potted plants. Large windows allow for ample natural light, framed by coastal live oaks in the background.
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 favorite
The living area showcases a dark leather sofa adorned with colorful pillows, paired with a light wooden coffee table. A ceiling fan hangs above, and a large television is mounted on the wall. The space features original pine flooring and a decorative non-functioning fireplace.
Apartment 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 favorite
A two-story villa with a light blue exterior features multiple balconies and arched entryways. The front is adorned with white railings and a stone pathway, complemented by landscaped areas with greenery. A mix of cloudy and clear skies enhances the welcoming appearance of the home.
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 favorite
A comfortable living area is captured with soft blue sofas, a wooden coffee table, and a large television. Natural light fills the room through expansive glass doors that lead to a deck, surrounded by lush greenery and palm trees.
Home in Palm Coast
4.95 out of 5 average rating, 182 reviews

Oceanside Breeze & Views for the Family

DavidRating, 5 stars2 months ago
This house was well equipped with all the essentials need for a lengthy stay. It was convenient with a short walk to the beach and several restaurants within a short distance. We enjoyed our stay and highly recommend to any family that wants to be by the beach. We will defiantly be returning in the future. The Steiners from South Carolina.
Guest favorite
The exterior of the turquoise tiny house is presented, featuring a welcoming front porch with wooden railings. Lush greenery and palm trees surround the home, creating a serene atmosphere. The entrance is highlighted by a small set of steps leading to the porch.
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 favorite
A wooden gate opens to reveal a serene backyard with a heated saline pool surrounded by landscaped greenery. A shaded seating area and lounge chairs are visible near the pool, along with a dining space and umbrella, providing a relaxed outdoor ambiance.
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
A balcony view showcases the tranquil ocean during sunrise, with two adirondack chairs placed on either side of a small table. Coffee cups are positioned on the table, surrounded by lush greenery and the gentle waves in the distance.
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
A large heated pool is featured at the property, surrounded by several lounge chairs arranged neatly along the deck. An umbrella provides shade for those seeking relief from the sun. A view of the ocean and palm trees can be seen in the background under a clear sky.
Condo 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 favorite
A private pool area is surrounded by a wooden fence and tropical landscaping. A ladder leads into the clear blue water, inviting relaxation. Sunlight filters through the trees, creating a serene atmosphere. A sign indicating 'Beach Access' is prominently displayed.
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 favorite
A community pool is framed by lush palm trees and features lounge chairs arranged along the edges. The pool area is enclosed by a black fence, with a green gazebo visible in the background, creating a relaxed outdoor atmosphere.
Condo in St. Augustine Beach
4.94 out of 5 average rating, 193 reviews

The Beach Retreat!

SheridanRating, 5 stars4 weeks ago
We had a great time! Being so close to the beach, pier and restaurants was perfect.
Guest favorite
An aerial view captures the oceanfront outdoor pool, surrounded by lounge chairs, palm trees, and pathways leading to the beach. The expansive sandy shore and ocean waves are visible in the background, emphasizing the relaxed coastal atmosphere.
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
An outdoor swimming pool is visible, surrounded by palm trees and tropical vegetation. Lounge chairs are arranged neatly on the pool deck, offering shaded seating. The pool's clear water reflects the blue sky, with steps leading into the shallow end. A gated enclosure ensures privacy.
Condo in St. Augustine
4.74 out of 5 average rating, 73 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 favorite
An inviting heated pool is surrounded by a stone-paved area, featuring six lounge chairs positioned nearby. Lush greenery and a privacy fence provide a tranquil backdrop, enhancing the outdoor relaxation space.
Home in St. Augustine
4.87 out of 5 average rating, 334 reviews

Pure Relaxation: heated pool, beach, cabana & more

JenniferRating, 5 stars3 weeks ago
This was our 2nd visit!! Everything was good as before. Clean and comfortable. A keurig coffee machine would be a great addition!! The dryer door needs to be reversed .Nice location and good communication if you have questions or issues.
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.

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