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Family-friendly vacation rentals in Fleming Island

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Fleming Island family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Home in St. Augustine
4.75 out of 5 average rating, 4 reviews

Beachfront Getaway Directly on St. Augustine Beach

DaphneRating, 5 stars4 months ago
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.
Guest favorite
Home in St. Augustine
4.93 out of 5 average rating, 164 reviews

5*Pool Oversized Home*Beach*Walk to all

TomRating, 5 stars3 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.
Top guest favorite
Home in Southeast Jacksonville
4.85 out of 5 average rating, 197 reviews

Private FL Home with Pool, Hot tub & Luxury Master

DanielRating, 5 stars1 month ago
we had some car troubles right before traveling for vacation and was a stressful few days. felt great to walk into the Airbnb and everything was just right. clean looked as advertised and felt homey right away. the kids had an absolute blast even on days we just hung out at the house. nice quite neighborhood not to far from things to do. would recommend to friends and family for sure and or stay again. thanks for topping off our vacation with the perfect place to stay!
Top guest favorite
Villa in St. Augustine
4.89 out of 5 average rating, 87 reviews

St Augustine Villa | Pools, Hot Tub & Beach Access

DavidRating, 5 stars3 weeks ago
Short walk inside the gated community to the beach. Very clear directions from the host for parking and walking to the pool and beach. The indoor pool was great for the winter vacation, and the beach was very calm and we spent long time walking on the beach everyday. It is short drive to the historical city and other beaches. The kitchen and dining area felt a bit crowded, but there's plenty of patio space and double bunk beds are great for families. We enjoyed the stay.
Guest favorite
Guesthouse in St. Augustine
4.91 out of 5 average rating, 560 reviews

Captain's Quarters Tiny House

SilviaRating, 5 stars3 weeks ago
Tom and Diane where Great Host. Helpfull and very very nice. Good tips for Dinner and things to do. We loved the location so close to Downtown and the beaches. Easy to get with the bikes The Tony House was Cozy and the outside welcoming. The outside shower was amazing. So all was great and we had a wonderfull time at Captains Quarter
Top guest favorite
Condo in Saint Augustine Beach
4.9 out of 5 average rating, 323 reviews

Beach side condo

ErikaRating, 5 stars1 month ago
Doug and Lori’s place was perfect! Clean, quaint and had everything you needed! Check in was so simple and the communication was amazing! Great location, close to restaurants, coffee shops and everything you would need. Definitely would stay here again on our next visit to St. Augustine
Guest favorite
Condo in Saint Augustine
4.99 out of 5 average rating, 73 reviews

Sand In My Shoes -1 min to Beach-Close to Downtown

DeniseRating, 5 stars8 months ago
Sand in My Shoes was a great place to stay! Short walk to the beach, pools and gym. About 15 minutes to downtown St. Augustine. The townhouse was well stocked with everything we needed. We would definitely stay there again!
Top guest favorite
Home in Saint Augustine
4.88 out of 5 average rating, 326 reviews

Direct Ocean & Beach View Home

CharlesRating, 5 stars1 week ago
David was awesome. The house was amazing. Great location, super convenient and our entire party was very happy.

Family- and pet-friendly home rentals

Guest favorite
Home in Southeast Jacksonville
4.85 out of 5 average rating, 175 reviews

Mandarin. Modern and Cozy!

HeatherRating, 5 stars2 months ago
This home was very clean spacious and cozy. It was a great fit for the 5 of us and our Great Pyrenees. We loved being close to family and lots to do. Micklers Landing ( beach) was 35 min away, easy parking, dog friendly and a nice beach for the kids. Host was friendly and very responsive. We will definitely be back!
Top guest favorite
Apartment in St. Augustine Beach
4.88 out of 5 average rating, 274 reviews

Low Tide - Beach Bungalow

MandyRating, 5 stars2 months ago
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!
Superhost
Apartment in Riverside
4.78 out of 5 average rating, 237 reviews

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

MikeRating, 5 stars14 months ago
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.
Top guest favorite
Home in Saint Augustine
4.99 out of 5 average rating, 397 reviews

Your Home Away From Home

AvisRating, 5 stars1 month ago
This airbnb is perfect. Close to St augustine in distance but miles away in peace and quiet. Hosts are wonderful, intent on their guests having a wonderful tilme Want to come back !!!!!!!
Guest favorite
Home in St. Augustine
4.88 out of 5 average rating, 327 reviews

Pure Relaxation: heated pool, beach, cabana & more

SaraRating, 5 stars2 weeks ago
We had a great stay. We love this quiet, walkable neighborhood that is just steps away from Cap’s on the Water and the beach. The weather didn’t cooperate during our visit for us to use the pool but it was still nice to look at. The house was exceptionally clean and organized and had everything we needed. We would definitely stay at Greg and Pia’s again and would definitely recommend it.
Top guest favorite
Vacation home in St. Augustine
4.97 out of 5 average rating, 119 reviews

1st Street Retreat, Dog Friendly Updated Apartment

CatalinaRating, 5 stars1 month ago
We love this Airbnb!! It’s our second time here and we will come back every time we are in St. Augustine. The place is so clean and tidy. Perfect for the two of us and our two dogs. Very dog friendly with the area in the backyard for them and some nice lounge chairs. The beach is walking distance and we take our dogs there in the mornings! And for the cherry on top, Taco Shop is less than a minute walk across the street! We will be back a million times :)
Superhost
Apartment in Beaches
4.85 out of 5 average rating, 117 reviews

East of A1A Palm Trees & Ocean Breeze!

JoshuaRating, 5 stars1 month ago
perfect location about a block and a half from the beach. you can see the ocean from the porch. host is friendly and responsive and went the extra mile. will definitely stay here again, had a great time with the family!
Superhost
Apartment in St. Augustine
4.8 out of 5 average rating, 188 reviews

Comfy and Quiet 5 min Walk to Historic Downtown

KarenRating, 5 stars1 week ago
Great space! Perfect for one and room for two. Very clean. Great location. Quiet neighborhood yet very walkable to the historic district, good restaurants and lots of fun. Host very responsive . Hope to stay again.

Family-friendly home rentals with a pool

Superhost
Home in Saint Augustine Beach
4.83 out of 5 average rating, 42 reviews

Forever Sunshine

AllenRating, 5 stars16 months ago
Perfect location near the beach, quiet, plenty of room for a group of 9 adults and 1 child, use of an elevator for we seniors and transport of groceries and luggage, plenty of privacy for reading, rest, and conversation with numerous decks, a widow's walk, and pool area. This beautiful home is well designed, spacious, and comfortable. In addition, Jamie and her team of property managers are very responsive, capable, and accommodating. We couldn't have had a better place for a family reunion.
Superhost
Condo in Beaches
4.85 out of 5 average rating, 62 reviews

D&G Beach House

KathyRating, 5 stars4 months ago
Staley’s rental was perfect for our 2 couples. Clean and comfortable with everything we needed. Loved the balcony view of the ocean and the easy accessibility! Beds were super comfy and nice to have our own bathrooms. We used the Beach Buggy service to get to the restaurants. Thanks Staley!
Superhost
Townhouse in St. Augustine
4.66 out of 5 average rating, 32 reviews

Poolside Dreamin' at Ponce Landing 30

NicoleRating, 5 stars2 months ago
Beautiful home and amazing access to the beach. We didn’t get to go to the beach but we were able to see fireworks close to the beach. I love how close restaurants and everything was. And literally minutes to historic downtown. Highly recommend
Guest favorite
Apartment in Saint Augustine Beach
4.94 out of 5 average rating, 180 reviews

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

MaryRating, 5 stars2 months ago
We had a great experience with our stay. Property was wonderful. Unfortunately weather did not allow us to enjoy the pool but it was very nice looking and clean. Hosts are wonderful - communication was perfect and just what we needed as far as timing and easy to understand. Will definitely be back when we're in the area again.
Superhost
Home in St. Augustine
4.67 out of 5 average rating, 238 reviews

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

JenniferRating, 5 stars3 months ago
Great location. Host was very nice and quick to respond. Sleeps a large group very comfortably. Eating area and kitchen are a little small for a big group. But overall wonderful.
Guest favorite
Cottage in Saint Augustine
4.71 out of 5 average rating, 204 reviews

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

MainaRating, 5 stars2 months ago
I love that the location was a few minutes from the tourist attractions! In addition the home was so cozy I felt so right at home! We just left the car at the house and saved money walking everywhere. I had a few destinations in mind to explore in st Augustine but I was so thankful to get other recommendations from Renee! We had extra time in our itinerary to check it out and they were all great 😊 would highly recommend for anyone looking to feel right at home and comfortable as well as ease of access to nearby tourist attractions.
Top guest favorite
Condo in Ponte Vedra Beach
4.99 out of 5 average rating, 147 reviews

Gated Sawgrass Beach Club - WALK to BEACH!

SergioRating, 5 stars3 weeks ago
What attention to detail ! The layout is excellent ! Walk right to the beach ! Very nice quiet community ! Couldn’t have asked for more. Thank you so much we will be back ! Vanessa was awesome
Top guest favorite
Condo in St. Augustine
4.94 out of 5 average rating, 285 reviews

Gorgeous Sea Place Ocean View Condo

RebeccaRating, 5 stars1 month ago
What a wonderful birthday weekend in St Augustine. This condo was super cleaned, well stocked, and the most beautiful beach views. Host was super communicative and wonderful. Highly recommend this condo. Loved the townhouse feel and having the bedrooms upstairs. The beds and couches were so comfortable. So nice and relaxing. Thanks again Elaine!! We will be back. 🩷😎🩷

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