Family-friendly holiday 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

Guest favourite
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.
Guest favourite
Apartment in Beaches
4.93 out of 5 average rating, 28 reviews

Breathtaking Oceanfront Views!

ErinRating, 5 stars5 months ago
We love this building, its view, the amenities and this condo. Spacious and clean. Super happy with the cable package for watching sports. Beach towels and wagon were super helpful.
Top guest favourite
Home in Jacksonville Beach
4.95 out of 5 average rating, 189 reviews

The confetti house - 1 mile from the Mayo clinic!

TracyRating, 5 stars3 weeks ago
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+
Top guest favourite
Apartment in St. Augustine Beach
4.9 out of 5 average rating, 332 reviews

Beach side condo

RickRating, 5 stars3 days ago
Very clean and welcoming. Lots of fun stuff around the place to look at. Easy check in and a short walk to the beach.
Guest favourite
Flat in St. Augustine
4.93 out of 5 average rating, 169 reviews

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

CarrieRating, 5 stars3 months ago
Beautiful condo with lovely views of the ocean. Complex had great hot tub and pool, tennis courts and easy access to beach. Highly recommend Colony Reef Club for its proximity to historic st. Augustine, gold courses, and restaurants.
Guest favourite
Home in St. Augustine
4.93 out of 5 average rating, 134 reviews

Hawaiian Island Escape ~ Heated Pool/Spa/Beach

GilbertRating, 5 stars1 week 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
Apartment in St. Augustine
4.99 out of 5 average rating, 74 reviews

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

DeniseRating, 5 stars11 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!

Family- and pet-friendly home rentals

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 stars5 days 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.
Guest favourite
Apartment in Beaches
4.92 out of 5 average rating, 102 reviews

Beachfront Luxurious Charming 2BR Condo

CathyRating, 5 stars2 weeks ago
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!
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 stars2 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
Guest suite in Beaches
4.86 out of 5 average rating, 522 reviews

Beach Cottage Style Studio Apt.

BrooklynRating, 5 stars1 month ago
This place was a perfect place to stay by Jax beach. We were able to walk to restaurants and they even offered us bikes. They were super friendly and made sure we had a great stay. I would definitely stay here again. Very nice neighborhood. We had a very nice weekend getaway.
Guest favourite
Flat in Beaches
4.86 out of 5 average rating, 122 reviews

East of A1A Palm Trees & Ocean Breeze!

MonaRating, 5 stars2 weeks ago
Our stay was very relaxing. This place is two minutes away from the beach! The best part was the porch where you could sit for hours to enjoy the cool breeze, loved it. Unfortunately there was construction going on in the area most of the days so make sure to look at the host's description before you book it. I missed it. Despite the morning noise, the place was a gem.
Guest favourite
Townhouse in St. Augustine
4.9 out of 5 average rating, 136 reviews

Paradise Retreat*Vilano Beach*Sand & Ocean Breeze

MarRating, 5 stars4 weeks ago
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.
Guest favourite
Bungalow in Butler Beach
4.94 out of 5 average rating, 184 reviews

Crescent Moon: soft sand beach, pets welcome

SallyRating, 5 stars3 weeks ago
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!
Guest favourite
Tiny home in Lincolnville
4.8 out of 5 average rating, 739 reviews

The St Augustine Tiny House - park and walk 2 town

JenniferRating, 5 stars2 weeks ago
We look forward ved staying at Brandon’s Tiny home. We love the Iceplant so its a plus and downtown is a short walk. This tiny home is perfect for a great getaway, is clean and has a great outside space.

Family-friendly home rentals with a pool

Guest favourite
Apartment in St. Augustine
4.93 out of 5 average rating, 103 reviews

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

LindaRating, 5 stars2 weeks ago
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!
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 stars1 week 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 favourite
Apartment in St. Augustine Beach
4.94 out of 5 average rating, 193 reviews

The Beach Retreat!

SheridanRating, 5 stars3 weeks ago
We had a great time! Being so close to the beach, pier and restaurants was perfect.
Guest favourite
Home in St. Augustine
4.87 out of 5 average rating, 334 reviews

Pure Relaxation: heated pool, beach, cabana & more

KarenRating, 5 stars3 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!!!!
Guest favourite
Flat in St. Augustine Beach
4.94 out of 5 average rating, 184 reviews

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

CarolynRating, 5 stars1 month ago
Exactly what we needed. Quiet, comfortable and so close to the ocean.
Guest favourite
Apartment in St. Augustine
4.85 out of 5 average rating, 272 reviews

Direct Oceanfront ~ Fantastic Views!

MeganRating, 5 stars1 week ago
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
Guest favourite
Flat in Lincolnville
4.95 out of 5 average rating, 111 reviews

F2 Downtown, POOL, beaches, free parking!

AlaneRating, 5 stars1 month ago
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.
Top guest favourite
Home in St. Augustine
5 out of 5 average rating, 140 reviews

Southern Charmer w/Pool - Walk to Everything!

TiffanyRating, 5 stars2 months ago
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 holiday rentals that are family-friendly in Fleming Island

  • Total rentals

    20 properties

  • Nightly prices starting at

    ₹6,923 before taxes and fees

  • Total number of reviews

    960 reviews

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    10 properties include access to wifi

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