Family-friendly vacation rentals in Fleming Island

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Popular amenities for Fleming Island family-friendly rentals

Family-friendly home rentals with a hot tub

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 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 favorite
Villa in St. Augustine
4.88 out of 5 average rating, 93 reviews

St Augustine Villa | Pools, Hot Tub & Beach Access

YariRating, 5 stars1 week ago
Exactly as described. Cozy and comfortable for our large family. Walking distance to the beach and close to all local attractions. We enjoyed our stay! Thank you!
Guest favorite
Condo 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 favorite
Home in Jacksonville Beach
4.95 out of 5 average rating, 189 reviews

The confetti house - 1 mile from the Mayo clinic!

TracyRating, 5 stars2 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 favorite
Condo in St. Augustine Beach
4.9 out of 5 average rating, 331 reviews

Beach side condo

SarahRating, 5 stars1 week ago
We enjoyed our stay! Not sure if it was just the dates we went, but it seemed as if we were on the less busy end of the beach which was a huge plus! Super relaxing stay!
Guest favorite
Apartment 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 favorite
Home in St. Augustine
4.93 out of 5 average rating, 134 reviews

Hawaiian Island Escape ~ Heated Pool/Spa/Beach

GilbertRating, 5 stars3 days 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
4.85 out of 5 average rating, 234 reviews

1st street, Cedar Beach House Retreat

JohnRating, 5 stars3 weeks 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

Superhost
Bungalow in Jacksonville
4.81 out of 5 average rating, 272 reviews

San Marco Area Bungalow * Cozy Screened Porch*

KellyRating, 5 stars3 weeks ago
Amy’s place was perfect! Clean, well located and nicely decorated. Her house had everything we needed! We will definitely be back!
Guest favorite
Apartment in St. Augustine
4.95 out of 5 average rating, 282 reviews

FREE BIKES Dog-friendly apt in the heart of St A

RussellRating, 5 stars1 week ago
We really enjoyed our stay here. The apartment was super clean and had a lot of charm. The backyard was cozy and great for our dog to hang out. Location was perfect—just 5-7 minutes from downtown St. Augustine, but in a quiet neighborhood that felt relaxed and safe. Gina and Benoit were quick to respond and easy to communicate with. Would definitely stay again.
Guest favorite
Condo in Beaches
4.92 out of 5 average rating, 102 reviews

Beachfront Luxurious Charming 2BR Condo

CathyRating, 5 stars1 week 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 favorite
Vacation home in St. Augustine
4.98 out of 5 average rating, 127 reviews

1st Street Retreat, Dog Friendly Updated Apartment

SarahRating, 5 stars1 week ago
Exactly what we needed for a weekend in St Augustine - extremely thankful that the dogs were able to join us and weren’t made to feel like they were an inconvenience. Wonderful space, easy to walk to the beach and an incredible taco spot across the road.
Guest favorite
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 favorite
Townhouse in St. Augustine
4.9 out of 5 average rating, 135 reviews

Paradise Retreat*Vilano Beach*Sand & Ocean Breeze

MarRating, 5 stars2 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.
Top guest favorite
Bungalow in Butler Beach
4.94 out of 5 average rating, 184 reviews

Crescent Moon: soft sand beach, pets welcome

SallyRating, 5 stars2 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!
Superhost
Home in St. Augustine
4.88 out of 5 average rating, 186 reviews

Crescent Beach House

DianeRating, 5 stars1 week 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

Top guest favorite
Home in St. Augustine
4.94 out of 5 average rating, 132 reviews

The Lazy Anchor-Pool-Walk to Beach-Dog Friendly

LazaraRating, 5 stars2 weeks ago
I'm using the translator and I hope it works well, from check-in to check-out. Wonderful house, clean, has everything to make you feel comfortable, the pool is spectacular, the beach is close to the house. Delary is very attentive and quick to respond to any message. I want to return soon. I felt at home.
Guest favorite
Condo in St. Augustine
4.93 out of 5 average rating, 103 reviews

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

LindaRating, 5 stars1 week 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 favorite
Condo in St. Augustine Beach
4.94 out of 5 average rating, 192 reviews

The Beach Retreat!

KerryRating, 5 stars3 weeks ago
Stephani did a wonderful job creating the perfect beach rental! The decorations are adorable, and the amenities are exactly what you would want. From having a well-stocked kitchen (including a coffeemaker and coffee) to a wheeled cooler for the beach, and plenty of extra towels, she really thought of everything.
Guest favorite
Home in St. Augustine
4.88 out of 5 average rating, 332 reviews

Pure Relaxation: heated pool, beach, cabana & more

KarenRating, 5 stars2 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 favorite
Apartment in St. Augustine Beach
4.94 out of 5 average rating, 184 reviews

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

CarolynRating, 5 stars3 weeks ago
Exactly what we needed. Quiet, comfortable and so close to the ocean.
Guest favorite
Condo in St. Augustine
4.85 out of 5 average rating, 271 reviews

Direct Oceanfront ~ Fantastic Views!

MeganRating, 5 stars4 days 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
Superhost
Condo in Treasure Beach
4.91 out of 5 average rating, 148 reviews

"Captain Jacks" First Floor 2BR/2Bath Condo

SusanRating, 5 stars1 month ago
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.
Superhost
Apartment in Treasure Beach
4.94 out of 5 average rating, 179 reviews

Updated and clean, private beach access condo

KerriRating, 5 stars2 months ago
We really enjoyed our week stay and hope to return next year. Susan was a very responsive host and condo was comfy and nicely decorated with coastal decor. We especially loved the beautiful, private beach…well worth the walk!

Quick stats about vacation rentals that are family-friendly in Fleming Island

  • Total rentals

    20 properties

  • Nightly prices starting at

    ﺩ.ﺇ294 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

Destinations to explore