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
4.8 out of 5 average rating, 5 reviews

Beachfront Getaway Directly on St. Augustine Beach

DaphneRating, 5 stars5 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 stars4 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
Home in Southeast Jacksonville
4.85 out of 5 average rating, 201 reviews

Private FL Home with Pool, Hot tub & Luxury Master

CarmelRating, 5 stars4 weeks ago
Amazing spaces indoor and out. The Airbnb pictures don’t do it justice. 3 bedroom, 3 bath, pullout couch. Sleeps 8 adults (willing to share beds) and 4 children (pullout couch and blow up mattress). Plenty of room for cooking, dining, well-equipped kitchen w/ air fryer, 2 coffee makers, crock pot and more. Great location 20 minutes from anything. Walked to stores (1.5 miles each way). Games and puzzles. Great master suite. Takes a few minutes to get hot water to back bathrooms, but be patient, it’s worth it. This could be a repeat for us!
Guest favorite
Villa in St. Augustine
4.88 out of 5 average rating, 92 reviews

St Augustine Villa | Pools, Hot Tub & Beach Access

LoganRating, 5 stars4 weeks ago
We had a blast! Close to everything you’d want to see, so short drive times to everything we did. End unit so a little more private than the other condos in the community. Easy walk straight from condo to beach.
Guest favorite
Guesthouse in St. Augustine
4.91 out of 5 average rating, 569 reviews

Captain's Quarters Tiny House

JenniferRating, 5 stars5 days ago
I would like to say first and foremost this was THE MOST COMFORTABLE BED we’ve slept in an air bnb and the place would be a top choice just for that alone. We had access to the hot tub that was much needed after sight seeing. We enjoyed the outdoor showering area as well. We had everything we needed for the few days we were there visiting. We will be back !
Top guest favorite
Condo in St. Augustine Beach
4.9 out of 5 average rating, 326 reviews

Beach side condo

GosiaRating, 5 stars1 week ago
The apartment was very nice and clean. Everything was there. We miss only more toilet paper rolls and shower soap in kids bathroom. The resort is perfect to spend nice time: very nice and clean 2 pools, spa and tennis/pickleball courts. The privat beach acces was fabulous with a tourtle direct close to boardwalk. We tried a few restaurants during our stay, and fall in love with one direct over the fence-Santiago's FloridaKitchen: perfect fresh homemeda food and very nice fast service. And you can not forget the Mayday ice cream. A lot of things to do around. We will definitely love to come back.
Guest favorite
Home in St. Augustine
4.93 out of 5 average rating, 132 reviews

Hawaiian Island Escape ~ Heated Pool/Spa/Beach

RamonRating, 5 stars2 months ago
The place is amazing having a 10 out of 10 for the pool and the hot top. House very beautiful and clean. Abrina and her husband are very friendly. They bring you fresh bread and butter in the morning. For sure I would recomend this peaceful place for vacaciones with the family
Guest favorite
Condo 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 stars10 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 favorite
Home in Southeast Jacksonville
4.85 out of 5 average rating, 178 reviews

Mandarin. Modern and Cozy!

RogerRating, 5 stars1 month ago
Great location and neighborhood. Good amenities. Host is very responsive and helpful.
Superhost
Apartment in Riverside
4.78 out of 5 average rating, 237 reviews

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

MikeRating, 5 stars15 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 St. Augustine
4.99 out of 5 average rating, 403 reviews

Your Home Away From Home

AshleyRating, 5 stars1 week ago
I cant say enough good things about Fred and Lynn's home away from home. I've stayed at a few locations in St Augustine, but they deserve more than 5 stars. My family enjoyed every second of their peaceful surroundings. The home was gorgeous, pool felt amazing, and hosts and fur babies were super friendly. We are definitely planning on returning now that we have found this hidden gem. Close enough to great restaurants, but so private that deer felt safe enough to lay in their yard. Fred met us as soon as we arrived with Ellie and they gave us the grand tour, checked in during our stay to make sure we were comfortable, and Lynn came out to have conversation and offered my daughter a pool float. Even making sure she had sun screen. It was the little moments like that that made this place so special!! I said several times "reminds me of grandma's house as a kid." Thank you again Fred, Lynn, Ellie, and Boo. We miss yall already!
Superhost
Home in St. Augustine
4.91 out of 5 average rating, 216 reviews

The Anastasia House Close to Downtown and beaches

TammyRating, 5 stars11 months ago
Great place to stay close to the historic area and lots of places to eat. close to beaches. The place was cute and clean great enclosed patio should def rebook next time we are in St Augustine
Guest favorite
Apartment in Beaches
4.86 out of 5 average rating, 120 reviews

East of A1A Palm Trees & Ocean Breeze!

IlyaRating, 5 stars1 month ago
Our stay at this apartment was absolutely wonderful! The location near the ocean was perfect, and the place was spotlessly clean and very cozy. The kitchen was well-equipped with everything we needed, making cooking easy and enjoyable. A special thanks to the host—very responsive and attentive, always ready to help. I highly recommend this place and would gladly stay here again!
Guest favorite
Bungalow in Butler Beach
4.94 out of 5 average rating, 176 reviews

Crescent Moon: soft sand beach, pets welcome

JulianaRating, 5 stars2 weeks ago
A great, quirky, perfect located property with everything you need! Really enjoyed our stay, will be coming back!
Top guest favorite
Apartment in St. Augustine
4.94 out of 5 average rating, 335 reviews

The Rohde House, The Rohde Guest House

StephanieRating, 5 stars1 week ago
We had such a wonderful stay. The location cannot be beat and we walked everywhere. The cottage was very well stocked which was great. There was even a box of bandaids in the medicine cabinet. We enjoyed coffee in the private yard area while our little dog searched for lizards. Such a great place and I’d highly recommend. We will definitely be back.
Superhost
Home in St. Augustine
4.78 out of 5 average rating, 191 reviews

Oceanfront home with large deck.

TraciRating, 5 stars6 days ago
Greg’s place is spectacular. This house is right on the beach. The beach was always quiet even over the holiday weekend. The layout is great. My fiancé and I were upstairs and my sister, brother-in-law and niece had plenty of space downstairs. There are beach towels, beach, chairs, beach mats to lay on. They also had a canopy. The upper back deck had 2 loungers so you could lay down and relax. Plenty of outdoor seating on all of the decks. Spectacular view of the beach. Kitchen well equipped. Tons of bath towels. Greg offered shampoo/conditioner, body wash, dish soap, hand soap, tp, paper towels, dish washer pods paper towels, plenty of cleaning products on both floors of the house in case you need anything..dryer sheets &tide. There’s basically two living rooms one upstairs and one downstairs both with nice televisions with plenty to watch.. The upstairs, ocean front bedroom has a tv as well. The house is very spacious. Greg was a great host! We will definitely return! Thanks Greg!

Family-friendly home rentals with a pool

Superhost
Condo in Beaches
4.85 out of 5 average rating, 65 reviews

D&G Beach House

KatieRating, 5 stars1 month ago
this place was perfect for our group of four! walkable to everything and right on the beach. The space was clean and private and exactly what the pictures showed. We couldn't have been happier. Staley was also super nice and responsive and had great recommendations for places to eat in her welcome book. We definitely will stay here again!
Superhost
Condo in St. Augustine
4.82 out of 5 average rating, 136 reviews

Oceanfront 1 BR Condo w/Private Balcony 2nd Floor

AliciaRating, 5 stars1 month ago
Had a great stay in St. Augustine. Peaceful and just what we needed for a quick getaway
Guest favorite
Apartment in St. Augustine Beach
4.94 out of 5 average rating, 182 reviews

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

LoriRating, 5 stars3 weeks ago
Mark and Melanie have a GEM at St Augustine Beach! The kitchen is so well stocked there is nothing missing. The seaside decor sets the tone for a very comfortable and relaxing getaway! The unit is clean, bright, well designed and the walkout patio directly to the beautiful Pool is a highlight ! The condo complex is securely gated. And extremely well maintained. And they’ve thought of everything , all The beach chairs, toys and towels are included which makes packing for a beach vacay a breeze. Melanie was very responsive and prompt with checkin instructions and local Recommendations. The beach is our favorite with white sugar sand , rolling surf, shells and it Is perfect for daily walks. We’ve stayed at many condos in St Augustine and this is by far the favorite ! We’ve reserved for a return trip next year and look forward to the sun, ocean, and relaxing here again !
Top guest favorite
Condo in Ponte Vedra Beach
4.99 out of 5 average rating, 154 reviews

Gated Sawgrass Beach Club - WALK to BEACH!

StefanieRating, 5 stars1 week ago
Vanessa's place was perfect for our long weekend. It is across the street from the beach, had all the things we might need for the beach or for cooking and it was very clean! Vanessa was also very helpful with advice or answering questions. The space is small but perfect for 2. Highly recommend!
Superhost
Apartment in St. Augustine
4.94 out of 5 average rating, 178 reviews

Updated and clean, private beach access condo

KerriRating, 5 stars3 weeks 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!
Guest favorite
Condo in St. Augustine
4.93 out of 5 average rating, 143 reviews

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

JoeyRating, 5 stars7 months ago
We really enjoyed our stay at Matthew's condo. It had everything we needed and the beach was only about a 5 minute walk away. There are some fairly steep stairs to navigate to get to the beach behind the condo , but it's not too bad. Would definitely stay here again.
Top guest favorite
Condo in St. Augustine
4.94 out of 5 average rating, 291 reviews

Gorgeous Sea Place Ocean View Condo

CynthiaRating, 5 stars3 weeks ago
Elaine's condo is beautifully decorated and she goes above and beyond with all the extra touches to make you feel welcome and right at home. The kitchen is well stocked with anything you need and it is nice quality. The condo was spotlessly clean with nice towels and linens to make your stay enjoyable and peaceful. This host was very accommodating and quick to respond with any questions we had about our stay. We will definitely keep this condo on our list to stay again when we are in St. Augustine.
Top guest favorite
Condo in St. Augustine
4.95 out of 5 average rating, 106 reviews

Sea Place Ocean View

DianaRating, 5 stars1 month ago
This condo is perfect. It met our needs and is located in beautiful St. Augustine. Great location. Ocean views. Peaceful.

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

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