Family-friendly holiday rentals in Flanders

Find and book unique family-friendly homes on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Flanders family-friendly rentals

Family-friendly home rentals with a hot tub

Top Guest favourite
Home in North Fork
4.97 out of 5 average rating, 206 reviews

Private Oasis W/Stunning Vinyard and Pool Views

RebeccaRating, 5 stars1 month ago
We loved staying at this home - it was the perfect place for our group of ten. The outdoor space was definitely the highlight, with the pool & spa being our favorite part of the trip. The only thing to note is that we weren’t supplied quite enough toilet paper or paper towels, though I did not reach out for more - It was the last evening when we ran out and we were leaving early the next morning. The trash requirements were a surprise after booking, but going to the transfer station was easy enough, and it is listed on the house rules. Overall, an excellent stay and would absolutely return!
Top Guest favourite
Cottage in Southampton
4.96 out of 5 average rating, 187 reviews

Secluded Southampton Cottage w/Pool & Spa

AmandaRating, 5 stars1 month ago
This house was the perfect place to enjoy a peaceful stay with our three young daughters. The grounds were in beautiful bloom during our time which made all of the outdoor time even more enjoyable. From the large yard, to the hot tub and the fire pit we enjoyed staying at the property as much as exploring the area. I appreciated the well equipped kitchen and the high quality bedding. Would love to return during the summer when the pool is open and the patios were all ready for the warm weather.
Superhost
Home in Shippan Point
4.94 out of 5 average rating, 116 reviews

OCEAN COAST LUXURY BEACH HOUSE/45 min to NYC

DebraRating, 5 stars2 months ago
Victoria's place was wonderful! It was spacious and comfortable and gave our family plenty of room to spread out and enjoy our visit. Victoria was a very responsive host and made check in and check out stress free and easy! There was ample parking for our cars and the house was private - it was the "house behind the house" so we weren't subject to busy traffic noise on the street. (Got a little confusing for DoorDash drivers but we worked it out :D). I will book this same place next time I am up for an extended weekend with the family. Highly recommend!
Top Guest favourite
Home in Stonington
4.97 out of 5 average rating, 228 reviews

Perfect New England Getaway has a pool/ hot tub

DestinyRating, 5 starstoday
Had booked a girls getaway at Tracy and Patrick’s place and it was perfect, even with gloomy weather! The house perfectly matches all pictures and descriptions and has everything you’ll need and more for the perfect relaxing and fun getaway! We even got a cute surprise visit from their furry friends which is always loved!! There are also shops and beaches a short drive away, we just didn’t happen to go visit because we were enjoying our cozy time at the home. Thank you again Tracy and Patrick:) we would totally recommend and want to come back!
Top Guest favourite
Apartment in Fire Island Pines
5 out of 5 average rating, 102 reviews

"NORTH APT." Renovated 1 Br Apt. In Great Location

WilliamRating, 5 stars5 days ago
Fantastic absolutely amazing experience. Jaime was beyond great when it came to professionalism and kindness and responsiveness. Super clean beautiful apartment didn’t miss a trick when it came to anything you might need. This was a top-notch experience. Amazing customer service, beautiful location. Beautiful pool and spa overlooking the ocean We will definitely be back.
Guest favourite
Home in East Hampton
4.94 out of 5 average rating, 163 reviews

1800 Historical East Hampton Home, 1 Mile to Town!

JoshRating, 5 stars1 month ago
This was a great find for a long weekend! It was perfect for our dog as the front- and backyards are fenced in. Wonderful kitchen, great pool and close to town which made for a perfect stay. Cindy gives good recommendations on restaurants and activities and is very responsive if you have any questions.
Guest favourite
Villa in East Hampton
4.98 out of 5 average rating, 51 reviews

Luxe| Pool| GOLF Sim| HotTub| Movie|Arcade|Firepit

KateRating, 5 stars1 week ago
We had such a wonderful stay at Ann Marie’s Airbnb! From the moment we booked, she was incredibly kind and responsive, making everything so easy and welcoming. The house itself was spotless, beautifully maintained, and had every amenity we could possibly need — it truly felt like a home away from home. The location was perfect — close enough to town that everything was easily accessible, but just far enough out that we avoided all of the typical Hamptons traffic. We even walked around the neighborhood every morning! We couldn’t have asked for a better balance of convenience and tranquility. Highly recommend this stay, as someone who frequents the hamptons — we’d come back in a heartbeat!
Top Guest favourite
Home in North Fork
4.96 out of 5 average rating, 56 reviews

Mattituck Dream House - Summer Rental Opportunity

CharlesRating, 5 stars3 days ago
Hi, we had a great stay with plenty of space for all of us. We all loved the fresh flowers on the living room table. The roses were a beautiful touch! The place was very clean to which my mother-in-law said it at least 4 times a day! LOL The bedrooms were set up so neatly when we arrived (very impressive). The kitchen had all the necessary utensils we needed and more. Great weekend! Thank you.

Family- and pet-friendly home rentals

Superhost
Apartment in Port Jefferson Station
4.84 out of 5 average rating, 293 reviews

The Palm Tree Extended Stay

NatashaRating, 5 stars3 weeks ago
Clean, spacious, private basement apartment with some natural light. Very comfortable bed. Lovely backyard. Quiet, green residential neighborhood. Within 10 minute driving distance from Port Jefferson town center.
Top Guest favourite
Home in East Hampton
4.95 out of 5 average rating, 233 reviews

Private beach, fully updated house, on 2 acres.

TenleyRating, 5 stars3 weeks ago
The house was clean, well-decorated, had all the things we needed, and private, with a long wooded lot leading down to the bay. We women friends were totally comfortable there. When we couldn’t find the entrance to the driveway off the main road, she stayed on the phone & directed us until we found it. Excellent choice!
Guest favourite
Apartment in Shelter Island Heights
4.91 out of 5 average rating, 247 reviews

Squire Chase House

PaigeRating, 5 stars1 week ago
Jason was a great host. Very responsive to any questions we had while staying on Shelter Island. The location is great - easy walk from the North Ferry and central to great restaurants. Airbnb was exactly as pictured. Would definitely stay again! Thanks again Jason!
Guest favourite
Home in North Fork
4.93 out of 5 average rating, 114 reviews

Maritime Village Getaway with Backyard

LauraRating, 5 stars3 weeks ago
I stayed at Mary's rental with my sister's family including a 4yo and 6yo, as well as my 72yo mother and the house was a perfect fit! The downstairs bedroom and full bath were perfect for mom to avoid the steep stairs, and the house was well equipped with a ton of kids books and some toys. Proximity to town was the highlight, we were easily able to walk with the kids which was perfect since the weekend was too chilly for the beach. Mary was responsive if needed but the house is well stocked and easy to navigate so we felt at home right away. I will absolutely be renting from Mary again!
Guest favourite
Guest suite in North Fork
4.92 out of 5 average rating, 157 reviews

GREENPORT RETREAT- PRIVATE 2 BR APT w/ PRIV BEACH

AmberRating, 5 stars3 weeks ago
We love staying at George’s place, it feels just like home away from home for us. We’ve visited this property several times over the years, most recently with our son who’s now old enough to fully enjoy the yard on his own. He had a fantastic time playing outside, talking to the deer and rabbits that came to visit. We even saw some turkey vultures! Overall a solid place to stay and it’s become somewhat of a family tradition. Thank you George!
Guest favourite
Cottage in Guilford
4.93 out of 5 average rating, 273 reviews

Charm + location. Walk to beach, town, & harbor.

MaryRating, 5 stars2 weeks ago
Jeanne's place was perfect for my trip to Guilford. Excellent location, close to the Green and to the water, quiet, peaceful. The house had everything I needed and more, Jeanne was super responsive and kind, and the bed was comfortable.
Guest favourite
Guesthouse in Groton
4.94 out of 5 average rating, 452 reviews

Quiet studio with sleeping loft and deck

JessicaRating, 5 stars2 days ago
This is the cutest Airbnb! Everything you need in a little niche of love, convenience, and comfort! A wonderful location and neighborhood! When visiting family, I will certainly be back to stay here. 💖
Guest favourite
Cottage in Montauk
4.91 out of 5 average rating, 598 reviews

Montauk Oceanview

SusanRating, 5 stars1 month ago
Always love staying at Ron’s. It’s so peaceful. Perfect location and beautiful Ocean views with a short ride if you need to go to town. Montauk Music Fest is a must. Amazing talent and great way to see all Montauk venues. Ron so great to have as a host!

Family-friendly home rentals with a pool

Superhost
Home in New London
4.88 out of 5 average rating, 179 reviews

Waterview Cove 1 @ Ocean Beach: 6 Queen 1 Sofa Bed

CraigRating, 5 stars2 months ago
This place is perfect for a large group with lots of queen size beds. Easy walk to Ocean beach.
Top Guest favourite
Barn in Bethel
4.98 out of 5 average rating, 237 reviews

Escape to a Restored New England Antique Milk Barn

GavinRating, 5 stars3 weeks ago
My girlfriend and I had a great stay here. The place was cozy, well-equipped, and perfect for a relaxing getaway. The outdoor area was the true highlight — from the spacious patio to the beautifully maintained landscaping, the property felt peaceful and private. There’s also a pool that looked amazing, even though we couldn’t enjoy it due to the weather. We had some trouble during check-in after a delayed flight and arrived around midnight, but the property owners were just a phone call away and quickly helped us get settled, which we really appreciated. Overall, it was a great experience and we’d absolutely recommend this spot to anyone looking for a quiet, scenic place to unwind.
Guest favourite
Home in East Hampton
4.91 out of 5 average rating, 113 reviews

Private & Pristine with Pool and Kid’s Playard

BridgetRating, 5 stars1 week ago
Marta could not have been more accommodating! She was responsive and provided everything we needed. She even went the extra mile and insta cart-ed garbage bags and paper towels when we ran out. She could not have been a kinder host! We had the best weekend and would HIGHLY recommend staying at Marta’s place! We will definitely be back!
Guest favourite
Home in North Fork
4.87 out of 5 average rating, 127 reviews

The Perfect North Fork Escape

JodieRating, 5 stars2 weeks ago
Everything was perfect for our girls weekend. This is the 3rd time we’ve used Laurie’s house and there’s obviously a reason we keep coming back. Can’t wait to go again.
Superhost
Home in East Hampton
4.88 out of 5 average rating, 110 reviews

Gorgeous East Hampton Getaway

LisaRating, 5 stars10 months ago
Wendy’s house is immaculate, tastefully decorated, very spacious and extremely comfortable. Her instructions were clear and her responsiveness immediate. We would absolutely consider staying there again.
Top Guest favourite
Home in Monroe
4.97 out of 5 average rating, 201 reviews

Garden Level Suite with Beautiful Pool

GraceRating, 5 stars3 months ago
We had an amazing time at Marybeth’s suite—it truly felt like a winter wonderland. Our kids had a blast "swimming" in the snow and "rolling" over the gentle hills. Every moment was filled with joy, whether we were relaxing in the sunroom, playing in the snow, or swinging outside. The time spent together as a family, along with our conversations with Marybeth and her family, was truly precious. We can’t wait to return in the summer!
Guest favourite
Home in Sag Harbor
4.86 out of 5 average rating, 269 reviews

Exclusive Sag Harbor Compound

Amy RoseRating, 5 stars2 weeks ago
Ben is a super host. His home is absolutely beautiful and well managed. His thoughtful recommendations and well timed check ins and reminders were the height of polished professionalism. We felt right at home, down to the bins of toys in the living room that our toddler and baby played with every day.
Superhost
Guesthouse in Shelter Island
4.96 out of 5 average rating, 115 reviews

Waterfront carriage house studio

FernRating, 5 stars9 months ago
John was a perfect host! Friendly, responsive and made us feel welcome. I took my 9 year old son and we had a great time fishing off the dock and kayaking. The kitchenette is lacking if you want to cook any meals but it didn’t matter in our case. Absolutely beautiful location!

Destinations to explore