Family-friendly holiday rentals in Lake Montauk

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Lake Montauk family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Home in Cutchogue
4.97 out of 5 average rating, 203 reviews

Private Oasis W/Stunning Vinyard and Pool Views

KimRating, 5 stars5 months ago
This is the 2nd Thanksgiving weekend we spent at Deeanna's. Her home is beautiful, comfortable and each detail is thought though in the best way. Deeanna went above and beyond to accommodate my family and we are so grateful to her. The kitchen is perfection and the bedrooms are lovely and comfortable. The scenery and views are breathtaking. Overall, this home is a total gem. Thank you, Deeanna! We hope to come back next year!
Top Guest favourite
Home in Stonington
4.97 out of 5 average rating, 221 reviews

Perfect New England Getaway has a pool/ hot tub

JenniferRating, 5 stars1 week ago
We had such a nice time at Tracey and Patrick's. The house was perfect for our family and two little dogs. There was plenty of space for everyone, and anything we could've possibly needed was there and easy to find. The location was perfect in a nice quiet neighborhood that was just a short distance drive from anything you might want to do during your vacation. What a wonderful . We all agreed we would definitely like to visit again and would certainly stay at Tracey and Patrick's if available. Thank you so much for all the great memories! Jen & Co.
Guest favourite
Cabin in Riverhead
4.86 out of 5 average rating, 102 reviews

Beach & Woods: Cozy Cabin, Hot tub, Peloton, Oh My

AllisonRating, 5 stars3 months ago
We had a fabulous time! Can't wait to come back. Was equally perfect for two toddlers as it was for four adults! Beautiful property, amazing hot tub, comfortable beds, great kitchen... everything was lovely.
Guest favourite
Home in East Hampton
4.94 out of 5 average rating, 161 reviews

1800 Historical East Hampton Home, 1 Mile to Town!

RichardRating, 5 stars1 month ago
Cozy and pretty home, all ready for a chill weekend. Cindy is super nice and easy to work with. Very generous too. The 2 pups loved the fenced in yards. Kitchen/dining room space is big and bright and awesome to hang out or read in the corner nook. I am sure the backyard and pool would be great in summer. Beds were comfortable. Thank you Cindy!
Guest favourite
Home in Shelter Island
4.88 out of 5 average rating, 24 reviews

Newly Renovated w/ Pool, Hot tub & Fireplace

AliciaRating, 5 stars6 months ago
We had a wonderful stay at Jennifer’s place. It was.l beautiful, immaculate, and incredibly well equipped—especially for kids with the plethora of games and toys. Jennifer was responsive and a great host. The house is on a serene, dead-end street, and outdoor area is perfect for kids.
Guest favourite
Home in East Hampton
5 out of 5 average rating, 16 reviews

Captains Quarters | July avail!

PeterRating, 5 stars2 months ago
This house served our family very well for a multi-month stay. The house and property are just like the photos and all the amenities were great to have. Would recommend staying here if you are looking for a quiet place near the water in East Hampton. Petra was always very responsive with anything we needed and was an excellent host.
Superhost
Home in Southampton
4.83 out of 5 average rating, 210 reviews

Cozy & Chic Summer Getaway near village/beaches

JamesRating, 5 stars7 months ago
We loved our stay at Chandra’s place, it was peaceful, super comfy and was close to everything we needed. It was great to enjoy a few runs locally and come back to the private garden and hot tub in the evening. The property was beautiful and well stocked with towels, soft bedding and kitchen equipment. I’d love to come back again in the future
Guest favourite
Home in Westhampton Beach
4.92 out of 5 average rating, 144 reviews

Hampton's Haven

ZacharyRating, 5 stars7 months ago
This home is top notch!! Esther is truly amazing and everything was excellent. The kitchen is amazing, the basement play area was awesome and the rooms were perfect! I will be staying here again!

Family- and pet-friendly home rentals

Guest favourite
Cottage in Riverhead
4.97 out of 5 average rating, 151 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

RashaRating, 5 stars2 weeks ago
We absolutely loved our quick getaway from the city at Kate’s lovely home. It is hard to articulate in words just how beautiful of a home and location this was. It was truly magical. We were very comfortable as a family traveling with young children. Despite the weather being a bit chilly, we had a wonderful time soaking the views and discovering “treasures” by the water. We cannot wait to come back again soon.
Guest favourite
Home in Narragansett
4.95 out of 5 average rating, 129 reviews

The Landing

JenniferRating, 5 stars4 weeks ago
The Landing was perfect for our weekend getaway. We stayed during the quiet season and felt like we were the only ones around. The house is designed to maximize the view of the water from where ever you are. Our weather was rainy and cold but we stayed cozy and warm by the fire. Being able to bring our older dog was a plus. With clear instructions and everything we needed in the house, we did not have to reach out to John much, but when we did, he was prompt and helpful. We would definitely rent again!
Guest favourite
Home in Hopkinton
4.88 out of 5 average rating, 122 reviews

Large estate with pond near beaches

SaraRating, 5 stars5 months ago
This was a fabulous destination! We were looking for a big place to have a special anniversary party weekend with extended family, and this house had everything we needed. Plenty of bedrooms upstairs and first floor, many common gathering areas, large kitchen and dining room tables, and lots of Space. (And this doesn't even include the explorable property outside.) The dozens of photos in the listing were very helpful, as well as the detailed descriptions. We had specific needs for elderly relatives with disabilities, and owner Lynne was so responsive in her replies to my many messages with varied questions. Truly, Lynne, you deserve a gold star from Airbnb for promptness and offering up ways and help that made our stay both easier and fulfilling.
Top Guest favourite
Home in Stonington
4.98 out of 5 average rating, 387 reviews

Historic Seaside 4BR Mystic Home | Walk to Seaport

JamieRating, 5 stars2 weeks ago
Great Gull property is amazing! We loved staying at this seaside inspired home. The thoughtful design reflected the area, and the location was amazing—5 minutes away from the aquarium, walkable to restaurants, and near historic downtown too. We loved the lake just steps away from the house, and were pleasantly surprised that they provided kayaks and bikes too! We also didn’t realize there was a little cottage in the back with bunks and a bathroom—my kids loved staying in here! This was a fun treat. Everything about the house was so comfortable and well stocked and furnished. Thank you for being a great host!
Guest favourite
Home in Sag Harbor
4.85 out of 5 average rating, 160 reviews

Sag Harbor House for rent.

MichaelRating, 5 stars8 months ago
Ed was great at communicating, house was everything we could have asked for. Would definitely book again!
Guest favourite
Guest suite in Greenport
4.92 out of 5 average rating, 155 reviews

GREENPORT RETREAT- PRIVATE 2 BR APT w/ PRIV BEACH

MoranRating, 5 stars8 months ago
We had a wonderful stay at George’s. The unit is exactly as described, don’t be deterred by the adherence to the house, it’s completely private. It’s at a great location for north fork explorations and the amount of towels was outstanding!
Guest favourite
Home in Greenport
4.91 out of 5 average rating, 104 reviews

Cozy Farmhouse Retreat in North Fork, NY

MarisaRating, 5 stars1 month ago
This was a great find! I booked this Airbnb for myself and 4 other girls and there was plenty of room and space for us to hangout, sleep, and get ready. Walkable to town. Extremely clean and had all the amenities you would need for a short weekend getaway. Marianne and Steven were very responsive whenever I had a question. I would totally book this Airbnb again!
Guest favourite
Guesthouse in Groton
4.94 out of 5 average rating, 443 reviews

Quiet studio with sleeping loft and deck

DiannaRating, 5 stars1 week ago
I will book again and again. The comfort of the bed and shower was fantastic. The appliances were updated and I will recommend this little piece of solitude Heaven. It’s like a wee nature refuge and Perfect location. The hosts were attentive and kind. A million thanks!

Family-friendly home rentals with a pool

Guest favourite
Home in Montville
4.92 out of 5 average rating, 268 reviews

Casino Wine Down House

MarkavaRating, 5 stars1 week ago
Friendly and prompt responder. Really clean. The kids more than loved the game room. And I personally loved the decor. Only objection is it’s kinda out of the way and you’d have to drive to do any activities, but other than that a really great stay.
Top Guest favourite
Home in Cutchogue
4.88 out of 5 average rating, 123 reviews

The Perfect North Fork Escape

EricRating, 5 stars8 months ago
We had a wonderful stay. Cute and comfortable house in an amazing location. Very comfortable for a family of 4.
Superhost
Home in Hampton Bays
4.95 out of 5 average rating, 128 reviews

Peaceful Retreat in Immaculate Architect’s House

TheanoRating, 5 stars2 weeks ago
We had an amazing stay at Michael’s Airbnb this past weekend! The space was exactly as described—clean, cozy, and well-equipped with everything we needed. Michael was a fantastic host: super responsive, thoughtful, and made us feel completely at home. The location was perfect for a relaxing getaway, and the setting was even more beautiful in person. Would absolutely stay here again—thank you for a wonderful experience, Michael!
Guest favourite
Cottage in Montauk
4.92 out of 5 average rating, 267 reviews

Montauk Oceanview Studio 6

LissaRating, 5 stars1 week ago
This place is amazing. The beach is a 3 minute walk through the dunes. The beach itself is in an area with less density. The space of the studio itself is bigger than comes through in the photos with high ceilings and perfect set up for a peaceful and relaxing beach get-away. Comfortable bed.
Top Guest favourite
Home in Hampton Bays
4.98 out of 5 average rating, 126 reviews

Beach House Feel - newly renovated backyard Oasis

LaurenRating, 5 stars8 months ago
We absolutely loved staying at Christine’s beautiful home! The place was immaculate, and we particularly enjoyed the pool and fire pit. The location was perfect—situated in a quiet neighborhood, close to great restaurants, and within walking distance of the water. Christine was an amazing host, letting us check in early and check out late. She also texted to make sure we had everything we needed and were enjoying our stay. She even stopped by to share some great recommendations and ensure we knew how to use the house and pool code. We had a fantastic experience and would highly recommend this Airbnb to anyone looking for a relaxing and enjoyable stay!
Top Guest favourite
Cottage in Montauk
4.92 out of 5 average rating, 159 reviews

Montauk Cottage Escape

JulieRating, 5 stars6 months ago
Wonderful time staying at Milton and Megan's. The location was perfect and the home had everything we needed and more to work remotely for the week. Thank you!
Guest favourite
Home in Southampton
4.96 out of 5 average rating, 169 reviews

Waterview+Pool, FreeForDogs! Kayaks/PingPong/Bikes

ChristiRating, 5 stars1 week ago
We had a wonderful two day stay at Roger and Amy’s place. It was fantastic- such a beautiful, inviting home. Our kids had a blast in the heated pool- we could barely get them to come out despite it being under 60 degrees out! The kitchen was stocked with more than just kitchen basics- the spice cabinet had soo many different choices ! It was probably the most perfect AirBnb experience I’ve had and we travel plenty.
Guest favourite
Home in East Hampton
4.93 out of 5 average rating, 148 reviews

Large heated pool, games room, near private beach

AnuradhaRating, 5 stars2 weeks ago
We had a fun weekend at Abigail 's place. The house is in a quiet cul de sac - exactly what we were looking for. There is a private beach a 15 min walk away that the kids loved. Host was very responsive and house was clean and stocked. thanks for having us!

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