Family-friendly holiday rentals in Amagansett

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Top-rated family-friendly rentals in Amagansett

Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite

Home in The Hamptons

4.95 out of 5 average rating, 465 reviews

Silver House: 3BR Home with Private Beach Access

Located on a half-acre property surrounded by tall oak trees, this three-bedroom, two-bathroom home is the perfect getaway. The house is part of the Clearwater Beach community with private beach access. The recently renovated kitchen and bathrooms are modern and minimal. Natural light floods the space throughout the entire house. Here is your perfect getaway from the chaos of city life The fireplace is NOT available for guest use. Early check-in and late check-out are NOT available in season

Guest favourite

Cabin in The Hamptons

4.95 out of 5 average rating, 488 reviews

Tiny Cottage in Hither Woods, Montauk

A little cabin on our property in Hither Woods. A cozy hideaway conveniently located 12 minutes walk from Gurney's Beach Resort, 16 minute walk from public path to beach, and 6 minutes drive from Montauk town for restaurants and nightlife. Good for couples and solo adventurers, the space is private and homey, with outdoor shower and Chimenea fire pit. The main house is 65ft away, but we honor your privacy. The cottage comes with WiFi, window A/C and complimentary coffee or tea. Parking for 1 car

Superhost

Home in The Hamptons

4.87 out of 5 average rating, 213 reviews

CozyFallRetreat,Walk2Beach,FencedYard4Pup,Spotless

Meticulously cleaned home.Tranquil family neighborhood in historic artist's beach community.Heated saltwater pool.Wood burning fireplace.Private fenced-in backyard.Half mile to private bay beach. Bike great trails & savor delicious meals prepared in fully equipped kitchen.Enjoy Clearwater Beach's renowned sunset. Easy living home.We welcome all respectful guests.East Hampton's best restaurants are nearby.Smoke free.Small dogs permitted.Cell reception booster! Ask about EVcharger.RentalR-25-705

Guest favourite

Home in The Hamptons

4.94 out of 5 average rating, 313 reviews

Amazing Home close to Everything -

Elegantly designed home featuring modern appliances, a seasonal heated pool, and situated just moments away from ocean beaches, Wolffer Vineyard, and the vibrant Bridgehampton/Sag Harbor villages. Set within meticulously curated landscaping, this property embodies perfection and meticulous attention to detail. Familiarize yourself with our disclosures, guidelines, and house rules. We maintain a strict no events, no parties, and no smoking policy — our home and property grouds are smoke-free.

Top Guest favourite

Condo in The Hamptons

5 out of 5 average rating, 239 reviews

Montauk Waterfront Condo w/ Sunset Views

Modern 1 Bedroom Condo in gated community (Rough Riders) with sunset views from beautiful deck. The community has multiple tennis courts, pool, jacuzzi, and sauna (pool / sauna / jacuzzi only open Late May - early October). The property is great for walks along the boardwalk and many guests enjoy swimming off the pier. The unit is less than a 5 minute car / Uber ride to town and a short 5-10 minute walk to Navy Beach and Duryea's. Strong wifi in unit, Smart TV ( Netflix, etc, - no cable)

Guest favourite

Guesthouse in The Hamptons

4.82 out of 5 average rating, 335 reviews

Detached bungalow w/ private bath

Cozy, simple living, in separate guest house with use of amenities (shared with our family of 4). The bungalow/guesthouse features a Queen bed, its own private bathroom (shower), small kitchenette (countertop oven, micrwave, Keurig coffee maker & small fridge) and loveseat for relaxing. There is a dedicated separate outdoor seating area for guests. 2 Adult guests ONLY (no children) due to size of guesthouse and proximity to the pool. Please NO pets allowed since owners have pets.

Guest favourite

Home in The Hamptons

4.94 out of 5 average rating, 133 reviews

Sag Harbor Village Cottage with Pool

Situated on a half-acre of land, this classic shingle cottage with brand new designer interiors offers the ideal Hamptons getaway. Located in the picturesque village of Sag Harbor, less than a mile from town, bay beaches, and tennis. 10 minute drive to Wolffer & ocean beaches. 4 bedrooms, 2 modern bathrooms and pool with mature landscaping offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

Guest favourite

Condo in The Hamptons

4.83 out of 5 average rating, 192 reviews

Coastline View Studio

This sun drenched studio apartment is perfect for families, couples or friends looking to get away and discover Montauk! Located in Montauk's harbor district. This unit is perfectly located to experience all that Montauk has to offer... Sit back on the balcony and enjoy a glass of wine as the sun sets perfectly over Culloden Point. A short walk to the Harbor, the Dock, Gosmans, TTs, Salivars, Sunday Funday, La Fin, Viking Fleet (fishing, Whale watching & Ferry).

Guest favourite

Home in The Hamptons

4.98 out of 5 average rating, 101 reviews

Sea Roost

This private, two-cottage property contains a few of the last remaining original fisherman cottages at Hither Hills built in the 1940s. Set on a lush, private knoll - South of the Highway - Sea Roost boasts mature landscaping and is located steps to Montauk's quiet and secluded Hither Hills Beach. The property consists of a 2 bed/2 bath cottage with separate artist studio (Qn bed, kitchenette & full bath). Dogs negotiable with pet fee. IG @searoosts

Guest favourite

Guest suite in The Hamptons

4.97 out of 5 average rating, 173 reviews

Be our guest King bed 2 bths Fireplace convenient

Beautiful, bright, spacious King suite w fireplace, two bathrooms & private separate poolside entrance. We are just minutes to beaches, boating, golf, hiking, biking, yoga and wineries. Play games, grill or cozy up fireside w a good book/movie! The space is creatively designed with a nod to natural elements and luxe comfort. Sleep your very best on our super deluxe king sized bed w/your choice of pillows. Complimentary coffee/tea/treats

Guest favourite

Home in The Hamptons

4.86 out of 5 average rating, 273 reviews

Exclusive Sag Harbor Compound

A private country compound in heart of Sag Harbor. House just gut renovated with all top of line (all Wolf and Subzero appliances). The main house is 3 bedrooms, 3.5 bath main house PLUS separate large guest cottage (with a King bed, bar fridge, and full bathroom). Gunite pool (i.e., salt chlorinated which makes it feels like clean freshwater). Walk to town, bay beach, public tennis courts, 1000 acre nature preserve.

Guest favourite

Cottage in The Hamptons

4.97 out of 5 average rating, 345 reviews

Carriage House - Cottage in East Hampton Village

Darling cottage in East Hampton Village. Situated in a historic picturesque tree-canopied neighborhood. Easy stroll to Newtown Lane and Main Street shops. (1/2 mile). Classic atmosphere. Very comfortable, bright, and clean. A perfect place from which to enjoy East Hampton and the surrounding area. Fully renovated (2019).