Family-friendly holiday rentals in North Sea

#2 Milford Beach (across street) Charles Isle 2BR

Welcome to your perfect Milford beachfront escape! This beautifully furnished 2-bedroom, 1-bath 2nd floor unit sits directly across from the beach, with beautiful water views. Just 100 yards from Silver Sands State Park, you’ll have easy access to its beaches, nature trails, and famous boardwalk. This unit offers beach gear, private yard for sunset dining, and proximity to Milford’s lively downtown. Whether here for a romantic getaway or family retreat, this spot offers relaxation or adventure!

Kiddo Approved! Heated Pool/Hotub Renovated Home

Family friendly Sag Harbor one level beach house close to Main Street. Heated pool (for a fee), hot tub, enclosed grass yard, kids play area with sandbox and toys, crib, highchair, outdoor fireplace, outdoor shower, yard is fenced and gated with separate safety fence and gates around pool. Backs up to a nature preserve for privacy. Quiet Neighborhood. Short drive to the beach and Main Street. Pool open April 13th-Oct 1. Pool can be heated June-August (for a fee). Hot Tub open April- November.

Tiny Home in Prime Spot in Southampton Village

Located in the heart of Southampton Village, this intimate, centrally-located cottage is the perfect getaway! Nestled in an easily accessible, safe, and well-lit neighborhood, it is ideal for those with or without a vehicle. Only a 5 min. walk from the train station and a 5 min. walk to town, which includes premier shopping and restaurants. Enjoy nearby wineries, museums, and pristine, top-ranked beaches. Be close to everything Southampton has to offer while enjoying absolute peace and quiet!

A-Frame cabin with private beach & epic sunsets

Just a 1.5 hour drive from NYC, this home is the perfect beach getaway spot, with a few steps from the deck to the private beach with its beautiful view across the Great South Bay. Remote work with stunning water views through the wall of windows & in cold weather light a fire while sunlight floods the living space. Two queen bedrooms & bunk bed room sleeps 6 guests, great for families or a small gathering of friends. 5 min drive to ocean beach with great swimming & surfing at Smith Point.

Hamptons Waterfront- Relax & Getaway!

My place is right on the water with your own sandy beach. A quick walk to the restaurant and dining. No worries about having a drink and getting home. You’ll love my place because of the location and the ambiance. My place is good for couples, solo adventurers, business travelers, and families (with kids). Conveniently located just minutes from the center of town for all your shopping needs; grocery store, Starbucks, 7-11, rite-aid, bagel cafe, pizzaria, farmers market and more.

Aqua Vista

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

Cozy guesthouse in an English style Tudor house

Light and airy, lots of blue and white (think Ralph Lauren) cozy and country feeling cottage in an English tudor house. The perfect place for a relaxing stay in Montauk. Reminiscent of an English county cottage with all its charm and imperfections. Its the perfect spot for a BBQ and relaxing outside with the sounds of birds chirping and the leaves rustling. 20 min walk to town, 25 min walk to the beach. I hope you'll enjoy your stay :)

Waterfront carriage house studio

Access to endless pool/spa, private beach around corner, breathtaking views, access for kayak, sup etc on property, playful friendly dog, easy access to all including sunset beach, beautiful breeze, private location, 46 foot classic powerboat available for charter at discounted rate w/ rental

Southampton Village Studio

Location, Location, Location!!!! New renovated stand along Studio Apartment in the heart of Southampton Village. Private with lots of light, Cable TV and living room area. Located in wonderful Southampton Village location, only 1 mile to village shops and 2 miles Coopers Beach. Wi-Fi