Kid-friendly holiday rentals in Fire Island

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!

Clarissa's Paradise

RESERVE NOW: This ideally located five-bedroom totally renovated home is the perfect spot for a family fun vacation. Located within walking distance of the well known playground and spray ground. The home features a spacious patio, central air conditioning, baseboard heating, WiFi, and Cable tv. The open layout provides perfect gathering spaces for your family, and all bedrooms are spacious and comfortably appointed. 4 full bathrooms . Sleeps 10. PLEASE NO PARTIES ARE STRICKLY PROHIBITED

Private & Pristine with Pool and Kid’s Playard

INSTANT BOOK/ dates are current. Private and Pristine 3 bed / 2 bath home in the heart of East Hampton set on 1.3 acres. Home features a chef's kitchen, in-ground gated pool, and pure privacy and relaxation. Close proximity to East Hampton Village (5 mins) and East Hampton, Amangansett and Bay Beaches (7mins), Montauk (20 mins), Sag Harbor (15 mins). Kids adore the huge playground! Entire property fenced-in to ensure the safety of kids! Heated Pool open: Memorial Day - Sept 30.

Granite Bay Getaway - Private Studio Apartment

Enjoy Long Island Sound in this cozy getaway. Three block walk to shore. Quiet residential neighborhood. Private deck with lovely afternoon light. Private entrance. Fully equipped eat in kitchen. Picturesque shoreline town of Branford. Many wonderful restaurants, 2 within walking distance. Land trust hiking trails at end of street. Ten minutes to New Haven, Yale & Avelo airport. Train station 2 miles away with connections to New York City and Boston. ½ mile from CT Hospice.

Room for everyone! Ocean Beach!

Convenient to everything Southeastern CT has to offer. Short drive to renowned Ocean Beach Park(two complimentary parking passes w/stay. Allows up to 10 guests) 20 mins to Mystic, Niantic, Mohegan Sun resort and casino. 5 mins to downtown New London and Block Island ferry. Walking distance to Thames river w/ excellent restaurants. Home provides room for multiple families and generational families. Charming New England neighborhood perfect for morning and afternoon strolls.

“Fantastic” apartment in “beautiful” townhouse

This is a sunny, spacious and private, top floor-through apartment in an owner-occupied Victorian townhouse. There is a large master bedroom, a bunk room, living and dining rooms. You also will enjoy the well-equipped kitchen and renovated bathroom with skylight. This apartment is in a prime uptown Hoboken location close to transportation to Manhattan and local restaurants, coffee houses and shopping. Perfect for families, professionals, Stevens visitors and couples.

NoFo Family Beach House — Walk To Private Beach

Nestled on the beautiful North Fork of Long Island, our family-friendly vacation home is a tranquil haven for wine enthusiasts and beach lovers alike. This updated, four-bedroom home offers the perfect blend of comfort and charm, ensuring a memorable escape for your family and friends. Explore the region's wineries and vineyards, savor in local farm to table cuisine, and create special memories with your loved ones.

There's a Beach Getaway!

Welcome to our family-friendly oasis just two blocks from beautiful beaches! Our house offers an open space living area, an expansive yard, fire pits, and a basement with a playroom and workout area. Enjoy our quiet neighborhood. We provide kid-friendly toys, beach gear, bicycles, and more. Sleeps six, with additional options available for larger parties. Cleaning fees for winter stays are 0$.

Entire One Bedroom Home on a Cobble Stone Street

Private sun filled duplex on a quiet and historic cobble stone street. Enjoy a private entrance where you go up the stairs to a fully equipped kitchen. On the third floor is your bedroom, a large bathroom and a living room where skylights and windows abound. This home is located within walking distance to all Hoboken has to offer which includes many forms of transportation to New York City.