Family-friendly holiday rentals in Long Island Sound

Luxury cottage by the sea with hot tub and pool

We built this guest cottage to provide an ultimate luxury experience for people wanting to escape from hectic life!With incredible coastal views, this home is a haven of tranquility. It sits on a special stretch of the Connecticut coast, with spectacular bird and wild life-watching year-round. Enjoy great shopping in Guilford's boutiques around the historic town green. Watch the sun set over the water and relax in the hottub for some night time star gazing year round (pool open June-beg/mid Oct)

Indoor spaces · Kitchen · Pool

Cheerful 3 Bedroom Cottage with Fire Place

We are happy to still offer some dates for September. Come enjoy the solitude of the beach as the tide ebbs & flows. Reconnect with loved ones in this family-friendly place. Enjoy strolls on the beach located just out the back door or a sunset meal on the back porch. This wonderful cottage offers everything you will need during your stay. Including, comfortable beds, beach strolls and a bright upgraded kitchen with many amenities. The 3 bedrooms will fit up to 8 people comfortably.

Kitchen · Indoor spaces · Location

Modern farmhouse w/ pool, beach, horses and winery

A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.

Indoor spaces · Family · View

Designer Beach Retreat on Exclusive Cedar Beach

Welcome to your own slice of heaven! Enjoy dinner in your Chef's kitchen while watching one of the most radiant sunsets you will ever see. Stunning views from the private rear deck or snuggled on the couch inside the living room. Wade into Long Island Sound with semi-private beach access 250 feet away. The property is 5 doors down from the CT Audubon Society, known for its epic views and wildlife watching. The sunrises & sunsets are beautiful! 15 minutes to Yale. We can't wait to host you!

Indoor spaces · Family · Nearby

Serene East Hampton Escape - Warm Pool til Nov

A luxuriously curated woodland escape with massive pool (heated and open May through October), fully fenced and just minutes from EH Village & Ocean Beaches. This impeccably renovated four-bedroom, four-and-a-half-bath home offers refined comfort in a serene, private setting. Sunlight floods the expansive interiors, featuring rich luxurious finishes, a separate office with queen sofa bed, a freestanding soaking tub, and a designer chef’s kitchen with a custom dining table for ten or more.

Family · Indoor spaces · Hospitality

Savor Ocean Sunsets at a Soothing Beachfront Haven

Newly renovated and featured as a top Airbnb by New York Magazine, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Stay on the property for swimming, beach walks, sunsets and BBQs - or venture out to enjoy all the North Fork has to offer.

Family · Kitchen · Pets

Steps to Beach • Hot Tub • Game Room • Water Views

Beautiful coastal beach house directly across from a private beach and tennis club with complimentary guest access. Backing up to a serene marsh with stunning views, this home offers a peaceful, upscale setting perfect for families and groups. Relax in the hot tub with outdoor TV, fire pit, and kayaks. Inside features 4 bedrooms, a workspace, and a new game room with a 100” TV, pool table, shuffleboard, and darts. Minutes from Branford’s town center, dining, and waterfront attractions.

Family · Kitchen · Check-in

The Cove Cabin

An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, two SUP, and two two-person kayaks are available for use from May 1 to November 1.

Kitchen · Family · Long stay

Luxury Hamptons Home with Heated Saltwater Pool

Get away from it all in this meticulously renovated Westhampton Beach home. Pull up to the cottage in the heart of Westhampton Beach, a place that delivers all the Hamptons have to offer, all while being within a two hour drive of NYC. No detail was overlooked in the renovation of this cottage… the beauty is only matched by the comfort and function. With the open floor plan, sunny kitchen, furnished open air patio, you won’t want to leave.

Kitchen · Family · Location

Luxury modern farmhouse with heated pool & hot tub

*Pool is now open until late October This beautiful modern farmhouse is located on a one-acre lot and features a custom designed open-concept living space with vaulted ceilings that opens directly into a pool area. Hidden behind a bookshelf, you'll find a gorgeous game room with a piano and a pool table that can be easily converted into a ping pong table or working space. Please note that we do not allow weddings and events at this time.

Family · Indoor spaces · Comfort

Peaceful Light-Filled Guesthouse salt pool/sauna

Step into a peaceful, well-appointed home nestled on 14 acres of ancient trees, stone walls, and meadows in Pound Ridge, NY. This light-filled guesthouse is designed for relaxation, with a heated saltwater pool available in summer, sunbathing under a majestic maple tree, and evening stargazing by the outdoor fire pit, or unwind in the pool side sauna. Perfect for families, small groups, or couples seeking a peaceful nature retreat.

Kitchen · Family · Sleep quality

Charming Historic Cottage in the Redwoods

Travel back in time to Marchant Farm and enjoy an authentic farm life experience in the historic, newly restored Sunflower Cottage. Whether you need a place to recharge or to reconnect with nature, you will find it here. Relax and unwind in the stunning floor to ceiling cedar living area. With 2 air conditioned bedrooms, each with full beds, and the children's magical loft space with two twin beds and play area.

Family · Indoor spaces · Decor