Holiday rentals in South Shore

Captain's House 1750 In town

Our 1750 house is just over a block from the cobblestones of Main St. and only one block from the harbor. You can walk from the Hy-Line Ferry. At night, just walk home from dinner at any restaurant in town. There are 3 bedrooms (1 has a bunk bed) and two and a half baths. In the morning, walk next door for great coffee and cinnamon muffin. Have a cookout and eat in our small backyard area. Come for a visit! (Restaurants, Buses and Cars can cause some noise FYI) Drip coffee maker/filters too!

Cuddle In Cottage near Surfside Beach

This charming Nantucket chic decorated cottage is your ideal vacation spot. Perfect for 2 and a max of 4 people. The cottage is less than a mile from Surfside Beach, voted the islands favorite, and across the street from a bike path offering biking to the beach or town a safe and easy option. The cottage boasts privacy with fully stocked kitchen, in and out door shower, radiant heat, AC unit in the bedroom, 2 flat screen TV's, top drawer linens, towels, beach chairs and an out door grill.

Spouter Cottage

A unique upside down two bedroom cottage with a deck and a view of the Harbor. A curated space with antique beams, handcrafted doors, flooring and cabinetry, antiques and fine art. It all lends a vintage feel to an up to date with all the amenities home. There is a private small side yard and garden with outdoor grill and seating. This is not a party house, it’s a sensitive house, my husband and I live right on the property, adjacent to the cottage, you have full privacy but no shenanigans.

“Somer Sweet” is Moments Away to the Beach!

So close to the beach! 2nd floor apt with private entrance decorated with vacation in mind offering an open living, dining and kitchenette area with cathedral ceilings. Beautiful bedroom with a queen bed, bureau and closet. A hall bathroom with a new tiled shower and vanity with marble top. In the hallway is a laundry area with full size washer/dryer. 2nd floor private entrance is located over our two bay garage which is attached to our home. Super location just .2m to beach road!

South of Town Surf Shack. Best Deal on Island.

Redecorated for summer 2025 with all new linens and amazingly comfortable Casper beds! While the exterior is the picture perfect Nantucket cottage-style home surrounded by hydrangeas, you will be surprised by the casual, surf-vibe of the decor. Enjoy the best of Nantucket by walking to Town (under 1 mi) at this prime location property. The lot has privacy hedges and borders conservation land. This property has a separate living area home to two of the homeowner's employees.

Madaket Bright and Airy Guest Cottage

Escape to this charming guest cottage in Madaket, just a short walk from Madaket Beach, known for its stunning sunsets. This peaceful retreat offers a cozy, light-filled space with a well-equipped kitchen and comfortable sleeping arrangements. Enjoy mornings on the private patio, bike scenic paths, or dine at Millie’s. Easily explore Nantucket’s shops, restaurants, and history. End your day with a breathtaking sunset—your perfect island getaway awaits!

Our Three Suns

Nantucket house with community access to pool, tennis courts, bike path This 4 bedroom, 3 1/2 bath house is located in the desirable family friendly community of Naushop. The house includes all the amenities Naushop offers; a community pool, two tennis courts, a pickle-ball court, playground and renovated clubhouse. The community is located on the bike path providing easy access to the beach (1.5 miles), town (2 miles), and other amenities.



Charming 4 bedroom home in Miacomet!

This 4 bedroom, 2.5 bathroom home is located in the Miacomet area of Nantucket. About 1.5 miles to the beach, 1 mile to Cisco Brewery, 167 Raw and Bartlett's Farm, and 2 miles to town, the location of this home cannot be beat! No car? The Nantucket WAVE bus (free!) stops at the end of the road, with a direct connection to Town. Nantucket is also extremely bike friendly!

Private 1 Bedroom Walk-Out Basement Apt

Convenient mid island location. We are within walking distance to town, Surfside Beach and numerous restaurants. The bus stop is right on our doorstep and the bike path is directly across the street.