Vacation rentals in South Shore

South of Town Surf Shack. Best Deal on Island.

Redecorated for summer 2025 with new linens and Casper beds! While the exterior is the picture perfect Nantucket cottage 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. No parties, dinner parties, or events are allowed.

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.

Updated, modern and charming condo!

Updated, modern and charming condo in central Nantucket. 1,120 square feet, totally accommodates 8 people. Living room has a cozy electric fireplace for chilly Nantucket nights. Full kitchen .Lush private back yard with a patio, grill, hammock, and a relaxing outdoor shower. Two parking spots in the front of the house. Central location is walkable to downtown, grocery stores, coffee shops, restaurants, and night clubs.Close to a couple of bus stations taking you to all parts of the island.

“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!

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, I live right on the property, adjacent to the cottage, you have full privacy but no shenanigans.

Mid Island Crash Pad

A conveniently located mid-island Crash Pad for the all movers and shakers that visit Nantucket! This gorgeous, newly built one bedroom studio with its own exterior entrance is just a few steps from the bike path and shuttle that takes you right into town. This location and space offer everything you need to be comfortable in between beach jaunts or shopping trips to town. Like a hotel room, we offer a simple and affordable place to stay on ACK.

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.



Great Condo In Town!

Great two bedroom condo in town renovated in winter 2025 - new kitchen and updated bathroom. If arriving by ferry, you're just a ten minute walk from dropping off your bags and being on vacation. Convenient to restaurants, bars, shopping and everything town offers. Queen bed in master and single in second bedroom. Couch in living room is a pullout as well as option for blow up mattress. The condo is on the second floor.

BRIGHT & STYLISH 2BD,1BT with deck & BBQ

Newly renovated 2BD, 1BT first floor in convenient mid island area that is great for a family or small group of friends. Great living area,TV. Dining table and chairs, laundry W/D, fully equipped kitchen(fridge/freeze, oven, microwave, coffeemaker, toaster), window units A/C. Could sleep up to 5 people. Deck with outdoor shower and BBQ. Parking for 1 car.The bus stop is right on the corner.

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!

"Sweet Pea" - Designer 5BR Home Close to Town

Welcome to "Sweet Pea", a renovated designer home located a 15 min walk to Town! The 5 bedroom/3 full bath property has been designed for groups & families. The home feels comfortably Nantucket with designer touches including Matouk linens, Circa Lighting, Casper beds, custom cabinetry & cultivated antiques. Relax on the outdoor patio or take a house bike to Town!