Holiday 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.

SUNNY second floor 2BD, 2BT

Newly renovated, bright and well designed 2BD, 2BT in convenient mid island area that is great for family with kids or a small group of friends. Could sleep up to 4 people. Private entrance.1Spacious BD with king bed, a couch, BT/shower, a desk. Another room with queen bed, couch, TV, dining table&chairs, 2nd BT/bathtub, W/D, fully equipped kitchenette( fridge/freeze, conv. oven, microwave, coffeemaker, toaster, hot plates burner), A/C.Bath & beach towels, chairs,umbrella and linens provided.

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.

Martha's Vineyard Getaway Cottage

Contemporary cottage on quiet, private, wooded lot. Pristine, bright & comfortably furnished. Open living area, hardwood floors, vaulted ceilings, indoor/outdoor fireplaces, well appointed kitchen, washer/dryer, cable/internet/phone with unlimited national calling, SmartTV with Netflix and additional internet streaming services. Walk or bike to beaches and trails, 5 minute drive from downtown shops and restaurants. Property abuts West Chop Woods with lovely, quiet walking trails.

Charming 3BR Nantucket Cottage by Town/Beach

Elegant, charming rose-covered cottage on Nantucket. Three-bedroom, 2-1/2 bath (plus outdoor shower), sleeps 5, walkable to town and beach. Open floor plan, eat-in kitchen. Beautiful English gardens. “Pebble Cottage” is practically across the street from Something Natural, a wonderful deli/bakery. In the summer, there is a shuttle bus to town and beach that stops right outside on Cliff Road. Parking space available. Pebble Cottage is the smaller of the 2 houses on the property.

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.

Brand New modern 2 bedroom 2nd floor apartment

Brand new 2nd floor modern and upscale apartment 2 bedrooms with queen beds plus an extra floor,mattress if required for kids etc. 1 big bath with double sinks plus a big shower with seat, 2 rain shower heads plus a handheld - big enough for the whole family-:) Big open modern living room/kitchen with cathedral ceilings and gas fireplace to keep you nice and cozy for those colder nights. 65 inch 4K tv with 5.1 surround in case you feel like relaxing at home

The Luxury Vineyard Yurt

Discover this exceptional Luxury Yurt firsthand! Upon entering, you will be welcomed by a distinctive experience, featuring textured concrete radiant floors and a four-foot circular central skylight. Every aspect has been meticulously designed, allowing you to relax in a generous private yard. Enjoy your evenings under the stars, utilize the complimentary paddling, practice yoga in the spacious loft, and indulge in the beauty of your private island Yurt!

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.

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.

Quiet Cul-de-Sac near Sconset

Located on a quiet cul-de-sac across from Sconset Golf Club, this classic Nantucket home offers a peaceful retreat with views of Sankaty Head Lighthouse. Just a ten-minute bike ride to Sconset village and a short walk to the free island shuttle. Filled with natural light, the home features a spacious yard, outdoor shower, and all the essentials for an easy summer stay—beach gear, bikes, and more included.