Holiday rentals in South Shore

A charming Cape Cod-style home is surrounded by well-maintained greenery and blooming hydrangeas. The exterior features light gray shingles and white window shutters. Two Adirondack chairs are positioned on the front lawn, offering a relaxed spot to enjoy the peaceful surroundings.

5.0 out of 5 average rating, 44 reviews

*Parker House*/Nantucket/Newly Updated

NEWLY UPDATED family friendly home located just outside the hustle and bustle of town. Brand new central A/C! Bikes, beach chairs and towels included. Convenient to bike paths, grocery shopping, and the town shuttle. However you spend your day on Nantucket, you’ll be happy to come home to the comfort of Parker House. Refresh in the outdoor shower, enjoy a meal cooked in the fully equipped kitchen or out back on the grill, unwind with a drink on the deck. The peace and charm of the island awaits!

An aerial view captures the surrounding landscape of a Nantucket cottage-style home. Lush greenery and vibrant trees envelop the property, which is bordered by neighboring homes. A glimpse of the coastline and water can be seen in the distance, highlighting the location's proximity to scenic views.

4.91 out of 5 average rating, 33 reviews

Bright South of Town Surf Shack Cottage-Gym Access

Classic Nantucket meets modern surf luxury. Behind cedar shingles and hydrangeas lies a designer retreat with Restoration Hardware decor, Casper beds, and Dan Lemaitre art. Bordering conservation land for wildlife viewing and privacy, yet <1 mile to Town. Complimentary EZIA Athletic Club gym access included! Message me for car ferry assistance by 1/18. Note: Professional staff reside in a separate basement unit to ensure a pristine stay. Quiet enjoyment is a priority; no parties or events.

A well-lit bedroom features a spacious bed with soft linens and decorative pillows. A wooden bedside table holds a lamp and a potted orchid. A small desk with a mirror and a light with a decorative shade adds functional elegance, complemented by a cozy blue armchair.

4.96 out of 5 average rating, 336 reviews

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.

4.95 out of 5 average rating, 217 reviews

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.

5.0 out of 5 average rating, 17 reviews

Apres Sea

Beautifully renovated 2-bed, 2-bath cottage, blends modern comfort with Nantucket charm. Nestled in a quiet neighborhood, it features an open-concept living area, high-end kitchen, and tasteful finishes. The spacious primary suite includes a private bath as does the second bedroom. Enjoy a private screened-in porch for outdoor dining, walk to Surfside Beach and enjoy easy access to town and mid-island amenities via the “Wave”, the islands free shuttle service. A perfect island getaway!

5.0 out of 5 average rating, 38 reviews

A private back yard is displayed, featuring two hammocks gently suspended between trees. Lush green grass surrounds the area, with a stone path leading to outdoor seating, visible through open doors of the cottage. Sunlight bathes the scene, creating a serene ambiance.

Cottage in Nantucket

Cisco Surf Shack

This recently renovated guest cottage is a cozy place to pause between your days on the beach. The house has fresh, laid-back interiors with all the modern amenities you would want for living by the water. The private and sunny back yard is complete with hammocks and a chiminea and is perfect for relaxing. A fabulous home right on the bike path close to Cisco beach (3/4 mile) , Bartlett Farm (1 mile) , Cisco Brewery(3/4 mile) , Miacomet Golf ( 2 miles) , and only 2.5 miles to town!

A cozy living area features a white sofa adorned with patterned throw pillows and a soft blanket. Intricately woven silver side tables sit on a textured area rug. Natural light enters from a nearby window, illuminating the wood-paneled walls and highlighting the adjacent kitchenette.

5.0 out of 5 average rating, 95 reviews

“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!

5.0 out of 5 average rating, 26 reviews

Downtown Condo 3 minute walk from Ferries.

Stay in the best location on Nantucket! This stylish downtown condo has Ocean views and is a 4-min walk from ferries and steps from top restaurants, shops, and nightlife. Perfect for couples, friends, or solo travelers. Enjoy a private entry, self check-in, and a fully equipped space with WiFi and AC. Walk to cafés, museums, and galleries, with easy access to bikes, buses, and taxis for beach trips. No car needed! 2nd floor unit with deck. Fully equipped Kitchen.

A spacious open-concept living area features high cathedral ceilings and neutral tones. A dining table accommodates multiple guests, while barstools line the kitchen island. A modern gas fireplace is integrated into the wall, enhancing the room's contemporary design.

4.95 out of 5 average rating, 110 reviews

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

4.95 out of 5 average rating, 127 reviews

A charming cottage exterior features a shingle facade and a spacious wooden deck. Two lounge chairs are arranged invitingly beside a potted plant. Large glass doors offer a view into the interior, while a grill is positioned nearby for outdoor cooking.

Guest house in Nantucket

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!

5.0 out of 5 average rating, 58 reviews

A private outdoor patio is equipped with a wooden dining table and chairs, shaded by a large umbrella. A grill is positioned nearby, and planters with greenery are placed at the base of the fence, enhancing the secluded atmosphere.

Cottage in Nantucket

Brand new upscale cottage-great location

Enjoy a stylish stay at this centrally-located 2 bedroom cottage. Patio dining table, grill, fire pit, outdoor shower. Private driveway. Rain shower, double sink, soaking tub. Master bedroom with king bed his and hers closet tv. Guest bedroom 2 twins. Living room fireplace WIFI. Fully equipped kitchen. Washer and dryer. Toiletries. Beach chairs, umbrella, cooler. Pack and play and baby chair. Security camera on driveway no other cameras on property