Vacation rentals in South Shore

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, 34 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.

The exterior of a charming cottage is surrounded by vibrant gardens featuring colorful flowers and lush greenery. A paved walkway leads to the front door, which is framed by a large round window and flanked by multi-paned windows on either side, enhancing the inviting facade.

4.93 out of 5 average rating, 129 reviews

Charming 3BR Nantucket Cottage by Town/Beach

Elegant, charming rose-covered cottage on Nantucket. Three BR, 2-1/2 bath + outdoor shower, sleeps 6 (w/one fold-out bed). 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.

4.95 out of 5 average rating, 220 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, 19 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!

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.

5.0 out of 5 average rating, 38 reviews

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!

The living area features high, sloped ceilings supported by wooden beams. Large windows allow natural light to brighten the space, and a working fireplace is positioned on one wall. A comfortable seating arrangement includes light-colored sofas, and a small TV sits on a side table.

4.97 out of 5 average rating, 199 reviews

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.

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, 111 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

A light-filled living area features a large gray sectional sofa and a round, textured coffee table. Shelving displays decorative items and a welcoming atmosphere is created by a modern chandelier overhead. Natural light streams through multiple windows, enhancing the bright ambiance.

4.97 out of 5 average rating, 73 reviews

Your family will be close to everything when you stay at this centrally-located Nantucket gem. Walk from the ferry with your belongings and then walk to town for ice cream and dinner. Or walk 100 yards down the road to Francis St beach! This recently renovated four bedroom, two and one half bath home features a new kitchen, large marble baths, gas fireplace, air-conditioning, porch, outdoor shower, large yard and sought after in-Town off street parking .

4.94 out of 5 average rating, 290 reviews

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.

4.95 out of 5 average rating, 84 reviews

Townhouse in Nantucket

Quiet Cul-de-Sac | AC | Top-Rated Nantucket Stay

Welcome to "You've Got Whale", your bright, beachy Nantucket escape. Relax around the patio fire pit, load up the beach gear, and explore Nobadeer or Surfside Beaches, just minutes away. Located at the end of a cul-de-sac in a picturesque enclave of 13 homes, this home with 4 levels of livings space can sleep up to 7 and is centrally located, near pristine beaches, hiking, parks, great restaurants and historic downtown Nantucket.

A modern kitchen features soft green cabinetry and a white countertop, complemented by natural wood beams overhead. Pendant lights illuminate the space, and a vase with fresh flowers rests on the kitchen island, adding a touch of color to the functional design.

4.91 out of 5 average rating, 178 reviews

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.

Popular amenities for South Shore vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in South Shore

4.99 out of 5 average rating, 80 reviews

Guest suite in Nantucket

Private studio

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.

5.0 out of 5 average rating, 58 reviews

Brand new upscale cottage-great location

A spacious outdoor view features a gravel driveway leading to a charming farmhouse nestled among trees and natural landscaping. The sky above is filled with clouds, while sunlight highlights the surrounding greenery, creating a serene atmosphere.

4.93 out of 5 average rating, 42 reviews

Nantucket Farmhouse-Walk to Beach-Near Sunset

4.96 out of 5 average rating, 51 reviews

A wooden deck extends over the water, featuring two classic Adirondack chairs facing the harbor. The serene view includes calm water reflecting the sky, with small boats visible in the distance. Tall grass lines the edge, adding a natural touch to the waterfront setting.

Condo in Nantucket

Spectacular Waterfront Townhouse

A vibrant outdoor space features a spacious yard with lush green grass and a blooming pink tree, providing a lively focal point. A pergola with seating is located to the left, while stepping stones lead through the yard towards the home, enhancing the tranquil atmosphere.

4.96 out of 5 average rating, 91 reviews

3 Bedroom with fenced in yard in Surfside Area

4.95 out of 5 average rating, 19 reviews

A large deck is visible, furnished with a table and chairs, surrounded by greenery. A charcoal grill sits nearby, and planters with flowers add color to the space. The cottage features wooden shingles, with sliding doors leading into the interior.

Home in Siasconset

Pristine Sconset Ctr Cot with AC

The exterior of a charming cottage features weathered shingles adorned with climbing greenery and blooming flowers. A bright blue door complements the natural tones, while a white picket fence encloses the garden space, inviting visitors to explore the tranquil ambiance of this retreat.

4.82 out of 5 average rating, 51 reviews

Tranquil House In Town