Vacation rentals in South Shore

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.

Location · Family · Outdoor spaces

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.

Location · Value · Comfort

Beach "Loft"

Enjoy The Beach Loft Apartment's convenient proximity to beaches, town and S’conset. Located 4 miles from the ctr. of the Historic District and 1 mile to Nobadeer beach our lofty spacious 900 sq. ft., 10 foot ceiling height apartment is the lower level (basement) of our home. Yet you will have complete privacy with separate parking as well as separate entrance and your own outdoor deck. The neighborhood is 3 acre zoning. It is secluded and quiet with many pine trees, oak and sassafras trees.

Location · Value · Outdoor spaces

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.

Family · Location · Decor

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!

Family · Value · Parking

“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!

Family · Value · Decor

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.

Family · Location · Heating

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

Value · Family · Hospitality

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!

Location · Value · Hospitality

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.

Family · Value · Shared spaces

Private Beach Cottage in Historic Sconset!

Charming one bedroom beach cottage in Codfish Park, Siasconset Local Realtor says "You have climbing roses and hydrangeas in the summer, you can walk up the shell path up to the Sconset Market — it's Norman Rockwell at its finest, a really magical Sconset spot," he said. "Wake up in the morning, walk up to the store for your coffee and the paper, then take a little stroll down to the beach, which you can see from the property!”

Location · Family · Nearby

The Mermaid Suite, walk to Beaches, 15 min to town

The Mermaid Suite is an efficiency apartment within walking distance to Nobadeer, Stones and Fisherman's Beaches. Well equipped with queen bed, desk, galley kitchen, full bath, outdoor shower, private entrance, linens, towels, parking, a/c and heating, etc. The Studio is a spacious 400 sq. ft. Secluded, private location. Comfortable, Cozy, and convenient.

Value · Location · Indoor spaces