Holiday houses 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.

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.

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.

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.

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!

"Upon a Rock" Peace & Quiet - Mid island retreat!

Our guest suite is a separate wing on the main house. It is separated by a locked door. You have your own separate private entrance. You must come into the backyard of the main house. Look for the arbor with BAIRD written on top. These is an extra charge for any guests after the first 2 guests.,$150 per guest per night. Our guest suite is not suitable for children. We do not allow pets. If you were bringing a car please let us know in advance so we can make parking arrangements

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.

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

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!

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.

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!”

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.