Holiday rentals in South Shore

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.

Nantucket Farmhouse-Walk to Beach-Near Sunset

The Nantucket Farm House was built in 1840 and was completely renovated and refurnished in 2023. If you are having trouble with ferry reservations and need a car, please let us know. We might be able to help. The home very private and is very close to beaches, bike paths, and the Nantucket public transportation stop. We are experienced Air BnB Superhosts and are committed to excellent service and guest satisfaction. We also have a full-time caretaker on island for your convenience.

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!

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!

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.

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.

Beachfront Cottage w. Yard + Town Access

Welcome to The Mizzen Cottage! Updated 1930's cottage on an ocean front compound on beautiful Chappaquiddick. Complete with a picturesque porch overlooking the outer harbor, side deck, outdoor shower, washer/dryer, dishwasher. Stunning views of the Edgartown lighthouse and Cape Poge. Access to a private beach. Access town with just a 10 minute walk (or 1 minute drive) to the Chappaquiddick Ferry, and be in downtown Edgartown in 15 minutes or less!

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!”

Beautiful Cottage, Historic Home

This quaint cottage is located Mid Island approximately one mile from Downtown, making it an ideal Nantucket home base for your group. With 2 bedrooms and 1 bathroom, the home comfortably accommodates up to 4 guests. Amenities include a private hot tub and a patio with an outdoor dining area. Inside, the professionally designed interiors feature coastal inspired décor with classic blue and white accents.