House 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.

Family · Location · Check-in

Walk to EDG Wharf - Outdoor Shower, AC, and Grill

Just a short walk to Edgartown's shops & restaurants, this cape style home features open concept living, stainless steel appliances, bamboo floors, oversize 2 car garage, washer/dryer and outdoor shower! The master suite includes a sitting area, walk in closet & attached bath with walk-in shower, soaking tub & double vanity. Additional 3 BRs include queen/twin beds & 2 full baths. Kitchen sliders lead to outdoor brick patio with BBQ and dining area. Outdoors games and four bikes included.

Value · Location · Biking

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.

Family · Value · Nearby

Pipe Dream - Madaket

Even on the busiest of summer days, you can escape the congestion of town and unwind at this peaceful Madaket oasis. The home is a short bike ride to Millie's and Madaket Harbor and enjoy's easy access to Smith's Point for a day of fishing and swimming. With 3BR/2BA, a new outdoor shower, wraparound porch and decking, an updated kitchen and upstairs bathroom, a home office and workout space in the newly constructed outbuilding, you have everything you need for a memorable Nantucket vacation.

Family · Location · Condition

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.

Location · Value · Biking

Large yard, deck & hot tub 4 bedroom, sleeps 8

**Min stay: peak season 5 nights / shoulder season 4 nights/ off season 3 nights** Tucked in off the road lies a 4 bedroom home with a spacious yard, hot tub, fire pit, and deck suitable for dining or entertaining. The modest upstairs expands to a basement with a large living area, two bedrooms, and a kitchenette. The large deck is equipped for dining or entertaining. It also features an outdoor shower for after a long day at the beach. **House is winterized for cold weather stays**

Location · Family · Outdoor spaces

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.

Family · Location · Sleep quality

"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

Location · Family · Shared spaces

Home in Nantucket

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 .

Location · Value · Backyard

The Luxury Vineyard Yurt

Discover this exceptional Luxury Yurt firsthand! Upon entering, you will be welcomed by a distinctive experience, featuring textured concrete radiant floors and a four-foot circular central skylight. Every aspect has been meticulously designed, allowing you to relax in a generous private yard. Enjoy your evenings under the stars, utilize the complimentary paddling, practice yoga in the spacious loft, and indulge in the beauty of your private island Yurt!

Family · Location · Backyard

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.

Location · Value · Quiet

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!”

Family · Value · Biking