House vacation rentals in South Shore

4.96 out of 5 average rating, 111 reviews

A clear view of Vineyard Sound is visible through the surrounding trees, showcasing the serene blue waters extending to the horizon. The gentle outlines of land can be seen in the distance, framed by lush greenery and a tranquil atmosphere.

Home in West Tisbury

Lambert's Cove Retreat, Water view, Beach pass

Enjoy stunning views of Vineyard Sound from this cozy three bedroom two bath home in a quiet neighborhood just minutes from Lambert's Cove Beach. This upside down house has one bedroom on the main level along with a full bath and open kitchen, dining, and family room. The downstairs has another living space, two bedrooms, laundry room, and full bath. Enjoy family time in the open upstairs with water views, or retreat to the lower level living room for some separation, quiet time, or work space.

4.94 out of 5 average rating, 203 reviews

The exterior of a charming house is shown, featuring a gray shingle facade and a welcoming covered porch. Lush greenery and ornamental shrubs frame the entrance, while a gravel driveway leads up to the front door, creating an inviting approach.

Home in Oak Bluffs

Spectacular beach & pool combo; beautiful sunsets!

Close to airport, you’ll love backyard beach, water view, pool/grass yard, ambiance and outdoors space. Beach & Pool (POOL HEAT STARTS SUMMER, ENDS 9/1) is a hard to find combination!! Location is private, yet it's close to the 3 largest towns on Martha's Vineyard. Great for couples, families (with kids), and big groups. Enjoy dinner with the indoor/outdoor Sonos music system during a beautiful sunset! NOTE; Rate increase in high season, pool/spa is a combined unit & ONLY heated in summer!

A living area features a comfortable sofa adorned with decorative pillows and a glass-top coffee table. Two bar stools are positioned at a nearby counter, and a chair is set to the side. Natural light streams through large windows showcasing plants in the outdoor space.

4.85 out of 5 average rating, 117 reviews

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.

A charming entrance to a coastal home is highlighted by a set of steps leading to a pastel blue door. Flower pots are positioned on either side of the door, and a wooden railing frames the steps, adding a welcoming touch.

4.9 out of 5 average rating, 103 reviews

Captain's House 1750 In town

Our 1750 house is just over a block from the cobblestones of Main St. and only one block from the harbor. You can walk from the Hy-Line Ferry. At night, just walk home from dinner at any restaurant in town. There are 3 bedrooms (1 has a bunk bed) and two and a half baths. In the morning, walk next door for great coffee and cinnamon muffin. Have a cookout and eat in our small backyard area. Come for a visit! (Restaurants, Buses and Cars can cause some noise FYI) Drip coffee maker/filters too!

5 out of 5 average rating, 281 reviews

The exterior of a classic Cape Cod home is framed by a grassy yard under a partly cloudy sky. White wooden adirondack chairs sit on the lawn, and the house features a cozy front porch, shutters in a deep hue, and multiple windows allowing natural light.

Home in Yarmouth

The Pearl: 3 Bedroom 500 steps to Englewood Beach!

The Pearl is a classic Cape Cod 3-bed home 500 steps to Lewis Bay. Walk through the marsh path on your way to Englewood Beach, a number of small beaches, & Colonial Acres! Seagull Beach is 2 miles away. • Mesh WiFi, 2 Smart TVs • Central Air Conditioning • Large 2nd-floor bedroom • Big yard on a quiet dead-end street • Original wood floors/trim • Living/Dining rooms • Outdoor shower, grill, deck, firepit • Equipped kitchen • Linens/towels provided • Washer/Dryer in basement • Work from home

A private outdoor area features green lounge chairs arranged around a small table, with a patio woven into the grassy landscape. A barbecue grill is positioned nearby, and the exterior of the cottage is framed by lush hedges and a pergola, creating a serene environment.

4.94 out of 5 average rating, 195 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.

4.89 out of 5 average rating, 109 reviews

Home in Yarmouth

Cheerful, renovated 2 bdrm-block to beach. Dog ok.

ARTIST and AUTHOR'S Cape Cottage! Dog Friendly-Freshly decorated Introductory Rates! Located .2 miles from the beaches in South Yarmouth. Be among the first to enjoy "My Two Cents" aka "Poppie's Place"- a quintessential, cheerfully remodeled home surrounded by hydrangeas, roses, and colorful perennials. Tucked off Seaview Avenue on a private lane you will enjoy easy access to several beaches, shops, Captain Parker's, Skipper’s and other great restaurants, Pirate's Cove mini golf, museums.

A bright and airy guest suite features a spacious bed with decorative pillows, set against light-colored walls. Sheer curtains allow soft natural light to fill the room. Wooden flooring complements the light decor, while a dresser and small cabinet provide additional storage space.

4.98 out of 5 average rating, 165 reviews

"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

4.98 out of 5 average rating, 320 reviews

A spacious living room features modern furnishings arranged for comfort. A large flat-screen TV is mounted above an electric fireplace. Natural light enters through multiple windows, and a playful dog portrait decorates the wall. A patterned rug anchors the seating area.

Home in Falmouth

The Driftwood Home, 5 min from Mashpee Commons, AC

- NOW PET FRIENDLY! - 15 min to Old Silver, South Cape, and Falmouth Heights beaches - 5 min to Mashpee Commons - 15 min to Falmouth Main St - 1600 square feet, built in 2014, w/ central AC - Large kitchen w/ all cookware and utensils - Outdoor deck with seating, fire pit, and grill - 55” Smart TV - 10 min to Shining Sea Bike Trail - Less than 10 min to Falmouth, Cape Cod, and Quashnet Valley Country Clubs - Centrally located to all of the Upper Cape - No parties or events!

A cozy sleeping area features a spacious bed with blue and white striped bedding. Natural light enters through two large windows, illuminating the light-colored walls and ceramic tile floor. A wooden bench at the foot of the bed complements a stylish lamp and decorative wall art.

4.94 out of 5 average rating, 242 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.

The charming beach cottage features blue shingle siding and a distinctive red door. Flower boxes beneath the windows are filled with colorful blooms. A brick chimney rises from the center, surrounded by well-maintained landscaping including small shrubs and flags.

4.99 out of 5 average rating, 108 reviews

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!”