Beachfront holiday rentals in South Shore

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Top-rated beachfront rentals in South Shore

Guests agree: these beachfront homes are highly rated for location, cleanliness and more.

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Guest favourite

A round black table is positioned between two comfortable chairs adorned with patterned upholstery. Atop the table, a decorative floral arrangement includes blue and white flowers, complemented by greenery. A couple of neatly stacked books are also visible.

Apartment in Oak Bluffs

Serenity on Martha's Vineyard

This 2BR, 2 Full Bath Condo with air condition (AC) and elevator access is located across the street from State Beach (AKA the "Ink Well") in Oak Bluffs. It's on the top floor, recently redecorated, with all the amenities for a wonderful vacation. Both bedrooms have Smart TVs & AC. Free Wi-Fi. Great location, within walking distance to the ferry, beach and downtown Oak Bluffs, restaurants and shops. Car not needed! Get ready to relax and unwind. It's the perfect location! Welcome to Serenity!

4.82 out of 5 average rating, 56 reviews

A covered balcony is seen from the exterior, featuring a small bistro dining set. Adjacent to the balcony, a path leads to the beach, with unobstructed views of the ocean. Lush greenery and white gravel enhance the outdoor setting.

Apartment in Oak Bluffs

Breezy Oak Bluffs Condo - Steps to Inkwell Beach!

Planning a family or couple's getaway to Martha's Vineyard? Then you'll love calling this delightful Oak Bluffs vacation rental your home-away-from-home. The quaint 2-bedroom, 2-bath condo offers beautiful beach views, cozy nautical decor, and a covered balcony perfect for socializing with a nice glass of wine. When it's time to explore the island, peruse the shops, restaurants, and lighthouses, or take a ride on the famous Flying Horses Carousel. A memorable Massachusetts vacation starts here!

4.88 out of 5 average rating, 24 reviews

Top guest favourite

A kitchen area features a bar with three wooden stools, inviting casual dining. Hanging pots and pans are showcased above the counter, while a vase of red roses adds a touch of color. A brick wall complements the white cabinetry and appliances.

Flat in Tisbury

Harbor view apartment, a quick walk from the ferry

This is a great one bedroom apartment on the second floor of a house. My place is close to the beach, public transport, the Steamship Authority ferry, Black Dog Tavern, Main Street Vineyard Haven, Stop & Shop grocery, and lots of great shopping. You’ll love the convenience! Walk to the apartment right off the ferry boat. Lots to do in walking distance, and onsite parking. The Martha's Vineyard Museum is a 5 minute walk, down the same street. My place is great for couples and solo adventurers.

4.93 out of 5 average rating, 150 reviews

Guest favourite

An aerial view captures the layout of Madaket village, showcasing houses and roads along the coastline. The expansive ocean stretches into the horizon, with gentle waves visible near the shore. Lush greenery adds a natural contrast to the sandy beach area.

Cottage in Nantucket

Exquisite Oceanside Madaket Getaway

Location-Location-Location! The best way to experience Madaket Beach, Smith's Point, and More! Beach access at your finger tips. Take in ocean views and sunsets. Enjoy the perfect blend of modern comforts/upgrades and preservation of details that evoke the history and spirit of this seafaring island. Beautiful original hardwood floors, tasteful touches of a bygone nautical era, and more pair with exquisite furnishings, elegant kitchen and living room appliances, hydrangea gardens, and more.

4.93 out of 5 average rating, 71 reviews

Top guest favourite

A serene view of the ocean is framed by white wooden architecture. The calm water reflects a clear blue sky, while a sandy beach lies in the foreground, accompanied by a stone jetty. Benches are positioned along the walkway, inviting relaxation.

Apartment in Oak Bluffs

FABULOUS OCEAN VIEWS-Oak Bluffs Condo Across Beach

Enjoy one of the most desirable locations on the Vineyard!! Enjoy AMAZING sunrises & gorgeous ocean views from this lovingly kept, super clean condo. Literally across the street from town beach, adjacent to Waban Park, a few blocks to Ocean Park, Flying Horses, Steamship Authority & downtown Circuit Avenue (restaurants, shops)! Bring a car (one unreserved parking spot) or walk over from the boat. Bike delivery & storage available. We hope to see you this summer in this fantastic summer condo!

5.0 out of 5 average rating, 34 reviews

Guest favourite

A beachfront cottage is framed by a vibrant landscape of flowering plants. The structure features a sloped roof and a welcoming porch with several blue chairs. Large windows provide views of the ocean, enhancing the connection with the natural surroundings.

Home in Nantucket

Swept Away - Madaket Beachfront

This beachfront cottage is the best way to experience all that Nantucket and Madaket have to offer! Just steps away from the Atlantic Ocean, with sweeping ocean views and sunsets from the second floor deck. Located on iconic Smith's Point, the cottage offers the perfect combination of modern comforts and the historic touches that make Nantucket so authentic. Beautiful original hardwood floors, tasteful furnishings, surrounding gardens, and more will make this a serene and memorable getaway.

4.94 out of 5 average rating, 17 reviews

Guest favourite

An aerial view captures a cozy cottage surrounded by lush greenery and a serene waterfront. The calm water reflects the clear blue sky, and the distant shoreline is lined with gentle waves. The natural landscape invites exploration and relaxation.

Home in Chappaquiddick

Waterfront Oasis

Located on Chappaquiddick a small, remote island with easy access to Edgartown. A short walk to the ocean & the entire OSV Trails. The cottage in not a luxury retreat, it's simple and full of old-fashioned charm. A cozy, no-frills getaway where the real amenities are right outside your door: Dike Bridge, Pocha Pond, East Beach and some of the most beautiful scenery around. Come for the views, private access to Pocha Pond inlet and the magic of the location- this is simply your home base.

4.88 out of 5 average rating, 16 reviews

Holiday home in Nantucket

Nantucket Beach House with Private Beach - 6 BR

6 Queen BR, 4 ½ BA beach house. Private beach. Light-filled, open floor plan. Large deck overlooking ocean, with 2 outdoor dining areas and sitting area. Primary BR on 2nd floor has office, private BA, and 2 private decks offering sweeping views. New furniture, stove, fridge, organic mattresses & bedding. Satellite TV and internet. Outdoor shower. Renovated 2025. Large lower level with high ceilings and lots of natural light from windows & glass double door. Beach steps shared w neighbor.

5.0 out of 5 average rating, 7 reviews

Top guest favourite

The cottage exterior is framed by lush greenery and stone landscaping, featuring a welcoming porch with rocking chairs. Colorful flower pots and pumpkins are placed around, while a serene view of the water is visible in the background.

Cottage in Oak Bluffs

The WestLake

This unique 3-level Vineyard style cottage perched on a 25' bluff offers you a panoramic view of the Lagoon's shimmering waters, and private beach access to the Nantucket Sound. From across the bay, you can see and faintly hear the Vineyard Haven Ferry departing. Simply follow the wooded path leading to over 110 feet of your own sandy beach with clean, calm waters which allows for safe kayaking and canoeing yet has the perfect breezes for windsurfing and sailing from your own mooring.

5.0 out of 5 average rating, 12 reviews

Top guest favourite

A cozy living area features a lightweight sofa adorned with colorful cushions, complemented by a pink upholstered chair. Large windows reveal ocean views, allowing natural light to fill the space. A small table holds fruit and a book, creating a welcoming setting.

Cottage in Chappaquiddick

Beachfront Cottage + Studio w. Town Access

Welcome to The Rudder Cottage! Fully renovated 1930's cottage on an ocean front compound, with a picturesque porch overlooking the outer harbor, full basement with washer/dryer and central air. An additional detached studio provides a third bedroom/work space. Stunning views of the Edgartown lighthouse and Cape Poge. Access to 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!

5.0 out of 5 average rating, 35 reviews

Guest favourite

A two-story beach house is shown, featuring a wooden porch and a large grassy area in front. The exterior is clad in siding, with a simple color palette. Soft outdoor lighting illuminates the surroundings, enhancing the welcoming feel at dusk.

Home in Falmouth

Walk to 3 Beaches from 6br+ w/huge outdoor shower

Location, location, location! Enjoy the ocean breeze from our 6+ BR/2 BA home that sleeps 14. Surrounded by water on 3 sides, this quintessential beach house is perfect for your get-away. Walk-able in less then 3-5 minutes to 3 different Falmouth beaches. We have a huge outdoor shower, 2 patios and gas grill to make outdoor enjoyment easy. Our 6+ BR sleeps 14 comfortably in beds- 1 King, 2 Queens, 1 Full and 6 twins. This is a BYO sheets, towels and toiletries property.

4.95 out of 5 average rating, 22 reviews

Guest favourite

The exterior of the house is surrounded by lush greenery, featuring a spacious yard with a picnic table and a stone wall. A guest cottage is visible, alongside a deck with outdoor seating and an umbrella. Tall trees provide shade on a sunny day.

Home in Oak Bluffs

First-class 4+ BR Lagoon Pond Camp

Ultimate getaway house! Situated on Lagoon Pond in Oak Bluffs. Sleeps 10 plus 2 in the optional guest cottage. The house is under 2 miles from OB center - convenient for walking and bike riding. Beach access! The house boasts a pizza oven, outdoor nooks (hammocks!), and a spacious yard. There are amenities galore including, but not limited to: an outdoor shower, grill, board games, wifi, towels, linens, etc. 1 week min stay, Sunday turnovers in July & August.

4.94 out of 5 average rating, 67 reviews