Last Updated August 13, 2021 8/13/2021

Top 12 Martha’s Vineyard Luxury Vacation Rentals

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Martha’s Vineyard has been a “secret” summer hideaway for the rich and famous for decades, so it’s no surprise that the island has many luxurious homes that serve as vacation rentals. If you’re looking for an amazing East Coast escape where you can enjoy a laid-back lifestyle, beautiful beaches and charming villages, along with plenty of high-end amenities, you’ll find all that and more. These properties come in all types and sizes, but they all have one thing in common: pure luxury.

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Luxurious 12-Bedroom Captain's Mansion Near Waterfront, Town, & Beaches
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Luxurious Captain's Mansion

Luxurious 12-Bedroom Captain's Mansion Near Waterfront, Town, & Beaches

The Captain Morse House is a 12-bedroom mansion that can accommodate up to 26 guests. Built in 1845 by whaling captain John Morse, it sits along the waterfront within walking distance of beaches and shopping. It includes two expansive porches framed by Doric columns where you can relax with a gorgeous view of the harbor. In the large back yard and garden you can enjoy peaceful solitude. There’s also a tool shed with complimentary bicycles, beach chairs, and lawn games for guest use. Ideal for entertaining, inside you’ll find two full kitchens, dining rooms, and living rooms along with plenty of upscale features and all the essentials.

Luxury Home with Pool and Foosball
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Luxury Home with Pool and Foosball

Luxury Home with Pool and Foosball

There aren’t many rentals with private pools in Martha’s Vineyard, but this luxurious home comes with one that’s heated from Memorial Day through the end of October. It also has an outdoor shower, garden and large terrace ideal for evening cocktails. Located on the northern edge of Manuel F. Correllus State Forest, you’ll be just a short drive from downtown Vineyard Haven, Oak Bluffs, Edgartown, and multiple beaches. It sleeps up to 10 in five bedrooms and also includes a foosball table, full kitchen, and satellite TV with a Blu-ray player.

Home with Pool Close to Edgartown
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Home with Pool Close to Edgartown

Home with Pool Close to Edgartown

This large Dutch Colonial home offers five bedrooms for up to 10 guests and is just a short walk to historic downtown Edgartown while beaches like South Beach are a quick drive away. It sits at the end of a private road, providing a more secluded feel and plenty of privacy along with an outdoor heated pool, available from June through September. There are outdoor decks and open covered porches for gatherings and meals, a grill and a gourmet kitchen that’s sure to please any cook, and seven cable TVs. Other features include beach chairs, an outdoor shower, and gorgeous grounds.

Chic Waterfront Home with Kayaks and A/C
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Chic Waterfront with kayaks and ac

Chic Waterfront Home with Kayaks and A/C

This enchanting waterfront home offers the ideal space for a fun escape with family or friends. It accommodates 11 guests in four bedrooms, all of which come with picturesque water views and their own private bathroom. Just some of the activities that can be enjoyed right out your door include swimming, boating, and clamming. You’ll have an outdoor grill for cooking up meals that can be enjoyed on a large blue stone patio with a teak dining set as well as a covered porch ideal for sipping your morning coffee, watching colorful sunsets and bird watching.

Architect's Stunning Home
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Architect's Stunning Home

Architect's Stunning Home

This spectacular four-bedroom home is not only an architectural gem with a suspended walkway that connects the three upstairs bedrooms, but it sits on five wooded acres close to Tisbury Great Pond, ensuring a tranquil escape away from the chaos of summer crowds. Your host has thoughtfully included many complimentary extras like an umbrella and beach chairs, boogie boards and towels. Enjoy gorgeous views of the treetops, particularly from the master bedroom that sits in the “the octagon” and includes a skylight and balcony. Other notable features include a full kitchen, grand piano, and fireplace.


Edgartown Beauty -- In Town and Close To Beaches
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Edgartown Beauty

Edgartown Beauty -- In Town and Close To Beaches

This four-bedroom saltbox-style home will put you just a short walk from the restaurants and shops on Main Street Edgartown or a pleasant two-mile bike ride from South Beach with bike rentals available in town. It includes a large three-season screened porch that opens to a patio and beautiful landscaping,  You’ll have a well-stocked kitchen, washer/dryer, Wi-Fi, and all the essentials too.

In-Town Luxury with Water Views
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In Town Luxury

In-Town Luxury with Water Views

The Captain Spring House offers sweeping views of Vineyard Haven Harbor and four levels of stylish living space. It’s just a short walk from the ferry, beach, and town, which means there’s no need for a car. There are many luxurious features too, like two rooftop decks, a tournament pool room, a fully-equipped wet bar, and home theater. It includes four bedrooms, accommodating up to eight, all of which have full marble baths with a tub and shower, and flat screen TVs. The Master Suite on the second floor even has a whirlpool tub for soaking with a harbor view.

Beautiful Martha's Vineyard Getaway on the Beach
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Martha's Vineyard Getaway on the Beach

Beautiful Martha's Vineyard Getaway on the Beach

This property includes two houses, the main house that sleeps up to 12 and a separate private cottage accommodating two. It’s ideal for a large group getaway, set on a lagoon pond complete with your own private beach. You’ll be just a 10-minute drive from the center of Oak Bluffs while enjoying all the comforts of home like a spacious kitchen, washer/dryer, a/c, and cable TV. You’ll want to spend plenty of time on the spacious deck, relaxing with water and sunset views.

Waterfront Beach House
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Waterfront Beach House

Waterfront Beach House

This waterfront home sits on the lagoon in Vineyard Haven within walking distance to town. It comes with your own private beach area and dock along with complimentary kayaks to paddle around. Rentals like paddle boards, skiffs, and boats can be delivered right to the waterfront. It sleeps up to 12 in six bedrooms and includes multiple decks, a large bluestone patio area on the waterfront with a grill, fire pit, and outdoor dining area. There’s also a chef’s kitchen, an additional large family room with a media area and 65” TV, and much more.

Mid-Century Modern All Glass House
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Mid-Century Modern All Glass House

Mid-Century Modern All Glass House

Designed by a Frank Lloyd Wright apprentice, you know this one is going to be special. It’s an all-glass, mid-century home — meaning there are floor-to-ceiling windows in every room. Located just minutes from Lucy Vincent Beach or the town of Menemsha, it includes a wrap-around deck that runs around the entire exterior, another around the interior open-air courtyard area, along with a large outdoor shower and stone sink. There are distance water views of the vineyard sound and Elizabeth Island too, plus all the usual desirable amenities.

Vineyard Haven Beach House
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Vineyard Haven Beach House

Vineyard Haven Beach House

This two-bedroom beach house sleeps six and boasts fabulous views from every room. It includes Wi-Fi, cable TV, and Apple TV for streaming, along with a full kitchen and living room stocked with games you can play while enjoying a water view. Outside you can relax on the decks while gazing out at the water or take advantage of walk-out access to a patio with stairs leading down to the private beach. You’ll be able to swim in the lagoon, have kayaks dropped off from a rental company to paddle around, or just kick back on the lounge chairs.

Historic Lambert's Cove
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Historic Lambert's Cove

Historic Lambert's Cove

This stunning, historic vacation home was once the island’s oldest Methodist Church, built in 1846. Today guests can enjoy the ambiance of the Romantic Era and an elegant contemporary design on a three-quarter acre property. It accommodates six and includes two residential buildings. The two-bedroom Parsonage has French doors that open from the living and dining areas onto the furnished granite patio with a fire pit and grill. The Church is a master suite with a king-sized bed, kitchenette, and full bath with soaking tub and shower. Many of the historic features have been preserved like the wide plank wood floors, pressed tin ceiling, and the bell in the tower that can still be rung.

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