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Your connection to all Martha's Vineyard Real Estate and Vacation Rentals
508-693-7832
Karen M. Overtoom Logo
508-693-7832


Martha's Vineyard Vacation Rental Properties







Waterview Farms, Prime Bike Trails, Martha's Vineyard!

"Oak Bluffs Rental, Fabulous Waterview Farms Contemporary, Association Beach And Dock."

Located in Waterview Farms, this four bedroom home features a private beach on Sengekontacket Pond, private dock access to Land Bank boat launch and several beautiful trails. The association water front beach is about 1/3 of a mile from the house as the the bird flies. You can also drive your car do... Read the full description.


Cozy Cottage Nestled on Edgartown Great Pond

"Waterfront Cottage on Martha's Vineyard"

This charming one bedroom cottage on the pond is the perfect get-away. Thoughtful decor fills every inch of this lovely home away from home. Features include a spacious and sun-splashed living room with fabulous views across the pond and a cozy but fully equipped kitchen. There is also an brand ne... Read the full description.


Beautiful Tashmoo Wood Condo!

"3 Bedroom Condo Rental With Association Tennis And Private Beach. Close To Down-Town Vineyard Haven."

This three bedroom two bath condo is a very short distance to association tennis, pool and the beach. Comfortable easy summer living with outdoor shower, spacious deck, and central AC for those really hot August days!


Private Makonikey Short Distance To Beach!

"Makonikey 4 Bedroom Home. Huge Yard, Minutes To Association Beach."

Fabulous custom designed and decorated four bedroom home is located in a wooded setting that offers total privacy and is with-in walking distance to a private association beach. And yet is only 3 miles from downtown Vineyard Haven. This lovely home offers a gourmet eat-in kitchen with top of the lin... Read the full description.


Martha's Vineyard Rental In Nat's Farm!

"Charming Country Home Close To Beaches, Bike Paths And West Tisbury Village."

Charming three bedroom home located in a private neighborhood close to bike path, trails and public tennis courts. Just a short drive to Lambert's Cove Beach, West Tisbury Village and down island restaurants and shops.


Aquinnah Waterview Rental

"Fabulous waterviews from this privately located, 3 bedroom contemporary."

Uniquely designed, 3-bedroom, 2 full bath contemporary home, divided between three floors and set upon an acre of lush grounds with waterviews overlooking Vineyard Sound and the Elizabeth Islands. Privacy enhanced with large tracts of conservation land nearby and walking distance to Lobsterville Bea... Read the full description.


Close To Town And Beach!

"Charming 3 Bedroom Home, One Mile To Lake Tashmoo, Close To Beaches and Downtown Vineyard Haven."

This charming 3 bedroom home offers open living, dining and kitchen space that open to a screened-in porch and patio. You are located in a peaceful setting yet a close distance to Lake Tashmoo, town beaches, and the Vineyard Haven Village for dining, shopping and theater.


KATAMA CONTEMPORARY!

"Close To South Beach In Katama, Lovely 4 Bedroom Edgartown Contemporary"

This updated contemporary is located in Katama area and a short bike ride to South Beach. There are 4 bedrooms, 1 down and 3 up, and a beautiful kitchen/dining which opens to a large living room. The house has a nice deck on the front and owners have added a deck off the kitchen as well.There is a ... Read the full description.


Beachy Katama Bay House!

"Vacation By South Beach! Smell the Salt Air!"

Vacation by the beach in a relaxed contemporary home offering fabulous panoramic views of Edgartown Harbor, Chappaquiddick, Katama Bay and South Beach. Our Katama Bay home is located off of Edgartown Bay Road at the quiet cul-de-sac,close to the beaches and boat launch access. For those who love the... Read the full description.


Oak Bluffs Waterfront With Boat Mooring!

"Fabulous Waterfront Home With Sandy Beach And Views Across The Lagoon."

Feel the ocean breezes from this classic waterfront home. There are four bedrooms, an open living room and dining room that open up to large deck overlooking beautiful views across the Lagoon. There is a path to private sandy beach. Landlord provides mattress pads, pillows, pillow protectors, dish t... Read the full description.


Spectacular Waterfront With Deep-Water Dock!

"Brand New Oak Bluffs Rental, Luxury, Waterfront With Deep Water Dock, Mooring, And Private Beach."

This home offers a spacious open floor plan providing a comfortable yet elegant retreat, truly an upscale surprise, perfect for relaxing or entertaining. With an expansive mahogany wraparound deck, sweeping views and a screened-in porch, enjoying the evening sunsets while grilling and dining al fre... Read the full description.


Chilmark Waterview Rental With Beach & Tennis!

"Beautiful Spring Point Contemporary Home With Panoramic View Of The Vineyard Sound!"

Gracefully situated atop the hills of Spring Point in Chilmark, the 4-BR (sleeps 8-10) home features panoramic water views sweeping from Gay Head Light to the Elisabeth Islands and east. This 4.750 sf family sanctuary was designed to balance inside and outside family gathering spots with private sp... Read the full description.


In-Town Edgartown Home!

"Close To Restaurants, Theater, And Edgartown Village Shopping."

This four bedroom Victorian home is located close to the Edgartown Village for shopping, theater or restaurants. Close to Fuller Street Beach. All new appliances have been added recently as well as a number of room AC units throughout the house.


West Tisbury Village Charming Farmhouse and Converted Barn

"Restored West Tisbury Farm House. Antique Furnishings, Open Floor Plan, Large Deck."

Mill Pond House is a completely restored 1840s farmhouse originally adjacent to the famous Mill Pond in historic West Tisbury on the island of Martha’s Vineyard. It was remodeled by the present owner, an interior designer. It is beautifully appointed with antiques, charming accessories, and comforta... Read the full description.


Chilmark Waterview With Beach And Tennis!

"Fabulous Spring Point Home With Breathtaking Waterviews, Private Association Beach & Tennis!"

Fabulous Chilmark home offers two levels of living space. On the first floor there is a fully equipped kitchen open to the dining room, a living room with fireplace, built-ins and sliders to a deck overlooking a meadow and the most incredible water views. There is a half bath, a master suite with pr... Read the full description.


Seven Gates Farm Rental With Waterviews!

"Rustic Home In Seven Gates Farm With Waterviews, Trails, And Private Beach Association."

This charming rustic home is set within Seven Gates Farm in West Tisbury. Enjoy the beautiful private association beach a very short distance away. There are shared tennis courts and miles of trails.


Katama, Easy Bike To Beach & Town!

"This 3 Bedroom, Newly Decorated Home Is Close To South Beach."

Lovely Edgartown Bay Road area. This 3 bedroom newly decorated home is very close to South Beach. Easy access to town. Large grassy yard for the kids to play on.


Panoramic Chilmark Waterviews With Private Association Beach!

"Unbeatable South Shore Views, Pond Access, Zack's Cliffs Beach Pass, Lucy Vincent And Squibnocket!"

Sweeping views of Squibnocket Pond, Dunes, the South Shore, Nomans Land, to sunsets over Aquinnah. A great family getaway with access to Chilmark's famed Lucy Vincent and Squibnocket Beaches as well as a private association beach in Aquinnah. Roomy and inviting, this house offers 5 five bedrooms all... Read the full description.


Chilmark House and Guest House With Atlantic Ocean Views!

"Gracious Vineyard Home with Sweeping Views of Keith Farm land and Atlantic Ocean."

This gracious Vineyard elongated Cape overlooks the Keith Farm and the Atlantic Ocean beyond. The gourmet kitchen has just been beautifully renovated and is a dream. The living areas are all decorated with charm and all have views. The separate main house, with four bedrooms, and guest house, with t... Read the full description.


Mink Meadows, Association Beach, In-Ground Pool!

"Mink Meadows Golf, In-Ground Pool, Beautiful Trails. Close To Down-Town Vineyard Haven."

Located in Mink Meadows Association, this wonderful four bedroom, three full and one half bath home has many nice features that include a large eat-in kitchen/family room, a more formal living room with fireplace, dining room and den. Televisions in every bedroom, living room and den. Laundry room... Read the full description.


Mink Meadows Cottage!

"Two Bedroom Cottage Just Minutes To Vineyard Haven Town"

This two bedroom cottage is set in a private setting in the woods, just a short distance to downtown Vineyard Haven. Sleeps four comfortably, open living space, deck and outside shower. If rented with the main house, access to private association beach and golf would be included.


Mink Meadows House & Guest House!

"Fabulous Rental, Heated In-Ground Pool, Private Association Beach, Nearby Vineyard Haven And Golf!"

Located in Mink Meadows Association, this wonderful four bedroom, three full and one half bath home has many nice features that include a large eat-in kitchen/family room, a more formal living room with fireplace, dining room and den. Televisions in every bedroom, living room and den. Laundry room i... Read the full description.


Oyster Pond Beauty!

"Elegant Edgartown Home In Oyster Pond with Heated Pool And Guest Suite."

Newly renovated architect designed home with every amenity. Cook's gourmet kitchen, open plan living/dining room, second living room, office for work and lots of outdoor patio and deck space. Set in a private 7 acre property with wildflower meadow. Relax around the beautiful in ground pool surround... Read the full description.


West Chop Beauty With Hancock Beach Key!

"Located A Short Distance To Down-Town Vineyard Haven."

This beautifully furnished West Chop home is elegant, sophisticated and pristine with wonderful artwork throughout. A fabulous well-equipped kitchen with custom cabinetry opens in to the dining area. The living room is perfect for relaxing. Both bedrooms are spacious, each with their own sitting are... Read the full description.


Farm House in Menemsha with North Shore Views!

"Sweeping Views from this Menemsha Farm House!"

Style, warmth, and comfort define this delightful farm house in Menemsha with a water view to the Vineyard Sound. The property is spacious and private. Features include a newly constructed private pool. The house comes with a key to a beach in Aquinnah on Moshup trail and a shared key to Quansoo ... Read the full description.


Private Menemsha Rental Close To Harbor, Town And Beach!

"Great Location, Mile to Menemsha Beach And Watch The Sunset!"

Located on Flanders Lane, this house sits up the hill and looks toward Menemsha. There is a window a/c unit in the upstairs bedroom and another one in a downstairs bedroom. Two of the bedrooms on the lower level have ensuite half bathrooms. The large primary bedroom on the second floor has an ensui... Read the full description.


Steps to South Beach!

"The Perfect Katama Family Vacation Rental. Located near Bike Path To Downtown Edgartown"

A stunning great room with cathedral ceiling is the heart of this sun-drenched “upside-down” house in Katama near South Beach. A well-stocked kitchen with stainless appliances and island, large dining table, comfy living area with TV and a handy half-bath are surrounded by panoramic windows and glas... Read the full description.


Waterfront Beach Cottage!

"Waterfront Rental With Views Of Vineyard Sound And Elizabeth Islands. Private Sandy Beach!"

Idyllic location right above a sandy private beach on the North Shore. This beach cottage affords views of the Sound and the Elizabeth Islands with a front row seat to unrivaled sunsets. Newly built with a large screened porch overlooking the view. Enjoy an unforgetable getaway with the beach at you... Read the full description.


Waterfront West Tisbury!

"Secluded Home Perched Above Private Beach With Spectacular Waterviews."

Prime beachfront residence perched on a bluff with an unsurpassed panoramic view of Vineyard Sound and the Elizabeth Islands. Spacious 2 bedroom main house and 2 bedroom guest house. Both are single story. Interiors newly renovated with new appliances and ceiling fans. Beautifully furnished and appo... Read the full description.


West Tisbury In-Town With Pool

"Lovely In-Town West Tisbury 3 Bedroom Home With Pool And Access To Lambert's Cove Beach!"

Let the stress roll off your shoulders. You have now arrived at your summer home-away-from home. This vintage 1830's farmhouse is the quintessential Martha's Vineyard experience. A peaceful, pastoral setting, across the road from a sheep meadow in the historic district of beautiful West Tisbury, a ... Read the full description.


Contemporary Waterfront in Squibnocket!

"Features Waterfront Panoramic Views, Well Equipped Kitchen, 5 Ensuite Bedrooms, & 6 Person Jacuzzi!"

Newly constructed home has open concept living area with 270 degree water views, abundant natural sunlight, central AC, high end appliances, hardwood floors, rooftop deck with seating to view gorgeous island sunsets, access to several private beaches,and high speed internet wifi.


Makonikey with Private Association Beach Nearby

"Beautifully Appointed 4 Bedroom, 2 & Half Bath Home with Central Air!"

This beautiful home has lots of open space for cooking, yard activities or just plain relaxing. Private association beach overlooking the Elizabethan Islands. Plan a sunset picnic on the beach or stroll down in the morning to see the rays of sun break on the water. Enjoy the large open concept livi... Read the full description.


Edgartown Harbor Waterfront

"Immaculate Luxury Waterfront Home With Space & Views Abound!"

This gorgeous waterfront home is well equipped with gourmet kitchen, stone fireplace, numerous sitting areas, and multiple decks each with water views over the Edgartown Harbor. Both the main and upper level have beautiful master suites and also washers & dryers. Easy access to downtown Edgartown, S... Read the full description.


Classic Vineyard House Close To Long Point Beach

"Sun Splashed Yard In A Quiet Neighborhood Only Minutes Away From The Beach & Bike Path!"

Well appointed Farmhouse Colonial, on two private acres on private road. Conveniently located in Vineyard Meadow Farms abutting the entrance to Long Point Beach, considered by many to be the best beach on the Island. Home was built for families in mind, with three bedrooms upstairs, primary bedroom ... Read the full description.


Idyllic Chilmark Home with Spa Pool!!

"Beautiful Chilmark Home"

At the quieter end of the Island, this one-level, 4 bedroom, sun-splashed home holds court atop a hill in Chilmark. Near Menemsha, the charming fishing village that will steal your heart, this gem is one mile from world-class Lucy Vincent Beach and surrounded by a network of wooded hiking trails. En... Read the full description.


Lovely Home with nearby Dock

"Fully Equipped Home Away From Home"

This cute cape is privately set with direct water access to Town Pond and a water view through some bushes and reeds along the edge. You can dock your canoes and kyacks here and access to Tisbury Great Pond and approximately a 2 mile boat ride to South Beach. There are four good sized bedrooms and a... Read the full description.


Wonderful Oak Bluffs Condo With Pool

"Stunning 3 Bedroom condo with pool"

Welcome to "Shangrila" A beautiful townhouse condominium end unit with magnificent views. Located midway between Oak Bluffs and Edgartown. You can enjoy the beautiful pool or one of the close local beaches. You will want to sit and enjoy the water views on the deck. The townhouse has a great livin... Read the full description.


Idyllic Vineyard Escape

"Spacious Country Farmhouse & Barn"

Set on 12 acres of peaceful woods, meadows, stone walls and its own pond, this charming 18th century 4 bedroom farmhouse and 3 bedroom rustic barn sleeps 12 and is perfect for larger groups wanting peace and tranquility all within a short distance to private swimming beaches. The setting offers mile... Read the full description.


Luxurious Water View Town Home

"Exquisite Home Very Close to Downtown Vineyard Haven!"

With sweeping views of Vineyard Haven Harbor, this recently built, in-town luxury home, combines water views with four levels of sophisticated and stylish living space, including two roof top decks, Home Theater, tournament Pool Room, Penthouse Lounge, and more. The main floor of Captain Spring Hous... Read the full description.


Bright Open Edgartown Home

"Lovely Open Concept Property Close to Town!"

This is an inviting and affordable home with air-conditioning. As you see from the pictures the sun is welcomed through many sliders and windows. Inside the furnishings are simple but well chosen. There is a splitter in the living area that cools the downstairs. The kitchen is fully equipped. The l... Read the full description.


Gracious Oak Bluffs Home

"Elegant with Private Beach and Guest House"

Newly updated gracious house and guest house with a total of five bedrooms and a brand new screen porch. Private beach access and tennis / pickle ball courts. This home has a reverse design that has been fully renovated and thoughtfully decorated. There is a large deck overlooking gardens and a pee... Read the full description.


Luxury Home with Private Heated Pool!

"Gorgeous Newly Updated 6 Bedroom Craftsman Home."

Beautiful bright sunny home with open concept living. Main floor features a gourmet kitchen with stainless appliances, breakfast bar and formal dining table to seat 10. Large glass sliders open up to expansive views of the deck, pool and pasture beyond. Also on the main level is a separate living... Read the full description.


Elegant Home with Heated Saltwater Pool !!

"Stunning Katama home close to South Beach Possible Ferry tickets available!!!"

Enjoy the pool with this Stunning custom designed and professionally decorated Tri Level contemporary home with open floor plan. Once inside you will be captivated by the dramatic open spaces, soaring ceiling and walls of glass. Located in a high end neighborhood only a mile to South Beach. The yard... Read the full description.


Water Front on Tisbury Great Pond!

"Gorgeous Water Views On The Great Pond"

This lovely new build house on the Tisbury Great Pond features 3 bedrooms, and 3 bathrooms. There is a full gourmet kitchen open to the dining, living and patio areas. French doors off the living area open up to a beautiful blue stone patio complete with breath taking water views. All three bedroom... Read the full description.


Sophisticated Chilmark Charmer

" Across From Great Rock Bight Beach!"

A modern summer retreat is nestled high on a knoll off North Rd in picturesque Chilmark. Here in this stunning contemporary ranch you will find the utmost in luxury. Each room is exciting, charming and stylish. Each room also has a portable air conditioner that does an excellent job of cooling the ... Read the full description.


Pristine Oak Bluffs Home

"Great location in Oak Bluffs with central air conditioning!"

For 2018, an expansion has been completed to create a new architecturally designed living space with complete central air conditioning system throughout the home. The dining room has seating for 6 with plenty of room for more. The new living room, has picture windows throughout, allowing views of th... Read the full description.


Storybook Cottage in Chilmark

"Adorable one bedroom cottage that is beautifully decorated!!!"

Chilmark Cottage Perfection!!! You will love this quaint Vineyard Style Cottage that has been meticulously designed to include all the amenities one could imagine. This vintage charmer really boasts a lot of Style. Inside you will find really beautiful hardwood floors, a fully equipped kitchen, an... Read the full description.


Victorian Cottage Overlooking Nantucket Sound

"Victorian Cottage in the Heart of Oak Bluffs"

Victorian Cottage located on Ocean Park in the heart of Oak Bluffs with fully equipped and updated kitchen, five bedrooms and three baths, cozy living spaces and multiple amenities will accommodate your family and friends. Smell the sea air and watch the waves break from your front porch. This char... Read the full description.


Elegant Refinished Barn & Bunkhouse in West Tisbury

"Peaceful retreat for family and friends in the center of West Tisbury."

This stunning sanctuary offers a unique balance of simplicity and sophistication. There is a lot of room for family and friends to enjoy both indoors and out. Main house has a dreamy bedroom with a queen bed plus and ensuite bath and the separate bunkhouse has three additional bedrooms. There is ... Read the full description.


Waterfront with Dock and AC Overlooking Katama Bay

"Fantastic Waterfront Property with Private Beach!!"

Private Beach, Waterfront, Mooring and Dock!! Spend your days looking at beautiful Katama Bay. Dock your boat or relax at your private beach. This large Classic Vineyard Home sleeps 10, has two living rooms, protected porch area and a really great front yard leading to the beach. The location is c... Read the full description.


Luxurious Home In Katama

"Prime Location Between Downtown Edgartown and South Beach!"

Gorgeous 4 bedroom 4 bath home with a separate guest suite above the detached garage. Top of the line finishes and appliances. Gourmet kitchen, screened in porch with fireplace and TV. Pool with swim up bar, hot tub and grilling area. This is a cream of the crop Katama house just a short distance ... Read the full description.


Perfect Summer Retreat!

"Beautiful Meadow & Peak of Water View From Middle Road!"

Water views, 3 acres and stone walls. At the end of a lane, enjoy the privacy offered by 49 acres of conservation land complete with walking trails. This house is a short distance from Lucy Vincent beach, as well as from Menemsha and Squibnocket. This spacious four bedroom, 2 bath home has an expans... Read the full description.


Lovely Private Home on Harlock's Pond

"Chilmark Estate with Private Beach and Water View"

Relax and enjoy this majestic estate you will call home during your stay. This slice of paradise in the coveted Seven Gates Association gives you access to two miles of private beach just half a mile away, with tennis courts also nearby and 1000 acres of conservation land. The house is exquisitely... Read the full description.


Picturesque Water View Home

"Gorgeous Atlantic Views!"

Windy Knoll is a 3BR, 2Bath home located in Aquinnah on a secluded lot off State Road with 160 degree views of the Atlantic Ocean. Approximately 1 mile to Philbin Beach similar distance to Moshup Beach and Lobsterville beach. Take the bike ferry over to Menemsha and enjoy sunset on the beach. Outdoo... Read the full description.


Gorgeous Remodeled High End Chilmark Home

"Bright, Crisp Home In The Heart Of Chilmark!"

Just a short distance from the iconic Chilmark Store, this newly remodeled home features three bedrooms and 2.5 baths, blending high-end finishes with a relaxed, beachy island aesthetic. The thoughtful layout begins on the first floor with a spacious primary suite featuring an en-suite bath for ulti... Read the full description.


Central Location for Your Vacation

"Nicely Furnished Two Bedroom in Peaceful Neighborhood"

This bright contemporary home is in the perfect central location to downtown of Vineyard Haven, Oak Bluffs and Edgartown. Explore and enjoy the vibrant and colorful life of towns, nature trails, beaches and peace of indoors. Two bedroom raised ranch with plenty of deck space at the end of a woode... Read the full description.


Wonderful open spacious home in Chilmark

"Open, bright home with Beautiful Gardens"

Set high on a hill in picturesque Chilmark is this absolutely wonderful 3 bedroom home with a finished walk out that has a sofa bed. Each bedroom has a window A/C unit. The grounds are beautiful. Wonderful screen porch for your morning coffee or sit in the back yard and enjoy the view. Short driv... Read the full description.


Makonikey 14 Acre Waterfront Home

"Private Beach & Hot tub Overlooking the Sound"

Waterfront home in spectacular location overlooking the Vineyard Sound and the Elizabeth Islands. This casual and comfortable single level 4 BR 3 bath home has central air and heat. Set on 14 private landscaped acres. View gorgeous evening sunsets on your secluded private 325 foot beach. Enjoy summe... Read the full description.


Turtle Pond Farm

"Lovely pastoral setting. Elegant farmhouse & guest house."

Lovely pastoral setting with an elegant farm house and guest house. Abutting Land Bank property on two sides. Quiet privacy, yet just minutes to Lambert’s Cove Beach. The four bedroom house and separate guest house are impeccably decorated and the floor plan lends itself to congregating with the fam... Read the full description.


Katama House and Guest House

"Adorable Katama House and Guest House"

Perfectly located close to South Beach and Edgartown is this absolutely wonderful 3 bedroom home with a separate guest quarters that has two queen size beds, kitchenette and bath. The main house has a formal dining room right off of the kitchen, a bright sunny porch, cathedral ceiling in the livin... Read the full description.


Beautiful Oak Bluffs Home on Lagoon

"Waterfront with Private Heated Pool"

This is a beautiful waterfront home with a pool on the Lagoon. Enter through the impressive foyer with waterviews over the pool and lawn. There is a large living room with cathedral ceilings and dining area on the main level. There is a gourmet kitchen with eat-in dining overlooking the pool. The fi... Read the full description.


Lovely Home, Near Bike Paths & with Lambert's Cove Beach Access!

"Contemporary Home with Air Conditioning, Sleeps 8!"

Inside the front entrance is a large open living room with a comfortable L-shaped couch facing the floor to ceiling windows which look out onto the spacious tree lined back yard and a wall mounted flat screen television. Off the open concept living/dining room is a large Primary bedroom and private... Read the full description.


Beautiful Cottage Close to Town

"Renovated and Spacious East Chop Home Close to Everything"

Wonderful, fully redecorated Gingerbread house on East Chop, just minutes from the excitement of Oak Bluffs. There are three bedrooms and two full baths. The interior is clean and crisp, with beach cottage décor and beautiful bamboo floors. Entertainment options include high-speed wifi, Sonos, cable... Read the full description.


Spectacular Water Views!!

"Beautiful Views High on a Hill"

Some of the finest Views on the Island!! This house is set high on a hill surrounded by nature. The expansive views, inside and outside, from this house are spectacular. Enjoy the large deck or the screened porch and gaze upon one of the most amazing Vineyard views available. It is a short dista... Read the full description.


Beautiful Spacious Home with Heated Pool and AC!

"Backyard Oasis with large enclosed pool area!"

Are you looking for the perfect back yard Oasis? Well here it is!! Surrounding a large pool you will be able to relax on the expansive deck with lots of areas to relax, a hard piped gas firepit and an outdoor shower with HOT water! Inside is an amazing kitchen with every amenity you could want. Co... Read the full description.


Panoramic Views Of Vineyard Sound

"Dramatic Sunsets and Sandy White Beaches!"

Set on the highest island point at Upper Makonikey Head in West Tisbury, this property has commanding panoramic views . “ STUNNING”, is the most frequent description of perhaps the best views on the North Shore and possibly the whole island. At 110 feet above sea level, these breathtaking we... Read the full description.


Luxurious Rental in Historic Edgartown Village

"Close to Lighthouse and Fuller Street Beaches as well as downtown Edgartown."

Newly renovated historical home in the heart of Edgartown Village, close to Fuller Street & Lighthouse Beaches. Beautifully designed interior with open gourmet kitchen and pickled hardwood floors, marble countertops, top of the line appliances and a large center island. Cozy family room with firepla... Read the full description.


Exceptional Menemsha Views

"Classic Vineyard charm and stellar sunsets."

This spacious two bedroom home is filled with classic Vineyard charm. Each room features spectacular views overlooking Vineyard Sound, as well as stellar sunsets in the evening. Close to Menemsha Village and public beach as well as access to Lucy Vincent and Squibnocket beaches.


Longview Retreat

"Large New Home Near Lambert's Cove Beach!"

Nestled in the Longview neighborhood of West Tisbury lies this brand new beautiful three bedroom home all en suite with an additional detached bedroom suite. Enjoy the quaint atmosphere of island life with all the modern amenities. High speed mesh internet throughout the house and detached suite al... Read the full description.


Lamberts Cove Estate with Pool, Tennis Court & Dock!

"Extraordinary Vineyard Haven estate with pool, tennis and access to Lake Tashmoo"

This Historic property has been meticulously and tastefully restored to preserve the historic character and grandeur yet offers all of today's modern amenities. This gracious home is in pristine condition and features 6 bedrooms, 5 full baths, 3 half baths, several sitting rooms, a more formal livin... Read the full description.


Custom Built Carriage House

"Centrally located custom built Carriage House in West Tisbury"

Custom built Carriage House in West Tisbury with one bedroom and a spacious loft. This newly built home features beautiful wood work throughout. Enjoy entertaining on the private second story deck or the grassy yard. This sun filled property has up island feel yet is centrally located, just 3 miles ... Read the full description.


Charming Aquinnah Cottage

"Classic Vineyard cottage with access to Philbin and Lobsterville Beaches"

Charming three bedroom cottage set on a hill overlooking a tranquil meadow just 1 & 1/2 miles to Aquinnah Cliffs. Enjoy access to town beaches. Philbin and Moshup Trail Beach passes bought separately. There is a front and back porch with rocking chairs to take in the landscape and enjoy the breeze... Read the full description.


Waterfront Lake Tashmoo

"Waterfront Lake Tashmoo rental with private dock and beach."

Enjoy privacy and comfort in this quintessential Vineyard property on Lake Tashmoo. This peaceful property boasts a private dock and sandy beach on the property for kayaking, swimming and relaxing. The recently renovated open floor plan features wood floors and cathedral ceilings in the living room,... Read the full description.


Breathtaking Waterfront Property

"Mesmerizing Views of Menemsha Pond and Ocean"

Breathtaking water views from this contemporary home located on Menemsha Pond and recently renovated with new kitchen and baths. This four bedroom retreat offers the perfect place to come during the summer months or even enjoy during the shoulder season while sitting by the fire with a warm cup of y... Read the full description.


Waterfront Estate on Vineyard Sound

"Spectacular Views"

Classic vineyard cottage with large open indoor and outdoor spaces to choose from while you and your family create memories to last a lifetime. Enjoy creating appetizers or three course meals in the newly renovated kitchen, bask in the light filled sun room or one of several covered porches while y... Read the full description.


Chilmark Estate with Waterviews

"Association Tennis and Beach"

Expansive home in North Abels Hill association with water views, private association beach and tennis. Centrally air conditioned, this family home has been well appointed with a large living room featuring fireplaces at both ends, a formal dining room, a first floor primary bedroom with en suite as... Read the full description.


Lovely Edgartown Condo

"Association Pool Just Steps Away!"

Enjoy this well appointed and immaculately clean two bedroom condo located just steps from the association pool and a short drive to South Beach with its gorgeous white sands. An open living room, kitchen and dining room with walk-out access to the deck and back yard offer plenty of gathering space... Read the full description.


Downtown Oak Bluffs!

"Quintessential Cottage Charm Close to Circuit Ave and Inkwell Beach!"

Newly renovated, Great for Family Gatherings, Corporate Retreats, Central Air & Heat, very close to Circuit Ave and Beach, 5 Bedrooms, 3 full baths, galley kitchen, new appliances, dining room, family room, Flat Screen TV, FREE Wifi, washer & dryer, bay window breakfast nook, Oak and Pine wood floor... Read the full description.


Elegant Home Perfect for Fall Wedding Season

"Swimming Pond and Hot Tub!"

This beautifully updated contemporary home is set amidst impeccably landscaped lawns and gardens. The outdoor living space is a true sanctuary, featuring a private swimming pond, a hot tub, and two outdoor showers—one fully enclosed for privacy and a second open-air shower conveniently located by t... Read the full description.


Great Edgartown Rental!

"Near Bike Path and Downtown"

Thoughtful additions and renovations, including central air have transformed the living spaces of this charming bow-roof cape style home. Conveniently located less than 1.5 miles from Morning Glory Farm via the MV bike path and close to South Beach and downtown Edgartown, this is the perfect vacatio... Read the full description.


Main Street Charmer

"Easy Access to Town & Beaches"

This newly renovated 4 bedroom 3 bath home is close to beach, restaurants, shops, and ferry. First floor primary with full bath, dining room and efficiant kitchen the Second floor features 2 nice size bedrooms that share a bath. There is a separate guest suite with kitchen, full bath and living spac... Read the full description.


Wonderful Chilmark Retreat

"Centrally Located off Middle Road"

Come experience the rest and relaxation of slowing down in this adorable well appointed and air conditioned family home in the heart of Chilmark surrounded by rolling fields and beautiful stone walls. Tucked back off Middle Road, this four bedroom two bath rental comes with linens and towels, high ... Read the full description.


Close to West Tisbury Village

"Access to Great Pond"

This well appointed home offers many attractive qualities including proximity to the West Tisbury village and less than a mile to an association dock on the Tisbury Great Pond. The main part of the home has two A/C mini splits which cool the entire area including an updated living area with a large... Read the full description.


West Tisbury Waterfront House & Guest House

"Comes with Quansoo Beach Key!"

This serene family compound with gorgeous landscaping on the Tisbury Great Pond is the perfect place to relax and enjoy your vacation. Expansive water views from the large living room in the main house, plus a fully equipped kitchen and primary bedroom with a queen bed, full ensuite bath and outdoor... Read the full description.


Impeccable Chilmark Home

"Beautiful Outdoor Spaces"

This remarkable single story home features a large living and dining room with post and beam cathedral ceilings. Floor to ceiling glass doors open onto the outdoor deck overlooking the gorgeous rolling meadows and trees. At the center of the home is the beautiful kitchen with ample work space for ... Read the full description.


Outstanding Chilmark Guest House

"Cozy and Modern Interior"

Sun splashed Chilmark guest house with post and beam cathedral ceilings throughout. Large living and dining room with glass doors onto the outdoor deck overlooking the peaceful pastoral surroundings. Efficient and sleek kitchen fully equipped for all your culinary needs. One bedroom has a set of ... Read the full description.


Classic Vineyard Home

"Exquisite Vacation Experience!"

This bright Vineyard colonial has been thoughtfully updated and stylishly designed to preserve many of it's original features. Located on Mill Pond just around the corner from the center of town, tenants here will enjoy proximity to Alley's General Store, the West Tisbury Farmers Market, as well as... Read the full description.


Picturesque West Chop House & Guest House

"Perfect Place for Vacation!"

Stunning house and guest house perfect for your family vacation on Martha's Vineyard! Enter the front door into the expansive light filled open concept living area with seating around a nice coffee table and stone fireplace, gorgeous fully equipped gourmet kitchen with high end appliances and a rou... Read the full description.


Beautiful New Guest House!

"Gorgeous Katama Rental!"

This thoughtfully crafted one bedroom guest house is the perfect place to enjoy a fun and relaxing vacation, close proximity to the town of Edgartown where you will find diverse shopping and dining experiences from take out to fine dining, art galleries, waterfront strolls, a short ferry ride to exp... Read the full description.


Classic Martha's Vineyard Retreat

"Privately Sited Close to West Tisbury Village"

This island retreat is located close to the West Tisbury Village, Alley's General Store, the Yoga Barn and lambert's Cove Beach just over 2 miles away. the everyday world. This Classic Cape is true Vineyard, very charming with a rustic flare. The cozy living room opens to a spacious deck overlookin... Read the full description.


East Chop Waterfront

"The Boat House"

Located on majestic East Chop and only a mile and a half from both Vineyard Haven and Oak Bluffs, this rustic ocean front cottage offers a unique Martha's Vineyard experience. Whether you relax on the the private beach and watch mesmerizing sunsets, visit the East Chop Lighthouse, or head only a ... Read the full description.


The Sea Owl House

"Sophistication Near the Sea"

Newly built custom post and beam home with bright open concept living, dining and kitchen. Bright and light filled home with high ceilings, wood floors, and soothing neutral tones make this the perfect place to gather with family and friends for a fun and relaxing vacation. Enjoy a peak of the wate... Read the full description.


Contemporary Beachfront Retreat

"Waterfront on Menemsha Pond!"

Overlooking Menemsha Pond with breathtaking water views from every room of the classic contemporary home with whole house air conditioning, this enchanting Chilmark property sits perched on a rise with a short path down to the beach that is shared with one neighbor. Central to this incredible prope... Read the full description.


West Tisbury Village with Lambert's Cove Beach Access!

"Martha's Vineyard Vacation House & Guest House!"

Centrally located in West Tisbury Village, this property has a spacious main house and cozy guest house. Enjoy fun filled quality time with loved ones in the sun-splashed living and dining room on the lower level with easy access to the outdoors via sliding glass doors that open to an expansive deck... Read the full description.


Gorgeous Edgartown Cape

"Close to Town and Beach!"

Beautifully updated three bedroom oasis with thoughtful touches and handsome landscaping giving vacationers an enjoyable indoor and outdoor living and dining experience. This property will truly become a home away from home that you'll be eager to return to year after year.


Close to Town and Beaches!

"Beautiful Modern Home Away from Home"

Enjoy this sleek and stylish three bedroom home with it's proximity to the Steamship, center of town and beaches. Tisbury Town Beach is under a quarter of a mile away! High ceilings and modern amenities offer guests a taste of luxury with comfortable living and dining both indoors and out. Large d... Read the full description.


Aquinnah Cottage Retreat

"Perfect Aquinnah Retreat Close to Philibin Beach"

Peaceful and private, recently updated cottage nestled on over 2 acres of land in Aquinnah. The house is bright and airy with all the amenities you need to feel at home on the Vineyard. The space Sleeping arrangements include a queen bed in the large second floor bedroom, and a comfortable full si... Read the full description.


Luxury Home with Beautiful Pool!

"Close to Town and Beach!"

With a lush green front lawn and a private saltwater pool, this beautifully appointed five-bedroom home offers ample space for friends and family. The interior has been fully renovated in a sophisticated coastal scheme. Enjoy multiple living areas for downtime, central air conditioning, and an invit... Read the full description.


Chic & Sophisticated Colonial

"Elegant and Spacious"

Perched upon a gentle rise in an enviable location, this spectacular four-bedroom Colonial is the coastal retreat you've been waiting for. With public tennis courts, a boat launch, and pristine local beaches just up the road, effortless recreation awaits right outside your door. Downtown Vineyard H... Read the full description.


Edgartown Estate with Private Guest House

"Katama Family Vacation"

Welcome to your quintessential Martha's Vineyard escape, perfectly situated just one mile from the vibrant heart of Edgartown. This beautifully landscaped and meticulously maintained property—featuring a generous main house and a fully updated private guest house—is designed for large gatherings and... Read the full description.


Year-round rental, close to downtown, in ground pool

"Fully renovated 3 bedroom year round rental with in ground pool"

Located off of Edgartown-Vineyard Haven Road, close to down-town and bike path, this 3 bedroom, 2 bath property is being offered year round to the right tenants. The home has been completely renovated, is being offered fully furnished and features an in-ground pool in the backyard. Available Septemb... Read the full description.


West Tisbury Vacation Oasis

"Idyllic Island Setting!"

This modern barn-style residence stands as a peaceful Vineyard retreat, defined by thoughtful design and a profound sense of place. The architecture reflects the local ethos—where the land meets the sea—inviting you to experience the island’s authentic character. Perfectly situated to embrace the... Read the full description.