Flanders Up-Island Real Estate
Escape to the island of Martha's Vineyard for an unforgettable vacation. Over 85 years in business, our extensive inventory of rental listings continues to grow. Specializing in Aquinnah, Chilmark and West Tisbury, our inventory ranges from pond side camps to high end waterfront properties. Enjoy the seclusion of Lucy Vincent, Squibnocket, Philbin's, Lobsterville, Lambert's Cove and Long Point beaches. Partake in the charms of the Vineyard by visiting up-island Farmer's Markets, Flea markets, or enjoying activities such as birdwatching, beachcombing, kayaking,
or surfing to name a few. Additionally, our listings include high end rentals in Edgartown,
Vineyard Haven and Oak Bluffs. Let us help you find your perfect island getaway.
Listed below is only a limited portion of our full inventory.
Click on the Advanced rental search tab above to search our listings.
We are available to answer questions and assist you in finding the property that meets your needs.

		Enjoy views over Chilmark Pond and the Atlantic and th eocean only steps from your door at this Abel's Hill Home. Link to Property

		On the Brink of Vineyard Sound. Lovely summer home and guest cottage. Link to Property

		Amazing Stonewall home with fabulous views. All possible amenities surrounded by tasteful living. Link to Property

		Quitsa Pond frontage. Home filled with character, great for entertaining and the views are endless...not to mention Dock Space and Private beach access! Link to Property

		Amazingly situated 4 bedroom modern Aquinnah Home. Perched on a hill with far reaching waterviews, pond access, inground pool and more. Link to Property

		Quansoo Home, newly built and beautifully furnished. A main house and Guest House situated next to the Great Pond. Link to Property

		Located on Stonewall Pond. Excellent views, comfortable home all within walking distance to Stonewall beach. Link to Property

		Vintage Chilmark home in pristine condition...Pond views...walk to Squibby Link to Property

		This large home, Guest house and Bunk House overlook stunning views of the Atlantic shore from Highmark Hill in Chilmark. Link to Property

		A family retreat in Prospect Hill, perfect for the tech savvy nature lover. Work from home surrounded by hiking trails and beaches. Link to Property

		Charming Chilmark home situated off a quiet Lane off of Middle Road. Views toward South Shore. Link to Property

		Large Home just off of Moshup Trail. Complete with private south shore beach access only steps from your front door. Link to Property
		Private, contemporary and in immaculate condition. A beautiful home with breathtaking views. Link to property.
		Views from Menemsha Pond to the Elizabeth islands. This quality constructed four bedroom home in Aquinnah sits atop a secluded hill. Link to Property

		Aquinnah Main and Guest House, wonderfully appointed and set in peaceful surroundings with views. Link to Property

		Unsurpassed views from this rambling five bedroom home located only a short distance from menemsha. Link To Property

		Striking four bedroom home. Nicely furnished, large open living room and well manicured grounds.. Link to Property

		Located down Stonewall Road, complete with access to the beach, this large 5 bedroom house has all the necessary amenities. Link to Property

		Wonderfully appointed South Abel's Hill Property. Expansive Atlantic Views, private beach access. Link to Property

		Ideally located off of Middle Road in Chilmark. Lovely 3 bedroom home with bunkhouse. Serene and private setting Link to Property

		Recently renovated quality four bedroom, three bathroom home located down a quiet Chilmark Lane. Distant North and South views. Link to Property

		Aquinnah cottage...2 Bedroom home situated only steps from Menemsha Pond Link to Property

		Chilmark Cottage, only a short distance to Menemsha and walk to conservation beach. Link to Property

		Stonewall pond at your yard's edge. Three spacious bedrooms and a home with every needed amenity. Link to Property

		Large rambling Chilmark Farmhouse nestled in a hill overlooking Squibnocket. Link to Property

		Open and sun filled with unmatched views over Squibnocket and Noman's Land. Link to Property

		With the Tiasquam river streaming through your backyard, this 3 bedroom is an ideal getaway. Link to Property

		A 4 bedroom contemporary gem situated at Quitsa Pond's edge. Complete with deep water dock. Link to Property

		Immaculate 4 bedroom home, overlooking chilmark meadows and south shore. Link to Property

		Situated on its own private peninsula, this Chilmark home offers astounding views and seclusion. Link to Property

		Remarkable Views from this 3 bedroom cottage, comes with dock access. Link to Property

		Custom Architectual home with 4 bedrooms, Open airy feel. Views of the Atlantic Ocean and walk to Private south shore beach. Link to Property