Martha's Vineyard

Unfussy New England island retreat of presidents, painters, and generations of summer people.

6638 waterfront rentals·19 shores·Every listing on the water·Updated 2026-11-03

The Vineyard's 100 square miles cover six towns, each with its own character. Edgartown for captains' houses, Chilmark for cliffs, Oak Bluffs for gingerbread cottages, Aquinnah for red clay bluffs. Rentals concentrate in July-August; May and September are cheaper and quieter.

StateMA
Peak seasonJuly to August
Best forWaterfront stays
Featured15 rentals
The curated list · 15 rentals

Where we would stay in Martha's Vineyard.

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PRIVATE CHAPPY WATERFRONT-360o WATERVIEWS/SAILBOATS, KAYAKS, PADDLEBOARDS
No. 01

PRIVATE CHAPPY WATERFRONT-360o WATERVIEWS/SAILBOATS, KAYAKS, PADDLEBOARDS

Beachfront
6 bedroom sleeps 14

A rare beachfront property in the area - enjoy direct access to the beach and sea.

Luxury 3 Field Club Compound with Pool and Barn
No. 02

Luxury 3 Field Club Compound with Pool and Barn

Beachfront
5 bedroom sleeps 8

This Martha’s Vineyard compound features two master suites and three additional bedrooms, along with a luxurious pool and spa.

Classic Modern House on its Own Point of Land with Astounding Views
No. 03

Classic Modern House on its Own Point of Land with Astounding Views

Beachfront
5 bedroom sleeps 11

A rare beachfront property in the area - enjoy direct access to the beach and sea.

Modern Saltbox in Edgartown Village
No. 04

Modern Saltbox in Edgartown Village

Vacation Home
4 bedroom sleeps 8 Beachfront

Modern Saltbox in Edgartown Village offers direct beachfront access and a sun terrace.

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725 Acre Chilmark Estate Hot Tub, WFH & Parking
No. 05

725 Acre Chilmark Estate Hot Tub, WFH & Parking

Holiday home
4 bedroom sleeps 8 Beachfront private pool

725 Acre Chilmark Estate offers beachfront access and a swimming pool with stunning views.

Oceanfront Home - Walk to Everything
No. 06

Oceanfront Home - Walk to Everything

Beachfront
4 bedroom sleeps 9

A rare beachfront property with endless water views, fully updated and steps from a sandy beach excellent for swimming.

Beachfront Aquinnah home. Beautiful views!
No. 07

Beachfront Aquinnah home. Beautiful views!

Beachfront
4 bedroom sleeps 8

Beachfront home on Lobsterville Beach in Aquinnah, featuring spacious bedrooms, ocean views from every room, and a private deeded beach dune path.

Classic Chappy Beach House, big water views, near the water
No. 08

Classic Chappy Beach House, big water views, near the water

Beachfront
4 bedroom sleeps 8

A rare beachfront property in the area - enjoy direct access to the beach and sea.

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15
curated rentals in Martha's Vineyard
Steps to Beach: Martha's Vineyard Private Retreat!
No. 09

Steps to Beach: Martha's Vineyard Private Retreat!

Vacation Home
3 bedroom sleeps 6 Private beach access

Steps to Beach: Martha's Vineyard Private Retreat! in Vineyard Haven offers a spacious holiday home with three bedrooms and two bathrooms.

Fabulous Waterfront 3-Bedroom Martha's Vineyard Cottage
No. 10

Fabulous Waterfront 3-Bedroom Martha's Vineyard Cottage

Beachfront
3 bedroom sleeps 6

This quintessential Vineyard cottage was built in the 1920's, and retains most of its original charm and character. Located in the desirable East Chop neighborhood, this little cottage is known for its appearance in the Jaws movie.

House in Chilmark/Menemsha, Martha's Vineyard w/ Private Beach, Sunset View
No. 11

House in Chilmark/Menemsha, Martha's Vineyard w/ Private Beach, Sunset View

On beach
3 bedroom sleeps 6

Discover paradise at this top rated beach location with rare beachfront access.

Stunning Location, Oceanfront Home Chilmark
No. 12

Stunning Location, Oceanfront Home Chilmark

On beach
3 bedroom sleeps 8

A rare beachfront property in the area - enjoy direct access to the beach and sea.

On the water
Rent a boat on Sailo

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Vintage 1920s House W/Beach Path & Glorious Sunset Water Views
No. 13

Vintage 1920s House W/Beach Path & Glorious Sunset Water Views

Beachfront
3 bedroom sleeps 8

This quintessential Up-Island 1920s summer house has panoramic water sunsets thanks to its hillside position overlooking the Vineyard Sound.

Breezy Oak Bluffs Condo - Steps to Inkwell Beach!
No. 14

Breezy Oak Bluffs Condo - Steps to Inkwell Beach!

Apartment
2 bedroom sleeps 4 Beachfront

Beachfront location with direct access to Inkwell Beach.

Bonita Springs vacation rentals
No. 15

Bonita Springs vacation rentals

Beach

Welcome to Bonita Springs, where sun-soaked beaches and lush parks create an idyllic escape for families and friends alike.

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