Holiday rentals with a pool in Dukes County

Chic Oak Bluffs Home with Hot Tub, Walk to Town

A chic coastal escape where upscale comfort meets effortless Vineyard charm. Nestled in the heart of Oak Bluffs and just a 15-minute stroll to Circuit Avenue and the beach, this 3-bedroom, 2-bath home is designed with elegance and ease in mind. Enjoy a serene coastal palette, brand new furnishings, a spacious deck for outdoor dining, and generous yards perfect for barbecues, games, and slow summer mornings. This cozy retreat is ideal for families or couples. It's a modern twist on island living!

Beach house in Great Harbors, association pool

Discover the perfect Cape Cod getaway in sought-after Great Harbors community. This charming, sun-filled A-frame welcomes you with a bright atmosphere & relaxed coastal vibe that makes summer on the Cape so special. Spend your days exploring nearby beaches, kayaking on Great Pond, biking through the neighborhood, or enjoying all that Falmouth has to offer. Guests have the option to access the Great Harbors Clubhouse, featuring swimming pools, tennis courts, & additional recreational amenities!

Spectacular beach & pool combo; beautiful sunsets!

Close to airport, you’ll love backyard beach, water view, pool/grass yard, ambiance and outdoors space. Beach & Pool (POOL HEAT STARTS SUMMER, ENDS 9/1) is a hard to find combination!! Location is private, yet it's close to the 3 largest towns on Martha's Vineyard. Great for couples, families (with kids), and big groups. Enjoy dinner with the indoor/outdoor Sonos music system during a beautiful sunset! NOTE; Rate increase in high season, pool/spa is a combined unit & ONLY heated in summer!

Seaside Luxury Home

Your ultimate Dream Home! Sip cocktails on the new deck while watching boats pass by on Nantucket Sound, take a dip in the in-ground pool surrounded by lush gardens and make family memories playing foosball by the bar or in the game room equipped with air hockey, a ping pong table & basketball shoot-out! Perfect for large family gatherings. The home is within a short stroll to the New Seabury Golf Course, Country Club, Beach Club & the Popponesset Marketplace. Opt. pool heat additional fee

WestTisbury Charm, Carroll House

Car Ferry ticket 8/28 or 9/4 weeks! Late summer and Sept are best times on MV- this oasis nestled in the woods has close bike path, nearby association pool, tennis, lamberts cove beach pass avail., conservation trails . Chickens with fresh eggs right outside. Wonderful outdoor patio, shower and sunset soaking tub! Central Martha's Vineyard location offers easy access to mid and up island delights avoiding traffic. Peaceful wooded property, with comfortable beds and tv room to unwind !

Lovely two - story private cottage. Katama quiet!

Private beach cottage offers comfort and style. Oversized 2nd floor bedroom with queen bed. Lovely layout w/full bath, w/d and showers (in and out). Nicely furnished and over 900 sf. Quilts and beauty rest bed a hi-lite! Nice grilling area in back. It sits equi-distant - 1.5 miles to downtown Edgartown and south beach. And a convenient 5 min walk to bike path or bus route. Perfect location! We’re open to welcoming May and June 2 Renters - special discount for the month Of May/June.

Heart of VH, w/ac, pool & harborview

Enjoy your stay on Martha’s Vineyard in Causeway Harborview condos with this 2 bedroom/1 bathroom unit. - Views of the harbor from the unit - Pool & Laundry on-site - Parking on-site - Walk to ferry, restaurants, shops and beach - Bike to Oak Bluffs - All linens provided - Fully equipped kitchen with coffee and tea provided - Beach gear provided My goal is to provide guests with a 5-star experience, if there is anything that can improve your experience that isn’t listed, just ask!

Private 3bdrm Condo Tashmoo Woods

This 3 bedroom (3 king) 2 1/2 baths newly renovated condo is in a private setting with screened in porch. New kitchen, gas grill on deck, outdoor shower. -Access to the Tashmoo Woods Association pool, tennis courts and play ground. -Close to West Chop beaches. -Two miles from downtown Vineyard Haven. On bus route, but best to have a car. -The primary bedroom (king bed) is downstairs and the 2 upstairs bedrooms share a bath (shower only). Minimum rental 5 days, 1 week in summer.

Falmouth/Woods Hole Charming Cottage By the Sea

Welcome to our Cottage By The Sea Rental located only minutes from the quaint village of Woods Hole, Falmouth and the Martha's Vineyard Ferry. We are located in the perfect setting to relax and enjoy all the area has to offer. Come enjoy The Shining Sea Bike path which is 10.7 miles , Sandy beaches, lively restaurants & local music scene, shopping on historic Main Street, Farmers Markets & more. Your sure to fall in Love with " Ole Cape Cod " when you visit our home and area

Cozy downtown apartment

Well appointed one bedroom condo in the heart of downtown Edgartown. Walk to restaurants, shopping, the beach and the lighthouse! Top floor, corner unit overlooks the saltwater pool. Living room is flooded with southwest sun. AC units in both living room and bedroom. Sleeping: - Bedroom: queen bed and a fold out single bed - Living room: fold out couch (queen) Condo amenities include: - salt water pool - picnic tables and grills (first come first serve) - playground

Sunny condo with pool, central to beach & town

We all want maximum time enjoying with minimal time waiting in lines and traffic, right? Your family will be close to everything and fully equipped when you stay at this centrally-located oasis. Just three miles from both State and South Beach, and away from triangle traffic. Property access to a large, heated salt water pool to lounge with ease. A few minutes from the bike path, with a few bikes to choose from to use (no waiting in rental lines!)

Cool, Mid Century House -- Lucy Vincent Beach!

Flooded with Light! Gracious, Simple but Elegant. All on one floor. This Elegant Mid Century house offers 4 bedrooms; 3 baths, full AC, a roomy outdoor shower and more. Lounge by the 4' deep spa pool. Enjoy world-class Lucy Vincent Beach located just one mile away (beach pass required). The quaint fishing village of Menemsha and the wonders of Chilmark all at your disposal. Elegant and special; you will love your time here.