Vacation 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!

Cozy Home w/Pool by South Beach

Beautiful and cozy home with in-ground pool is located in the Katama area of Edgartown, close to South Beach. Home features a lovely living room, spacious first floor family room, an office area, large eat-in kitchen, finished basement with TV, playroom, and sleeping area. First floor master suite. Two spacious bedrooms with a shared bath on the second floor. Take a spiral staircase to a large sleeping loft. Multiple outdoor decks overlook the pool. Very large yard w/fire pit for outdoor fun.

Oak Bluffs Renovated Retreat

Fully renovated for 2025, this 3-bed, 2.5-bath townhome invites you to unwind with a community pool, tennis courts, and direct access to Sengekontacket Pond. Inside, a custom chef’s kitchen, new baths, and luxury furnishings set an upscale coastal tone. The main level flows from a sun-lit living room to dining area / deck, and powder room. The entire second floor is reserved for the primary suite. The walk-out lower level offers two guest bedrooms, a full bath, laundry, and a private patio.

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

Brand New 2BR Condo w/ Pool. No Pets!

This beautifully renovated condo is in the heart of Edgartown. 5 min walk to downtown shops, restaurants, and waterfront. This unit has 2-bedrooms & 1.5-baths. The master has a king bed and half bath, and the second bedroom features a queen bed and full bath. Enjoy a spacious living room with high ceilings, a full kitchen, and access to outdoor spaces with a pool. Sleeps 4, this condo is the perfect base for your Martha's Vineyard adventure!

Ocean Front Resort Studio Unit

Studio unit in ocean front time-share resort with beach access and pool. Studio is ideal for two people, but will sleep up to four people with a pull down, double murphy bed & full size sleep sofa (note, that the primary bed is the full size, pull-down murphy bed, see pictures ). Kitchen area with bar seating and equipped with kitchen basics. Resort location is fabulous overlooking Nantucket sound in Falmouth Heights near the harbor.

Modern & Spacious Edgartown Home with Pool

Enjoy your vacation in this wonderfully charming three bedroom home with an in-ground heated pool. Head to the beach or stay at home and go for a swim in your own backyard. There is plenty of dining room & deck space to entertain. The bike path and bus shuttle are at the end of the road (a two minute walk away). Downtown Edgartown is less than two miles away for you to enjoy shopping and multiple dining choices.