Holiday rentals with a pool in Dukes County

West Tisbury Gem with Deck + Association Pool

Spacious, secluded yet close to everything, this light-filled gem began renting in summer '23. Each bedroom has its own bath so you get maximum privacy. Gorgeous landscaping, steps from trails to State Forest, 9 mins to one of MV's most stunning beaches, Lambert's Cove. 5-10 mins to the VH ferry, grocery, airport. Fully stocked chef's kitchen + basement for kids to play ping pong while you sun on the deck after an outdoor shower. *** Please inquire about monthly discounts in the off season.

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!

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

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 5 bikes to choose from to use (no waiting in rental lines!)

WestTisbury Charm, Carroll House

Oasis Nestled in woods near bike paths! Enjoy Fall 2026 Sept -Oct open! A 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.

This private beach cottage offers comfort and style. Oversized 2nd floor bedroom with queen bed (Designer quilts) full bath and shower (in and out) Nicely furnished over 900 sf and And immaculately kept. Nice grill And sitting area in back. And please Use the built in pool! It sits equi-distant 1.5 miles to downtown Edgartown and south beach. And convenient 5 min walk to bike path or bus route. Perfect location!

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.

Spacious 2BR by the Sea in Falmouth

This inviting 2-bedroom condo at Beachside Village Resort offers comfort and charm with Queen beds, twin beds, a sleeper sofa, and a fully equipped kitchenette. Ideal for up to 6 guests, enjoy ocean views, air conditioning, and access to the resort's pool and BBQ area. Just steps from Surf Drive Beach and close to Cape Cod's top attractions, it's perfect for a relaxing family or group escape.

Edgartown Harbor King Suite

Martha’s Vineyard has plenty of family-friendly activities, a fantastic array of dining options and much more. Situated on Edgartown Harbor among flowering English gardens, this property is ideally located on Martha's Vineyard. Guests will enjoy watching the boats come and go as they listen to the peaceful sounds of the ocean while sitting harbor side.

Waterside Guest House

Clean, oceanfront, cozy guesthouse located steps from ocean and beach. Sleeps 2-4. Panoramic views of Martha's Vineyard & Vineyard Sound. Tennis Court, Wifi, Cable, & your own private heated outdoor whirlpool are available year round; swimming pool seasonal. Pricing is wide ranging - from $99/night in winter to $499/night in mid-summer.

Relax....You're on Island Time......

Its a short walk from the ferry...Please be our guest on the Vineyard! There is a very comfortable Vineyard cottage feel to our two b harbour-view condo. Our sunny unit is just steps to the lovely pool. The property grounds are spacious and beautiful