Holiday rentals with a pool in Dukes County

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

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!

Deluxe Studio Steps From Surf Drive

Stay in our deluxe studio at Beachside Village in Falmouth, MA—ideal for couples or families of four. Each unit features a Queen bed, Queen sleeper sofa, air conditioning, and a kitchenette with a dining area. Enjoy views of Martha’s Vineyard, stroll through nearby village shops, and unwind on Surf Drive Beach just steps away. Your perfect Cape Cod retreat awaits with a touch of coastal history and comfort.

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.

Beautiful Edgartown Colonial with heated pool.

Stunning 5 bedroom, 10 room, 3500 square foot colonial in beautiful area. Gourmet kitchen, dining room, living room, den, family room with ping pong. Huge deck, private yard with fire pit and outdoor shower. 30 x 16 x 4 heated in ground pool. Central air. Kayaks, bikes. Seven passenger Toyota Highlander available to rent May- October.

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