Holiday rentals with a pool in Dukes County

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.

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

Home with pool, close to Long Point Beach

Lovely and spacious pool home in a centrally located neighborhood. Biking distance and access to Long Point Beach. 5 bedroom, 3.5 bath beautiful home situated on 2 acres that back up to private conservation land. Huge backyard with a fully enclosed pool, outdoor shower, fire pit and dining area ideal for the perfect Vineyard summer vacation. The home is perfect for large groups and families with a fully finished basement, dining rooms that seats 10, and an open kitchen.

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 - please Use the built in pool! 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 and the 4.5 bike path surrounds! Perfect location!

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!

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 3500 sq ft home, 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

Beautiful Family Friendly House with Pool

Indian Hill Cape with Pool and Privacy Hidden away down a quiet road in gorgeous West Tisbury, our house is located on a lovely historic dead end road that leads to the Cedar Tree Neck Sanctuary- often voted the best place to hike on the island.