Holiday rentals with a pool in Dukes County

Edgartown Designer Retreat With Pool & Hot Tub

Located in Katama, this 3,000-square-foot home has undergone a complete renovation, and offers privacy and easy access via bike path to downtown Edgartown and South Beach. Everything is brand new. There is a salt water heated pool & hot tub! Highlights include 8 inch wide white oak flooring, a custom marble vanity, ultra thick quartz countertops, custom lighting, high end art throughout, all new high end appliances and designer furniture, outdoor shower, gym, and 4 bedrooms / 3.5 bathrooms.

Island Inn - Two Bedroom Suite - 1A - Oak Bluffs,

Your stay in this charming first-floor corner two-bedroom, one-bath unit is made comfortable with all the essentials. The cozy living and dining area features a TV for relaxing downtime, while WiFi keeps you connected with loved ones and helps you plan your island adventures. The kitchenette is equipped with an apartment-sized fridge, stove, microwave, and coffeemaker, along with silverware, plates, cups, cookware, and utensils—everything you need to enjoy a convenient and stress-free stay.

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

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!

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!

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.

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.