Vacation rentals with a pool in Dukes County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Dukes County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

A large outdoor pool reflects clear blue water under the sun, surrounded by green trees and neatly trimmed hedges. Several white lounge chairs are visible nearby, offering a space for relaxation. The pool area is well-maintained, with a smooth deck and designated swimming lanes.

Home in West Tisbury

5 out of 5 average rating, 10 reviews

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.

Superhost

A cozy living and dining area features a light-colored sofa with decorative throw pillows, complemented by a wooden dining table surrounded by four chairs. A fireplace, framed art, and a warm-toned lamp enhance the space, while a patterned rug adds a touch of comfort.

Condo in Oak Bluffs

4.67 out of 5 average rating, 3 reviews

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.

Guest favorite

A clear blue swimming pool is surrounded by lounge chairs positioned for relaxation. Lush greenery provides a natural backdrop, while a shaded area offers protection from the sun. Steps lead from the pool to a nearby structure, adding convenience for guests.

Condo in Tisbury

4.92 out of 5 average rating, 49 reviews

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.

Guest favorite

A colonial saltbox style home is shown with light wood siding, complemented by multiple windows. A deck is visible on the side, leading to a swimming pool surrounded by lounge chairs. Lush greenery frames the property, enhancing the outdoor space.

Home in Edgartown

4.95 out of 5 average rating, 20 reviews

Quintessential Vineyard House, Brand new pool!

Just Renovated! This colonial saltbox style Martha's Vineyard home is perfect for a family of eight with its four bedrooms 3.5 bathrooms. Brand new pool. It is in a great family friendly neighborhood with access to tennis. Inside you will find a comfortable living area which is open to the dining area and the kitchen. The lower level is complete with ping pong and a flat screen TV. This property is only minutes to South Beach, State Beach, Morning Glory Farm and downtown Edgartown.

Top guest favorite

A well-maintained saltwater pool is surrounded by manicured lawns and natural landscaping. The pool area includes comfortable seating with lounge chairs and umbrellas positioned under clear skies. A spa area is integrated into the design, with stone pathways leading around the space.

Guesthouse in Falmouth

5 out of 5 average rating, 61 reviews

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

Superhost

A bright living room is showcased, featuring white sofas and a light wood coffee table. A decorative shelving unit lines the wall, filled with various items. Large windows allow natural light to fill the space, and soft curtains frame the view of the outdoors.

Condo in Edgartown

4.8 out of 5 average rating, 5 reviews

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!

A swimming pool is visible, with clear blue water reflecting sunlight. In the background, a person is seen jumping into the pool, showcasing a playful moment. A white lounge chair is positioned next to the pool, surrounded by lush greenery.

Home in West Tisbury

5 out of 5 average rating, 3 reviews

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 !

Guest favorite

A clear blue swimming pool is framed by a lush green tree and surrounding foliage. Poolside lounge chairs are positioned around the edge, alongside an umbrella providing shade. The vibrant sky is dotted with fluffy white clouds, enhancing the serene outdoor setting.

Cottage in Edgartown

4.98 out of 5 average rating, 99 reviews

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!

Guest favorite

An inviting in-ground pool is situated within a meticulously maintained grassy area, surrounded by trees. The pool area features slate-like patio stones and is complemented by six lounge chairs organized neatly under a shaded umbrella.

Home in Edgartown

5 out of 5 average rating, 16 reviews

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.

Superhost

An aerial view captures the quaint charm of the Beachside Village Resort, showcasing its coastal architecture. The vibrant green lawn is bordered by neatly trimmed shrubs, and outdoor seating areas are visible. The ocean sparkles in the background, with the road leading to the beach nearby.

Condo in Falmouth

4.88 out of 5 average rating, 8 reviews

1BR w/ Fireplace & Beach Access | Pool + Hot Tub

Stay in a cozy 1-bedroom condo at Beachside Village Resort in Falmouth, MA. Enjoy a Queen bed, sleeper sofa, fireplace, and outdoor seating with ocean views. This charming retreat sleeps up to 4 guests and offers 2 full bathrooms, a kitchenette, air conditioning, and beach access. Perfect for couples or families seeking a relaxed Cape Cod experience near historic attractions and local seafood restaurants.

Superhost

A serene outdoor pool is surrounded by well-kept lawns and colorful flower beds. The pool area features numerous lounge chairs and umbrellas. In the background, Edgartown Harbor is visible, with boats moored and gentle waves reflecting the clear blue sky.

Apartment in Edgartown

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.

Top guest favorite

A spacious colonial house is framed by lush green grass and mature trees. The exterior features dark shingles with multiple windows reflecting natural light. A winding driveway leads to the entrance, while a wooden fence provides privacy at the rear.

Home in Edgartown

4.92 out of 5 average rating, 51 reviews

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.