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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Top guest favorite

Home in Oak Bluffs

4.94 out of 5 average rating, 194 reviews

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!

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

4.91 out of 5 average rating, 47 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 sandy beach stretches along the shore, bordered by smooth stones leading into the calm water. The expansive sky is filled with soft clouds, creating a serene atmosphere. Old pilings can be seen further out in the water, enhancing the coastal view.

Apartment in Falmouth

4.91 out of 5 average rating, 22 reviews

Studio- Beachside Village, Falmouth MA - Cozy!

Explore beautiful Cape Cod from the Beachside Village Resort. Once a cozy seaside mansion for a well-to-do boat captain, the property was converted into the charming resort it is today with extraordinary views of Martha’s Vineyard across Falmouth Harbor. Spend your days on the soft sand beach watching the rolling waves, wandering through the surrounding seaside village shops, or treat yourself to the freshest seafood and other New England favorites offered throughout the area.

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, 52 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 light and airy studio unit featuring a spacious bed against a wall, with a full-sized leather sleep sofa positioned opposite. A dining table with four chairs and a kitchenette area with essential appliances are visible. A flat screen TV is placed on a white console.

Condo in Falmouth

5 out of 5 average rating, 4 reviews

InnSeason Resorts HarborWalk Studio

Walk out the door, cross the street and catch the Island Queen ferry to Martha's Vineyard. This resort is directly across from Falmouth Harbor, at the center of it all. Just minutes from the beach, you also have easy access to fishing and boating, and it's only a short walk to shopping, dining and more on bustling Main Street. When it's time to take a break, take your beach bag to the on-site tanning deck and enjoy the lovely harbor views.

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, 97 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!

Superhost

An outdoor seating area features a round table surrounded by several cushioned chairs on a blue area rug. Green decorative pillows add a pop of color, while trees provide a natural backdrop in a peaceful setting. The railings enhance the open, inviting space.

Home in Falmouth

4.92 out of 5 average rating, 13 reviews

Jaws House - Great Harbors

Your family will be close to everything when you stay at this centrally-located place. This fully renovated ranch is close to beaches and Great Bay. Downtown shopping is a 10 minute drive away. If you like to golf there are 5 golf courses within 20 minutes of the home. Great community neighborhood with a clubhouse, pool, and tennis courts.

Guest favorite

A private yard features a heated in-ground pool surrounded by manicured green grass. Lounge chairs are positioned near the poolside, while flowering shrubs add color to the landscape. A basketball hoop stands nearby, providing a recreational option for guests.

Home in Edgartown

4.91 out of 5 average rating, 47 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.