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

Home in Oak Bluffs

4.94 out of 5 average rating, 191 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

Home in Edgartown

5 out of 5 average rating, 16 reviews

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.

Guest favorite

Cottage in Edgartown

5 out of 5 average rating, 14 reviews

2br Cottage Steps to Beach w/pool

Welcome to Lighthouse Cottage the best location on island! This amazing XL deluxe cottage in the Harbor View Resort has it all with 2 King bdrms/2 master baths with outside shower all on the first floor! Walk to Lighthouse and Fuller beaches to take a swim in the ocean and play in the sand! Downtown Edgartown and lighthouse are just steps away with quaint shops and restaurants. Come jump in the pool, have a drink at the bar and dine at the restaurants on site. Come enjoy Vineyard lifestyle!

Superhost

Home in Edgartown

4.78 out of 5 average rating, 111 reviews

Katama gem.

Select Dog friendly, - mile from downtown, mile from south beach, steps to bike path, fenced in yard.. Gorgeous pool, w/a seperate pool house with flatscreen, mini fridge, and fold out queen. Downstairs the "cave", there is bar, pool/ping pong, flatscreen, pull out queen. Basic gym w/flatcreen.. Four bedrooms- one with private deck, and an upstairs office, five using very private pool house . The pool is sublime, hot tub is new, large yard, upstairs bathrooms with heated floors,

Guest favorite

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

Rental unit in Falmouth

4.9 out of 5 average rating, 20 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

Guesthouse in Falmouth

5 out of 5 average rating, 51 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

Guest favorite

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

Condo in Falmouth

5 out of 5 average rating, 8 reviews

Beachside Villiage-Oceanfront

Located across from the popular Surf Drive Beach, Beachside Village Resort is built in true Cape Cod style all rooms being outfitted in comfortable East Coast furnishings. The beach is just a few short steps away. At Beachside Village you get the homey comfort of an East Coast Bed and Breakfast with the amenities and privacy of a resort.

Guest favorite

Home in Edgartown

4.91 out of 5 average rating, 46 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.

Superhost

Home in Falmouth

4.93 out of 5 average rating, 15 reviews

Gorgeous Cape Cod Property!

This gorgeous rambling Cape has been beautifully maintained and upgraded inside and out! Fabulous location with wonderful pool views from almost every room and just 200 yds to private sandy beach. We can also be found on the we need a vacation site - this is quintessential Cape Cod at it’s best!