Holiday 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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Superhost

Home in Mashpee

4.84 out of 5 average rating, 19 reviews

Seaside Luxury Home

Your ultimate Dream Home! Sip cocktails on the new deck while watching boats pass by on Nantucket Sound, take a dip in the in-ground pool surrounded by lush gardens and make family memories playing foosball by the bar or in the game room equipped with air hockey, a ping pong table and basketball shoot-out! Perfect for large family gatherings. The home is within a short stroll to the New Seabury Golf Course, Country Club, Beach Club and the Popponesset Marketplace. Opt. pool heat additional fee

Guest favourite

Home in Oak Bluffs

4.93 out of 5 average rating, 181 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 favourite

Apartment in Tisbury

4.91 out of 5 average rating, 46 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 favourite

Rental unit in Falmouth

4.88 out of 5 average rating, 8 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 favourite

Home in Edgartown

5 out of 5 average rating, 12 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, outdoor shower, and high end designer furniture throughout.

Guest favourite

Guest house in Falmouth

5 out of 5 average rating, 49 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 favourite

Home in Chilmark

4.95 out of 5 average rating, 37 reviews

Cool, Mid Century House -- Lucy Vincent Beach!

Gracious, one-level living, flooded with Sunlight! This Elegant Mid Century beach house offers 4 bedrooms; 3 baths, full AC, a roomy outdoor shower and more. Lounge by the 4' deep spa pool. Enjoy world-class Lucy Vincent Beach located just one mile away (beach pass required). The quaint fishing village of Menemsha and the wonders of Chilmark all at your disposal. Elegant and special; you will have lovely memories of your time here.

Superhost

Apartment 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 favourite

Home in Edgartown

4.91 out of 5 average rating, 45 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.

Cabin in Falmouth

4.64 out of 5 average rating, 513 reviews

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.

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!