Vacation rentals with a pool in Dukes County

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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 West Tisbury

5 out of 5 average rating, 8 reviews

West Tisbury Gem with 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.

Guest favorite

Home in Oak Bluffs

4.94 out of 5 average rating, 190 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.

Vacation home in Mashpee

5 out of 5 average rating, 4 reviews

Capecation! 3-bedroom condo with heated pool

It's the perfect time for a Capecation! Our spacious 3-bedroom condo is perfect for a multigenerational family vacation or a girls weekend away. This rental comes with your own private heated pool(thru September), two mountain bikes and a paddleboard for your use. We provide sheets, towels, beach chairs & a gift basket. We are located about a mile from South Cape Beach and Popponesset Marketplace. It's about a 10 minutes to all the shops, restaurants and movie theatre at Mashpee Commons.

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

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

Superhost

Condo in Falmouth

5 out of 5 average rating, 4 reviews

InnSeason Resorts Captains Quarter's

Located across the street from Falmouth Heights Beach, this is the perfect spot for your escape to Cape Cod. This spacious One Bedroom Suite includes an efficiency kitchen, whirlpool bath and a fireplace. After checking in you can relax in our large outdoor heated pool and take in the sweeping views of Vineyard Sound. The Resort offers two BBQ area's and picnic tables. The friendly and knowledgeable staff is there to assist you in making your stay a memorable one!

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.

Cabin in Falmouth

4.65 out of 5 average rating, 534 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!