Holiday rentals with a pool in Nantucket County

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Top-rated rentals with a pool in Nantucket County

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

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Top guest favourite

Home in Barnstable

4.95 out of 5 average rating, 115 reviews

Private Pool, near beaches, 3 BR/3 BA, Central Air

Enjoy the Barnstable historic seaside village of Cotuit in this sprawling house with central air, nestled in the pines on a quiet street with private gated (unheated) pool, lg. backyard, firepit, ample parking, just blocks from Main St, Ropes Beach, scenic ocean views, fort playground, and Kettleer baseball. Each bedroom has a TV and ensuite bathroom! Relax in the seasonal sunroom overlooking the pool; grill burgers on the patio. Max. 9 (6 adults). Pool open 6/20-9/15/24. The reviews tell all!

Top guest favourite

Home in Oak Bluffs

4.93 out of 5 average rating, 199 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

Home in Mashpee

5 out of 5 average rating, 13 reviews

18 Menemsha Rd., Popponesset, Pool, 3-Beds, 4 bath

This home was custom built in 2022, and is designed to provide comfort, luxury and loads of charm for the discerning vacationer. New construction with a nod to the Nantucket Sea Captain's houses of yesteryear. Professionally decorated and landscaped, offering every amenity you could possibly desire; from an in-ground, heated, saltwater pool (with electric cover), hot tub, outdoor shower, fire-pit, and even a cabana with a sink, refrigerator, and smart TV. Just a 3 min walk to private beach.

Guest favourite

Home in Mashpee

5 out of 5 average rating, 21 reviews

Exclusive New Seabury Home w/ Heated Pool ⛳️🏖🦞☀️🐠

~~ You Have Arrived! Welcome to "The Fore Seasons" in desirable New Seabury on Cape Cod. ⛳️🏖🌸☀️ You will be sure to fall in love with old Cape Cod in this 4,500 sqft private home located on the 10th hole fairway of the championship golf course. With its 4 bedrooms, 4 bathrooms, Heated Inground Pool, Outdoor Shower, Putting Green, Ping Pong table and Ctrl Air there is enough room for the largest families. Pool is open from Mid-May until end of Sep. Available year round for all gatherings!

Guest favourite

Home in Nantucket

5 out of 5 average rating, 7 reviews

Secluded guesthouse with salt pool, close to beach

Take it easy at this unique and tranquil getaway. This is a private studio guesthouse in a secluded area. Wake up to beautiful sunrises: the property is surrounded by conservation land with pasture and distant ocean views. Enjoy semi-private saltwater pool and spa (May-September) and patio grill! The studio consists of a Queen bed, a sleeper sofa, TV, fridge and basic kitchenette amenities, a deck overlooking conservation land and a full bathroom. Hiking, beach walks, biking and a lot more!

Guest favourite

Home in Mashpee

5 out of 5 average rating, 12 reviews

Cape Gem in New Seabury with private heated pool

Our Pristine, Newly Renovated, Patio home with Private heated Pool, located in the Mews of New Seabury, offers the privacy and peacefulness for the perfect vacation. The sandy local beaches—South Cape Beach and Popponesett—are both very short drive away (5-10 minutes)! Highlights of the seashore resort community of New Seabury: Mashpee Commons (fine dining, shops, movie cinema), golf courses, boating, walking trails, close proximity to ferries to Nantucket and Martha’s Vineyard.

Top guest favourite

Guest house in Falmouth

5 out of 5 average rating, 53 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 Falmouth

4.95 out of 5 average rating, 38 reviews

Dog Friendly Cape Oasis | Pool+Beach |Tennis Court

This newly renovated beach cottage, designed by Wil&Co. Homes, is the perfect getaway for Cape lovers. Walk to the private association beach, bring you kayaks or canoes and launch them from the many water access points, and enjoy access to the association pool and tennis courts. This airy retreat has room for the whole family (including dogs) or group of friends with a fire pit, large backyard and game room. 7 Min Drive to Menauhant Beach 13 Min Drive to Downtown Falmouth

Top guest favourite

Home in Nantucket

5 out of 5 average rating, 29 reviews

Our Three Suns

Nantucket house with community access to pool, tennis courts, bike path This 4 bedroom, 3 1/2 bath house is located in the desirable family friendly community of Naushop. The house includes all the amenities Naushop offers; a community pool, two tennis courts, a pickle-ball court, playground and renovated clubhouse. The community is located on the bike path providing easy access to the beach (1.5 miles), town (2 miles), and other amenities.  

Guest favourite

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

Flat in Falmouth

5 out of 5 average rating, 3 reviews

Deluxe Studio Steps From Surf Drive

Stay in our deluxe studio at Beachside Village in Falmouth, MA—ideal for couples or families of four. Each unit features a Queen bed, Queen sleeper sofa, air conditioning, and a kitchenette with a dining area. Enjoy views of Martha’s Vineyard, stroll through nearby village shops, and unwind on Surf Drive Beach just steps away. Your perfect Cape Cod retreat awaits with a touch of coastal history and comfort.

Top guest favourite

Apartment in Mashpee

4.98 out of 5 average rating, 140 reviews

Sleep 6 @ New Seabury w/ Pool Access, All Seasons!

Welcome to Your Coastal Getaway at The Mews, New Seabury – Mashpee, MA Tucked inside the beautiful New Seabury Country Club, our cozy Cape-style condo offers the perfect balance of relaxation and adventure on Cape Cod. Enjoy access to a private condo association pool just a 3-minute walk away, and a beach only 5 minutes away by car or bike.