Vacation rentals with a pool in Nantucket

Surfside Heaven (w/ Pool in the summer)

Welcome to 43 Boulevarde, a serene home just a half mile from Nobadeer and Surfside Beaches. This spacious four-bedroom, four-bath retreat features a pool, spa, and a half-acre private fenced backyard. Enjoy beach chairs, books, and an outdoor shower. Relax on private balconies or the deck with a new Webber BBQ. A 10-minute drive or 20-min. bike ride to the town of Nantucket , with a few great nearby cafés. Perfect for families, pets, and beach lovers. Book now for a blend of relaxation and fun!

Nestled 5 bedroom, 2.5 bath home in Naushop!

Spacious 5-bedroom, 2.5-bath home in a private community on Nantucket, perfect for families, kids, and pets. Enjoy access to a community pool, tennis, pickleball, playground, and clubhouse. Includes two off-street parking spaces. No car? We’re steps from a free Wave shuttle stop that travels island-wide. This is a well-loved family/pet friendly home with normal wear. We will always provide a clean, comfortable, and welcoming home for you and your loved ones to enjoy your vacation on Nantucket!

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!

Stunning Ocean View Cottage

Enjoy ocean views in this beautifully decorated 2-bedroom, 2-bathroom cottage, just steps from the beach. The first floor features a cozy living room with a flat-screen TV, snack station, and a queen bedroom with a private bath. Upstairs, a well-equipped kitchen with ocean views leads to a bright living area with deck access. The second bedroom offers a queen bed & private bath .Includes yard space, parking, pool, and firepit. Beach access 200 yards away. Please note, no pets allowed.

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.



Gorgeous 5 bd, pool & tennis close to town & beach

Our recently upgraded, spacious, award-winning house and community is in the ideal location in Nantucket- a short distance from Town/ Main Street and Surfside beach. The charming community is quintessentially Nantucket- with white picket fences, tennis and swimming. The house comes fully-equipped with everything from a lobster pot and brand-new grill to tons of beach equipment. 5 spacious bedrooms + 6th bonus room with a daybed.

Pool! Large 4 bedroom+bunk room mid-island!

Spend your days on Nantucket relaxing POOLSIDE at Third Wind. This Mid Island paradise is close to everything. Walk to Stop n Shop and the world-famous Chicken Box while being conveniently located 1.5 miles from downtown. Third Wind offers easy living for you and your whole family, featuring accommodations for 10+ people, 3 full bathrooms, and a wonderful backyard with a deck and pool. Please enjoy our home as much as we have!

Beautiful home in Naushop

A well appointed Nantucket house for 10 guests, centrally located on the island. There is easy bike or car access to town and beaches. Although most families would want to visit during late spring, summer, or early fall, the property is available throughout the year. We have gone to great lengths to make the home comfortable and accommodating to our guests’ wishes.

Well appointed 3 bedroom condo

Bring the whole family to this great place with lots of room for fun. Newly renovated 3 floors of living space and a private back patio. Condo boast a heated pool and a green for family fun. Close to public transportation and bike paths. Smoke free and pet free condo

Family Home for Nantucket Getaway

Silent Sea is the perfect home for a family looking to enjoy Nantucket's many attractions. This three bedroom, two and a half bathroom home with central air-conditioning is ideally situated in the Nashaquisset community.

Boutique Garden Apartment with Great Location

Full kitchen / Living room with Tv. One bedroom with Queen size bed and the other is with Bunk Beds. Outdoor patio with swing and outdoor dining table. Parking available for your stay. One or two cars.

Two-bedroom home in Naushop

Two-bedroom, newly furnished condo in the Naushop community. Private patio, access to community pool & tennis courts, close to bike paths. 2 miles to Town and nearby beaches.