Holiday rentals with a pool in 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!

Conveniently close and quietly Tucked away!

Tucked Away is a great vacation getaway. Hidden away on a quiet circle, this spacious property borders the Miacomet golf course and miles of Land Bank land. With a trail out the back it's only a short walk to the Cisco beaches and Miacomet pond. The home has all the modern comforts expected for a great vacation. Step outside to the quiet and private rear of the property and dip in the pool and spa. The front of the property has an expansive lawn as well, great for kids to play around on.

Villa Ackscape

Experience Nantucket living in this newly built 2025 luxury 5BR, 4.5BA retreat, centrally located minutes from Town, Surfside & Cisco. Perfect for families or groups, it features dual primary suites plus a private in-law level with separate access, kitchen, bedroom & bath. Nearly every bedroom has its own bath. Enjoy exclusive heated pool access across the street, an outdoor shower, parking for 3+ cars, direct bike path access, and all-new designer furnishings for a truly indulgent stay.

A Children’s Paradise

Elegant over-sized colonial in Naushop! The open concept first fl boasts bedroom with en-suite. The second fl has an additional primary bedroom with en-suite, as well as king & queen bedroom that share a newly redone soaking tub. The children will have sleepovers of their dreams, in the attack with a 75” TV. Newly redone in June 2022 basement includes an arcade, in home theater, and twin beds. Entertainers backyard, community tennis courts, pool, & playground for your family to enjoy!

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.

Family-Friendly 5bd w/ Pool, Patio, Central AC

Sit back and relax by your private, fenced in pool or secluded yard guarded by a mature evergreen hedge. Take a stroll down quiet Pine Crest Dr with your better half, or walk down the street with the kids to the incredible Hinsdale Park playground. 92 Old South has 5 bedrooms, 3 full baths, 6 beds (one with a trundle) and comfortably sleeps 10. The open kitchen flows into the family room with vaulted ceiling, separated by a breakfast bar.

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.

rel-ACK-s Here, Bike Everywhere!

Relax here on Nantucket! Quaint community nestled mid island next door to parks and nature. Only 10min. car / 20min. or less bike ride on dedicated paths to town, beaches, restaurants, and shops. 7 cruiser bikes provided. Wave shuttle picks up across Nobadeer Farm Road. No arguing over rooms, with themed Whaling, Nobadeer, and Gallery rooms, allowing all the Nantucket vibes.

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.