Holiday rentals with a pool in Nantucket County

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!

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.

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.



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

2026 Availability Details: - 3 night minimums for weekend stays - Thurs-Sun, June / September / October (2 night minimum during the week) - 7 night minimums, Fri check-in / Fri check-out only, June 26th - Sept 4th 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.

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.

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.