Holiday rentals with a pool in Nantucket

Private Poolside Nantucket Retreat Near the Beach

Private Nantucket retreat with a saltwater pool, spa, large sun-filled deck, grilling area, and peaceful conservation surroundings. This rental includes a detached studio plus a private lower-level suite in the main residence, each with its own separate entrance Ideal for families or small groups who want flexible sleeping space, outdoor living, and a quiet setting close to the beach. Spend the day at the ocean, come back for pool time, grill dinner on the deck, and enjoy the spa in the evening

Location · Family · Getting around

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!

Value · Location · View

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.

Family · Location · Comfort

Naushop: Pool, Pickleball, Private Detached Office

In the heart of Naushop, this home offers a quiet, charming location close to beaches, town, and bike paths. Relax in your private backyard sanctuary, or take advantage of the fully detached private office—perfect for working remotely while on vacation. Guests enjoy access to Naushop’s exclusive amenities, including a pool, pickleball & tennis courts, and a neighborhood playground. The perfect mix of Nantucket charm, convenience, and work-from-home flexibility.

Family · Location · Biking

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 · Location · Pool

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!

Family · Location · Hospitality

Salt Air Suite | Private Nantucket Retreat

Welcome to Salt Air Suite, a newly built private lower-level guest retreat near Surfside Beach. Guests enjoy a private entrance, living room, kitchen, dining area, bedroom, bathroom, Wi-Fi, and access to the HOA pool, grills, clubhouse, and mini golf. Located near beaches, Meat & Fish Market, Cisco Brewery, and bike paths. Please note the suite is attached to our family home, Quiet hours are respected. Thanks

Location · Getting around · Cleanliness

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.

Family · Location · Laundry

Ultimate relaxation spot close to beach

Discover your own private retreat on Nantucket Island! This inviting summer rental features a spacious lower level suite with a pool table for entertaining and a rejuvenating steam room for relaxation. Nestled in a serene setting close to the beach. Experience luxury and tranquility in this secluded hideaway. Book your summer escape now!

Location · Family · Hospitality

Tuck'd Away in Surfside

Enjoy the best of Nantucket from this modern, stylish, and conveniently located private guesthouse. Walk one block to Surfside beach, bike to Cisco Brewery or the shops and restaurants in town, and kick back in the expansive, private and beautifully landscaped yard with pool and hot tub(open in season), firepit, and sports court.

Family · Location · Outdoor spaces

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

Location · Value · Condition

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.

Location · Decor · Cleanliness