Vacation rentals with a pool in Nantucket

Rustic home w private pool & hot tub near downtown

Rustic cozy 3 bedroom 2 bathroom house located about a mile from downtown Nantucket and 2 miles from several beaches (Surfside, Jetties, Steps, etc). The house is on a private quarter acre lot with a big front and back yards including 16x32 heated play pool (3’6-5’6 depth) and a hot tub. The backyard includes a sun deck with lounge chairs, outdoor shower, dining table, a grill, a lounge area with a fire pit and an outdoor projector. The house is next to a bike path and quaint cafes/restaurants.

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.

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!

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.

Clean, family-friendly with heated saltwater pool

First time listing our former year-round residence, Happy Campers is bright, clean, and perfect for groups who love to spend time in and around the pool. Located just minutes from south shore beaches and easy access to town via the bike path or free Wave shuttle bus. Sleeps up to 10 comfortably. New carpet and furniture in bedrooms and fresh paint in May 2026. Please note, this is a non-smoking property. POOL WILL BE OPEN & HEATED MEMORIAL DAY THROUGH OCTOBER

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!

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

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.

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!

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.