Holiday 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.

Family · Location · Outdoor spaces

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!

Family · Location · Outdoor spaces

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.

Location · Family · Hiking

Historic Island Home, Heated Pool

This luxury historic home is located Mid Island approximately one mile from Downtown, making it an ideal Nantucket home base for your group. With 4 bedrooms plus a loft and 3 bathrooms, the home comfortably accommodates up to 9 guests. Amenities include a private heated pool, gas fire pit, outdoor shower, and a patio with a spacious outdoor dining area. Inside, the professionally designed interiors feature open concept layouts, classic Nantucket architecture, and coastal inspired décor.

Location · Hospitality · Indoor spaces

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!

Location · Family · Walkability

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 · Layout

Nantucket Steps from Beaches & Town

Enjoy your stay , comfortable Nantucket home! Featuring two cozy bedrooms, a living room with sofa bed, renovated bathroom, and fully equipped kitchen, Relax outdoors on your private deck with grill and hot tub, just minutes from beaches, shops, and restaurants. I have bicycles so you can explore the island. My pleasure it’s in my guest happy I know what’s a special time😊🏄🏼‍♂️☀️🌈🌝🍀 Welcome! Hot tub available Maio–September.

Location · Family · Cleanliness

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 · Walkability · Quiet

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.

Value · Family · Hospitality

rel-ACK-s - Spotless Secluded Getaway Near Town

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.

Family · Location · Getting around

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!

Family · Location · Sleep quality

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 · Cleanliness