Vacation 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

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.

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.

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.

Beautiful Historic Home, Heated Pool & Hot Tub

This luxury historic retreat is just steps from Downtown, making it the perfect Nantucket home base for your group. With 6 bedrooms plus a loft and 4 full bathrooms, the property comfortably accommodates up to 13 guests. Amenities include a heated pool, hot tub, fire pit, and two outdoor dining patios. Inside, the professionally designed interiors showcase open concept layouts, classic Nantucket architecture, and coastal inspired décor.

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.

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.

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.