Holiday rentals with a pool in Nantucket

Surfside Heaven (w/ Pool in the summer)

Welcome to 43 Boulevarde, a serene home just a half mile from Nobadeer and Surfside Beaches. This spacious four-bedroom, four-bath retreat features a pool, spa, and a half-acre private fenced backyard. Enjoy beach chairs, books, and an outdoor shower. Relax on private balconies or the deck with a new Webber BBQ. A 10-minute drive or 20-min. bike ride to the town of Nantucket , with a few great nearby cafés. Perfect for families, pets, and beach lovers. Book now for a blend of relaxation and fun!

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.

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.



The Miro

Mid-Island Chic with Private Patio & Parking. Stylish, renovated condo in a quiet Nantucket neighborhood near parks and beaches. Minutes to downtown, yet peaceful and private. Bright open living space, full kitchen, 3 levels with a primary suite, guest room, and third floor with queen bed + sofa. Private fenced patio with grill, 2 bikes, parking, pool access, and easy access to The Wave shuttle. Perfect for a relaxed island getaway.

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.

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.