Vacation rentals with a pool in Nantucket County

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Top-rated rentals with a pool in Nantucket County

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Guest favorite

Home in Nantucket

4.96 out of 5 average rating, 27 reviews

Serene 5000sf Sanford Farm Estate - Pool & Hot Tub

This beautifully lit 5,000 sqft home offers the perfect blend of privacy and convenience. Nestled amidst 1,200 acres of conservation land stretching to the oceanfront, the property boasts breathtaking views. Just 2.5 miles from town, you'll enjoy easy access to local attractions. Nature lovers will appreciate direct access to the Madaket Bike Path. Unwind on the back patio and soak in the stunning vistas and trails that connect to the Head of the Plains Trailhead, ideal for hiking and exploring

Guest favorite

Townhouse in Nantucket

5 out of 5 average rating, 26 reviews

Airy Nantucket Escape in Historic Downtown!

Venture out on a quaint island escape with a few loved ones and stay at this 1-bedroom, 2-bath escape on Main Street! Nestled in the heart of Historic Downtown, easily stroll the cobbled streets, pop in and out of local shops, or dine along Nantucket Harbor from this light-filled vacation rental. Grab some coffee at a nearby cafe, followed by a leisurely day soaking up the sun at a nearby beach. Later, enjoy a beer at Cisco Brewery or whip up a farm-fresh recipe in the townhome's full kitchen!

Guest favorite

Rental unit in Nantucket

5 out of 5 average rating, 7 reviews

Ultimate relaxation spot with pool close to beach

Discover your own private retreat on Nantucket Island! This inviting summer rental features a spacious lower level unit with a pool table for entertaining and a rejuvenating steam room for relaxation. Nestled in a serene setting close to the beach, it offers shared access to a pool and spa for ultimate indulgence. Experience luxury and tranquility in this secluded hideaway. Book your summer escape now! **this unit can be rented with the studio subject to availability, to sleep up to 8 people

Home in Nantucket

4.96 out of 5 average rating, 25 reviews

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.

Guest favorite

Villa in Nantucket

5 out of 5 average rating, 13 reviews

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!

Superhost

Home in Nantucket

4.76 out of 5 average rating, 46 reviews

Rustic home with new pool and hot tub near downtown

Cozy and rustic 3 bedroom 2 bathroom house with attached bungalow 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. All new sun deck with lounge chairs, umbrella and outdoor shower. There’s also a dining table and a grill. The house is next to bike path and quaint cafes and restaurants.

Home in Nantucket

5 out of 5 average rating, 5 reviews

Quiet and Private Cottage with Pool on Nantucket

The house was built spring 2018.... 4 Bedrooms,3 Bathrooms Sleeps up to 8 people. Beautiful Custom Kitchen Custom Interior Design Beautiful yard with pool,sun loungers,picnic table,barbecue and outdoor shower.Sunbathe by the pool in the afternoon sun or relax with a book under the pergola. Secluded location yet also walking distance to all local amenities including beaches, bike paths,dining,gourmet supermarkets, yoga studio, health food store. Perfect family summer getaway!!

Home in Nantucket

4.94 out of 5 average rating, 31 reviews

Family-Friendly 5bd w/ Pool, Patio, Central AC

Sit back and relax by your private, fenced in pool or secluded yard guarded by a mature evergreen hedge. Take a stroll down quiet Pine Crest Dr with your better half, or walk down the street with the kids to the incredible Hinsdale Park playground. 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.

Home in Nantucket

4.8 out of 5 average rating, 15 reviews

Gorgeous 5 bd, pool & tennis close to town & beach

Our recently upgraded, spacious, award-winning house and community is in the ideal location in Nantucket- a short distance from Town/ Main Street and Surfside beach. The charming community is quintessentially Nantucket- with white picket fences, tennis and swimming. The house comes fully-equipped with everything from a lobster pot and brand-new grill to tons of beach equipment. 5 spacious bedrooms + 6th bonus room with a daybed.

Guest favorite

Home in Nantucket

4.93 out of 5 average rating, 14 reviews

Heated pool through October! Mid island oasis

Spend you days on Nantucket relaxing POOLSIDE at bACK At It. 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. bACK At It features easy living for you and the whole family with accommodations for 6 plus people, 2 full baths, and a wonderfully zen backyard and pool. Please enjoy our home as much as we have!

Guest favorite

Guesthouse in Nantucket

5 out of 5 average rating, 7 reviews

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.