Vacation rentals with a pool in Nantucket County

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Top-rated rentals with a pool in Nantucket County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Nantucket

5.0 out of 5 average rating, 21 reviews

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

*7 night minimum - 6/21-8/30. Friday check-in / check-out* 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 bdrms, 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.

Oct 25 – Nov 1

$853 per night

Home in Nantucket

New place to stay

An adorable studio

Take it easy at this unique and tranquil getaway. This is a private studio over a garage in a secluded area. Wake up to beautiful sunrises: the property is surrounded by conservation land with pasture and distant ocean views. Enjoy the pool and spa during the summer months and patio grill! The studio consists of a Queen bed, a sleeper sofa, TV, fridge, microwave oven, coffee maker, toaster oven, a deck overlooking conservation land and a full bathroom. Hiking, beach walks, biking and a lot more!

Jan 11 – 18

$671 per night

Guest favorite

Townhouse in Nantucket

5.0 out of 5 average rating, 19 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!

Mar 13 – 20

$735 per night

Guest favorite

Home in Nantucket

5.0 out of 5 average rating, 23 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.

Oct 1 – 8

$800 per night

Home in Nantucket

4.67 out of 5 average rating, 3 reviews

Home on Private Lane W/New Addition, Pool, & Spa

New listing! Fully renovated home at end of a private lane with extensive, brand-new addition with covered porch, pool and hot tub, central A/C. Over 3500 square feet of living space with perfect layout to accommodate large and multigenerational families. A peaceful oasis, beautifully landscaped, abutting Land Bank and Conservation land with direct access to miles of hiking and bike trails through the Middle Moors. Ideally situated - close to town, beaches, and mid-island conveniences.

Feb 18 – 25

$1,000 per night

Guest favorite

Home in Nantucket

4.86 out of 5 average rating, 37 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.

Oct 8 – 15

$757 per night

Guest favorite

Home in Nantucket

4.96 out of 5 average rating, 23 reviews

Recently renovated, great mid-island location!

Recently renovated home in the beautiful and unique Nashaquisset community. Offering family-friendly club amenities including community swimming pool and two well maintained tennis courts for use during the summer season. Fantastic mid-island location. Approximately 1.5 miles from town, 2 miles from Surfside Beach, and 1 mile from the grocery store. Two bikes available. Outdoor shower. Saturday to Saturday weekly rentals during the summer months.

Nov 9 – 16

$800 per night

Home in Nantucket

New place to stay

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.  

Nov 30 – Dec 7

$546 per night

Home in Nantucket

4.75 out of 5 average rating, 8 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.

Apr 25 – May 2

$785 per night

Guest favorite

Home in Nantucket

5.0 out of 5 average rating, 17 reviews

rel-ACK-s Here, Bike Everywhere!

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.

Sep 4 – 11

$900 per night

Guesthouse in Nantucket

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 (open in season), firepit, and trampoline.

Jan 5 – 12

$750 per night

Home in Nantucket

4.8 out of 5 average rating, 5 reviews

Beautiful Historic Home | Heated Pool & Hot Tub

We offer a collection of handcrafted homes designed to bring your group together. This beautifully preserved historic home includes a main home and guest cottage. Our spaces are more than just a place to stay. They are a source of lasting memories. Your redefined sense of travel.

Mar 21 – 28

$697 per night