Vacation rentals with a pool in Nantucket

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Nantucket

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

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A saltwater pool set within a well-maintained lawn features a spa at one end. Four lounge chairs with blue cushions are positioned under a navy umbrella, providing shade. Lush greenery and a protective fence surround the area, creating a serene outdoor space.
Home in Nantucket
4.96 out of 5 average rating, 26 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.

Home in Nantucket
New place to stay

Villa Ackscape

Experience Nantucket living in this newly built 2025 luxury 5BR, 4.5BA retreat, centrally located minutes from Town, Surfside & Cisco. Perfect for families or groups, it features dual primary suites plus a private in-law level with separate access, kitchen, bedroom & bath. Nearly every bedroom has its own bath. Enjoy exclusive heated pool access across the street, an outdoor shower, parking for 3+ cars, direct bike path access, and all-new designer furnishings for a truly indulgent stay.

A two-story cottage is surrounded by lush greenery and features a large covered porch with white railing. The light gray exterior complements the blue sky, and windows provide glimpses of the interior. A spacious yard leads up to the cottage, enhancing the coastal charm.
Home in Nantucket

Stunning Ocean View Cottage

Enjoy ocean views in this beautifully decorated 2-bedroom, 2-bathroom cottage, just steps from the beach. The first floor features a cozy living room with a flat-screen TV, snack station, and a queen bedroom with a private bath. Upstairs, a well-equipped kitchen with ocean views leads to a bright living area with deck access. The second bedroom offers a queen bed & private bath .Includes yard space, parking, pool, and firepit. Beach access 200 yards away. Please note, no pets allowed.

Top guest favourite
The exterior of a light blue house is visible, framed by an array of colorful hydrangeas and shrubbery. The structure features a symmetrical façade with multiple white-framed windows. A welcoming front door, flanked by lanterns, is set against a backdrop of clear blue sky.
Home in Nantucket
4.98 out of 5 average rating, 41 reviews

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.



A bright living area features white walls and natural wood flooring. A comfortable white sofa is positioned near large glass doors leading to the pool. A circular woven coffee table is centered on a blue and white patterned rug, with decorative pillows and artwork adding subtle color.
Home in Nantucket
4.87 out of 5 average rating, 47 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.

The view captures a well-maintained hotel with white siding, surrounded by lush gardens. A centrally located pool is framed by lounge chairs and umbrellas. The harbor is visible in the background, showcasing numerous boats and a serene sky, contributing to a tranquil atmosphere.
Apartment in Edgartown

Martha’s Vineyard King balcony suite harbor view!

4th floor with large balcony overlooking harbor and pool! Harborside Inn is an excellent choice for rest and rejuvenation. Well-known for its historic environment and proximity to great restaurants and attractions, Free wifi is offered to guests, and rooms at Harborside Inn offer a flat screen TV, a refrigerator, and air conditioning. Very helpful concierge. While staying at Harborside Hotel, you have access to all owners privileges

A charming two-story house features a light blue exterior with white trim, surrounded by lush greenery. A white picket fence encloses the front yard, with colorful flowers near the entrance. The door is centered, leading to a welcoming entryway.
Home in Nantucket
4.75 out of 5 average rating, 20 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.

A comfortable seating area is presented on a wooden deck, facing a clear blue pool. Sunlight reflects off the water, while lush greenery frames the space, providing a sense of privacy. A stylish patterned rug enhances the inviting outdoor atmosphere.
Home in Nantucket
4.77 out of 5 average rating, 26 reviews

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!

Guest favourite
The exterior of the cottage is shown, featuring a shingle-clad façade. Two tall windows frame the front door, while well-maintained shrubs line the path. Sunlight casts gentle shadows on the manicured lawn and surrounding trees, creating a serene outdoor setting.
Cottage in Edgartown
4.98 out of 5 average rating, 100 reviews

Lovely two - story private cottage.

This private beach cottage offers comfort and style. Oversized 2nd floor bedroom with queen bed (Designer quilts) full bath and shower (in and out) Nicely furnished over 900 sf and And immaculately kept. Nice grill And sitting area in back. And please Use the built in pool! It sits equi-distant 1.5 miles to downtown Edgartown and south beach. And convenient 5 min walk to bike path or bus route. Perfect location!

Guest favourite
A charming blue door is framed by lush greenery and climbing vines, creating an inviting entrance to the home. Soft pink roses are visible in the foreground, adding a touch of color to the well-maintained garden.
Home in Nantucket
4.94 out of 5 average rating, 77 reviews

Beautiful home in Naushop

A well appointed Nantucket house for 10 guests, centrally located on the island. There is easy bike or car access to town and beaches. Although most families would want to visit during late spring, summer, or early fall, the property is available throughout the year. We have gone to great lengths to make the home comfortable and accommodating to our guests’ wishes.

Superhost
An aerial view showcases the property nestled along Edgartown Harbor, surrounded by lush greenery. Boats are docked along the marina, with well-maintained gardens visible near the buildings. The architecture reflects the local charm, complementing the serene waterfront setting.
Apartment in Edgartown

Edgartown Harbor King Suite

Martha’s Vineyard has plenty of family-friendly activities, a fantastic array of dining options and much more. Situated on Edgartown Harbor among flowering English gardens, this property is ideally located on Martha's Vineyard. Guests will enjoy watching the boats come and go as they listen to the peaceful sounds of the ocean while sitting harbor side.

The entrance features a set of wooden steps leading to a glass door framed by gray shingle siding. A doormat is positioned at the threshold, offering a welcoming touch. Lush greenery is visible in the background, contributing to a serene environment.
Condo in Nantucket
5 out of 5 average rating, 6 reviews

Well appointed 3 bedroom condo

Bring the whole family to this great place with lots of room for fun. Newly renovated 3 floors of living space and a private back patio. Condo boast a heated pool and a green for family fun. Close to public transportation and bike paths. Smoke free and pet free condo

Popular amenities for Nantucket rentals with a pool

When is the best time to visit Nantucket?

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Avg. price$2,099 CAD$1,575 CAD$1,750 CAD$1,615 CAD$2,099 CAD$2,528 CAD$2,602 CAD$2,661 CAD$2,100 CAD$1,407 CAD$1,587 CAD$1,888 CAD
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Quick stats about vacation rentals with a pool in Nantucket

  • Total vacation rentals

    Explore 130 vacation rentals in Nantucket

  • Nightly prices starting at

    Nantucket vacation rentals start at $168 CAD per night before taxes and fees

  • Verified guest reviews

    Over 2,310 verified reviews to help you choose

  • Family-friendly vacation rentals

    110 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wifi availability

    130 of Nantucket vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Nantucket rentals

  • 4.9 Average rating

    Nantucket stays are highly rated by guests—averaging 4.9 out of 5!