Holiday rentals with a pool in Nantucket

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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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Guest favourite

Home in Nantucket

5 out of 5 average rating, 6 reviews

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!

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.

Top guest favourite

Home in Nantucket

4.97 out of 5 average rating, 58 reviews

L0W TIDE, with Private Pool

Home located 6 miles from town, has 5 bedroom, 4.5 bath, 2 wings with central living space. Smart TVs/streaming and pool. Beach 2 miles away. FREE EV Charging. Part of a 2 home compound, houses can be rented separately or together, separated by trees and fencing. Pool Opens Memorisl Day Week 2025, closes Sept 15, 2025. We have Car Ferry tickets available for these dates, at face value Friday July 4 return Thursday July 10 Sunday July 6- Sunday July 13 Sunday July 13 – Sunday July 20

Apartment in Oak Bluffs

4.92 out of 5 average rating, 13 reviews

Spectacular Martha's Vineyard Island Home!

This is our beautiful Hidden Cove home on Martha's Vineyard we call Shangri-La! Spectacular setting with a great peaceful view overlooking Sengekontacket Pond with the Ocean beyond. The property features a shared Pool, Tennis Courts & Dock. Our house is conveniently located midway between the Oak Bluffs & Edgartown town centers. When the presidents visit the Vineyard this is the area they come to relax (at the Farm Neck Golf Club which is right up the street).

Guest favourite

Home in Edgartown

5 out of 5 average rating, 6 reviews

Sunny condo with pool, central to beach & town

We all want maximum time enjoying with minimal time waiting in lines and traffic, right? Your family will be close to everything and fully equipped when you stay at this centrally-located oasis. Just three miles from both State and South Beach, and away from triangle traffic. Property access to a large, heated salt water pool to lounge with ease. A few minutes from the bike path, with 5 bikes to choose from to use (no waiting in rental lines!)

Top guest favourite

Home in Nantucket

5 out of 5 average rating, 23 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.  

Home in Nantucket

4.94 out of 5 average rating, 32 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.

Guest favourite

Cottage in Edgartown

4.98 out of 5 average rating, 97 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

Home in Edgartown

4.91 out of 5 average rating, 47 reviews

Beautiful Edgartown Colonial with heated pool.

Stunning 5 bedroom, 10 room, 3500 square foot colonial in beautiful area. Gourmet kitchen, dining room, living room, den, family room with ping pong. Huge deck, private yard with fire pit and outdoor shower. 30 x 16 x 4 heated in ground pool. Central air. Kayaks, bikes. Seven passenger Toyota Highlander available to rent May- October.

Guest favourite

Guest house 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.