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Vacation rentals with a pool in West Tisbury

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in West Tisbury

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

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Guest favorite
The expansive pool, surrounded by a landscaped yard, features a vibrant blue surface reflecting the clear sky. Comfortable lounge chairs are positioned alongside, inviting relaxation. A floating inflatable adds a playful touch to the tranquil setting.
Home in Cotuit
4.95 out of 5 average rating, 128 reviews

Private Pool, near beaches, 3 BR/3 BA, Central Air

Enjoy the Barnstable historic seaside village of Cotuit in this sprawling house with central air, nestled in the pines on a quiet street with private gated (unheated) pool, lg. backyard, firepit, ample parking, just blocks from Main St, Ropes Beach, scenic ocean views, fort playground, and Kettleer baseball. Each bedroom has a TV and ensuite bathroom! Relax in the seasonal sunroom overlooking the pool; grill burgers on the patio. Max. 9 (6 adults). Pool open 6/20-9/15/26. The reviews tell all!

Top guest favorite
A serene backyard features a heated pool surrounded by paved stone decking. Multiple lounge chairs are positioned for comfort, offering views of the lush greenery. The two-story home is visible in the background, with a deck equipped for outdoor relaxation.
Home in New Seabury
5 out of 5 average rating, 15 reviews

New Seabury Oasis with Pool!

Relax with the whole family at this peaceful New Seabury retreat. 5 bedrooms, 3 bathrooms with separate living rooms on each floor. Newly updated backyard and heated pool. Backs up to 10th/11th hole of the Ocean Course at New Seabury. Great for a large family or two families to share. Master bedroom has built in desk space to allow to work from home, as needed. Walk to Popponessett marketplace and all the beautiful outdoor space New Seabury has to offer. Short drive to South Cape beach.

Guest favorite
A modern outdoor space is highlighted by a fresh salt-water pool surrounded by sleek lounge chairs and umbrellas. The pool area is complemented by lush greenery and well-maintained landscaping, offering a serene ambiance for relaxation.
Home in Edgartown
4.97 out of 5 average rating, 33 reviews

Edgartown Designer Retreat With Pool & Hot Tub

Located in Katama, this 3,000-square-foot home has undergone a complete renovation, and offers privacy and easy access via bike path to downtown Edgartown and South Beach. Everything is brand new. There is a salt water heated pool & hot tub! Highlights include 8 inch wide white oak flooring, a custom marble vanity, ultra thick quartz countertops, custom lighting, high end art throughout, all new high end appliances and designer furniture, outdoor shower, gym, and 4 bedrooms / 3.5 bathrooms.

Top guest favorite
A modern home with light grey siding is featured in the background, surrounded by landscaped gardens. A heated saltwater pool, with clear blue water, is framed by grey stone paving. Lounge chairs and shaded seating are situated beside the pool, enhancing the outdoor space.
Home in Popponesset
5 out of 5 average rating, 19 reviews

18 Menemsha Rd., Popponesset, Pool, 3-Beds, 4 bath

This home was custom built in 2022, and is designed to provide comfort, luxury and loads of charm for the discerning vacationer. New construction with a nod to the Nantucket Sea Captain's houses of yesteryear. Professionally decorated and landscaped, offering every amenity you could possibly desire; from an in-ground, heated, saltwater pool (with electric cover), hot tub, outdoor shower, fire-pit, and even a cabana with a sink, refrigerator, and smart TV. Just a 3 min walk to private beach.

Top guest favorite
A spacious wooden deck is surrounded by trees, offering a serene view of the natural landscape. A small round table with drinks is set between two folding chairs. A gas grill is positioned against a wooden railing, with sunlight filtering through the foliage.
Apartment in Barnstable
4.95 out of 5 average rating, 57 reviews

Studio Apartment

Private Studio Apt on lower level of owner occupied House.Private deck overlooking Pond. Queen bed, single sofabed/and small sleeping loft. Very comfortable for 2 people but can sleep up to 4. Kitchenette w/dinnerware and cookware. Coffee maker, fridge, microwave, toaster oven, outside gas grill. Private bath/shower. TV, WiFi, A/C. Pond access, SUP, kayaks. Pool/hot tub on Main House level available for use on request. Sunrise view. Golfcourses, shopping, restaurants, beaches nearby.

Guest favorite
A clear blue swimming pool is surrounded by lounge chairs positioned for relaxation. Lush greenery provides a natural backdrop, while a shaded area offers protection from the sun. Steps lead from the pool to a nearby structure, adding convenience for guests.
Condo in Tisbury
4.92 out of 5 average rating, 49 reviews

Private 3bdrm Condo Tashmoo Woods

This 3 bedroom (3 king) 2 1/2 baths newly renovated condo is in a private setting with screened in porch. New kitchen, gas grill on deck, outdoor shower. -Access to the Tashmoo Woods Association pool, tennis courts and play ground. -Close to West Chop beaches. -Two miles from downtown Vineyard Haven. On bus route, but best to have a car. -The primary bedroom (king bed) is downstairs and the 2 upstairs bedrooms share a bath (shower only). Minimum rental 5 days, 1 week in summer.

Guest favorite
The exterior of the cottage features a well-maintained lawn with lush green trees in the background. A wooden deck extends from the house, along with patio chairs overlooking a tranquil pond surrounded by vibrant flowers and plants.
Cottage in Centerville
4.93 out of 5 average rating, 100 reviews

The Holly Cottage

Welcome to Centerville, enjoy this fully equipped 1 bedroom 1 bath home with an easy walk or ride to just about everything. Enjoy the nearby ocean and beaches, or take a ride downtown to Main Street for dining and entertainment. Only a short distance to the ferries for a day trip to the islands and you can be back in time to catch a concert at the Melody Tent. Enjoy your days by the pool and your evenings grilling out on the large deck or chatting with the koi fish.

Superhost
An indoor pool area features large windows and skylights that allow ample natural light. A tropical plant in a pot is positioned in the foreground. The pool is surrounded by a spacious deck with seating options, providing a relaxed environment for enjoyment.
Home in New Bedford
4.73 out of 5 average rating, 211 reviews

Poseidon's Palace - 2.0

Poseidon's Palace is a beach house just steps away from East Beach. Home boasts an indoor pool, all brand new stainless steel appliances, indoor electric fireplace ,sauna . Bring your family along to enjoy holidays, birthdays, weddings , family reunions. Home is on the corner lot of a serene neighborhood with lovely neighbors all around. The home can be a great refuge while you work from home & is ideal for entertaining . Tons of day activities to participate in.

Top guest favorite
A private deck is showcased with outdoor furniture, including a round table and chairs. A colorful striped umbrella provides shade, while surrounding greenery and flowers add a natural touch. The deck is well-lit by sunlight, creating a warm and inviting space.
Apartment in Hyannis Port
4.9 out of 5 average rating, 144 reviews

Great Location. Near Beach & Main Street. Unit M1

Our home-away-from-home accommodations include this charming studio with lawn space, a private deck with outdoor furniture and a gas grill. The cottage is comfortably furnished and features a small kitchen. This cottage has a queen bed and a table with sitting area. The kitchen is nicely updated with updated with beautiful granite countertops and stainless steel appliances including an stove/oven, microwave, mini-fridge, toaster, coffee maker. Keurig, and kettle.

Top guest favorite
A cozy studio space features sloped ceilings and warm wooden flooring. A spacious bed is dressed in white linens, with accent pillows adding a touch of color. A small kitchenette is visible beside a comfortable chair and a blue rug, offering a relaxed atmosphere.
Guest suite in Dartmouth
4.94 out of 5 average rating, 107 reviews

The Loft @ Beechwood. Private, comfy, coastal!

The Loft is a detached and private studio apartment with a private entrance, beautifully decorated with a coastal decor befitting nearby Padanaram Harbor & Village. The skylights and a 'really, really comfortable bed' will help you relax and enjoy all the area has to offer. Ideal for two guests, but able to accommodate a third, or two children, The Loft is a great home base to explore the local area or the Islands of Cuttyhunk, Martha's Vineyard & Nantucket.

Top guest favorite
Condo in New Seabury
4.97 out of 5 average rating, 172 reviews

New Seabury Cape Condo | Pool & Beach Escape

Welcome to your coastal getaway at The Mews in New Seabury, Mashpee—a refined Cape-style condo tucked within an intimate golf course community. This exclusive enclave of just 15 residences offers a peaceful, private escape with access to a shared association pool reserved solely for residents. Enjoy nearby beaches like South Cape Beach State Park and Mashpee Town Beach, both just minutes away, for the perfect Cape Cod retreat.

Guest favorite
A charming stone exterior features a distinctive arched design, with two red doors providing access to the private studio. Lush greenery surrounds the entrance, complemented by a gravel pathway and neatly trimmed bushes, evoking a sense of tranquility in the outdoor space.
Apartment in North Falmouth
4.8 out of 5 average rating, 114 reviews

Falmouth, Cozy Studio Near Old Silver Beach

This private studio is located in a quiet neighborhood. Located on the second floor, it has A/C, a skylight, Dish TV Amenities include a gazebo. The kitchenette includes a microwave, toaster oven and a Keurig coffee maker. The pool is NOT heated and is open seasonally (July 1 - Labor Day) Close to beaches! Please note there is NO STOVE in the unit.

Popular amenities for West Tisbury rentals with a pool

Quick stats about vacation rentals with a pool in West Tisbury

  • Total vacation rentals

    Explore 40 vacation rentals in West Tisbury

  • Nightly prices starting at

    West Tisbury vacation rentals start at ﺩ.ﺇ771 per night before taxes and fees

  • Verified guest reviews

    Over 480 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of West Tisbury vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across West Tisbury rentals

  • 4.9 Average rating

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