
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.

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!

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.

Mashpee Manor Pool House
A modern day-dream-house with a private back yard and a heated pool awaits you! A walk away from John's Pond, 1.6 miles to Mashpee Commons to shop, dine and play! Spacious living/dining/kitchen area, half bath with laundry and a first-floor home office that can double into an additional sleeping area. Upstairs landing a cozy family room, with three bedrooms, 2 with their own bathroom, one with a jacuzzi tub! Finished lower-level has a pool table, and a fourth bedroom great for the older kids!

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.

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.

Falmouth/Woods Hole Charming Cottage By the Sea
Welcome to our Cottage By The Sea Rental located only minutes from the quaint village of Woods Hole, Falmouth and the Martha's Vineyard Ferry. We are located in the perfect setting to relax and enjoy all the area has to offer. Come enjoy The Shining Sea Bike path which is 10.7 miles , Sandy beaches, lively restaurants & local music scene, shopping on historic Main Street, Farmers Markets & more. Your sure to fall in Love with " Ole Cape Cod " when you visit our home and area

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.

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.

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.

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.

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.

Quaint North Falmouth near Old Silver Beach
Located in the Quaint village of North Falmouth, yet close to beaches, this one-bedroom Apartment is a great place to relax. It has a tiled walk-in shower and heated floor in the bathroom. The kitchen includes a microwave, toaster oven, cook top stove, and a Keurig coffee maker. The pool is not heated and is open seasonally (July 1 - Labor Day) Very private location. Close to Old Silver Beach!
Popular amenities for West Tisbury rentals with a pool
House rentals with a pool

Renovated Cape Oasis W/ New Pool and Game Room!

Centerville Oasis, Heated Saltwater Pool!

Sunny Cape w/Private Pool, Steps to Private Lake

Coastal Retreat in Sandwich -Pool Access, Dogs OK!

The Plymouth Pool House

The Wakeby esCAPE ~ Pool & Walk to Beach!

Upscale Secluded Home w/Central AC, Pool & Firepit

Family Friendly Hideaway
Condo rentals with a pool

Relax....You're on Island Time......

Falmouth MA, Cape Cod Getaway

Lovely lakefront studio/condo with pool

1BR Condo with Balcony in Mashpee, MA

Two bedroom condo .on the water Falmouth, ma

Bright, Coastal Mashpee Condo Near the Commons

Condo in Falmouth MA

Spectacular Martha's Vineyard Island Home!
Other vacation rentals with a pool

Waterfront Home w/ Dock, Heated Pool, Kayaks & A/C

Cape Cabin, Pools, Hot Tub, Beach, Game RM, & More

Beautiful Mashpee Home with Pool

1 bedroom apartment located 5 minute walk to beach

Ocean Front Resort Studio Unit

West Tisbury Gem with Deck + Association Pool

Cape Cod Resort|Cabin w/Pool & Private Beach

Large Home Heated Swimming Pool Private Beach
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 $289 CAD 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 and kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
40 of West Tisbury vacation rentals include wifi 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!
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