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Vacation rentals with a pool in Tisbury

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Tisbury

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

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Top guest favorite

A spacious backyard is highlighted by a private, unheated in-ground pool surrounded by paved areas. Colorful lounge chairs and an inflatable float add to the inviting atmosphere. A patio table with patterned cushions is positioned nearby, offering a space for relaxation and outdoor dining.

4.95 out of 5 average rating, 127 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 6/20-9/15/24. The reviews tell all!

Top guest favorite

The outdoor pool area is surrounded by a black metal fence and features clear blue water. A swan-shaped float is situated on the water, while lounge chairs are positioned nearby. An umbrella provides shade, enhancing the inviting setting.

Home in North Falmouth

5 out of 5 average rating, 23 reviews

New Construction Home with Pool in N. Falmouth

Come relax in this new construction house, located in quaint North Falmouth. Decide to spend the day at home and hang by the pool and hot tub. Have the kids ride their scooters around the cul de sac while you watch the sunset on the front porch. If you decide to venture out, Old Silver and Megansett Beaches are approx. 2 miles away, and the Shining Sea Bikeway is at the end of the street that takes you all the way to Woods Hole. Whether you stay in or go out, living is easy with this rental!

An indoor heated saltwater pool is surrounded by large windows that invite natural light. The space is accented by sleek white walls and high ceilings with skylights. A hot tub is visible near the pool, contributing to a relaxing atmosphere.

Villa in New Seabury

4.98 out of 5 average rating, 52 reviews

Heated Indoor Pool & Spa - Golf Course View

CHERRY BLOSSOM RETREAT Cold days, raining days and power outage won't hinder your stay at this luxurious home, boasting an indoor heated salt water pool and hot tub fully equipped with a backup generator, overlooking the renowned 3-Hole Championship Golf Course. Our ultimate luxury home features an array of indoor entertainment options including arcades, air hockey, foosball PS5, Switch, etc. comfortably accommodating 6 to 8 guests, and merely a short drive to all all New Seabury's amenities.

Home in Oak Bluffs

4.93 out of 5 average rating, 204 reviews

Spectacular beach & pool combo; beautiful sunsets!

Close to airport, you’ll love backyard beach, water view, pool/grass yard, ambiance and outdoors space. Beach & Pool (POOL HEAT STARTS SUMMER, ENDS 9/1) is a hard to find combination!! Location is private, yet it's close to the 3 largest towns on Martha's Vineyard. Great for couples, families (with kids), and big groups. Enjoy dinner with the indoor/outdoor Sonos music system during a beautiful sunset! NOTE; Rate increase in high season, pool/spa is a combined unit & ONLY heated in summer!

The spacious outdoor area features a heated saltwater pool surrounded by paver stones. Lounge chairs are positioned around the pool, accompanied by blue umbrellas. A nearby cabana is visible, along with vibrant landscaping, providing a relaxing atmosphere for guests.

Home in Popponesset

5 out of 5 average rating, 16 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.

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.

A spacious in-ground pool is surrounded by a sunbathing area featuring a lounge chair and umbrella. Lush greenery and flowering bushes frame the backyard, while a pool house is visible in the background, equipped with comfortable seating. The pool area invites relaxation and enjoyment.

Home in Barnstable

4.83 out of 5 average rating, 29 reviews

Stunning Cape Home - Inground Pool, 5 Min To Beach

Stunning in-ground pool. Just 5 minutes from Craigville, Dowses and Covell's Beach! Perfect for mid-size groups or families, this home sleeps 8 and boasts a dreamy, private, fenced-in backyard w/ a, pool house w/ TV & bar, outdoor shower, and cozy patios. Complete w/ all your beach essentials. Conveniently located, we're 13 minutes from Mashpee Commons and 10 minutes from local grocery stores, local bakeries& restaurants. Central to all the Cape has to offer!

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, 103 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.

A clear blue swimming pool is framed by a lush green tree and surrounding foliage. Poolside lounge chairs are positioned around the edge, alongside an umbrella providing shade. The vibrant sky is dotted with fluffy white clouds, enhancing the 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!

Top guest favorite

A welcoming living area features a comfortable sectional sofa and two wooden armchairs arranged around a circular coffee table. Natural light fills the space, highlighting a large area rug on the hardwood floor. A well-equipped kitchen is visible in the background.

Condo in New Seabury

4.97 out of 5 average rating, 159 reviews

Sleep 6 @ New Seabury w/ Pool Access, All Seasons!

Welcome to Your Coastal Getaway at The Mews, New Seabury – Mashpee, MA Tucked inside the beautiful New Seabury Country Club, our cozy Cape-style condo offers the perfect balance of relaxation and adventure on Cape Cod. Enjoy access to a private condo association pool just a 3-minute walk away, and a beach that is 5 min drive or 10 min bike ride or 30 min walk (walk cuts through golf course-ask host for directions).

Home in Edgartown

5 out of 5 average rating, 17 reviews

Modern & Spacious Edgartown Home with Pool

Enjoy your vacation in this wonderfully charming three bedroom home with an in-ground heated pool. Head to the beach or stay at home and go for a swim in your own backyard. There is plenty of dining room & deck space to entertain. The bike path and bus shuttle are at the end of the road (a two minute walk away). Downtown Edgartown is less than two miles away for you to enjoy shopping and multiple dining choices.

A clear blue swimming pool is visible in the foreground, surrounded by a spacious deck with lounge chairs. The two-story building showcases multiple windows and a covered porch area, providing a view of the pool. A white fence encircles the pool area.

Condo in Falmouth

5 out of 5 average rating, 8 reviews

Spacious 2BR by the Sea in Falmouth

This inviting 2-bedroom condo at Beachside Village Resort offers comfort and charm with Queen beds, twin beds, a sleeper sofa, and a fully equipped kitchenette. Ideal for up to 6 guests, enjoy ocean views, air conditioning, and access to the resort's pool and BBQ area. Just steps from Surf Drive Beach and close to Cape Cod's top attractions, it's perfect for a relaxing family or group escape.

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Popular amenities for Tisbury rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Top guest favorite

An expansive outdoor area features a rectangular saltwater pool surrounded by a concrete deck. The historic house presents a mix of shingle-style architecture and modern updates. Lush greenery and trees frame the property, with clouds and blue skies providing a scenic backdrop.

Home in East Sandwich

5 out of 5 average rating, 42 reviews

XL Estate: 2 Homes-Pool-Tennis-Game Barn - 20 ppl

Home in New Seabury

5 out of 5 average rating, 7 reviews

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

A private backyard features a large swimming pool surrounded by a patio with stone paving. Lush greenery and low shrubs border the area, while a wooden table and chairs are positioned nearby. The house is visible in the background, framed by trees.

Home in Mashpee

4.91 out of 5 average rating, 22 reviews

Beautiful Mashpee Home with Pool

Home in Barnstable

4.59 out of 5 average rating, 32 reviews

Contemporary Gem with Private Pool!

The exterior showcases a contemporary home with a blend of stone and siding elements. Solar panels are visible on the roof, and a circular driveway leads to a welcoming entrance with double doors. Surrounding greenery enhances the property’s serene setting.

Home in Sagamore

4.96 out of 5 average rating, 23 reviews

XL Cape Retreat - Pool - Hot Tub - 5min to Beach!

An outdoor pool area showcases a heated inground pool with clear water, surrounded by a wooden deck. Sun loungers are placed nearby, and patio umbrellas provide shade. Lush greenery and trees line the background, offering a serene environment. A beach ball floats in the water.

Home in New Seabury

4.96 out of 5 average rating, 28 reviews

Exclusive New Seabury Home w/ Heated Pool ⛳️🏖🦞☀️🐠

A heated saltwater pool glistens under the sun, surrounded by a spacious paver patio. The fenced backyard provides privacy, while a light-colored house with a deck offers a welcoming ambiance. Lush trees stand in the background, enhancing the serene outdoor space.

Home in Barnstable

4.82 out of 5 average rating, 17 reviews

Centerville Oasis, Heated Saltwater Pool!

A spacious backyard is surrounded by trees, featuring a circular above-ground pool. Nearby, a hammock is hung between two trees. Several white lounge chairs are arranged on the grass, providing a relaxing spot in the sun.

Home in Mashpee

4.85 out of 5 average rating, 65 reviews

Sunny Cape w/Private Pool, Steps to Private Lake

Condo rentals with a pool

An outdoor swimming pool is surrounded by lounge chairs and umbrellas, providing a comfortable space for relaxation. Tall trees and greenery enclose the area, enhancing the tranquil atmosphere. Clear blue skies and well-maintained landscaping contribute to the inviting poolside setting.

Condo in Falmouth

4.83 out of 5 average rating, 18 reviews

Falmouth MA, Cape Cod Getaway

A clear swimming pool is surrounded by well-maintained grass and tall, green trees. Several lounge chairs are positioned around the pool's perimeter. A colorful float is visible in the water, and a shaded area is indicated by a large umbrella. The overall setting is peaceful and inviting.

Condo in Falmouth

4.65 out of 5 average rating, 51 reviews

Lovely lakefront studio/condo with pool

An indoor pool area is illuminated by large windows that provide natural light. White lounging chairs are arranged around the pool, and potted plants add a touch of greenery. The clear water reflects the inviting setting, creating a serene atmosphere.

Condo in Teaticket

4.63 out of 5 average rating, 8 reviews

InnSeason Resorts Surfside

Condo in Oak Bluffs

4.67 out of 5 average rating, 3 reviews

Island Inn - Two Bedroom Suite - 1A - Oak Bluffs,

A community pool is surrounded by a tan deck and green lounge chairs. The pool features clear blue water and a ladder for entry. Lush greenery provides a natural backdrop, with a few buildings visible in the distance, emphasizing a peaceful environment.

Condo in New Seabury

4.93 out of 5 average rating, 15 reviews

5 Mi to Mashpee Commons: Coastal Mashpee Condo

A relaxing outdoor pool area features lounge chairs arranged along the pool's edge. The surrounding building, showcasing spacious balconies, houses multiple units. Guests enjoy sunbathing and walking nearby, with clear skies overhead enhancing the scene.

Condo in Falmouth

5 out of 5 average rating, 4 reviews

Two bedroom condo .on the water Falmouth, ma

The entrance of the condominium is shown, featuring a wooden exterior with shingles. A pathway leads to the door, surrounded by neatly trimmed shrubs and grass. Bright sunlight highlights the clear sky and the inviting pathway.

Condo in Falmouth

4.71 out of 5 average rating, 28 reviews

Condo in Falmouth MA

Condo in Oak Bluffs

4.92 out of 5 average rating, 13 reviews

Spectacular Martha's Vineyard Island Home!

Other vacation rentals with a pool

An oval-shaped pool is surrounded by a wooden deck, featuring two lounge chairs positioned nearby. The pool is clear and inviting, with a pool ladder for easy access. Lush greenery can be seen in the background, adding to the natural setting.

Home in Vineyard Haven

4.88 out of 5 average rating, 8 reviews

Greenwood family fun.

A spacious backyard is featured, showcasing a heated pool and well-maintained lawn. A patio area with outdoor seating is visible, bordered by trees for privacy. The home in the background reveals a newly renovated exterior. Soft clouds drift overhead, adding a serene backdrop.

Home in Falmouth

5 out of 5 average rating, 5 reviews

Heated pool, walk to beach, town

A sunlit space features large glass windows providing views of the surrounding greenery. Two sofas, one with textured fabric and the other adorned with cushions and a throw, are arranged around a wooden coffee table. Natural light enhances the welcoming atmosphere.

Home in Edgartown

5 out of 5 average rating, 8 reviews

Sunny condo with pool, central to beach & town

The kitchen features a bright white color scheme with modern high-end appliances. An island with seating for four is highlighted, alongside a view of the outdoor patio through large glass doors. Light wood flooring complements the space, enhancing its expansive feel.

Home in East Falmouth

5 out of 5 average rating, 4 reviews

Summer 2025 Open!Walk to Great Pond, central a/c

Home in New Bedford

4.72 out of 5 average rating, 196 reviews

Poseidon's Palace - 2.0

A refreshing pool is surrounded by lush greenery, providing a tranquil setting. Two lounge chairs are positioned nearby, with a shaded dining area under an umbrella. A raised bed garden is visible in the background, enhancing the outdoor retreat.

Vacation home in West Tisbury

4.91 out of 5 average rating, 11 reviews

Beautiful Family Friendly House with Pool

Top guest favorite

An aerial view reveals a spacious bay front home surrounded by lush greenery. A large pool is visible in the backyard, with steps leading down to a beach area featuring kayaks. The residence is set in a tranquil, wooded environment.

4.95 out of 5 average rating, 21 reviews

ShoestringBayHouse, waterfront & pool in Cotuit

An aerial view captures the spacious property featuring a well-maintained in-ground pool surrounded by a fenced area. Lush gardens and trees in various autumn colors frame the grounds, with expansive fields visible in the background, offering a serene outdoor setting.

Home in East Sandwich

5 out of 5 average rating, 8 reviews

Saltfish Bay - Heated Pool and Beach Access

Quick stats about vacation rentals with a pool in Tisbury

Total rentals
50 properties
Nightly prices starting at
ﺩ.ﺇ551 before taxes and fees
Total number of reviews
860 reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace

Destinations to explore