Vacation rentals with a pool in Tisbury

4.76 out of 5 average rating, 33 reviews

An inviting outdoor space is depicted, featuring a spacious in-ground pool surrounded by lounge chairs. String lights are strung across the pool area, illuminating the backyard. A pool house and umbrellas provide additional amenities, while the home's facade is visible in the background.

Home in Barnstable

Heated Pool Oasis | 5 Min to Cape Cod Beaches!

Stunning in-ground pool HEATED in May, June, Sept, Oct only. 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!

4.95 out of 5 average rating, 128 reviews

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

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!

5 out of 5 average rating, 23 reviews

A sandy beach extends toward calm waters bordered by a tree-lined shore, creating a serene natural setting. The gentle curve of the waterway leads to a distant point, where lush greenery enhances the picturesque landscape. The bright blue sky adds to the tranquil atmosphere.

Home in East Falmouth

Renovated ranch with pool access

Renovated home in E. Falmouth offers endless relaxation and recreation: swim, bike, fish, kayak, walk, lounge. Short walk to Assoc beach or to the Seashores Clubhouse pool (seasonal). Bring your kayak: explore Washburn Island & Waquoit Bay. Sleeps 6 with 1-floor living, AC, laundry, large back deck, and outdoor shower. Nearby, you'll find dining/shopping areas, wineries/breweries, & more. A short drive to Woods Hole offers fast boats to Martha's Vineyard. Book now and enjoy Sandy Feet Retreat.

4.93 out of 5 average rating, 209 reviews

The exterior of a charming house is shown, featuring a gray shingle facade and a welcoming covered porch. Lush greenery and ornamental shrubs frame the entrance, while a gravel driveway leads up to the front door, creating an inviting approach.

Home in Oak Bluffs

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!

5 out of 5 average rating, 7 reviews

A three-story townhome is nestled among lush greenery, showcasing a muted gray exterior. Large windows bring natural light into the living spaces. A patio is visible on the lower level, furnished with outdoor seating, offering a tranquil view of the surrounding landscape.

Townhouse in Oak Bluffs

Oak Bluffs Renovated Retreat

Fully renovated for 2025, this 3-bed, 2.5-bath townhome invites you to unwind with a community pool, tennis courts, and direct access to Sengekontacket Pond. Inside, a custom chef’s kitchen, new baths, and luxury furnishings set an upscale coastal tone. The main level flows from a sun-lit living room to dining area / deck, and powder room. The entire second floor is reserved for the primary suite. The walk-out lower level offers two guest bedrooms, a full bath, laundry, and a private patio.

4.92 out of 5 average rating, 49 reviews

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

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.

5 out of 5 average rating, 64 reviews

The exterior of a spacious cottage is displayed, framed by vibrant green lawns and seasonal flowers. A stone pathway leads up to the entrance, with pumpkins placed decoratively in the garden area. The clear blue sky enhances the overall inviting presence of the home.

Guesthouse in Woods Hole

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

4.95 out of 5 average rating, 58 reviews

A view from the deck reveals a well-maintained pool area surrounded by lounge chairs and umbrellas. Adjacent to the pool is a tennis court, framed by greenery, providing a serene backdrop. The water sparkles under a clear blue sky, inviting relaxation.

Home in East Falmouth

Dog Friendly Cape Oasis | Pool+Beach |Tennis Court

This newly renovated beach cottage, designed by Wil&Co. Homes, is the perfect getaway for Cape lovers. Walk to the private association beach, bring you kayaks or canoes and launch them from the many water access points, and enjoy access to the association pool and tennis courts. This airy retreat has room for the whole family (including dogs) or group of friends with a fire pit, large backyard and game room. 7 Min Drive to Menauhant Beach 13 Min Drive to Downtown Falmouth

4.93 out of 5 average rating, 100 reviews

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

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.

Apartment in Hyannis Port

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.

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.

4.94 out of 5 average rating, 107 reviews

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

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.

4.97 out of 5 average rating, 165 reviews

Condo in New Seabury

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).

Popular amenities for Tisbury rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.99 out of 5 average rating, 90 reviews

A spacious backyard features a circular fire pit surrounded by Adirondack chairs in various colors. In the distance, an inviting in-ground pool is visible, complemented by lush greenery and trees lining the property, creating a serene outdoor setting.

Home in Sandwich

"Cape Escape" luxury home w/pool & beach access.

5 out of 5 average rating, 19 reviews

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

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

5 out of 5 average rating, 6 reviews

A welcoming exterior view of a modern house is presented, featuring a well-maintained path leading to the entrance. Flanking the walkway, neat landscaping includes flowering bushes and a lush green lawn. A bright sun casts a soft glow over the façade, enhancing the inviting atmosphere.

Home in Mashpee

Mashpee Manor Pool House

4.88 out of 5 average rating, 25 reviews

An aerial view of a spacious backyard features a heated pool surrounded by a grey stone patio. Lounge chairs and umbrellas are positioned around the pool. The house showcases multiple large windows and a deck, with green grass and trees creating a private setting.

Home in Plymouth

Mansion with Heated Pool Near Ocean

4.85 out of 5 average rating, 66 reviews

A charming Cape-style house is surrounded by lush green grass, featuring a well-maintained front yard adorned with flower beds and small American flags. The entrance is highlighted by a decorative door with a wreath, framed by neatly arranged bushes. A single-car garage is visible on the right.

Home in Mashpee

Sunny Cape w/Private Pool, Steps to Private Lake

4.93 out of 5 average rating, 54 reviews

A spacious colonial house is framed by lush green grass and mature trees. The exterior features dark shingles with multiple windows reflecting natural light. A winding driveway leads to the entrance, while a wooden fence provides privacy at the rear.

Home in Edgartown

Beautiful Edgartown Colonial with heated pool.

4.87 out of 5 average rating, 31 reviews

The exterior of a spacious home is depicted, featuring a peaked roof and well-manicured landscaping. Lush green shrubs and blooming hydrangeas frame the entrance, while a driveway leads to a two-car garage. A flag decorates the front, conveying a welcoming environment.

Home in Falmouth

Sippewissett Forest Magic by the Sea

4.91 out of 5 average rating, 35 reviews

An aerial view of a spacious property featuring a uniquely shaped heated saltwater pool surrounded by a stone patio. A large deck is positioned next to the pool, with several lounge chairs arranged nearby and greenery framing the area.

Home in New Seabury

Home w/ golf view, salted heat pool, mins to beach

Condo rentals with a pool

An inviting outdoor pool area is framed by neatly arranged lounge chairs under vibrant blue umbrellas. Surrounding trees provide shade, enhancing the tranquil setting. The pool invites relaxation and enjoyment, with sunlit water reflecting the clear blue sky.

Condo in Mashpee

4.67 out of 5 average rating, 3 reviews

2BR Condo in Cape Cod w/ Patio & Laundry

A spacious living area features a large dark leather sectional sofa with decorative pillows. The room is illuminated with natural light and displays coastal-themed artwork on the walls, adding a relaxed atmosphere. A sliding barn door is visible, contributing to the modern design.

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.

4.65 out of 5 average rating, 51 reviews

Lovely lakefront studio/condo with pool

A two-story building designed in a classic Cape Cod style is showcased, featuring a large balcony on the front. Lush green landscaping surrounds the building, enhancing the tranquil outdoor setting. Nearby structures are visible, displaying similar architectural features.

5 out of 5 average rating, 8 reviews

Beachside Villiage-Oceanfront

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.

5 out of 5 average rating, 4 reviews

Two bedroom condo .on the water Falmouth, ma

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

4.94 out of 5 average rating, 16 reviews

5 Mi to Mashpee Commons: Coastal Mashpee Condo

A circular seating area is arranged around a stone fire pit, featuring several wooden Adirondack chairs placed on a sandy surface. Lush greenery and distant water views create a serene outdoor setting, ideal for gatherings.

Condo in West Yarmouth

5 out of 5 average rating, 9 reviews

Memorial Day- Waterview Cove at Yarmouth- Cape Cod

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.

4.7 out of 5 average rating, 33 reviews

Condo in Falmouth MA

Other vacation rentals with a pool

4.96 out of 5 average rating, 24 reviews

The exterior of the house is presented, featuring a light-colored facade with a black roof and six front-facing windows. A porch is accessible with seating arranged nearby. A well-maintained lawn with flower beds is visible, complemented by a gravel driveway and American flag displayed.

Home in East Falmouth

Modern Cape Cod home steps to beach; pool access!

A spacious living area is furnished with a comfortable gray sofa and a dark wooden coffee table. A fireplace is positioned against the wall, and large windows with light, flowing curtains offer views of the outdoor space, including a pool and patio area.

Home in Vineyard Haven

4.88 out of 5 average rating, 8 reviews

Greenwood family fun.

5 out of 5 average rating, 7 reviews

A spacious deck features a wooden dining table with matching chairs, overlooking a private heated pool and serene water views. Lush greenery surrounds the area, while a private dock is visible along the shoreline.

Home in New Seabury

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

5 out of 5 average rating, 15 reviews

A charming single-story home is presented with a neatly manicured lawn, adorned with blooming blue hydrangeas. A flag is displayed on the front porch, and large windows provide a view of the inviting interior. The clear blue sky complements the home's fresh appearance.

Home in Hyannis Port

Renovated Cape Oasis W/ New Pool and Game Room!

4.56 out of 5 average rating, 9 reviews

A cabin with a light green exterior is framed by lush trees. Four adirondack chairs surround a stone fire pit set on a grassy area. A charcoal grill is positioned nearby, and a spacious deck is visible at the rear of the cabin.

Cabin in Falmouth

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

4.91 out of 5 average rating, 11 reviews

A swimming pool is visible with several lounge chairs arranged around it. The ocean can be seen in the background, along with a small gazebo. A clear blue sky complements the scene, enhancing the resort's coastal atmosphere.

Apartment in Falmouth

Ocean Front Resort Studio Unit

4.82 out of 5 average rating, 17 reviews

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

Centerville Oasis, Heated Saltwater Pool!