Holiday rentals with a pool in Oak Bluffs

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.

4.97 out of 5 average rating, 29 reviews

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

~~ You Have Arrived! Welcome to "The Fore Seasons" in desirable New Seabury on Cape Cod. ⛳️🏖🌸☀️ You will be sure to fall in love with old Cape Cod in this 4,500 sqft private home located on the 10th hole fairway of the championship golf course. With its 4 bedrooms, 4 bathrooms, Heated Inground Pool, Outdoor Shower, Putting Green, Ping Pong table and Ctrl Air there is enough room for the largest families. Pool open from Mid-May until through Columbus Day! Available year round for all gathering

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!

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.

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.

5 out of 5 average rating, 12 reviews

Home in Sandwich

Family Cape Cod Oasis-Pool-Hot Tub-Game&Kids Room

🏖🏝Welcome to your perfect Cape Cod escape - a beautifully updated 7-bedrooms and 3.5-bath home designed with both relaxation and family fun in mind. This private oasis is just minutes away from lakes, beaches, and shopping. This home offers the ultimate mix of comfort, entertainment, and kid-friendly amenities. Whether you are planning a family reunion, or a beach week with friends, this home is built to bring people together- comfortably and with style. Book your Cape Cod adventure today!

4.95 out of 5 average rating, 58 reviews

An indoor heated saltwater pool is showcased, surrounded by large windows that provide ample natural light and views of the landscaped garden outside. A hot tub is situated beside the pool, and indoor plants add a touch of greenery to the serene setting.

Villa in New Seabury

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.

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.

The exterior of the villa is framed by lush greenery and flowering shrubs. A brick pathway leads to a welcoming entrance, featuring a single red door. The home is situated in a peaceful residential area, surrounded by mature trees and landscaping.

4.94 out of 5 average rating, 16 reviews

Cape Gem in New Seabury with private heated pool

Our Pristine, Newly Renovated, Patio home with Private heated Pool, located in the Mews of New Seabury, offers the privacy and peacefulness for the perfect vacation. The sandy local beaches—South Cape Beach and Popponesett—are both very short drive away (5-10 minutes)! Highlights of the seashore resort community of New Seabury: Mashpee Commons (fine dining, shops, movie cinema), golf courses, boating, walking trails, close proximity to ferries to Nantucket and Martha’s Vineyard.

4.8 out of 5 average rating, 5 reviews

Condo in Edgartown

Brand New 2BR Condo w/ Pool. No Pets!

This beautifully renovated condo is in the heart of Edgartown. 5 min walk to downtown shops, restaurants, and waterfront. This unit has 2-bedrooms & 1.5-baths. The master has a king bed and half bath, and the second bedroom features a queen bed and full bath. Enjoy a spacious living room with high ceilings, a full kitchen, and access to outdoor spaces with a pool. Sleeps 4, this condo is the perfect base for your Martha's Vineyard adventure!

4.97 out of 5 average rating, 167 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).

Apartment in North Falmouth

A two-story, modern building features a stone facade and dark blue exterior accents. The front entry is framed by landscaped greenery. Stairs lead to an upper level, while large windows allow for ample natural light. The setting is surrounded by trees, offering a private atmosphere.

4.81 out of 5 average rating, 148 reviews

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 Oak Bluffs rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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.

4.91 out of 5 average rating, 22 reviews

Beautiful Mashpee Home with Pool

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.

5 out of 5 average rating, 7 reviews

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

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!

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.

5 out of 5 average rating, 6 reviews

Mashpee Manor Pool House

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!

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.

4.85 out of 5 average rating, 66 reviews

Sunny Cape w/Private Pool, Steps to Private Lake

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

5 out of 5 average rating, 25 reviews

A charming two-story house is featured, with a light gray exterior and blue front door. The inviting porch is furnished with wooden rockers, surrounded by manicured shrubs and vibrant pink flowers. Windows are symmetrically placed, creating a balanced, welcoming appearance.

Home in North Falmouth

New Construction Home with Pool in N. Falmouth

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

4.75 out of 5 average rating, 4 reviews

2BR Condo in Cape Cod w/ Patio & Laundry

A living and dining area features a light-colored stone coffee table and a wooden dining set with two chairs. A gray sofa with decorative pillows is positioned next to a lamp, while a coastal-themed artwork adorns the wall, contributing to a relaxed ambiance.

Condo in Oak Bluffs

Island Inn - Residential Suite - 35G - Oak Bluffs,

A serene saltwater pool is surrounded by lounge chairs and umbrellas, set among vibrant greenery. A colorful arrangement of blooming flowers frames the foreground, adding to the tranquil atmosphere of the outdoor area.

Condo in Mashpee

Cape Cod Townhouse w/ Patio & Kitchen

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

A cozy living and dining area features a light-colored sofa with decorative throw pillows, complemented by a wooden dining table surrounded by four chairs. A fireplace, framed art, and a warm-toned lamp enhance the space, while a patterned rug adds a touch of comfort.

Condo in Oak Bluffs

4.67 out of 5 average rating, 3 reviews

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

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

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

Bright, Coastal Mashpee Condo Near the Commons

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

4.7 out of 5 average rating, 33 reviews

Condo in Falmouth MA

Other holiday 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.

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

4.95 out of 5 average rating, 22 reviews

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.

Home in Cotuit

ShoestringBayHouse, waterfront & pool in Cotuit

4.83 out of 5 average rating, 6 reviews

Quaint, relaxing Cape Cod condo

4.91 out of 5 average rating, 55 reviews

Private POOL*New Seabury* 3 bedroom

A dining area features a wooden table surrounded by black spindle-back chairs, positioned on a blue and white chevron rug. Natural light streams through windows adorned with light blinds, illuminating the room's neutral walls and highlighting a small vase of flowers atop the table.

Home in West Tisbury

5 out of 5 average rating, 3 reviews

WestTisbury Charm, Carroll House