Vacation rentals with a pool in Edgartown

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!

5 out of 5 average rating, 5 reviews

Home in Vineyard Haven

Modern Family-home,POOL with lots of outdoor space

Staying in this spacious Martha's Vineyard home is extraordinary. With its modern structure, in both the main and guest house, not to mention the patios, and decks full of greenery and flowers. Enjoy the houses perks, check out the brand new hot tub, fire pit and outdoor grill! You'll love making memories with family and friends with all our outdoor accessories, like the showers and dining area (right next to the grill). And if your feeling extra active, enjoy a workout in the guest house gym.

4.95 out of 5 average rating, 57 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.

4.97 out of 5 average rating, 32 reviews

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

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.

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

May 26-27, 31; June 3-4 are $199/night July 26-Aug 1 available at $1575/night (6 nights) Please email me to discuss these dates and options. Memorial Day rentals commence: Saturday Welcome to ShoestringBayHouse, waterfront on Popponesset Bay. Our home overlooks the un-heated pool (opens May 15th), beach and bay. We include: Bikes, Kayaks, and a Barnstable beach pass. Pet friendly and spacious with 4 BR/ 4.5 baths is priced for six (6) adult guests. (other group size options available).

5 out of 5 average rating, 7 reviews

An inviting outdoor area features a heated in-ground pool surrounded by a wide patio of pavers. Sun loungers are positioned near the water, and a dining set is shaded under an umbrella. Lush greenery is visible in the background, providing a sense of privacy.

Home in Popponesset

49 Clover Lane, 3 beds, 3.5 baths, pool & firepit

Custom built home, nestled in the heart of the Popponesset. This exquisite property has a heated in-ground pool, surrounded by a spacious patio and gas fire pit. The pool, (seasonal) boasts a motorized cover, and a gas fire pit. The kitchen is complete with a central island, connected to the living room and breakfast area. Spacious bedrooms, fireplaced living room, with large screen TV. Experience the ultimate Cape Cod lifestyle, and a quick stroll to the Popponesset Inn and Marketplace.

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

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.

4.8 out of 5 average rating, 5 reviews

A bright living room is showcased, featuring white sofas and a light wood coffee table. A decorative shelving unit lines the wall, filled with various items. Large windows allow natural light to fill the space, and soft curtains frame the view of the outdoors.

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!

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.

4.91 out of 5 average rating, 35 reviews

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

Newly renovated home in the heart of New Seabury! You'll love the breathtaking golf course view from our backyard, where you can enjoy a heated saltwater pool, a large deck, and a patio with a fire pit. Our spacious home offers a fully equipped kitche, a coffee bar and plenty of open space for family gatherings. 5 minutes from the stunning South Cape beach, and surrounded by attractions like the Children's Museum and Mashpee Commons.

Popular amenities for Edgartown rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 23 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 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

4.91 out of 5 average rating, 22 reviews

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

Beautiful Mashpee Home with Pool

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

4.85 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

4.87 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, 26 reviews

An in-ground pool is surrounded by a spacious patio, featuring several blue lounge chairs. Lush greenery frames the area, with a clear blue sky overhead. The pool’s water reflects the sunlight, creating a refreshing ambiance for relaxation and entertainment.

Home in Hyannis Port

Hyannis Port Coastal Escape – Pool & Walk to Beach

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

4.96 out of 5 average rating, 24 reviews

A spacious pool area is enclosed by a white fence, surrounded by lush greenery. Lounge chairs are positioned around the edge of the inviting water, with trees and houses framing the scene in the background. The sky transitions to soft hues during sunset.

Condo in Vineyard Haven

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

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.

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

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,

4.63 out of 5 average rating, 8 reviews

An aerial view captures the resort's layout alongside the coastline. Sandy beach stretches along the water's edge, while the Atlantic Ocean meets a calm bay. Behind the resort, residential areas are interspersed with patches of greenery, illustrating the natural beauty surrounding the location.

Condo in Teaticket

InnSeason Resorts Surfside

A clear swimming pool is surrounded by a fenced area, with a light-colored deck. The two-story building in the background features balconies and outdoor seating. Lush greenery is visible nearby, creating a relaxing environment.

Condo in Vineyard Haven

4.78 out of 5 average rating, 23 reviews

Martha’s Vineyard Condo * Near Ferry

4.69 out of 5 average rating, 32 reviews

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

Condo in Falmouth MA

The exterior of the home features a sloping roof with multiple skylights and is surrounded by well-kept greenery. A paved pathway leads to the main entrance, set against a backdrop of bright blue sky and lush, manicured landscaping.

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

A private backyard features a heated pool surrounded by a spacious deck. The contemporary two-story home, with large glass windows and doors, provides views of the lush greenery. Lounge chairs and umbrellas are arranged for outdoor relaxation.

5 out of 5 average rating, 27 reviews

New Seabury pool/hot tub near beach,Popponesett

A heated in-ground pool is surrounded by a spacious patio, featuring a dining set with green chairs and an umbrella for shade. Lush trees are visible in the background, providing natural cover and enhancing the outdoor space's open feel.

5 out of 5 average rating, 3 reviews

Private home with heated pool near the beach!

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

5 out of 5 average rating, 12 reviews

The interior features a spacious living area with a cozy sectional sofa and two small tables. Skylights above provide natural light, illuminating the neutral-toned decor and textured rug. The open floor plan connects to the dining area and kitchen, visible in the background.

Home in East Falmouth

Sunny Loft - Seasonal Pool & Beach access

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

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

4.72 out of 5 average rating, 202 reviews

Poseidon's Palace - 2.0

5 out of 5 average rating, 11 reviews

The exterior of the home is surrounded by lush greenery and features a spacious deck. A retractable awning provides shade over the seating area, while the charming wooden siding and multiple skylights add character to the structure. The clear blue sky enhances the inviting atmosphere.

Home in West Tisbury

West Tisbury Gem with Deck + Association Pool