Holiday rentals with a pool in Edgartown

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, 14 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.

Superhost

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

NOTE: Summer calendar is blocked, you must inquire for accurate availability Waterfront w/ a private heated pool & private dock just off Ockway Bay that leads to Nantucket sound. The home consists of 5 bedrooms with water views (3 king beds & 6 twin beds), 2 kitchen areas, 2 living areas, and 3 full bathrooms. Enjoy the peaceful private setting on the waterfront decks, swim in the pool, or kayak to the beach. Central A/C & 2 kayaks provided. Boats may be docked at our dock w/ owner permission

5 out of 5 average rating, 22 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, 206 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, 18 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

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.

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 gem within the vibrant Cape Cod beach community of Seacoast Shores. Take a 2-min walk to the private beach where you can swim, sunbath and watch the boats go by or take a 15-min walk (3-min drive) to the community clubhouse with seasonal access to an Olympic sized pool, kids wadding pool and restaurant. After a day at the beach or pool, head back to the newly built “cape cod” style home with plenty of room to spread out. Cap off your day on the back patio with smores on the firepit.

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

Welcome to ShoestringBayHouse, waterfront on Popponesset Bay. Our home overlooks the un-heated pool, beach and bay. Includes: Bikes, Kayaks, and a Barnstable beach pass. Our pet friendly and spacious home with 4 BR/ 4.5 baths is priced for SIX adult guests but our home will accommodate up to eight (8) guests at additional cost (we do not count infants/toddlers) Pool, kayaks and bikes: May 15th to Oct 15th Guest is responsible for reading all guidebooks, descriptions and policies.

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.

Apartment 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.

Guest house in Woods Hole

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.

5 out of 5 average rating, 64 reviews

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, 55 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

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.