Holiday rentals with a pool in Martha's Vineyard

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Top-rated rentals with a pool in Martha's Vineyard

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

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Guest favourite

Home in Barnstable

4.95 out of 5 average rating, 113 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!

Guest favourite

Condo in Brewster

4.97 out of 5 average rating, 177 reviews

Ocean Edge Resort-Pool Access-End Unit-2 bdr/2 bth

2nd floor Ocean Edge end unit condo located in the heart of Brewster with access to OE resort amenities: pools, gyms, tennis courts, as well as access to resort activities (fees apply). Easy access to Cape Cod Rail Trail for bicycles. Scenic route 6A offers arts & crafts galleries and local shops. A 10 minute car ride to a 36 hole Captains Golf course. Short ride to 10 Brewster bay beaches famous for tidal flats. A 30 minute ride to Cape Cod National Sea Shore. Welcome to your Happy Place!

Guest favourite

Villa in Mashpee

5 out of 5 average rating, 41 reviews

Heated Indoor Pool & Spa - Golf Course View

CHERRY BLOSSOM RETREAT Cold days, raining days, power outage won't be an issue if you can steal away to this home, with an indoor heated salt water pool and hot tub fully equipped with a backup generator, with a view of the famous 13-Hole Championship Golf Course Cape Cod. Our ultimate luxury home is filled with arcades, air hockey, foosball and other indoor entertainments for guests to enjoy, comfortably sleeps 6-8 and just a few minute drive to all of the amenities New Seabury has to offer.

Guest favourite

Home in Oak Bluffs

4.94 out of 5 average rating, 189 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!

Guest favourite

Home in Edgartown

5 out of 5 average rating, 16 reviews

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.

Superhost

Home in Plymouth

4.9 out of 5 average rating, 183 reviews

Thanksgiving House Dining Table seats 12-14

This beautiful 2.5 acre fully fenced in private property has gardens, an in-ground pool & pool house with an outdoor heated shower. Our home offers 2 kitchens, dining room seating 12, a great room, 3 bedrooms with private sitting areas & lower level with 2 bunk beds (bottoms are full beds) & exercise area. Outside are 2 grills & chiminea. We are 3 miles from the beach, shopping/cafes, 45 minutes from Boston (on a train route) and 20 minutes to Cape Cod. POOL can be HEATED for $500.00/Visit.

Guest favourite

Cottage in Edgartown

5 out of 5 average rating, 14 reviews

2br Cottage Steps to Beach w/pool

Welcome to Lighthouse Cottage the best location on island! This amazing XL deluxe cottage in the Harbor View Resort has it all with 2 King bdrms/2 master baths with outside shower all on the first floor! Walk to Lighthouse and Fuller beaches to take a swim in the ocean and play in the sand! Downtown Edgartown and lighthouse are just steps away with quaint shops and restaurants. Come jump in the pool, have a drink at the bar and dine at the restaurants on site. Come enjoy Vineyard lifestyle!

Guest favourite

Home in Plymouth

4.89 out of 5 average rating, 238 reviews

Ocean Side, Amazing View, close to town/beach, Spa

PRICING IS FOR 2 GUESTS, 1 BEDROOM, 1 BATH ONLY, can add additional bed/bath for a fee, YOU WILL HAVE THE HOUSE TO YOURSELF. We only use this listing to fill gaps when the larger listing isn't rented & will decline ALL WEEKENDS, HOLIDAYS, PEAK times and will only accept mid-week, non summer/holidays. Please read additional info. OCEAN FRONT, HISTORIC SUMMER COTTAGE, AMAZING VIEWS, GREAT LOCATION, less than 1 mile walk to town and beach. Hot tub, fireplace, stocked kitchen, fresh linens.

Guest favourite

Condo in Tisbury

4.91 out of 5 average rating, 47 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.

Guest favourite

Home in Oak bluffs

4.95 out of 5 average rating, 44 reviews

Private Heated Pool, Wifi, AC, Grill & Firepit

This house is perfect for family gatherings, bachelorette parties and retreats! The private heated pool is located on a 1.2 acre, fully fenced in parcel, two miles from the heart of Oak Bluffs. Backyard Stone Fire pit & outdoor grill 5 bedrooms, 4 full baths, 1 half bath Large outdoor shower AC / heat split in every room Wireless Internet & smart TV in every interior room Basketball court in front yard Our private Pool is open & heated from May 15 to September 7! Hottub closes 11/15

Guest favourite

Condo in Mashpee

4.98 out of 5 average rating, 128 reviews

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

Welcome to our beautiful Cape Condo located in The Mews at New Seabury Country Club in Mashpee, MA. Our unit provides access to a private condo association pool a 3 min walk from the unit. Also, we have: -5 min bike/car ride to beach -Central air, wifi, cable, gas grill -Located on Championship Golf Course -Beach chairs, beach towels/toys -New Seabury Village restaurants, mini-golf, bowling, museums -20 min drive to Hy-Line Ferry to Nantucket/Martha's Vineyard

Guest favourite

Home in Nantucket

4.93 out of 5 average rating, 14 reviews

Heated pool through October! Mid island oasis

Spend you days on Nantucket relaxing POOLSIDE at bACK At It. This Mid Island paradise is close to everything. Walk to Stop n Shop and the world-famous Chicken Box while being conveniently located 1.5 miles from downtown. bACK At It features easy living for you and the whole family with accommodations for 6 plus people, 2 full baths, and a wonderfully zen backyard and pool. Please enjoy our home as much as we have!