Holiday rentals with a pool in Tisbury

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Top-rated rentals with a pool in Tisbury

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

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Top guest favourite

Home in Cotuit

4.95 out of 5 average rating, 115 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!

Top guest favourite

Flat in Barnstable

4.95 out of 5 average rating, 37 reviews

Studio Apartment

Private Studio apartment on lower level of Main House with deck overlooking Pond. Queen bed, single sleeper sofa and small sleeping loft. Very comfortable for 2 people but could sleep up to 4. Kitchenette with dinnerware and cookware. Coffee maker, full size fridge, microwave, toaster oven, outside gas grill. Private bath with shower. TV, WiFi, A/C. Pond access, SUP, kayaks available. Pool and hot tub at Main House. Sunrise views. Golf courses, shopping, restaurants, and beaches nearby.

Top guest favourite

Home in Oak Bluffs

4.93 out of 5 average rating, 199 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 Popponesset

5 out of 5 average rating, 13 reviews

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.

Guest favourite

Barn in Woods Hole

5 out of 5 average rating, 12 reviews

Falmouth/Woods Hole Carriage House Roost

Welcome to our Cozy Carriage House Apartment located only a few 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

Guest favourite

Apartment in Tisbury

4.92 out of 5 average rating, 48 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.

Superhost

Home in Plymouth

4.89 out of 5 average rating, 121 reviews

Seaview Summit | Ocean Views, Indoor Pool, Beach

Welcome to Seaview Summit House, where you can enjoy breathtaking panoramic ocean views, take a dip in our heated swimming pool, and take a short walk to the beach. Our spacious and beautifully decorated home features a large living area with comfortable seating, a fully equipped kitchen with all the essentials, and a dining area that seats everyone. You'll have plenty of room to spread out and enjoy your time together, whether you're lounging inside or soaking up the sun outside.

Top guest favourite

Guest suite in Centerville

4.99 out of 5 average rating, 76 reviews

Cape Cod Hideaway

Enjoy a bit of Cape Cod in a neighborhood of lush green trees , flower gardens, and a walking trail. Less than 1 mile from Centerville's shops and restaurants. Only 2 miles from Craigville Beach and its beachside walk up shanty’s for fresh seafood / burgers. Main street Hyannis is the "Hub" of the Cape and a quick 10-minute drive. Explore the many beaches and local fare by day and the lively clubs at night. Ocean docks, marinas, and ferries to the islands are a 10–15-minute drive.

Guest favourite

Home in New Seabury

5 out of 5 average rating, 12 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.

Superhost

Flat in Falmouth

5 out of 5 average rating, 3 reviews

Deluxe Studio Steps From Surf Drive

Stay in our deluxe studio at Beachside Village in Falmouth, MA—ideal for couples or families of four. Each unit features a Queen bed, Queen sleeper sofa, air conditioning, and a kitchenette with a dining area. Enjoy views of Martha’s Vineyard, stroll through nearby village shops, and unwind on Surf Drive Beach just steps away. Your perfect Cape Cod retreat awaits with a touch of coastal history and comfort.

Superhost

Flat in North Falmouth

4.83 out of 5 average rating, 138 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!

Top guest favourite

Apartment in New Seabury

4.98 out of 5 average rating, 141 reviews

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 only 5 minutes away by car or bike.