Vacation rentals with a pool in Martha's Vineyard

Chic Oak Bluffs Home with Hot Tub, Walk to Town

A chic coastal escape where upscale comfort meets effortless Vineyard charm. Nestled in the heart of Oak Bluffs and just a 15-minute stroll to Circuit Avenue and the beach, this 3-bedroom, 2-bath home is designed with elegance and ease in mind. Enjoy a serene coastal palette, brand new furnishings, a spacious deck for outdoor dining, and generous yards perfect for barbecues, games, and slow summer mornings. This cozy retreat is ideal for families or couples. It's a modern twist on island living!

“The Hideaway”Private Guest Suite/Pool/Beach Pass

Enjoy a bit of Cape Cod in a friendly and walkable neighborhood of lush green trees , flower gardens, and a walking trail. Less than 1 mile from Centerville's shops and restaurants. Less than 2 miles from Craigville Beach and its beachside walk up shanty’s for lunch. A small beach on Lake Wequaquet is only 2 miles down the road . Main street Hyannis, a walkable downtown with many shops and restaurants is a quick 10-minute drive. Ocean marinas, and ferries to the islands, are a 15 minute drive.

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 6/20-9/15/26. The reviews tell all!

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!

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.

"Cape Escape" luxury home w/pool & beach access.

Welcome to the Cape Escape! Enjoy views of Spectacle Pond from the 70 ft. deck of this recently renovated 5 bed/3 bath spacious home meeting all your needs! Relax by the in-ground pool in the private enclosed yard. Enjoy nights around the fire-pit. Directly across the driveway you can enjoy kayaking, sunbathing & swimming at the neighborhood beach. Within 6 miles of the home you will find the historic Sandwich boardwalk, Ocean beaches, Cape Cod Canal and more! Perfect for family gatherings!

In-Ground Pool Oasis | 5 Min to Cape Cod Beaches!

Stunning in-ground pool HEATED in May, June, Sept only. Pool is opened in May! 5 minutes from Craigville, Dowses and Covell's Beach! Perfect for mid-size groups or families, this home sleeps 8 and boasts a dreamy, private, fenced-in backyard w/ a, pool house w/ TV & bar, outdoor shower, and cozy patios. Complete w/ all your beach essentials. We're 13 minutes from Mashpee Commons and 10 minutes from local grocery stores, local bakeries& restaurants. Central to all the Cape has to offer!

Falmouth/Woods HoleCarriage 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

ShoestringBayHouse, waterfront & pool in Cotuit

Rent four nights: get the 5th night for $49 Prime Summer 2027: rates in the area of $10,000-13,775; please inquire Welcome to ShoestringBayHouse in Cotuit, waterfront on Popponesset Bay. It's all about the views. Our home overlooks the pool, beach and bay. We include: 2-Bikes, 2-Kayaks, and a Barnstable beach pass with beach chairs. Pet friendly and spacious with 4 BR/ 4.5 baths is priced for six adult guests plus children. Pool: May 15th through late October

The Holly Cottage

Welcome to Centerville, enjoy this fully equipped 1 bedroom 1 bath home with an easy walk or ride to just about everything. Enjoy the nearby ocean and beaches, or take a ride downtown to Main Street for dining and entertainment. Only a short distance to the ferries for a day trip to the islands and you can be back in time to catch a concert at the Melody Tent. Enjoy your days by the pool and your evenings grilling out on the large deck or chatting with the koi fish.

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.

New Seabury Cape Condo | Pool & Beach Escape

Top 5% of Air Bnbs! Welcome to your coastal getaway at The Mews in New Seabury, Mashpee—a refined Cape-style condo tucked within an intimate golf course community. This exclusive enclave of just 15 residences offers a peaceful, private escape with access to a shared association pool reserved solely for residents. Enjoy nearby beaches like South Cape Beach State Park and Mashpee Town Beach, both just minutes away, for the perfect Cape Cod retreat.