Vacation rentals with a pool in Martha's Vineyard

Find and book unique homes with a pool on Airbnb

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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Top guest favorite

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!

Top guest favorite

Home in Oak Bluffs

4.93 out of 5 average rating, 198 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 favorite

Home in Mashpee

5 out of 5 average rating, 12 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 favorite

Home in Mashpee

5 out of 5 average rating, 18 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 is open from Mid-May until end of Sep. Available year round for all gatherings!

Guest favorite

Apartment in Hyannis

4.89 out of 5 average rating, 123 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, and kettle. This studio has air conditioning.

Top guest favorite

Guest suite in Centerville

4.99 out of 5 average rating, 73 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.

Superhost

Home in Wareham

4.93 out of 5 average rating, 73 reviews

Edgewater Coastal Retreat with Heated Pool

Coastal farmhouse on salt water inlet off Buzzards Bay. Gourmet outdoor kitchen with commercial grill & stove/oven, sink & refrigerator. In-ground pool (heated for small feee). Outdoor game pavilion with ping pong table & foosball. Fishing & kayaking off back yard - kayaks & life jackets provided. Playground right next door. Minutes to down town stores/restaurants, public boat launch and many local beaches. Space for trailered boat at house. Come and relax and leave refreshed!

Guest favorite

Guesthouse in Falmouth

5 out of 5 average rating, 53 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

Guest favorite

Home in Oak Bluffs

4.96 out of 5 average rating, 47 reviews

Private Heated Pool, Wifi, AC, Grill & Firepit

FULL INTERIOR RENOVATION FOR SUMMER 2025! This home is being completely transformed with high-end finishes. Nestled on 1.2 fenced-in acres, just 2 miles from Oak Bluffs, it's perfect for family gatherings, bachelorettes, and retreats. Enjoy a heated pool (5/15-9/7), hot tub (closes 11/15), fire pit, grill, outdoor shower, AC/heat in every room, WiFi, smart TVs, and a half basketball court. A true Vineyard escape!

Guest favorite

Cottage in Edgartown

4.98 out of 5 average rating, 97 reviews

Lovely two - story private cottage.

This private beach cottage offers comfort and style. Oversized 2nd floor bedroom with queen bed (Designer quilts) full bath and shower (in and out) Nicely furnished over 900 sf and And immaculately kept. Nice grill And sitting area in back. And please Use the built in pool! It sits equi-distant 1.5 miles to downtown Edgartown and south beach. And convenient 5 min walk to bike path or bus route. Perfect location!

Superhost

Apartment in 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 favorite

Condo in Mashpee

4.98 out of 5 average rating, 135 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.