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.

Guest favorite
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 the outdoors space. Beach & Pool (POOL HEAT STARTS SUMMER, 6/21) 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!
Nov 4 – 11
$475 per night
4.93 out of 5 average rating, 164 reviews
Guest favorite
Cottage in Sandwich
Blue Anchor Cottage - private hot tub getaway!
This newly renovated cottage is an amenity-filled launching point to explore all of Cape Cod! Just 0.4miles to the beach and with our own salt water pool, you’ll be able to fully enjoy the Cape's most historic town. Some of our favorites nearby: 2min- your local coffee shop 2min- great fish tacos + bar 2min- nice conservation area hike 2min- local convenience store 7min- downtown Sandwich 7min- golf course 9min- Sandwich Boardwalk 10min- Heritage Museums & Gardens 22min- Cape Cod Rail Trail
Oct 20 – 27
$302 per night
4.92 out of 5 average rating, 112 reviews
Guest favorite
Home in Plymouth
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 and I 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.
Sep 18 – 25
$495 per night
4.89 out of 5 average rating, 199 reviews

Popular amenities for Martha's Vineyard rentals with a pool

House rentals with a pool

Guest favorite
Home in Plymouth
Our Secret Garden
Feb 15 – 22
$350 per night
4.92 out of 5 average rating, 166 reviews
Guest favorite
Home in Sandwich
Luxurious Cape Escape w/pool & beach access.
Apr 11 – 18
$475 per night
4.99 out of 5 average rating, 67 reviews
Superhost
Home in Plymouth
Seaview Summit House | 5BR steps from beach
Feb 19 – 26
$903 per night
4.89 out of 5 average rating, 46 reviews
Guest favorite
Home in Wareham
Edgewater Coastal Retreat with Heated Pool
May 27 – Jun 3
$889 per night
4.93 out of 5 average rating, 59 reviews
Superhost
Home in Oak Bluffs
Sea Glenn Flowers Private home new to market
Jul 22 – 29
$969 per night
4.83 out of 5 average rating, 6 reviews
Superhost
Home in New Bedford
Poseidon's Palace - 2.0
Nov 5 – 12
$631 per night
4.79 out of 5 average rating, 149 reviews
Superhost
Home in Barnstable
Contemporary Gem with Private Pool!
Apr 17 – 24
$491 per night
4.69 out of 5 average rating, 13 reviews
Guest favorite
Home in Bourne
Cape House with Pool by Canal
Nov 25 – Dec 2
$217 per night
5.0 out of 5 average rating, 19 reviews
Guest favorite
Home in Cotuit
ShoestringBayHouse, waterfront & pool in Cotuit
Oct 29 – Nov 5
$267 per night
4.9 out of 5 average rating, 10 reviews
Guest favorite
Home in Rochester
South Coast Serenity - Quintessential New England
Feb 6 – 13
$484 per night
4.95 out of 5 average rating, 60 reviews
Guest favorite
Home in Barnstable
Private Pool, near beaches, 3 BR/3 BA, Central Air
Nov 23 – 30
$375 per night
4.94 out of 5 average rating, 99 reviews
Guest favorite
Home in Plymouth
Our families slice of heaven
Jun 19 – 26
$525 per night
4.95 out of 5 average rating, 38 reviews

Condo rentals with a pool

Guest favorite
Condo in Vineyard Haven
Relax....You're on Island Time......
Oct 29 – Nov 5
$300 per night
5.0 out of 5 average rating, 17 reviews
Guest favorite
Condo in Tisbury
Private 3bdrm Condo Tashmoo Woods
Dec 19 – 26
$400 per night
4.91 out of 5 average rating, 45 reviews
Guest favorite
Condo in Mashpee
The Cape Escape with Private Pool
Sep 5 – 12
$461 per night
5.0 out of 5 average rating, 54 reviews
Guest favorite
Condo in Mashpee
Sleep 6 @ New Seabury w/ Pool Access, All Seasons!
Jan 22 – 29
$160 per night
4.97 out of 5 average rating, 98 reviews
Superhost
Condo in Barnstable
Beachfront Complex in Hyannis
Aug 3 – 10
$400 per night
4.93 out of 5 average rating, 15 reviews
Guest favorite
Condo in Yarmouth
Memorial Day Week- The Cove at Yarmouth, Cape Cod
Aug 15 – 22
$300 per night
5.0 out of 5 average rating, 8 reviews
Superhost
Condo in Dennis
Bright & Airy - Condo In The Heart Of The Cape!
Dec 29 – Jan 5
$253 per night
4.81 out of 5 average rating, 36 reviews
Superhost
Condo in Yarmouth
South Yarmouth July 20-27, 2024 Sleeps 8
Jul 20 – 27
$450 per night
4.75 out of 5 average rating, 4 reviews
Superhost
Condo in Yarmouth
Fabulous 1 BR Condo at The Cove at Yarmouth!
Jul 20 – 27
$390 per night
New place to stay
Condo in Tisbury
Martha’s Vineyard Ground Condo * Pool * Near Ferry
Jan 20 – 27
$139 per night
4.75 out of 5 average rating, 4 reviews
Guest favorite
Condo in Oak Bluffs
Dog-friendly 1st-Floor 1BR Near Beach/Park | Pool
Nov 18 – 25
$204 per night
4.97 out of 5 average rating, 31 reviews
Guest favorite
Condo in Tisbury
Heart of VH, w/ac, pool & harborview
Aug 29 – Sep 5
$390 per night
4.74 out of 5 average rating, 19 reviews

Destinations to explore