
Vacation rentals with a pool in Dukes County
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Top-rated rentals with a pool in Dukes County
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Popular amenities for Dukes County rentals with a pool
House rentals with a pool
Top guest favourite

Home in Falmouth
5 out of 5 average rating, 15 reviewsBrand new 4 BR, can walk to pool & close to beach!
BonnieRating, 5 stars9 months ago
Erin’s home is awesome! We rented it for our daughter’s and their families - 4 adults, 4 children shared the home for the week. The house was SPOTLESS at check in, and so well appointed, from kids toys, kitchen staples, beach chairs, beach towels, bicycles, a fabulous outdoor dining patio with large table/chairs/umbrella, quality bed linens, towels, etc. and rooms full of nice, comfortable furnishings. The neighborhood is fabulous, especially for families who want to enjoy the pool (which is awesome!)/playground/small beach area. It was quiet and relaxing and very walkable and there are also several larger Falmouth beaches you can drive to within a few minutes. Downtown is about a 5 minute drive to shops, restaurants and grocery stores. All in all, it’s a great house in a really great location!

Home in West Tisbury
5 out of 5 average rating, 5 reviewsCharming Getaway Post&Beam Home Cozy and Sweet
SarahRating, 5 stars9 months ago
Our family stayed at Madi's place for our summer vacation. Madi was very responsive and communicative prior to our stay with local recommendations and instructions for the home and beach passes. Our family of 5 was comfortable and we had a wonderful time on MV. Would definitely return to Madi's place.

Home in Falmouth
5 out of 5 average rating, 4 reviewsHeated pool, walk to beach, town
MaeveRating, 5 stars7 months ago
Perfectly located between beach and town. Backyard well manicured and welcoming.
Guest favourite

Home in Edgartown
5 out of 5 average rating, 6 reviewsSunny condo with pool, central to beach & town
JamesRating, 5 stars8 months ago
Exactly what we hoped for: Quiet, peaceful, friendly neighbors, and close to the restaurants in Edgartown. The pool was perfect for late afternoons/early evenings with the kids after long days at the beaches. Our hosts were very quick to respond to any messages or questions we sent. We loved our week here and look forward to coming back next year.

Home in Edgartown
4.56 out of 5 average rating, 9 reviewsMagical House & Pet Friendly! Swim Spa/Jacuzzi
RebeccaRating, 5 stars8 months ago
Alan was a fantastic host. The house felt much bigger than the pictures and smelled clean when we arrived. The pool was also great for our kids. We slept comfortably and it was a great quiet neighborhood to go for walks. Also, very close to south beach and easy to get into Edgartown. Would highly recommend!

Home in West Tisbury
4.75 out of 5 average rating, 8 reviewsWest Tisbury Beach House
CaryRating, 5 stars10 months ago
Lovely location and very clean. Good spot to travel qround island. Lambert Cove was beautiful at sunset. If you have a bad back you might want to bring a mattress pad.
Guest favourite

Home in West Tisbury
5 out of 5 average rating, 8 reviewsWest Tisbury Gem with Deck + Association Pool
SamanthaRating, 5 stars8 months ago
Rachel’s house was great, and had everything anyone would need… Beds were comfortable, water pressure in showers was perfect. Most importantly, Rachel was so lovely to deal with… She was very responsive and helpful. Highly recommend!!!
Condo rentals with a pool

Condo in Oak Bluffs
4.92 out of 5 average rating, 13 reviewsSpectacular Martha's Vineyard Island Home!
StephenRating, 5 stars24 months ago
Thank you for your hospitality. The stay was great and you were a pleasure to deal with.

Condo in Tisbury
4.7 out of 5 average rating, 23 reviewsHeart of VH, w/ac, pool & harborview
LaurenRating, 5 stars9 months ago
Great unit! Had everything we needed for a weekend stay, close to Vineyard Haven and the ferry. Unit was clean and Matthew was very easy to communicate with! Would stay again!

Condo in Mashpee
5 out of 5 average rating, 4 reviewsCapecation! 3-bedroom condo with heated pool
KarlRating, 5 stars8 months ago
We drove from Maryland up to the Cape, through lots of traffic. The host was great and responsive, suggesting great places for dinner. Our week was just amazing, wish we could have stayed longer. The pool was a perfect way to start and end the days and the bikes were a great way to explore the neighborhood. We really hope to return, just so much more we wanted to do.

Condo in Falmouth
5 out of 5 average rating, 3 reviewsTwo bedroom condo .on the water Falmouth, ma
RobertRating, 5 stars32 months ago
this is a great unit with lots of space for the family. so much to do on the cape and near by. but you can just park the car and just stay put with a beach and pool! everything went perfect

Condo in Oak Bluffs
New place to stayIsland Inn - Residential Suite - 35G - Oak Bluffs,
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- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Brown University
- Easton Beach
- Sandwich Glass Museum
- Owen Park Beach
- Sagamore Beach
- New Silver Beach
- Onset Beach
- Lighthouse Beach
- Roger Williams Park Zoo
- Oakland Beach
- Fort Adams State Park
- Pinehills Golf Club
- Nickerson State Park
- South Shore Beach
- Scusset Beach
- Grey's Beach
- Coast Guard Beach
- Oyster Harbors Beach