
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.
Vacation rentals for every style
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Popular amenities for Dukes County rentals with a pool
House rentals with a pool

Greenwood family fun.

Brand new 4 BR, can walk to pool & close to beach!

Charming Getaway Post&Beam Home Cozy and Sweet

Heated pool, walk to beach, town

Summer 2025 Open!Walk to Great Pond, central a/c

Magical House & Pet Friendly! Swim Spa/Jacuzzi

West Tisbury Beach House

West Tisbury Gem with Deck + Association Pool
Condo rentals with a pool

Surfside Resort Cape Cod, Falmouth MA

Spectacular Martha's Vineyard Island Home!

Heart of VH, w/ac, pool & harborview

1BR w/ Fireplace & Beach Access | Pool + Hot Tub

Island Inn - Residential Suite - 35G - Oak Bluffs,

InnSeason Resorts HarborWalk

InnSeason Resorts Surfside
Other vacation rentals with a pool

Cozy Studio Near Surf Drive Beach

1BR w/ Fireplace & Beach Access | Pool + Hot Tub

Private 3bdrm Condo Tashmoo Woods

Beautiful Edgartown Colonial with heated pool.

Waterside Guest House

Sunny 2bedroom condo w pool, walk to town

Sippewissett Forest Magic by the Sea

Spacious 2BR by the Sea in Falmouth
Destinations to explore
- Pet-friendly rentals Dukes County
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- Rentals with a patio Dukes County
- Rentals with a washer and dryer Dukes County
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- Rentals with lake access Dukes County
- Waterfront rentals Dukes County
- Apartment rentals Dukes County
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- Rentals with a hot tub Dukes County
- Rentals with beach access Dukes County
- House rentals Dukes County
- Rentals with pools Massachusetts
- Rentals with pools United States
- Cape Cod
- Sea Street Beach - East Dennis
- West Dennis Beach
- Brown University
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Onset Beach
- Point Judith Country Club
- Easton Beach
- Oakland Beach
- Coast Guard Beach
- Horseneck Beach State Reservation
- White Horse Beach
- Roger Williams Park Zoo
- Second Beach
- Chapin Memorial Beach
- Island Park Beach
- Pinehills Golf Club
- Nauset Beach
- The Breakers
- Lighthouse Beach
- South Shore Beach
- Inman Road Beach