Dukes County rentals with pool

We found 353 rentals with pool — enter your dates for availability

Where to?

Dates

Calendar
Flexible dates

October 2025

November 2025

Explore Dukes County rentals with pools

Outdoor pool

The Club at New Seabury

Sleeps 6

Pool

Premier Host

Modern 4 bed/3.5 bath Farmhouse, private HEATED POOL and AC on bike path

Sleeps 10 · 4 bedrooms · 3+ bathrooms

Find spaces that suit your style

House

Condo/Apartment

Rentals with Pool in Dukes County

Rentals with Pool in Oak Bluffs

Rentals with Pool in Aquinnah

Rentals with Pool in Chilmark

Rentals with Pool in Gosnold

Rentals with Pool in Edgartown

Rentals with Pool in Vineyard Haven

Holiday Rental options in Dukes County

Mountain holiday rentals in Dukes County

Oceanfront holiday rentals in Dukes County

Lake holiday rentals in Dukes County

Family-friendly holiday rentals in Dukes County

Beach holiday rentals in Dukes County

Pet-friendly holiday rentals in Dukes County

Ski holiday rentals in Dukes County

Holiday rentals with spa pool in Dukes County

d651e85d-57d4-f26c-f791-7e16a9ec7c6fcb7e5159-d778-4e2e-9cdc-0435a48f3c88