Gloucester County rentals with pool

We found 918 rentals with pool — enter your dates for availability

Where to?

Dates

Calendar
Flexible dates

November 2025

December 2025

Explore Gloucester County rentals with pools

Showing deals for: 30 Jan - 2 Feb

Premier Host

Squeaky Shores Gloucester, VA Waterfront York River Oasis

Sleeps 10 · 5 bedrooms · 4 bathrooms

for 3 nights, 1 home

AU$1,181 per night

includes taxes & fees

Wide water views looking out to the Chesapeake Bay from living room.

Premier Host

MILLION $ VIEWS NO EXTRA CHARGE! HOT TUB! POOL! BEACH! RESORT-LIKE AMENITIES!

Sleeps 6 · 3 bedrooms · 1 bathroom

for 3 nights, 1 home

AU$508 per night

includes taxes & fees

Gorgeous Waterfront Estate--Private Pool, Pier, Tennis Court, Firepit

Sleeps 12 · 5 bedrooms · 2 bathrooms

for 3 nights, 1 home

AU$1,062 per night

includes taxes & fees

Relax On Rappahannock, in Urbanna, Not Only For Oyster Fest, @ The Blue Tango!

Sleeps 5 · 2 bedrooms · 2 bathrooms

for 3 nights, 1 home

AU$217 per night

includes taxes & fees

Chesapeake Bay Cottage, Private Pool, Pier and Kayaks

Sleeps 6 · 3 bedrooms · 2+ bathrooms

for 3 nights, 1 cottage

AU$757 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Rentals with Pool in Gloucester County

Rentals with Pool in Gloucester

Rentals with Pool in Gloucester Point

Rentals with Pool in Hayes

Holiday Rental options in Gloucester County

Oceanfront holiday rentals in Gloucester County

Family-friendly holiday rentals in Gloucester County

Holiday rentals with spa pool in Gloucester County

Ski holiday rentals in Gloucester County

Monthly rentals in Gloucester County

Pet-friendly holiday rentals in Gloucester County

Lake holiday rentals in Gloucester County

Beach holiday rentals in Gloucester County

Mountain holiday rentals in Gloucester County