Photo by throwingsofas

Highland County rentals with pool

We found 12 rentals with pool — enter your dates for availability

Where to?

Dates

Calendar
Flexible dates

September 2025

23

October 2025

Explore Highland County rentals with pools

Exterior

All season getaway. Relax at The "Wilberness" Log Cabin close to Rocky Fork Lake

Sleeps 8 · 2 bedrooms · 1 bathroom

Terrace/patio

Premier Host

Amish-built cabin, serene and peaceful with pond and private dock for fishing.

Sleeps 5 · 2 bedrooms · 1 bathroom

This close-up view highlights the beautiful architectural design and bold contrast of the black metal roof and stone accents. The wide porch and symmetrical layout give the home a clean and inviting presence.

Country Cornerstone Retreat, Pool | Game Room | Theater | Hot Tub | Massage

Sleeps 8 · 3 bedrooms · 3+ bathrooms

Find spaces that suit your style

House

Condo/Apartment

Rentals with Pool in Highland County

Rentals with Pool in Greenfield

Rentals with Pool in Leesburg

Rentals with Pool in Lynchburg

Rentals with Pool in Highland

Rentals with Pool in Mowrystown

Rentals with Pool in Sinking Spring

Rentals with Pool in Hillsboro

Holiday Rental options in Highland County

Family-friendly holiday rentals in Highland County

Oceanfront holiday rentals in Highland County

Holiday rentals with spa pool in Highland County

Lake holiday rentals in Highland County

Beach holiday rentals in Highland County

Ski holiday rentals in Highland County

Mountain holiday rentals in Highland County

Pet-friendly holiday rentals in Highland County

07240a6f-37be-6c7e-17a1-74082fa0c62cd4830555-c6a4-4f27-8522-8b0ef9e7c924