
Holiday rentals with a pool in Maryland
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Maryland
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Maryland rentals with a pool
House rentals with a pool

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB

Bay Breeze Retreat

Gorgeous, waterfront home - Perfect for Families.

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit

Waterfront, pool, pickleball

Saybrook Hall | Pickleball + Pool + Hot Tub

Chester Riverfront At Kent Narrows

River Heights Retreat (pool and hot tub)
Apartment rentals with a pool

Oceanfront 2 Bedroom-Sleeps 6-Indoor/Outdoor Pool

Gone Coastal *Pool* Bayside with view* Top Floor

Ocean Pines Getaway

Direct Oceanfront with a View and Amenities Galore

Caramar Couples Retreat

Luxury Living at National Harbor

Water Front Condo w/Pool Short Walk to Beach

2BRCapri: Indoor Pool, Game Room, Massage Chair
Other holiday rentals with a pool

Flohom 1 | Breathtaking Skyline 360° Views

Luxury Farmette -Private & Secluded-1hr to DC

Premium 1 BR Apt w/ Balcony | Placemakr Columbia

Heron Roost

Historic Gatehouse Master Suite

Cozy Farm Stay •Baby Goats •Fireplace • Family Fun

Casa Blanca—Heated Indoor Pool!

Waterfront Poolside Escape
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