
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

Stoney Spring Overlook

Waterfront Paradise with a Private Pool

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

Bay Breeze Retreat

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit

Bury Oasis: Pool, Hottub, Movie Theatre, Game Room

5 BEDR, Inground Pool+Billiard Table, Close To D.C

Casa Blanca—where luxury meets tranquility
Condo rentals with a pool

Oceanfront Condo: Beach, Pool & Balcony Views!

DownByTheBay 4601-Midtown/Oversize Sleep 15 w/Pool

🌊Oceanfront studio w/ amazing views & amenities🏖

WraparoundBalcony-2 Bed-Sleeps 8-Pool-Laundry-WiFi

OCEAN FRONT Gem w/Pools, Movie Theater, Gameroom

🌊 NOTHING BEATS OCEANFRONT!!! 🌊

Direct Ocean Front/Gorgeous Views/Indoor Pool

Getaway in Ocean Pines
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