Vacation 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.
Vacation 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
Home in Ocean City
4.94 out of 5 average rating, 219 reviewsMad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB
Jan 15 – 22
Home in Kent Narrows
5.0 out of 5 average rating, 278 reviewsChester Riverfront At Kent Narrows
Oct 19 – 26
Home in Stevensville
5.0 out of 5 average rating, 101 reviewsChesapeake Bay Waterfront ARTectural Home w/ Pool!
Apr 3 – 10
Home in Oakland
4.95 out of 5 average rating, 192 reviewsPrivate|LAKE&Waterfalls|Firewood|HotTub|Comm. Pool
Mar 28 – Apr 4
Home in Chesapeake Beach
4.91 out of 5 average rating, 111 reviewsIndoor pool/spa nestled in Southern Md. woods.
Jul 7 – 14
Home in Edgewater
4.95 out of 5 average rating, 119 reviewsHouse in Edgewater Maryland
Jan 31 – Feb 7
Home in Saint Michaels
4.97 out of 5 average rating, 238 reviewsMiles Aweigh
Apr 4 – 11
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
Nov 15 – 22
Condo rentals with a pool
Condo in Ocean City
4.85 out of 5 average rating, 100 reviews2 Bdrm Oceanfront-Pool, Xbox, Pickleball, Gym, HBO
Oct 25 – Nov 1
Condo in Ocean City
4.97 out of 5 average rating, 225 reviewsDirect Oceanfront with a View and Amenities Galore
Nov 27 – Dec 4
Condo in Ocean City
4.94 out of 5 average rating, 169 reviewsGorgeous Oceanfront Condo- Beach, Pool, Hot Tub!
Nov 17 – 24
Condo in Ocean City
4.89 out of 5 average rating, 164 reviews🌊Oceanfront studio w/ amazing views & amenities🏖
Nov 26 – Dec 3
Condo in Ocean Pines
4.96 out of 5 average rating, 108 reviewsWaterview Retreat
Nov 1 – 8
Condo in Ocean City
4.91 out of 5 average rating, 256 reviewsOcean Front 802 Midtown Oasis Pool & Parking
Feb 5 – 12
Condo in Ocean City
4.82 out of 5 average rating, 137 reviewsRomantic Beach Inscape-Best Ocean View+Heated Pool
Feb 13 – 20
Condo in Ocean City
4.9 out of 5 average rating, 114 reviewsA Serene Beachfront Getaway - 2 BR St. Tropez OC!
Dec 1 – 8
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