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
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
19–26 Jan
Home in Stevensville
5.0 out of 5 average rating, 101 reviewsChesapeake Bay Waterfront ARTectural Home w/ Pool!
3–10 Sep
Home in Berlin
4.78 out of 5 average rating, 174 reviewsOC, Md great amenities in community, near beaches
5–12 Nov
Home in Oakland
4.95 out of 5 average rating, 192 reviewsPrivate|LAKE&Waterfalls|Firewood|HotTub|Comm. Pool
8–15 Jun
Home in Chesapeake Beach
4.91 out of 5 average rating, 111 reviewsIndoor pool/spa nestled in Southern Md. woods.
27 Jan – 3 Feb
Home in Edgewater
4.95 out of 5 average rating, 119 reviewsHouse in Edgewater Maryland
1–8 Feb
Home in Saint Michaels
4.97 out of 5 average rating, 238 reviewsMiles Aweigh
19–26 Jun
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
15–22 Nov
Apartment rentals with a pool
Apartment in Ocean City
4.85 out of 5 average rating, 100 reviews2 Bdrm Oceanfront-Pool, Xbox, Pickleball, Gym, HBO
25 Oct – 1 Nov
Apartment in Ocean City
4.97 out of 5 average rating, 226 reviewsDirect Oceanfront with a View and Amenities Galore
27 Nov – 4 Dec
Apartment in Ocean City
4.94 out of 5 average rating, 169 reviewsGorgeous Oceanfront Condo- Beach, Pool, Hot Tub!
17–24 Nov
Apartment in Ocean City
4.91 out of 5 average rating, 256 reviewsOcean Front 802 Midtown Oasis Pool & Parking
19–26 Jan
Apartment in Ocean City
4.89 out of 5 average rating, 164 reviews🌊Oceanfront studio w/ amazing views & amenities🏖
26 Nov – 3 Dec
Apartment in Ocean Pines
4.96 out of 5 average rating, 108 reviewsWaterview Retreat
8–15 Oct
Apartment in Ocean City
4.89 out of 5 average rating, 152 reviewsPrime Condo North OC 2 Blocks to Beach w/ Pool
21–28 Feb
Apartment in Ocean City
4.9 out of 5 average rating, 114 reviewsA Serene Beachfront Getaway - 2 BR St. Tropez OC!
2–9 Dec
Destinations to explore
- Rentals with pools United States
- Rentals with pools Washington
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