Vacation rentals with a pool in Southern Maryland
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Southern 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 Southern Maryland rentals with a pool
House rentals with a pool
Home in Harwood
4.94 out of 5 average rating, 117 reviewsLuxury Home, Sleeps 15, Private Pool, Close to DC
Jun 12 – 19
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
Nov 17 – 24
Home in Saint Michaels
4.97 out of 5 average rating, 238 reviewsMiles Aweigh
Sep 22 – 29
Home in Edgewater
4.95 out of 5 average rating, 119 reviewsHouse in Edgewater Maryland
Feb 2 – 9
Home in Hollywood
4.85 out of 5 average rating, 26 reviewsRiverhouse
Dec 18 – 25
Home in Montross
5.0 out of 5 average rating, 48 reviewsWaterfront+Kayaks+Gameroom+Pool+Firepit+EV/Dog OK
Dec 4 – 11
Home in Lusby
4.91 out of 5 average rating, 67 reviewsSpacious and private waterfront, sleeps 10
Oct 22 – 29
Home in Montross
5.0 out of 5 average rating, 7 reviewsThat 70's Hive - Retro Retreat w/ Beaches, Pool +
Jun 14 – 21
Condo rentals with a pool
Condo in West Springfield
4.84 out of 5 average rating, 170 reviewsBeautiful 2BR/1BA Renovated Condo near DC
Condo in Oxon Hill
4.88 out of 5 average rating, 132 reviewsModern Apartments available at National Harbor
Jun 15 – 22
Condo in McLean
4.82 out of 5 average rating, 126 reviews3 Bedroom/King-Master/Free-Parking/POOL (Rare)
Mar 4 – 11
Condo in Alexandria
5.0 out of 5 average rating, 6 reviewsQuiet Condo Near Alexandria ~ Ideal for long stays
Condo in Centreville
4.89 out of 5 average rating, 82 reviewsPeaceful resort- like patio condo
Aug 13 – 20
Condo in Colonial Beach
5.0 out of 5 average rating, 24 reviewsRooftop bay and river views
May 7 – 14
Condo in Alexandria
4.67 out of 5 average rating, 3 reviewsBeautiful 1 bedroom 1 bath apt in Alexandria VA
Aug 11 – 18
Condo in Annandale
4.84 out of 5 average rating, 19 reviewsModern Top-Floor Condo Nestled amongst Trees!
Destinations to explore
- Baltimore Vacation rentals
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- Rentals with pools United States
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