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.
Cottage in Cambridge
4.99 out of 5 average rating, 107 reviewsChurch Creek - waterfront cottage & pool - private
Close to Blackwater NWR and the Harriet Tubman Center, enjoy peaceful days at our secluded waterfront cottage on Church Creek. Two miles from a main road, and our closest neighbor is across a cove, our estate offers 50 acres of privacy and one of the best waterfront views on the Chesapeake. Enjoy a view from every window and nature all around you. Excellent walking, swimming (in-ground pool-May 3-Oct 1), great birding and bicycling. Launch your kayak from the backyard. Perfect private getaway!
Feb 28 – Mar 7
Cabin in Frostburg
4.92 out of 5 average rating, 133 reviewsBig Savage Guest Cabin
Nestled on 10 acres near the summit of Big Savage Mountain is our home site which includes our guest cabin. Warm summer days and cool evenings make for a great vacation spot. In the country but just 1 mile from down town. Your retreat is just 3 minutes from dining, biking, hiking, swimming, and live music. Fall brings beautiful foliage and winter plenty of snow. There is something for fans of all seasons. We are only 5 minutes from Frostburg State University & 30 minutes from Deep Creek Lake.
Aug 28 – Sep 4
Guest suite in Myersville
4.93 out of 5 average rating, 276 reviewsHarmony Lodge nestled in wooded tranquility!
Tranquil lodge nestled on 3 wooded acres in Myersville, MD. Relax by the heated pool, enjoy the warmth of the fire pit, or walk the grounds and enjoy Mother nature. Minutes away from downtown Frederick and Middletown restaurants, shops, and parks. Visit the local wineries and festivals. Tour historic battlefields. Go antiquing. Take in a round of golf, bike the C&O canal, hike the Appalachian trail, boat on the Potomac River, or go skiing. Bring your fur baby with you to enjoy the activities!
Feb 20 – 27
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 New Market
4.94 out of 5 average rating, 112 reviewsHistoric Peace and Plenty Farm: Pool House
Dec 21 – 28
Home in Chesapeake Beach
4.91 out of 5 average rating, 110 reviewsIndoor pool/spa nestled in Southern Md. woods.
Apr 19 – 26
Home in Saint Michaels
4.97 out of 5 average rating, 238 reviewsMiles Aweigh
Aug 12 – 19
Home in Oakland
4.95 out of 5 average rating, 192 reviewsCozy&Private|HotTub|CARC|Firewood|Essentials|5 Str
Apr 17 – 24
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
Apr 26 – May 3
Home in Ocean Pines
4.88 out of 5 average rating, 113 reviewsTortuga Cottage: Your All- Season Getaway
Aug 31 – Sep 7
Home in Edgewater
4.95 out of 5 average rating, 114 reviewsHouse in Edgewater Maryland
Oct 29 – Nov 5
Home in Oakland
4.96 out of 5 average rating, 180 reviewsAmazing Views! | 4BD/4.5BA | Dock, WISP, Hot Tub
Aug 9 – 16
Home in Shady Side
4.88 out of 5 average rating, 174 reviewsCattail Landing- Photographer's Waterfront Retreat
Jul 25 – Aug 1
Home in Berlin
4.78 out of 5 average rating, 174 reviewsOC, Md great amenities in community, near beaches
Aug 17 – 24
Home in Perry Hall
4.98 out of 5 average rating, 41 reviewsGunpowder Retreat
Feb 3 – 10
Home in Ocean City
5.0 out of 5 average rating, 3 reviewsEpic Luxurious Mansion Bayside Pools Tennis
Jan 2 – 9
Condo rentals with a pool
Condo in Ocean City
4.97 out of 5 average rating, 219 reviewsDirect Oceanfront with a View and Amenities Galore
Oct 13 – 20
Condo in Ocean City
4.94 out of 5 average rating, 160 reviewsGorgeous Oceanfront Condo- Beach, Pool, Hot Tub!
Feb 12 – 19
Condo in Ocean City
4.83 out of 5 average rating, 133 reviewsRomantic Beach Inscape-Best Ocean View+Heated Pool
Feb 8 – 15
Condo in Ocean City
4.89 out of 5 average rating, 163 reviews🌊Oceanfront studio w/ amazing views & amenities🏖
Apr 8 – 15
Condo in Ocean City
4.89 out of 5 average rating, 151 reviewsPrime Condo North OC 2 Blocks to Beach w/ Pool
Feb 14 – 21
Condo in Ocean City
4.92 out of 5 average rating, 248 reviewsOcean Front 802 Midtown Oasis Pool & Parking
Oct 11 – 18
Condo in Ocean Pines
4.96 out of 5 average rating, 102 reviewsPeaceful Water View Retreat
Oct 16 – 23
Condo in Ocean City
4.9 out of 5 average rating, 114 reviewsA Serene Beachfront Getaway - 2 BR St. Tropez OC!
Apr 8 – 15
Condo in Ocean City
4.95 out of 5 average rating, 190 reviewsCaramar Couples Retreat
May 9 – 16
Condo in Ocean City
4.94 out of 5 average rating, 110 reviewsOceanfrontStudio-Slps4-Pool-Pickleball-HBOMax-Dis+
Aug 1 – 8
Condo in Ocean City
4.95 out of 5 average rating, 221 reviewsNice 2 BR Oceanfront, Year Round Fun & Amenities!
Nov 4 – 11
Condo in Ocean City
4.84 out of 5 average rating, 306 reviews🌊 NOTHING BEATS OCEANFRONT!!! 🌊
Apr 25 – May 2
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