Vacation rentals with a pool in Assateague Island
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Assateague Island
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Assateague Island rentals with a pool
House rentals with a pool
Home in Ocean Pines
4.96 out of 5 average rating, 113 reviewsLittle house in Berlin, Md.
Dec 8 – 15
Home in Rehoboth Beach
4.99 out of 5 average rating, 119 reviewsSecluded beach beauty with private, heated pool
Sep 14 – 21
Home in Ocean City
4.86 out of 5 average rating, 159 reviewsBeach Paradise IV-Downtown Luxury Condo Bay View
Dec 7 – 14
Home in Ocean Pines
4.87 out of 5 average rating, 116 reviewsTortuga Cottage: Your All- Season Getaway
May 16 – 23
Home in Ocean City
4.94 out of 5 average rating, 221 reviewsMad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB
Apr 5 – 12
Home in Ocean City
4.98 out of 5 average rating, 109 reviewsStunning Bayview Home with Own Private Pool
Dec 23 – 30
Home in Ocean City
4.93 out of 5 average rating, 152 reviewsRight behind Alley Oops & Crab Bag. Walk to beach
Sep 14 – 21
Home in Greenbackville
4.92 out of 5 average rating, 49 reviewsStunning waterfront panoramic view getaway house
Sep 23 – 30
Condo rentals with a pool
Condo in Rehoboth Beach
4.98 out of 5 average rating, 164 reviewsCozy Creekwood - Relaxing Getaway
Sep 18 – 25
Condo in Rehoboth Beach
4.92 out of 5 average rating, 143 reviewsWelcome to The Getaway at Rehoboth Beach
Apr 8 – 15
Condo in Bethany Beach
4.93 out of 5 average rating, 280 reviewsSea Colony Premier Family Resort
Apr 25 – May 2
Condo in Ocean City
4.91 out of 5 average rating, 244 reviewsWight Bay Unit 245
Jun 13 – 20
Condo in Ocean City
4.85 out of 5 average rating, 103 reviews2 Bdrm Oceanfront-Pool, Xbox, Pickleball, Gym, HBO
Jun 3 – 10
Condo in Ocean City
4.79 out of 5 average rating, 351 reviewsOcean-Front Beach Condo with Ocean and Bay views
Sep 17 – 24
Condo in Rehoboth Beach
4.78 out of 5 average rating, 253 reviewsRight on Silver Lake walk to beach!
Nov 28 – Dec 5
Condo in Ocean City
5.0 out of 5 average rating, 67 reviews2BR Capri: Ocean Views/Indoor pool/Massage chair
Nov 7 – 14
Destinations to explore
- Rentals with pools United States
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