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, 112 reviewsLittle house in Berlin, Md.
Dec 8 – 15
Home in Ocean Pines
4.88 out of 5 average rating, 115 reviewsTortuga Cottage: Your All- Season Getaway
Oct 9 – 16
Home in Rehoboth Beach
4.99 out of 5 average rating, 119 reviewsSecluded beach beauty with private, heated pool
Sep 15 – 22
Home in Frankford
4.93 out of 5 average rating, 165 reviewsA Bethany Beach Gem
Apr 12 – 19
Home in Rehoboth Beach
5.0 out of 5 average rating, 172 reviewsBeautiful Beach House in Rehoboth
Mar 6 – 13
Home in Ocean City
4.98 out of 5 average rating, 109 reviewsStunning Bayview Home with Own Private Pool
Nov 15 – 22
Home in Ocean City
4.86 out of 5 average rating, 159 reviewsBeach Paradise IV-Downtown Luxury Condo Bay View
Mar 28 – Apr 4
Home in Ocean City
4.93 out of 5 average rating, 150 reviewsRight behind Alley Oops & Crab Bag. Walk to beach
Sep 16 – 23
Condo rentals with a pool
Condo in Ocean City
4.91 out of 5 average rating, 256 reviewsOcean Front 802 Midtown Oasis Pool & Parking
Mar 15 – 22
Condo in Dewey Beach
4.95 out of 5 average rating, 105 reviewsLuxury water-view condo with high-end finishes
Mar 12 – 19
Condo in Ocean City
4.99 out of 5 average rating, 180 reviewsCozy oceanfront condo with stunning ocean views
Jul 14 – 21
Condo in Rehoboth Beach
4.98 out of 5 average rating, 163 reviewsCozy Creekwood - Relaxing Getaway
Sep 14 – 21
Condo in Rehoboth Beach
4.99 out of 5 average rating, 168 reviewsComfy and Convenient 2 bedroom/2 bath condo
Sep 28 – Oct 5
Condo in Rehoboth Beach
4.92 out of 5 average rating, 143 reviewsWelcome to The Getaway at Rehoboth Beach
Feb 14 – 21
Condo in Bethany Beach
4.93 out of 5 average rating, 280 reviewsSea Colony Premier Family Resort
May 10 – 17
Condo in Ocean City
4.94 out of 5 average rating, 227 reviewsNice 2 BR Oceanfront, Year Round Fun & Amenities!
Mar 7 – 14
Destinations to explore
- Rentals with pools United States
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