Vacation rentals with a pool in Assateague Island

Find and book unique homes with a pool on Airbnb

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Popular amenities for Assateague Island rentals with a pool

House rentals with a pool

Top guest favorite
Home in Ocean Pines
5 out of 5 average rating, 18 reviews

Sunshine at Ocean Pines

PareseRating, 5 stars5 days ago
My family visits Ocean Pines every year. This was one of our favorite houses. The house has an open floor plan, is bright and spacious. We found the house to be very clean and have everything we needed. Access to the beach at ocean pines was a 12 min drive and parking pass was included with stay! Thank you, we had a great vacation!
Top guest favorite
Home in Bivalve
5 out of 5 average rating, 21 reviews

Family Retreat - Private Pool, 4 Bedroom, Fire Pit

AshleyRating, 5 stars1 week ago
Where do I start? My boyfriend and I randomly chose Ann’s place for a quick weekend getaway knowing nothing about the town or Bivalve. It was such a great trip! Very quiet little town with the nicest locals! Ann and Eddie came by and took us in the golf cart and sharing a little about the town. Ann’s space was PERFECT and CLEAN! So peaceful and relaxing. Having the pool was great for the few hot days we had. Absolutely loved and recommend visiting this quaint little town and staying at Ann’s if you get the chance!
Top guest favorite
Home in Ocean City
5 out of 5 average rating, 32 reviews

Direct Ocean Front - Beach Retreat Condo!

JacquelineRating, 5 stars4 days ago
We had such a great time at Chris and Loree’s! This was our second trip to ocean city, and their condo was just the right distance from everything there is to do! The view on the balcony was incredible and their place was spotless and comfortable. It was a nice size, loved having washer and dryer and two bathrooms, since it was just me and two teenage boys! There was a TV in the closet that could be rolled out to the porch, where I enjoyed my morning coffee or evening de winding. The pool was nice, but the kids didn’t use it too much as they werent allowed to jump or throw their ball. With the beach being just steps away, they didn’t mind at all! Absolutely would stay here again. Thank you so much Chris and Loree!!
Guest favorite
Home in Ocean City
4.91 out of 5 average rating, 58 reviews

Beachy Sunset Island Townhouse!

DevonRating, 5 stars1 week ago
Great place
Guest favorite
Home in Ocean Pines
4.95 out of 5 average rating, 21 reviews

Peaceful, pet and family-friendly beach retreat

JasonRating, 5 stars1 month ago
My first time staying at an Airbnb so wasn’t sure what to expect. Sara’s place exceeded all expectations. Always quick to respond when i had questions. Would not hesitate to book again.
Guest favorite
Home in Ocean Pines
4.88 out of 5 average rating, 145 reviews

Tortuga Cottage: Your All- Season Getaway

MariaRating, 5 stars2 weeks ago
This was our second stay at Tortuga Cottage. As spacious and clean for my husband, me, and our two young boys plus our Labrador retriever as we remembered it from 2 years ago. It is nestled in a friendly, shaded neighborhood that felt safe and welcoming to walk our dog around and explore the local restaurants, trails, and stores. Only 15 minutes from the beach with accessible parking and locker rooms. Kristy was great at communicating before, during, and leading up to departing from our stay. If you’re on the fence about booking this place, just do it! You’ll be overjoyed that you did.
Top guest favorite
Home in Berlin
5 out of 5 average rating, 11 reviews

Townhome in West OC with Lots of Amenities

AngieRating, 5 stars2 weeks ago
Loved our stay, highly recommend! We had such a great time at this beautiful beach-themed home! The house was spacious, clean, and perfect for our whole family. Kitchen was well equipped for cooking. The community has a dock with easy access for kayaks. We loved having access to the garage, which made it easy to store our kayaks! The location was ideal, it’s just a quick drive to Assateague Island or into Ocean City. Wendy was friendly and responsive, making sure we had everything we needed during our stay. We really appreciated her hospitality! Overall, it was a perfect getaway! Highly recommend this property for anyone looking for a relaxing beach vacation!
Guest favorite
Home in Ocean Pines
4.98 out of 5 average rating, 51 reviews

Ocean Pines-OCMD Bliss at the Beach- Sat. to Sat.

SadeeRating, 5 stars2 weeks ago
this place is such a serene gift! beth the host went above and beyond for us and the home is stocked with anything you could need. her reccomendations were helpful and spot on fun. we will absolutely be back! she communicated well and was so so kind and thoughtful. beautiful house and wonderful stay!!!!

Condo rentals with a pool

Guest favorite
Condo in Ocean City
5 out of 5 average rating, 12 reviews

Luxury Waterfront Beach Condo @ Coconut Malorie OC

GabrielRating, 5 stars1 week ago
Definitely will book again. Super clean! Locations is great. In walking distance to the beach. Walking distance to Fagers, awesome place for food and drinks. Short driving distance to miniature golf, bowling and other restaurants. Communication was excellent with Suzy and Jerry. We enjoyed the warm welcome.
Top guest favorite
Condo in Ocean City
4.98 out of 5 average rating, 40 reviews

Luxury Oceanfront Getaway!

ChristopherRating, 5 stars1 week ago
Shiri's place was perfect. My wife and I have both frequented OC since we were kids, and we both agreed that this was the nicest place we have ever stayed. Far enough from the boardwalk to be peaceful, close enough to travel to the boardwalk if we wanted. The condo was clean, there is a washer and dryer in the unit which is a plus, and a tv in both the living room and bedroom, which is something we always look for. There is plenty to do in the area! Unfortunately, it rained during our whole stay, but you have beach access just outside of the building! We are excited to stay at Shiri's place again (hopefully when it's not raining 😂) and spend some time on the beach! We sat on the balcony every morning and night and it was so peaceful. Shiri was always very helpful and kind - she is such a wonderful host!
Top guest favorite
Condo in Ocean City
4.99 out of 5 average rating, 223 reviews

Cozy oceanfront condo with stunning ocean views

AndreaRating, 5 starstoday
We had such a blast staying at Joe and Kristi’s place in Ocean City! The view was absolutely stunning, the ambience was perfect, and we really enjoyed checking out some of their food recommendations—everything was delicious. They were also super responsive and helpful throughout our stay, which made the whole experience even better.
Guest favorite
Condo in Ocean City
4.93 out of 5 average rating, 14 reviews

Extraordinary Oceanfront Penthouse - Unit 1210

HopeRating, 5 stars4 days ago
Wonderful, updated top-floor condo. Everything was as pictured- you won’t be disappointed. Great balcony view/furniture. Updated appliances. Great showers- strong water pressure. Higher end of rental cost in the area, but well worth it. Easy quick beach access- not overly crowded.
Superhost
Condo in Ocean City
4.83 out of 5 average rating, 283 reviews

🏖 *Ocean *Ocean *Ocean* 🏖 Beautiful Condo!!

ErinRating, 5 stars3 days ago
We had a fantastic stay at Adam’s place. Location was amazing and the description of the unit was exactly on point. Place was clean and comfortable and even had some toys and games for the kiddos! Great communication with the host and we’ll definitely be back!!
Top guest favorite
Condo in Ocean City
5 out of 5 average rating, 29 reviews

Direct Oceanfront with Pool - Steps To The Beach

Gennadiy VRating, 5 stars6 days ago
Wondering place we stayed at! Clean room, with some modern furniture. This room has everything we needed. Definitely will come back.
Superhost
Condo in Ocean City
4.87 out of 5 average rating, 199 reviews

🌊Oceanfront studio w/ amazing views & amenities🏖

VeronicaRating, 5 stars4 days ago
Lisa was an amazing host. My mother and I had a wonderful OCMD experience! Lisa was so kind and kept in touch throughout our visit. Thank you! We will be visiting again! 😊
Guest favorite
Condo in Ocean City
4.9 out of 5 average rating, 42 reviews

BaysideGetaway | 2 Blk to Beach & Boardwalk | Pool

AdamRating, 5 stars4 days ago
Nice place, in a good location for the beach and boards.

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