
Holiday rentals with a pool in Assateague Island
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Top-rated rentals with a pool in Assateague Island
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Popular amenities for Assateague Island rentals with a pool
House rentals with a pool

Sunshine at Ocean Pines
We had an amazing time at Phillip’s place in Ocean Pines! The home was clean, comfortable, and had everything we needed for a relaxing getaway. It’s located in a peaceful, wooded neighborhood that still offers easy access to Ocean City, beaches, and local restaurants. Phillip was a fantastic host—very responsive and thoughtful, making sure our stay was smooth from check-in to check-out. The back deck and cozy living space made it easy to unwind after a day of exploring. We would definitely stay here again and highly recommend it to anyone visiting the area!

New! Oceanfront at Marigot Beach
We enjoyed our stay with Oceans Edge Vacations at Marigot Beach Suites! The unit was very clean and in a great location with access to the beach in under 1 minute. The Host and Oceans Edge Vacations team was excellent! Upon check in Airbnb had an old # listed first on my account instead on my current #. My check in instructions was sent by Airbnb to the old # instead of my current #. The Oceans Edge Vacations staff was patient and attentive with me in solving the issue. Oceans Edge Vacations team sent me my check in instructions to my current # fast and explained how the issue can be fixed with Airbnb. Since my check in instructions was sent to a # that wasn't mine currently I requested a new access code be sent. The Oceans Edge Vacations staff changed my access code and sent it immediately. I was then free to enjoy my visit knowing no one but me had access to my unit. I can't say enough about the unit, Oceans Edge Vacations and it's Staff. I strongly recommend Oceans Edge Vacations.

Direct Ocean Front - Beach Retreat Condo!
We had a wonderful stay at Chris and Loreees place! Super responsive when needed and clear instructions for check in and out. Private, quite, clean building and condo and we had everything we needed. The views were stunning & exactly as pictured. Walking distance to many stores, restaurants, and 7-11 next door for convenience. I would recommend staying here!

Luxe Lewes Carriage House: Spa Hot Tub/Estate Pool
Let's see...if Martha Stewart had a rental cottage, it would look just like Lisa and Jay's carriage house. Everything from the splendid charcuterie board and Prosecco on ice that awaited us upon our arrival to the beautifully designed cottage and wonderful gardens helped create an amazing vacation that we will not forget anytime soon. Jay and Lisa truly paid attention to every detail right down to the perfectly placed English antiques, fresh cut flowers and towels so thick you could drown in them. Nothing was missing and their hospitality made you feel right at home. We had smiles on our face the entire time! This is now my new Happy place. The gold standard by which every rental will be judged....perfect hosts, perfect place..like I said...Martha Stewart. Thank you Lisa and Jay for making our stay a wonderful experience!! We will definitely be back to your Lewes Carriage House whenever possible!

Peaceful, pet and family-friendly beach retreat
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.

Assateague surf cottage!
Great place, would definitely booked again, Lee is a great guy, came to change lightbulbs that were missing, house is in a good location close to a lot of places.

Heartsong Farmhouse , a nature lover's retreat.
Sarah’s place is AMAZING! Sarah went above and beyond being they didn’t have time with the weather to set up the new pool but went and dropped off a sprinkler and water hose for my daughter to use even though the weather never quite cooperated for us to use! Sarah was very responsive and helpful with anything we needed as well as gave great recommendations for local things! We will definitely be returning & staying here!

Ocean Pines-OCMD Bliss at the Beach- Sat. to Sat.
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!!!!
Apartment rentals with a pool

Luxury Waterfront Beach Condo @ Coconut Malorie OC
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.

Luxury Bay & Oceanview Condo in the Heart of Dewey
It was truly the perfect location to stay for my son’s wedding which was at the Hyatt Place right next door! An amazing experience all around from the beautiful beach decor, lovely views of the bay & ocean & convenience of walking everywhere in Dewey! The condo was clean, nicely furnished & had a well-equipped kitchen to make us feel right at home. The host was very welcoming & quick to respond to any questions we had. The wedding venue was beautiful and our stay here made the weekend even more special! It will always be one of my favorite memories.

Cozy 1 BR Condo - 5 Minute walk to Beach, w/ Pool!
Our stay was very peaceful and relaxing all thanks to Clint’s place! We were able to walk to the boardwalk and restaurants. The place itself was clean and has everything you would need on vacation. Thank you Clint!

🏖 *Ocean *Ocean *Ocean* 🏖 Beautiful Condo!!
Our stay was amazing, and Adam was communicative and extremely helpful the entire stay! Beautiful place and great location.

Direct Oceanfront with Pool - Steps To The Beach
Wondering place we stayed at! Clean room, with some modern furniture. This room has everything we needed. Definitely will come back.

🌊Oceanfront studio w/ amazing views & amenities🏖
I had a peaceful, relaxing time and enjoyed the ocean view and the sound of the waves. Lisa was extremely communicative and made sure I had everything I needed for a great stay.

Romantic Beach Inscape-Best Ocean View+Heated Pool
The view and easy access to the beach make this perfect for a weekend getaway. Quiet in the offseason and close to tons of great local restaurants.

Direct Ocean Front/Gorgeous Views/Indoor Pool
My husband and I decided to go on a getaway last minute. We found Seth’s place and were able to book the unit for the days we had available. It was great and met all of our expectations. We have been to OC and Fenwick many times and knew this is where we wanted to stay. It did not disappoint and we hope to rent again in the near future.
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