Waterfront vacation rentals in Assateague Island

Find and book unique waterfront rentals on Airbnb

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Popular amenities for Assateague Island waterfront rentals

Waterfront apartment rentals

Guest favorite

Apartment in Ocean City

5 out of 5 average rating, 7 reviews

Luxury Waterfront Beach Condo @ Coconut Malorie OC

CynthiaRating, 5 stars5 months ago
Suzy and Jerry’s Oasis by the Sea is exactly how it sounds - it’s a hidden oasis by the sea! I loved how responsive and friendly the hosts were up to and throughout the AirBNB experience. This was my first time using AirBNB and it was an incredible experience. I felt like we were VIPs at the resort where this condo is located! The amenities were perfect. I loved the custom welcome sign for us when we walked in. Everything was spotless. The hosts were responsive with every question we had and were sympathetic when we shared a recent tragedy that occurred in our lives before coming to stay at the condo on vacation (unrelated to the experience). I can’t say enough about these hosts or the beautiful condo. It’s absolutely perfect for a vacation in Ocean City, Maryland. The hosts reminded us to check out the views and I’m so glad they did. Their condo balcony shows the sunset over the bay in a way I’ve never experienced. It was breathtaking. Thank you so much for this much needed respite!
Superhost

Apartment in Ocean City

5 out of 5 average rating, 4 reviews

The Pelican of Bahia Vista 3B/2b

TaraRating, 5 stars6 months ago
Outstanding communication and the stay was 100% as described. Beautiful place and the sites were amazing. I highly recommend Violet and her property! So very welcoming and clean! Just a short walk to the boardwalk and night life, then to be able to come back to have peace and quietness was so satisfying. Don’t hesitate to book this property! It’s a must!!
Guest favorite

Apartment in Ocean City

4.96 out of 5 average rating, 56 reviews

Canal Front Condo 2 Blocks 2 Beach & Park Sleeps 4

RachelRating, 5 stars5 months ago
We were looking for a Labor Day weekend getaway and stumbled upon this listing. We loved how close we were to an assortment of shops and even did some morning walks to Starbucks. We personally prefer the beaches farther away from the boardwalk so this was a perfect location for us! The hosts were amazing and answered us so quickly but also provided us with check in/ check out information before we even needed to ask. We had a wonderful time and would be back!
Guest favorite

Apartment in Ocean City

5 out of 5 average rating, 24 reviews

Bayside Bungalow - Waterfront

GregoryRating, 5 stars5 months ago
Felt super comfortable there. Everything was in walking distance beach, great restaurants bars and we even utilized the kitchen for breakfast and lunch. Loved the coffee set up and the quite seating area on the water out back. We def would recommend and would love to stay again!
Superhost

Apartment in Ocean City

4.8 out of 5 average rating, 10 reviews

Bayfront Ponte Vista ~ 211

JuanRating, 5 stars5 months ago
Amazing apartment with a fantastic view! Very clean and quiet, will deff come back to stay here again!
Guest favorite

Apartment in Ocean City

4.96 out of 5 average rating, 28 reviews

Driftwood Condo, 1BRTropical Bayside w/sunsetview

BrunoRating, 5 stars5 months ago
Steven’s place is so cozy, I definitely felt at home. Everything looks so clean and new. Beach access is walkable, and A LOT of options around the area to go walking or driving. I definitely can see me coming back!!! Thanks, Steven, for the wonderful time that I had with my family in OC.
Guest favorite

Apartment in Chincoteague

4.86 out of 5 average rating, 167 reviews

Sunset Haven Downtown

DaleRating, 5 stars1 month ago
Had a lovely stay. Home is by the river with peaceful views. The New Year celebration was in the park and lots of fun. Kitchen had everything we needed and even some local coffee. Very comfortable bed. Don's Seafood restaurant is next door and food was outstanding. Very short 5 minutes to other shops and restaurants and the Chincoteague Wildlife Refuge. We would stay here again.
Superhost

Apartment in Ocean City

4.71 out of 5 average rating, 28 reviews

3br Waterfront Assateague Island Best View

MikeRating, 5 stars7 months ago
Marcia was extremely responsive, on top of any question we had, and provided recommendations for restaurants and other activities. The location was perfect, we could almost walk anywhere we needed to go. The view is amazing and the condo was very clean!

Waterfront house rentals

Guest favorite

Home in Woolford

4.93 out of 5 average rating, 142 reviews

Waterfront Getaway with Dock

BrittanyRating, 5 stars1 month ago
We booked this place to stay while duck hunting. We enjoyed cooking at the house and relaxing by the water in the evening. Would recommend staying here.
Guest favorite

Home in Ocean Pines

4.99 out of 5 average rating, 119 reviews

Charming Waterfront Cottage w/2 King Suites + Dock

EricRating, 5 stars1 month ago
This is our third stay at Jennifer’s home, and wow, another 5 star stay. Woke up to 2025 and a placid bay view, great coffee, and a perfect night’s sleep! Gold star amenities, luxe beds, and insider tips on the places to go and eat. Book with confidence. 10 min from the ocean, ultra luxe accommodations.
Guest favorite

Home in Woolford

5 out of 5 average rating, 116 reviews

Starboard on McKeil Point, w/heated pool & hot tub

AshleyRating, 5 stars1 month ago
Kristin's home was the perfect setting for a peaceful family Christmas! It was a great size for my family (11 adults and 2 kids) to stay comfortably. The kitchen is set up nicely for large groups with 2 ovens, 2 dishwashers and 2 fridges. We spent most of our time relaxing in the large dining and sitting areas as well as enjoying bird watching from the backyard (bald eagles!). Kristin is extremely responsive -- even immediately responding to and helping to fix a plumbing issue (on Christmas Eve!). Would highly recommend this place for your next summer or winter getaway!
Guest favorite

Home in Reedville

4.95 out of 5 average rating, 232 reviews

Waterfront FamilyFriendly Home Improved for 2023

BarbaraRating, 5 stars1 month ago
This was a weekend getaway for my 60th birthday, and we made a great choice. It was the perfect place to kick back and relax. The house is comfortable and cozy. The view was beautiful-- be sure to get up for the sunrise.
Guest favorite

Home in Woolford

5 out of 5 average rating, 218 reviews

Newly Renovated Modern 3 bed 2 bath Water Front

SarahRating, 5 stars2 months ago
The Riverhouse exceeded our expectations and deserved the 5 or more rating! The place was immaculate, had a gorgeous river view, and the hosts were extremely accommodating and responsive! Highly recommended!
Guest favorite

Home in Bethany Beach

4.87 out of 5 average rating, 47 reviews

Waterfront, SUPs, Yaks, & Bikes! Walk 2 the Beach

FarmandRating, 5 stars5 months ago
We had the most amazing stay at Donna’s house! The place was spotless, super cozy, and so stylish, with plenty of room for everyone to kick back and relax. The quiet neighborhood made it the perfect spot to unwind and recharge. We absolutely loved hanging out on the outdoor decks, soaking up the views, and enjoying our morning coffee while watching the gorgeous sunrises over the canal. The screened porch was perfect for unwinding and catching the sunset. The beach was only a short distance away, and the kayaks and SUPs were such a fun way to explore the bay. Donna was an incredible host—always responsive and so helpful throughout our stay. We seriously can’t recommend her beach house enough!
Guest favorite

Home in Reedville

5 out of 5 average rating, 48 reviews

Private Waterfront KingBed Dock Firepit Kayak SUP

SkippyRating, 5 stars5 months ago
The place looks just like in the photo. The house is pristine clean and well decorated. Its surrounding is also beautiful and peaceful. We had fun with catching crabs and kayaking around from the dock in the backyard. The owner is very responsive and gave good instructions. We enjoyed our stay a lot. Will definitely keep the house in mind in our next visit.
Guest favorite

Home in Lewes

4.98 out of 5 average rating, 179 reviews

Beautiful Waterfront Home-Private, Clean, Relaxing

KarenRating, 5 stars1 month ago
What a charming lovely place to stay. Laura was so attentive and addressed any questions or concerns in a timely manner. The beds were so comfortable and the kitchen had everything we needed. We all agreed we would come back in a heartbeat.

Waterfront condo rentals

Guest favorite

Condo in Ocean City

4.95 out of 5 average rating, 39 reviews

Entire Downtown Bayfront Condo

HeatherRating, 5 stars6 months ago
This is a great location if you have kids. I love the fact that there was baby gates for the porch and also there was kid friendly cups plates, and utensils. it’s very close to the beach and it’s a very quiet location on the bay. We would definitely stay here again. The house was gorgeous. The beds were very comfortable and very clean. I can’t say not one negative thing about our stay. We would definitely book here again.
Superhost

Condo in Ocean City

4.88 out of 5 average rating, 51 reviews

Waterfront Condo w/ Balcony, Right on the Canal

AmyRating, 5 stars4 months ago
Very clean, nice view, host and hostess were quick responders:) a little far from our venue but we would def come back !:)
Superhost

Condo in Ocean City

4.85 out of 5 average rating, 40 reviews

Penthouse condo. Bayside with elevator. Wow Views!

VincentRating, 5 stars5 months ago
This was our 3rd stay at this location. It is the perfect location for us in OC. Having morning coffee on the balcony overlooking the marina is a relaxing way to start the day. Just a few short blocks to the beach and the boardwalk. Having a car in OC is a necessity and the free parking here comes in handy. Looking forward to our next stay.
Guest favorite

Condo in Ocean City

4.85 out of 5 average rating, 101 reviews

1st Floor 3 BR Condo close to Beach with Pool!

KellyRating, 5 stars5 months ago
Mike’s beach house is perfect for a family or group trip. More than enough space to fit everyone and the location is amazing. You’re less than a 5min walk to the beach but also return to a quiet dock rental. It was so calm sitting on the porch each morning looking at the water. Far enough from the hustle and bustle but close enough to enjoy the boardwalk and attractions when wanted. He’s super communicative as well. Would definitely stay again.
Guest favorite

Condo in Ocean City

4.87 out of 5 average rating, 71 reviews

UNIQUE Bay Front Sanctuary Condo

EdwardRating, 5 stars5 months ago
Great stay and location. Centralized to everything and everywhere I went.
Guest favorite

Condo in Ocean City

4.98 out of 5 average rating, 215 reviews

Direct Oceanfront close to Northside Park!

MonaRating, 5 stars1 month ago
This wasn't our first time at Stephanie's condo, and it won't be the last! It's clean, comfortable, quiet, and there's plenty of elbow room. Beautiful views right on the beach. Close to some of our favorite places to eat. Stephanie is a great host too!
Guest favorite

Condo in Ocean City

5 out of 5 average rating, 60 reviews

Blue Haven I Bay I Boatslip I BoardwalkI Inlet

AjRating, 5 stars4 months ago
We stayed at Julie’s place during Oceans Calling this year and have to say that it was a great location. Condo was beautiful and Julie took care of some of the dumb things you don’t think about like conveniently placed outlets and labeling things like switches for lights. There’s also a luggage cart and elevator to get your stuff to and from the condo which we weren’t expecting. Condo is spacious and didn’t feel cramped at all. All the three bathrooms can be accessed directly from a bedroom so that’s great too. View is fantastic and the location is very walkable to surrounding areas. We also found some street (non pay) parking around the adjacent streets near the oldest bar in OC which saved us some headaches for extra cars. Julie is a very responsive and thorough host. Overall very happy with this booking.
Guest favorite

Condo in Ocean City

4.88 out of 5 average rating, 129 reviews

Water Front Condo w/Pool Short Walk to Beach

ShawnRating, 5 stars3 months ago
This place was great for a little weekend get away. The place has a very homey feel. The location was great, nice and quiet. Brian was extremely responsive and friendly.

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