House vacation rentals in Ocean Pines

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Popular amenities for Ocean Pines house rentals

House rentals with a pool

Guest favourite
Home in Ocean City
4.86 out of 5 average rating, 73 reviews

Sunshine Retreat and Free Mini Golf /Huge Pool

BrianRating, 5 stars1 day ago
Had a great time and Tammy’s place was the perfect stay. 10/10 would recommend to any small family or trip if you want to stay a short walk away from the strip
Guest favourite
Home in Ocean City
4.92 out of 5 average rating, 39 reviews

West OC Bayside Getaway w/ pool

ZacharyRating, 5 stars4 months ago
House is in one of the best spots for easy in and out of inlet access to beach, shopping, and restaurants. Gives you an extremely personal, and private way to thoroughly enjoy beach life environment. Doug was absolutely amazing from start to finish. Hospitality beyond expectations, which made the stay that much more enjoyable.
Guest favourite
Home in Selbyville
5 out of 5 average rating, 5 reviews

Dogs WelcomeIBeaches|Nature Trails|Gym|Pool

AmyRating, 5 stars8 months ago
My family and I enjoyed our stay in Delaware! The home was clean, beautiful, and just as described. Serena was easy to work with and very responsive. With the pool, access to the bay, walkable neighborhood, and close proximity to restaurants and the beach, we would love to stay here again!!
Guest favourite
Home in Ocean View
4.9 out of 5 average rating, 21 reviews

5BR/4.5 BA/Pool Next to House/ 1.5 miles to beach

JessicaRating, 5 stars8 months ago
We had three families with five kids stay and the location was perfect! Having the pool next door was essential! The kids ran back and forth each afternoon! We had to drive to the beach but it only took us 10 minutes. layout was great. host was great. we will certainly be looking at this house again for future trips!
Superhost
Home in Ocean View
4.87 out of 5 average rating, 67 reviews

PRiVATE Pool, Peaceful, and Close to Bethany Beach

Phil Rating, 5 stars2 weeks ago
We stayed at Trina’s place on a resent golf trip. She was great, and her place is exactly as described. She reached out days before we arrived with clear directions for check in, which was a breeze. Trina responded very quickly to my question and I would highly recommend stay with her if you are traveling to the area.
Superhost
Home in Ocean City
4.81 out of 5 average rating, 52 reviews

Amazing Large 4 Bedroom West OC Town House, Pool!

CarlaRating, 5 stars5 months ago
My family and I enjoyed our stay. We didn’t want to leave. The location was excellent. It was close to boardwalk, restaurants and the outlet mall. I loved not having to drive far to places. We will be back.
Guest favourite
Home in Ocean City
5 out of 5 average rating, 11 reviews

Charming Condo with pool and 2 bedrooms

JpRating, 5 stars7 months ago
The unit was in great shape and in a very convenient location. Isabel was very accommodating to our schedule and made the whole process very easy. Thanks again!
Top guest favourite
Home in Ocean City
5 out of 5 average rating, 21 reviews

Large beachy feel 4 Bedroom

KerrynRating, 5 stars2 weeks ago
We were only there for a short stay to visit family, but Brian’s property was great and met all of our needs. Brian was a very responsive, accommodating, and helpful host!

Weekly house rentals

Top guest favourite
Home in Bethany Beach
4.94 out of 5 average rating, 112 reviews

Bethany Beach 116 5th St Oceanblock

FlorenceRating, 5 stars2 weeks ago
Stayed with grandparents, a child and pets and it never felt crowded! Paul answered any questions we had. We loved the decor and location, would definitely stay here again!
Superhost
Home in Frankford
5 out of 5 average rating, 3 reviews

Coastal Pines a 7 BR private beach retreat!

AlishaRating, 5 stars1 month ago
Thank you so much for providing a place for us to have a beautiful weekend! We will be looking to return back for a longer stay in the future!
Guest favourite
Home in Ocean Pines
4.97 out of 5 average rating, 33 reviews

WHAT DAY IS IT???????

KarinRating, 5 stars8 months ago
We had a wonderful stay at Brian’s place! The house was very comfortable, beautiful, clean and well equipped. The welcome basket and the baskets of samples in case you forgot something was a nice touch. He was very responsive to any questions I had. The beach parking pass was perfect - we took advantage of that on 2 days. I would definitely recommend this house. I wish we had more time at the house to enjoy it even more.
Guest favourite
Home in Ocean View
4.9 out of 5 average rating, 20 reviews

Boho Beach Golf Villa

CarmenRating, 5 stars3 weeks ago
This property was perfect as it was a place of celebration for my birthday and an anniversary. We had invited guests who were comfortably accommodated. Spacious and quiet with an enclosed porch/patio area. We socialized and enjoyed the media content provided on the screen in the living room, and in our bedroom. We felt right at home. We now have a memorable experience. Thanks to our precision oriented host.
Top guest favourite
Home in Bethany Beach
5 out of 5 average rating, 37 reviews

5 Bedroom Canal Front home- 3 min walk to beach

LauraRating, 5 stars1 month ago
Shelly’s house was the perfect place for our weekend retreat! The 5 of us all had our own spaces and could comfortably be in the perfectly furnished shared spaces! Everything is what I’d choose for my own home - comfortable, lovely without being fussy, makes being there easy. Highly recommend!
Superhost
Home in Bethany Beach
4.94 out of 5 average rating, 16 reviews

The Bethany Beach Comber

MaryRating, 5 stars2 weeks ago
We had a lovely stay. We booked last minute and John was super accommodating. The house is beautiful, very clean, and exactly as described. I would definitely stay here again! Thank you!
Top guest favourite
Home in Ocean Pines
5 out of 5 average rating, 50 reviews

OC Gateway: Modern 4BR/2.5BA home (dog friendly)

VickyRating, 5 stars1 week ago
This beautiful house is a 5 stars accommodation. An absolute pleasure to stay in and also to appreciate all the design and decor details. Very cozy and you feel right at home! Bedrooms and linens were so comfortable that it was hard to get up in the morning. Squeaky clean bathrooms with a hi-quality towels! Fully stoked kitchen with condiments and all the necessary dishes, appliances and equipment for a meal preparation and enjoying a family dinner around the counter or dinning table! We had a one year old with us and Steven provided a high chair, pack-n-play, and lots of toys and board games! Steven is a wonderful host, very professional and proactive, checked on us every day to make sure that we are good and don't need anything else. Highly recommend this place for a nice getaway to MD. Steven, we will be back!
Guest favourite
Home in South Bethany
4.91 out of 5 average rating, 34 reviews

BB’s Coastal Treehouse House at Sea Colony

MariiaRating, 5 stars7 months ago
Barbara is an AMAZING host and has a lovely home that we thoroughly enjoyed for this short but lovely family getaway. The place was spotless: clutter free, super clean and beautifully designed. We could tell that Barbara put her heart and sole into making her condo feel like home for every guest. The place is located in a beautiful area that is pedestrian friendly, which was super important to us as we travelled with a toddler. It’s also minutes away from the beach while at the same time far away from noisy streets. Barbara was extremely accommodating with the check in/out time and responded to all our inquiries within minutes. We would come back without a hesitation! P.S on a side note the place was very well adapted for a toddler with some books, toys and even noise machines in every room:) we found this to be a great bonus for our family!

Private house rentals

Top guest favourite
Home in Ocean Pines
5 out of 5 average rating, 16 reviews

Sunshine at Ocean Pines

HectorRating, 5 stars2 weeks ago
Absolutely loved our stay! Phillip was a fantastic host and super communicative both before our arrival and leading up to check-in, which made everything seamless and stress-free. The house itself was spotless, incredibly well- maintained, and thoughtfully organized. You can really tell he puts care into every detail! There were tons of games to keep us entertained, which made for some really fun evenings. I also appreciated how every light switch was clearly labeled (a small thing, but so helpful!), and the binder full of local attractions and amenities was a great touch. On top of all that, Phillip even offered us early check-in, which was such a nice bonus. Highly recommend staying here since we had such a great time and would definitely come back!
Top guest favourite
Home in Selbyville
4.9 out of 5 average rating, 173 reviews

Country Private Vacation House

ElizabethRating, 5 stars7 months ago
This was a great place to stay while we went to the Ocean’s Calling music festival in Ocean City. The location was great, away from everything but still only a short drive. As someone who easily gets grossed out by air bnbs, it was so clean and comfortable, with plenty of space! Thanks for an incredible stay, will definitely want to stay again if we come back to the area!
Guest favourite
Home in Ocean Pines
4.93 out of 5 average rating, 27 reviews

Beach Retreat is a 3 bedrooms2 baths beach house.

AmberRating, 5 stars7 months ago
Rosa’s home is a perfect getaways spot! It’s clean, spacious and quiet. Everything you need is in the home. The neighborhood is perfect for walking the dogs and everyone is friendly. It’s a quick 10-15 minute drive to the beach and boardwalk inlet. We definitely would stay here again when we need a place to stay. Rosa is super helpful and always responded quickly!
Superhost
Home in Berlin
4.8 out of 5 average rating, 5 reviews

Quiet Retreat near Assateague Main House

ZacharyRating, 5 stars45 months ago
What a truly incredible place and host! I can’t say enough about Kate’s responsiveness and the incredible space. We loved it and hope to be back again!
Superhost
Home in Ocean City
4.92 out of 5 average rating, 48 reviews

Newly built, modern home, short walk to the beach

JulieRating, 5 stars9 months ago
Second stay for us and we would go back again. We love that we can walk to the beach. Plenty of space for two families with young adult children. The screened in porch is great for morning coffee and relaxing in the evening. Hosts are super responsive and flexible.
Guest favourite
Home in Millville
4.85 out of 5 average rating, 60 reviews

Cedar Dr & Central Av 3 bedrooms Millville house

ChuckRating, 5 stars8 months ago
Very happy with our stay, close to grocery and restaurants. Owner communicated very well and had great recommendations. The house had great spaces for our group of 7 to spread out or all hang together. Thanks again for your hospitality.
Top guest favourite
Home in Ocean City
5 out of 5 average rating, 13 reviews

Beachfront 3BD/2BA Serenity on Boardwalk & Ocean

JohnRating, 5 stars7 months ago
Place was a great location, next to the beach, almost on the boardwalk. We walked pretty much everywhere the entire weekend. Host communicated well with all directions and instructions for the property. Would definitely recommend. Ty Shelly!
Guest favourite
Home in Frankford
5 out of 5 average rating, 49 reviews

My Happy Place - 10 min. to Beach. Quiet

NinaRating, 5 stars7 months ago
Bettina's My Happy Place was very enjoyable. My family especially loved the screened in gazebo, which does not include lights or electricity, but we loved that - PERFECT for unplugging! The outdoor shower was great for rinsing off after the beach. We loved the availability of beach chairs, beach toys, grill and fire chimenea (fire pit). We used the fire chimenea two nights. The location was FANTASTIC!!! I would have loved to have more pillows in the master bedroom. Wi-Fi was a little spotty if you had too many devices connected. The fire chimenea has seen better days, but still useable. Side Note: We were extremely pleased when we realize there were no bugs. The whole neighborhood was more or less flying bug free.

Quick stats about house rentals in Ocean Pines

  • Total rentals

    240 properties

  • Nightly prices starting at

    $55 CAD before taxes and fees

  • Total number of reviews

    6.2K reviews

  • Family-friendly rentals

    230 properties are a good fit for families

  • Pet-friendly rentals

    70 properties allow pets

  • Rentals with a pool

    120 properties have a pool

Destinations to explore

  1. Airbnb
  2. United States
  3. Maryland
  4. Worcester County
  5. Ocean Pines
  6. House rentals