Vacation rentals with a pool in Ocean Pines

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Popular amenities for Ocean Pines rentals with a pool

House rentals with a pool

Guest favorite
A light and airy deck features a rectangular dining table surrounded by aqua-colored chairs. A calm water view is visible beyond the railing, with flags gently waving in the breeze. Soft lighting is provided by string lights overhead, enhancing the inviting atmosphere.
Home in Ocean City
4.95 out of 5 average rating, 255 reviews

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB

ErikaRating, 5 stars3 weeks ago
Beautiful spot! Great location, close to all the happenings of Ocean City, but peaceful and quiet at the house…perfect set up. Great neighborhood. The house is beautiful, all the beds very comfortable. The back deck is gorgeous, thoroughly enjoyed that space and taking the kayaks out on the canal! It’s worth bringing your own linens and towels, we packed everything into a large tote and it worked out perfectly. Very responsive and friendly host! We had a great time here and plan to return. Highly recommend!
Guest favorite
A spacious outdoor deck is surrounded by lush trees, offering a serene atmosphere. Comfortable seating is arranged alongside a glass-top table, while string lights add a soft glow. A fenced-in backyard features a firepit area with seating for relaxation and gatherings.
Home in Ocean Pines
4.97 out of 5 average rating, 79 reviews

*Catch Me By The Sea*

AliciaRating, 5 stars3 weeks ago
We had a really lovely stay. We appreciated the thoughtful communication and local recommendations. We especially enjoyed the backyard and beach ammenities. Perfect little spot if you're looking to stay outside of the hassle and bussle of OC and in the quaint village of OP. Would highly recommend this spot for anyone looking for a good value in a sweet little town. 🦀
Guest favorite
A community pool is surrounded by concrete flooring and shaded by trees. In the background, a pavilion with picnic tables can be seen, along with mobile homes lining the area. Lifeguards are stationed under an umbrella, observing the calm waters.
Home in Berlin
4.94 out of 5 average rating, 51 reviews

Amazing 2 Bedroom home close to the beach!

MikeRating, 5 stars7 months ago
We needed a small place to stay for a few days and this was the perfect place for the two of us; it was cozy, spotless, well equipped for all that we needed and the decor was beachy which was perfect for the area. Jacob was quick and attentive to any question we had - it was so quiet and peaceful outside. It was a perfect getaway for us - we would highly recommend to anyone needing a nice, quiet place in the future. Thank you!!!
Guest favorite
A large swimming pool is surrounded by a concrete deck, with numerous white lounge chairs arranged along one side. The calm water reflects the clear blue sky, while the distant community homes are visible in the background, creating an inviting leisure space.
Home in Berlin
4.79 out of 5 average rating, 194 reviews

OC MD trip bayside, great amenities

CalistaRating, 5 stars1 month ago
Absolutely wonderful hosts!! Very responsive and helpful. There might have been an issue with the lockbox so they called ahead to make sure we could get in! I will definitely be booking with Shawn and Terri again!
Top guest favorite
A modern two-story home is situated on a tree-lined lot, featuring a welcoming front entrance. Brightly colored adirondack chairs provide seating in the gravel area by the driveway, which accommodates several vehicles. Natural light filters through the trees, creating a serene environment.
Home in Ocean Pines
4.97 out of 5 average rating, 32 reviews

Beautiful Spacious 4 Bedroom Home in Ocean Pines

DimitrisRating, 5 stars2 weeks ago
My family and I find this place to feel like home. Very clean the host was very responsive to any questions I had prior to the date of the event. The price was just right for all that we received. The place was private with much to do and the surrounding area. I definitely will be coming here when I visit Home again .This place was big enough for my family of eight to enjoy themselves to the fullest. Thank you again.
Guest favorite
A comfortable living room is highlighted by a large television set on a white cabinet. A soft blue couch and loveseat provide seating, complemented by a colorful coffee table featuring a coastal design. Two lamps illuminate the space, along with natural light from a nearby window.
Home in Ocean Pines
4.94 out of 5 average rating, 52 reviews

Close to OC, Family Friendly, Pool Access

TanieshaRating, 5 stars1 week ago
This was my very first time using an airbnb and Beth set the bar high! I honestly don't know if i could ever stay in a plan old hotel room ever again. She was helpful and responsive from the day we made the reservation all the way through and including our checkout. Beth created a welcome package that made acclimating to her home a breeze. Her house was clean, organized and stocked with all the essentials. What was advertised in the photos and description is exactly what was provided. She even had a wide variety of games to play! As far as location, it was just the right distance away from the hustle and bustle of the beach. We were able to go enjoy our day and then return to the quiet and peacefulness of her home to get a good night's sleep. Her home was also convenient to shopping within 15 minutes of driving. Checkout was easy and without a housekeeping cart sitting in the hallway, I didn’t feel rushed. So if you're planning to visit OC, Beth's house is right for you.
Guest favorite
A single-story beach house features a light grey exterior with white shutters and a welcoming front porch. Lush greenery and a gravel path enhance the charming entrance, while tall trees create a natural backdrop, providing a serene setting.
Home in Ocean Pines
4.93 out of 5 average rating, 44 reviews

Charming Home in a Beach Town Community!

ErinRating, 5 stars10 months ago
Ocean Pines is the perfect location- 20 minutes from the beach and lots of activities in Ocean City but a nice quiet and peaceful place to come back to to relax and enjoy the night with family. This house was a great size with really nice showers and plenty of space. We got the resident rate to visit the Ocean Pines pools which was very nice.
Superhost
The exterior of a two-story house is shown at dusk, illuminated by soft lights from the large circular windows. A front porch is visible, welcoming guests into the home. Lush greenery surrounds the property, creating a tranquil atmosphere.
Home in Ocean Pines
4.86 out of 5 average rating, 50 reviews

Entire Home w King Bed in Peaceful OceanPines 🌊🌲

JordanRating, 5 stars6 months ago
This was our second stay at this beautiful home that was perfect for my family to celebrate Thanksgiving! Fantastic location, 15 min to the beach, restaurants and stores a few minutes away, everything we needed if we forgot anything or didn’t feel like cooking. The beds were super comfortable and the open floor plan was perfect our family to hang out!

Condo rentals with a pool

Top guest favorite
A living area is shown, featuring two brown leather sofas arranged around a wooden coffee table. A lamp provides soft illumination, and a wall-mounted television is visible. A bookshelf filled with books and a decorative piece enhances the cozy environment.
Condo in Bethany Beach
4.93 out of 5 average rating, 299 reviews

Sea Colony Premier Family Resort

ReneeRating, 5 stars4 days ago
Great place to stay at Sea Colony. The place was very nice and looked just like the pictures, and the amenities at the resort were excellent. My husband loved the open pickleball play and we both liked the pools and tram. Great location between many beach towns and boardwalks.
Guest favorite
A light-filled living area features a soft, neutral-toned sectional sofa facing a wooden coffee table. Floor-to-ceiling windows showcase ocean views, with sunlight reflecting off the water. A flat-screen TV is mounted on a wooden entertainment unit, complementing the room's modern design.
Condo in Ocean City
4.91 out of 5 average rating, 310 reviews

Oceanfront Family Oasis: Pool, Beach & Parking!

JasonRating, 5 stars1 month ago
Great place to stay in Ocean City! clean and wonderful place situated right off the beach secluded and quiet. had lots of beach materials for use. would stay again.
Guest favorite
A comfortable living area is furnished with a large gray sectional sofa and an additional chair. A blue ottoman sits at the center, adorned with a decorative tray. Light pours in through large windows, highlighting a coastal-themed photograph on the wall.
Condo in Dewey Beach
4.94 out of 5 average rating, 65 reviews

Luxury Bay & Oceanview Condo in the Heart of Dewey

SueRating, 5 stars3 weeks ago
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.
Superhost
An open living space features large glass doors that lead to a balcony with ocean views. The balcony is furnished with metal chairs and a small table. A cozy white sofa is positioned nearby, with a decorative pillow adding a touch of color.
Condo in Ocean City
5 out of 5 average rating, 3 reviews

New Updated Direct Oceanfront Condo - Pool & Wifi!

KaraRating, 5 stars2 weeks ago
Listing is better than you think it is! Great location (I was nervous about it because we usually stay closer to 120th St) it was very private and peaceful. Big bonus that it is right over the bridge (no extra traffic lights!) The kitchen is fully stocked - we wound up bringing a lot that we didn’t need. The pullout couch is also one of the most comfortable I’ve ever been on. Beautifully decorated and updated. Might book again this season!
Top guest favorite
A cozy living area features a comfortable grey sofa adorned with beach-themed pillows. Light wood flooring complements the dining area, which includes a small table and four chairs. The open kitchen is visible in the background, equipped with white cabinetry and modern appliances.
Condo in Ocean City
5 out of 5 average rating, 44 reviews

Top Rated! Beautful Sunsets! Midtown Bayside Condo

LandonRating, 5 stars1 week ago
Raphaelle is a great host and our stay was amazing. With great views and an accommodating place, would certainly return!
Superhost
A sunlit indoor lounge area is surrounded by large windows, offering a view of the indoor pool. Rattan furniture with tropical-patterned cushions is arranged around a low table. Decorative plants enhance the green ambiance, contributing to a relaxing environment.
Condo in Ocean City
4.88 out of 5 average rating, 197 reviews

🌊Oceanfront studio w/ amazing views & amenities🏖

TeriRating, 5 stars3 weeks ago
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.
Guest favorite
A welcoming kitchen and dining area is displayed, with modern appliances and a wooden dining table. Colorful letters spelling 'Welcome' are arranged on a sideboard, while a refrigerator and seating area are visible in the background, enhancing the cozy atmosphere.
Condo in Ocean City
4.9 out of 5 average rating, 40 reviews

BaysideGetaway | 2 Blk to Beach & Boardwalk | Pool

ReginaRating, 5 stars1 month ago
Was an adorable place! It was perfect for the weekend away! It was within walking dostance of the beach and boardwalk. Matthew was amazing with his instructions on how to locate the home. He was very quick to respond and extremely kind. Highly recommend this place!
Guest favorite
An outdoor pool area features a rectangular pool with a clear blue surface. Sun loungers are positioned around the pool, and a glass enclosure creates a barrier against the elements. The building's multiple floors are visible in the background under a sunny sky.
Condo in Ocean City
4.97 out of 5 average rating, 126 reviews

Direct Ocean Front/Gorgeous Views/Indoor Pool

DianeRating, 5 stars1 week ago
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.

Quick stats about vacation rentals with a pool in Ocean Pines

  • Total rentals

    140 properties

  • Nightly prices starting at

    G$8,372 GYD before taxes and fees

  • Total number of reviews

    3.4K reviews

  • Family-friendly rentals

    140 properties are a good fit for families

  • Pet-friendly rentals

    50 properties allow pets

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

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