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 private pool is surrounded by a paved patio and lush greenery, providing a serene setting for relaxation. Adirondack chairs are positioned near the pool, while colorful flowers add visual interest to the landscape. The clear water reflects the bright blue sky and scattered clouds.
Home in Berlin
4.96 out of 5 average rating, 74 reviews

Private pool, waterfront, kayaks, bikes, firepits!

LenoreRating, 5 stars1 month ago
We can't wait to return to Golden Quarter Farm! Charming and expansive, the property has everything we were looking for in a place to spend a relaxing weekend with extended family. The historic house is bright and roomy with a well-appointed kitchen; the bedrooms are unique, comfortable, and private; and the living space homey and inviting -- perfect for spending time together. The beautiful views of the riverfront drew everyone outside for walks down the pier, through the fields, and down the sun-dappled forest trails. It was a bit too chilly during our April stay, but the possibilities for enjoying the river (canoe, kayay, SUP) and lovely pool were nonetheless enticing. Finally, I must mention that Evie and Mary were extraordinarily welcoming and accomodating, from communicating proactively to preparing the home for our stay and checking in to make sure everything was perfect. Highly recommend!
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 stars1 month 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!
Superhost
The A-frame cottage features large front windows, allowing natural light to fill the interior. Wooden siding blends harmoniously with the surrounding trees. A spacious deck is accessible, adorned with outdoor seating. Dappled sunlight casts shadows on the ground, creating a serene outdoor setting.
Home in Ocean Pines
4.88 out of 5 average rating, 32 reviews

Captivating A-Frame in beautiful, Ocean Pines

DevinRating, 5 stars1 month ago
Overall a great stay! The house was beautiful and in an awesome location. Lots of things provided free of charge, such as toiletries, frozen food, cleaning supplies, and others. These appeared to be leftover from previous tenants, but neatly tucked away. I like that they aren't wasteful with perfectly good supplies. One light in the kitchen appeared to have been turned on while we went out once. the rustic, retro style was a huge hit for us and we're very appreciative of the hospitality for the duration of our stay here!
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 stars1 month 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. 🦀
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 stars3 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, 53 reviews

Close to OC, Family Friendly, Pool Access

JackieRating, 5 stars3 days ago
Wonderful home in a very peaceful area. Beth was very responsive to questions we had and gave detailed instructions on checking in and out. The home is a perfect size, and we really enjoyed the three season room as a quiet area in the mornings.
Guest favorite
A well-maintained outdoor pool area is surrounded by a secure black fence. Numerous blue umbrellas provide shade over lounge chairs, creating a relaxed atmosphere. The clear blue sky reflects off the water, and nearby structures feature light-colored exteriors typical of resort styles.
Home in Ocean Pines
4.91 out of 5 average rating, 53 reviews

Private, pet-friendly, w/game room & new kitchen

MaureenRating, 5 stars1 week ago
Maria, the host was wonderful. Each time I sent a message she responded quickly. Had a beautiful week especially for the beach. Would definitely rent again and other properties owned by Maria. Nothing against the host, Airbnb fee should be less and the cleaning fee is to high
Guest favorite
The exterior of the home features a welcoming entrance with a covered porch and decorative seasonal wreath. A stone pathway leads to the front door, surrounded by lush plants and landscaping, framed by light-colored siding and a garage door.
Home in Ocean Pines
4.95 out of 5 average rating, 22 reviews

Robin Hood Retreat

DanyetRating, 5 stars1 month ago
Bill is a wonderful , polite. ,accurate and a cool host. The house was neat and clean. Bill made sure you have fresh linens for each bedroom. He was easy to get in contact with.Bill makes you feel at home.The house is beautiful and in a peaceful area!( The pictures does not do this house any justice) Bills house is safe and secure. Bill has many properties and I will be booking again. Thanks bill for everything. You are great!!

Condo rentals with a pool

Guest favorite
A scenic view of a pond is presented, bordered by residential homes that reflect a serene atmosphere. The sky is adorned with clouds, casting varying shades of blue and orange as the sun sets. A fountain can be seen in the pond, adding to the tranquil setting.
Condo in Frankford
4.92 out of 5 average rating, 13 reviews

Pondview Villa: Beach Club Gem

ShannonRating, 5 stars1 month ago
5 Star accommodations, like new! The kitchen had all of the tools, gadgets, pots, pans to help feel at home. We stayed off season (last week of April). We were the only people in the building. Note: for off season guests, the pool isn't open yet. The beaches, trails, and restaurants all nearby made it easy to explore and then return to relax in comfort. We sat on the deck, hung out by the pond with comfy chairs and enjoyed the sunsets. Our 1 1/2 year old Weim dog settled in nicely. We were grateful for water and food bowls provided. If you're staying with kiddos or friends, there is a hidden gem- lots of games tucked away in the coffee table. What a nice touch! All of the instructions for the home were simple, easy to follow. Note: This condo is on the 2nd floor. Easy for us, but may be difficult for some.
Guest favorite
Condo in Ocean City
4.91 out of 5 average rating, 273 reviews

Wight Bay Unit 245

JamieRating, 5 stars8 months ago
we had a great stay for Country Calling! highly recommend!
Superhost
A spacious outdoor deck features a woven seating arrangement, including two lounge chairs, a hanging chair, and a coffee table. Decorative pillows provide comfort, while a potted palm adds a touch of greenery. Glass doors lead to the interior space, allowing for natural light.
Condo in Ocean City
4.95 out of 5 average rating, 19 reviews

Luxury 2BD Condo, Walk to Beach, Pool&Tennis Court

KimberlyRating, 5 stars4 days ago
From the moment we walked in, we were blown away. This condo is gorgeous—beautifully decorated, modern, and clearly designed with adults in mind (no mismatched beachy knick-knacks here!). It strikes that perfect balance of cozy and upscale, with top-of-the-line appliances and thoughtful touches throughout. You can tell a lot of love and care went into creating this space. And the best part? It’s just a block from the beach! We felt instantly at home and didn’t want to leave. If you’re looking for a peaceful, stylish getaway in Ocean City—this is it. Can’t wait to come back!
Superhost
A spacious living area features a comfortable gray sectional sofa adorned with colorful cushions. An inviting lamp sits on a coffee table, while the light beige walls complement the tiled flooring. The open layout connects to the kitchen and dining space in the background.
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!!
Guest favorite
An aerial view captures a seasonal heated pool surrounded by lounge chairs under blue umbrellas. The beach and ocean are visible in the background, highlighting a stretch of sandy shore with colorful beach umbrellas. Parking areas are noted to the side of the building.
Condo in Ocean City
4.89 out of 5 average rating, 168 reviews

Oceanfront Condo: Beach, Pool & Balcony Views!

MichaelRating, 5 stars1 month ago
Spacious and great view! Appreciate the kid-friendly touches like dinnerware, cups.
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
4.87 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
An outdoor community pool is depicted, featuring a spacious area of clear blue water surrounded by lounge chairs. Sun umbrellas provide shade, and a diving board is visible. Lush greenery and a distant building are present in the background, enhancing the inviting environment.
Condo in Ocean City
4.96 out of 5 average rating, 95 reviews

Gone Coastal *Pool* Bayside with view* Top Floor

ShannonRating, 5 stars3 weeks ago
The place was amazing, easily fit my family (5) of us. The condo looks exactly like the pictures, very clean, had games in the closet. I would definitely come back here to stay in the furture.
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, 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.

Quick stats about vacation rentals with a pool in Ocean Pines

  • Total rentals

    140 properties

  • Nightly prices starting at

    ﺩ.ﺇ147 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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