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Vacation rentals with a pool in Ocean Pines

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Ocean Pines

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite

The spacious pool area is surrounded by shaded umbrellas and lounge chairs. A large group of individuals enjoys the water, with a vibrant blue sky above. Steps lead into the pool, providing easy access for guests. Lush greenery frames the scene, enhancing the sense of relaxation.

Condo in Ocean Pines

4.96 out of 5 average rating, 170 reviews

Getaway in Ocean Pines

Steps to 2 pools, 2 marinas, tiki bar and OP Yacht Club. Live music Thursday-Sunday evenings from 6-10pm, (in season). Beach day? Ocean City 15 min drive or walk to the marina and hop on a boat with friends and head across the bay into OC. Assateague Island is a 20 min drive. Crabbing? Fishing? Walk to one of the many Ocean Pines canals or ponds. Golfing? The links are just across the Parkway. Wedding party? Be footsteps away from make lasting memories. Free beach parking on 49th included

The exterior of the home is characterized by a light-colored facade with large windows allowing natural light to fill the interior. A welcoming porch features white railings, while a gravel pathway leads to the entrance. Surrounding greenery enhances the serene environment.

Home in Ocean Pines

5 out of 5 average rating, 10 reviews

Bimini Beach Bungalow w/ beach club pass

Welcome to Bimini Beach, tucked away on a quiet cul-de-sac in the serene community of Ocean Pines. The home includes a brand-new sofa & loveseat, with the rest of the home updated in 2021. The upstairs loft is complete with games, puzzles, books, & gaming rockers. Enjoy a fully stocked kitchen with island seating in addition to a dining table. Directly off the dining room is a screened in porch with picnic table. Linens, bathroom towels, & additional amenities are included for your comfort.

Top guest favorite

The exterior of a single-story house is visible, featuring a spacious front porch with white railings. Large windows allow natural light to enter, while a driveway provides parking for two vehicles. A wooded area surrounds the property, enhancing its peaceful setting.

Home in Ocean Pines

4.98 out of 5 average rating, 122 reviews

Camelot

HIGHEST RATED HOUSE IN OCEAN PINES! CHECK OUT OUR AMAZING GUEST REVIEWS :) Jumpstart your ultimate beach getaway at this impressive 3-bedroom, 2-bathroom retreat house! Complete with amenity-packed living spaces with vaulted ceilings and a serene location, you’ll never hunger for entertainment at this family friendly home. Grill out on the patio, roast marshmallows by the fire pit, tee off at a nearby golf course, or enjoy some retail therapy at Outlets Ocean City! A short drive to the beach!

An aerial view of a marina with multiple boats docked along a well-maintained pathway. The surrounding residential community and parking area are visible, as sunlight reflects off the peaceful water, highlighting the scenic environment.

Townhouse in Ocean Pines

4.95 out of 5 average rating, 60 reviews

OceanPinesFamilyBeachRetreat~JettdTub~KingBed~Golf

Immediate removal of stress at the front door. Being nestled in a marina’s serene waterfront & nature park is good for the soul. Relax in a jetted tub after a sun filled day & an al fresco meal on a back porch with charming outdoor dining. An open concept main level features large windows & comfortable seating through the entire property. 2 full bathrooms upstairs & a king sized bed provide maximum comfort & outdoor living on 2 balconies. Additional fees for pools, pets, >3 guests may apply.

A two-story blue house is framed by trees, with a well-maintained front yard. The home features black shutters and white steps leading to a central door. A porch flag and a welcoming bench are visible, enhancing the inviting exterior.

Home in Ocean Pines

4.95 out of 5 average rating, 129 reviews

Little house in Berlin, Md.

Our home is located in Ocean Pines, Maryland. Spend the day at the beach, golf, come back and relax on our spacious screened porch. The community has 5 pools, walking trails, Parks, and more. The house is a short drive to Ocean City, Md. (8 Miles) via Rt. 90 or Rt. 50. Assateague Island National Seashore is also just a short drive 12 miles. You can see wild horses, beautiful sunsets, ride bikes, or go to the beach. There are many golf courses within 15 miles of the house all very nice.

Top guest favorite

A bright, open kitchen area is visible, featuring modern appliances and a spacious countertop. Large windows allow natural light to fill the room. A comfortable chair sits beside a decorative rug, while a sleek ceiling fan contributes to the airy atmosphere.

Guest suite in Ocean Pines

4.99 out of 5 average rating, 121 reviews

Newly built bright and airy guest suite!!!!

Welcome to our new 2nd floor private suite with parking, patio/firepit, and self check-in private entry. We are located just minutes from the Ocean City beaches, quaint small town of Berlin, Ocean Downs Casino, Assateague, Windmill Creek Winery, restaurants, and outlets. Enjoy neighborhood amenities such as a breathtaking waterfront Yacht Club with restaurant and live music (seasonal), Robert Trent Jones Sr. golf, farm market, playgrounds, 5 pools/fee (4 seasonal), and racquet club.

Top guest favorite

A vibrant pool area features playful water structures, including a large mushroom fountain and spray jets. Children are seen enjoying the water, while sun umbrellas provide shade for nearby seating. Surrounding areas are lined with lounge chairs, enhancing the recreational atmosphere.

Cottage in Ocean Pines

4.96 out of 5 average rating, 28 reviews

Cozy Cottage near the Ocean and Wild Horses

Blissfully quiet 1000 sq. feet, 3 rooms (2 bedrooms, and 1 telework-ready study), 2 full bathrooms, and screened in porch. Surrounded by towering pine trees yet only minutes from the tranquility of Assateague National Park or the excitement of the Ocean City boardwalk, "Burr Hill" has it all. Easy access to fee-based amenities: 5 swimming pools, a golf course, pickle ball courts as well as nearby kayaking, a winery, multiple restaurants and Berlin voted Best Little Town in the US!

An inviting beachfront pool area is presented, featuring bright blue water surrounded by a spacious deck. Yellow umbrellas and lounge chairs are arranged around the pool, offering a comfortable space to relax. A clear view of the ocean is visible in the background under a sunny sky.

Condo in Ocean City

4.96 out of 5 average rating, 275 reviews

Direct Oceanfront with a View and Amenities Galore

Note: Must be 25 or older to rent our home. Beautifully renovated 2 bedroom beach front condo with views of both the beach and bay. Enjoy watching the waves roll in or a stunning sunrise through floor to ceiling windows without ever getting out of your king size bed. In the evening, open your front door to witness breathtaking sunsets over the bay. Or just relax with a drink on the beachfront balcony and listen to the waves with full 100% view of the beach and ocean.

Home in Ocean Pines

4.83 out of 5 average rating, 126 reviews

Peaceful Beach Cottage - Sanitized & WiFi!

Fully renovated clean, sanitized, quaint house in a quiet neighborhood minutes from the beach/ocean! Community offers many amenities such as pools, restaurants, playgrounds, etc. Have peace and quiet while only being minutes from the beach and main OC drag. Very close to the casino! Voted "#1 Safest Neighborhood in Maryland!" *June-August we only accept 7 day rentals with a Saturday check in* *Memorial & Labor Day weekends have 3 night minimum with Fri check in*

An indoor pool area is featured, with clear water and comfortable seating around the perimeter. The pool is surrounded by light-colored walls and large windows, allowing natural light to fill the space. Accessible steps lead into the water, contributing to ease of entry.

Condo in Ocean City

4.92 out of 5 average rating, 230 reviews

Sun, Sand & Sea | Your Cozy Oceanfront Hideaway

**2025 guests: Our pool and hot tub are in the process of being renovated and will be closed during your stay. This does not impact our condo, but you will not be able to use these amenities.** -Oceanfront -Indoor pool & Hot tub -Walk to local dining and shopping -Elevator accessible plus luggage carts -Full kitchen for cooking meals -Fast Wifi and Streaming TVs -Fully Stocked Home: Clean linens, towels, toilet paper, paper towels & more!

A blue water slide is displayed adjacent to a large indoor swimming pool. Brightly colored bunting decorations hang along the poolside. Nearby, lifeguard chairs and railings are positioned for safety, complementing the spacious and well-maintained aquatic environment.

Home in Ocean Pines

4.88 out of 5 average rating, 145 reviews

Tortuga Cottage: Your All- Season Getaway

This is an escape to reacquaint with family, nature, and your best self. Come home from the beach just a few miles away to enjoy the gas fire place, outdoor fire pit, and hot tub on chilly nights, fenced in back yard. Take advantage of the parks indoor outdoor pools golf yacht club, just moments from the cottage. Dogs are part of our family, and we are happy to consider canine guests on a case by case basis. Please see policies for breeds.

An outdoor swimming pool is framed by a wooden deck, providing ample lounge chairs for relaxation. Surrounding the pool, the building's balconies highlight the architecture, while greenery offers a touch of nature. The inviting water reflects the bright sky above.

Condo in Ocean City

4.96 out of 5 average rating, 121 reviews

WraparoundBalcony-2 Bed-Sleeps 8-Pool-Laundry-WiFi

Welcome to our stunning oceanfront retreat! This luxurious property offers the perfect combination of comfort, style, and breathtaking views. With a spacious J-shaped wraparound balcony, you can indulge in panoramic vistas of the sparkling ocean waves from every angle. Ideal for groups of up to 8 guests, this two-bedroom, two-bathroom getaway provides ample space for everyone to unwind. Book today for the vacation you'll never forget!

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Popular amenities for Ocean Pines rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

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

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*

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.

4.94 out of 5 average rating, 51 reviews

Amazing 2 Bedroom home close to the beach!

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.

4.79 out of 5 average rating, 194 reviews

OC MD trip bayside, great amenities

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

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

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!

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 🌊🌲

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

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!

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

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!

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

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🏖

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

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

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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