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.

1 of 1 pages1 / 1
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
4.94 out of 5 average rating, 284 reviews

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

After relaxing at the beach (just a 7 min walk away), unwind on our deck "watchin' the tide rollin' away!" Get the best of the bay & the beach with this dog-friendly hidden gem! Imagine evenings enjoying the bay breeze as you crack crabs on the deck! Relax inside our open-concept great room that allows everyone to be together. Fish on our private dock or use it for your own boat or jet-ski to dock there. Witness spectacular sunsets with our Kayaks. Enjoy a well lit, private work space to virtual work w/ high speed internet! A new wood CRIB now in master suite for restful sleep! The pools and tennis/pickleball courts are only a few blocks away for your enjoyment! Plus, a truly unique OUTDOOR MOVIE EXPERIENCE for all our guests to make for the best Vacay EVER!

Guest favorite
An open living area is presented, featuring a spacious sectional sofa, a light wood dining table with seating for six, and a modern kitchen. Natural light floods the space through large windows, enhancing the neutral color palette and warm wood accents.
Home in Ocean Pines
5 out of 5 average rating, 17 reviews

House with Fire Pit + Private Yard near Ocean City

Skies of Blue in Ocean Pines offers a 1400 sq ft spacious beach getaway for the entire family. With a bright open floorplan and 3 large bedrooms (King, Queen, 2 Twins + Full), this newly renovated home will meet all your vacation needs. The huge and private backyard is perfect for entertaining or relaxing, with a large deck, firepit, grill, sunroom, and a fenced yard. The house is just 7 miles from the shores of Ocean City and comes with a free beach parking pass at the OP Beach Club (49th ST).

Top guest favorite
Home in Ocean Pines
5 out of 5 average rating, 24 reviews

Whimsical Willow l Beach Club Pass and No Pet Fee

Discover this charming 3-bedroom home! With wood floors throughout, it features a king master suite, a queen bedroom, and a kids’ room with a twin-over-full bunk. Enjoy a fully stocked kitchen, fast WiFi, a screened-in porch, and a jetted tub for ultimate relaxation. Perfect for families or dual-family stays! Explore Ocean Pines or take a quick 10-minute drive to Ocean City for endless fun. Included is the Beach Club Parking Pass! Plus- A local manager is here to ensure everything goes smoothly.

Top guest favorite
A scenic collage features various images: a tranquil beach sunset, a lush golf green with a white sand trap, a wooden pier stretching over gentle waves, wild horses running along the shore, and a charming screened porch nestled among tall trees.
Home in Ocean Pines
4.97 out of 5 average rating, 61 reviews

Ocean Pines-OCMD Bliss at the Beach- Sat. to Sat.

Welcome to Bliss at the Beach, our charming 3br, 2ba home nestled in the desirable, beloved Ocean Pines community. Loved for its safe, quaint, family friendly neighborhoods. Find yourself less than 15 minutes away from the beautiful beaches and vibrant shopping, dining and boardwalk district of Ocean City. Enjoy the ease of the prepaid parking at the Ocean Pines Beach club on 49th street, just unload the family and walk on the beach!! Summer months Bliss is a 7-night minimum to guests 25+older

Top guest favorite
An A-frame structure is set amidst lush greenery, featuring a welcoming front porch with steps leading up to the entrance. Two bicycles are positioned nearby, and vibrant flowers adorn the edges. Sunlight filters through the leafy trees, enhancing the natural surroundings.
Home in Ocean Pines
5 out of 5 average rating, 52 reviews

hi-A-tus A-frame

Charming A-frame nestled in the heart of OP. Open floor plan, softest sheets, flat screen TVs, high speed WiFi, in an amenity filled community surrounded by multiple beaches. 10 min from OC & 15 min from Assateague! Sleeps 4 comfortably. Perf for 4 adults or fam. Must be 25 yrs old. Enjoy all that OP has to offer including 5 pools, multiple playgrounds, yacht club & farmers market. Weekly rental during the high season (6/6 - 8/29), Sat check-in/Sat check-out only! If you book diff, we'll cancel

Guest favorite
Home in Ocean Pines
4.96 out of 5 average rating, 49 reviews

Ocean Pines Chalet

Nestled in the tranquil Ocean Pines, MD, Ocean Pines Chalet is a picturesque 4-bedroom, 3.5-bath haven exuding coastal charm. This delightful retreat is surrounded by a plethora of local amenities including community pools, parks, tennis and basketball courts, skate parks, golf, and a yacht club. A 15-minute drive from the bustling Ocean City beaches, it offers the perfect blend of serene living and beachside excitement, making it an ideal getaway for those seeking both relaxation and adventure

Top guest favorite
A serene waterfront scene is captured at sunset, with vibrant colors reflected in the calm water. A charming building with large windows is illuminated, surrounded by lush trees, and boats are docked along the waterfront, creating a peaceful atmosphere.
Condo in Ocean Pines
4.97 out of 5 average rating, 216 reviews

Ocean Pines Yacht Club Getaway Waterview

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

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, 142 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!

Guest favorite
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
4.96 out of 5 average rating, 138 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.

Guest favorite
A modern kitchen is complemented by a spacious dining area and cozy living room with ocean views. White cabinetry and stainless steel appliances enhance the kitchen, while large windows allow natural light to fill the space, highlighting the wood-paneled ceiling.
Condo in Ocean City
4.95 out of 5 average rating, 178 reviews

Oceanfront 1 Bedroom, Balcony, Sitting Room, Pool

Opal Osprey: This OVERSIZE one-bedroom condo has been completely remodeled... giant oceanfront balcony PLUS a large patio room on the bayside! Expansive ocean views from every angle, super easy beach access, wonderful atmosphere in the quiet north end of OC. Linens included! Property Amenities - King size bed & queen sleeper - Large outdoor pool - Elevators - Dedicated high-speed WiFi and router w/ ethernet (Xfinity 100Mbps) - 2 Smart TVS with Xfinity, Roku - Keyless check-in 24/7

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, 137 reviews

Newly built bright and airy guest suite!!!!

FREE oceanfront parking pass with bookings. 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 waterfront Yacht Club with restaurant and live music (seasonal), golf, farm market, playgrounds, 5 pools/fee, (no pool on property) racquet club.

Top guest favorite
A charming house with a light blue exterior is surrounded by lush greenery. A spacious deck features potted plants and outdoor seating. Colorful Adirondack chairs in red and blue are placed around a small fire pit on a patterned stone patio, inviting relaxation.
Home in Ocean Pines
5 out of 5 average rating, 14 reviews

Cozy beach home away from home!

Welcome! Come enjoy a cozy experience at this centrally located home in the desired Ocean Pines Community! This home is near the playground and allows access to the on-site golf course, five pools (including indoor pool!) tennis courts, and marina for a small fee. Fun in the sun awaits 15 minutes away in downtown Ocean City, where you can stroll the boardwalk, lounge on the sand, or hit the amusement park. Plenty of restaurants, grocery stores and shopping within 15 minutes.

Popular amenities for Ocean Pines rentals with a pool

When is the best time to visit Ocean Pines?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price€145€135€142€160€180€208€239€237€189€171€141€151
Avg. temp3°C4°C7°C13°C18°C23°C26°C24°C21°C15°C9°C5°C

Quick stats about vacation rentals with a pool in Ocean Pines

  • Total vacation rentals

    Explore 170 vacation rentals in Ocean Pines

  • Nightly prices starting at

    Ocean Pines vacation rentals start at €43 per night before taxes and fees

  • Verified guest reviews

    Over 4,300 verified reviews to help you choose

  • Family-friendly vacation rentals

    170 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 50 rentals that welcome pets

  • Rentals with dedicated workspaces

    100 properties have a dedicated workspace

  • Wi-Fi availability

    170 of Ocean Pines vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Ocean Pines rentals

  • 4.8 Average rating

    Ocean Pines stays are highly rated by guests—averaging 4.8 out of 5!

Destinations to explore