Vacation rentals with a pool in Maryland Beach

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Maryland Beach

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

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Guest favorite

Home in Ocean City

4.94 out of 5 average rating, 219 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

Condo in Ocean City

4.89 out of 5 average rating, 152 reviews

Prime Condo North OC 2 Blocks to Beach w/ Pool

Pristine condo in North Ocean City with every amenity you can imagine welcomes guests over 21. Rare end unit offers more space than similar units. Two blocks from beach/park makes this the best location in town - fabulous sunset views and pool (Memorial thru Labor Day). 2 bedrooms and 2 stories offers spacious options for 6 guests to spread out. Full kitchen with everything, washer/dryer, central heat/air, Smart TV’s to access your streaming channels High Speed Internet and starter items

Guest favorite

Condo in Ocean City

4.91 out of 5 average rating, 256 reviews

Ocean Front 802 Midtown Oasis Pool & Parking

Wake up to the ocean sunrise in this modern 2 bedroom, completely renovated, condo. Prime location on 29th street, 2 blocks north of the famous OC Boardwalk, 2 blocks east of OC's premier amusement and water park along with two famous crab house and other restaurants within walking distance. One hassle free off street parking spot, free WIFI, full size washer & dryer, and a beautiful outdoor pool steps from the beach. Enjoy the bay sun set view out the front door and fall asleep to the waves.

Guest favorite

Condo in Ocean Pines

4.96 out of 5 average rating, 109 reviews

Waterview Retreat

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

Superhost

Condo in Ocean City

4.85 out of 5 average rating, 102 reviews

2 Bdrm Oceanfront-Pool, Xbox, Pickleball, Gym, HBO

Stunning newly renovated 2 bedroom oceanfront condo in the premiere Golden Sands! Blue Wave is known for its unique 3-tiered wave wall and incredible ocean views from the living room and primary bedroom. SmartTV w/Xbox! Wake up to the sun rising over the ocean right out your bedroom window, and after a cup of coffee on the balcony (included!) head to the building's sun deck,fitness center, lounge, arcades, tennis court, pickleball court,beach volleyball,or indoor/outdoor pools and tiki bar.

Guest favorite

Condo in Ocean City

4.79 out of 5 average rating, 103 reviews

Cozy Ocean Blk, Family Friendly, beach 2 min walk

4 ADULTS MAX. ( 2 queen size beds) No parties, or unauthorized guest allowed in the unit. PLEASE REVIEW RENTAL AGREEMENT BEFORE BOOKING, FOR ALL INFO ABOUT MY UNIT. My place is close to family-friendly activities (movies, mini-golf, beach), nightlife, public transportation, nice variety of places to eat . Its quite, cozy and a 2 minute walk to the beach. Great for couples, individuals, close friends and families (w/children). Only a few blocks from 127 St. Bayside park(family activities)

Guest favorite

Condo in Ocean City

4.94 out of 5 average rating, 227 reviews

Nice 2 BR Oceanfront, Year Round Fun & Amenities!

GORGEOUS kitchen & main areas renovation completed March ‘22!! 2 bedroom, 1.5 bath, direct oceanfront condo on 7th floor of Golden Sands building in OC. It’s clean, comfy, stylish, full of amenities & in a great location. Great WiFi, 3 TVs with cable, DVD, well stocked kitchen & stunning ocean view with large balcony. Top floor has indoor pool, fitness room, sauna & game room. Outdoor pool, tiki bar, gift shop, market & deli open weather permitting in May and then daily by Memorial Day.

Superhost

Condo in Ocean City

4.81 out of 5 average rating, 227 reviews

🏖 *Ocean *Ocean *Ocean* 🏖 Beautiful Condo!!

Oceanfront OCMD! An Awesome 2 Bedroom & 2 FULL Bath Condo in the Atlantis Condominium. Perfect for Families, that sleeps 8! This Beautiful Condo is Self Check-in and is walking distance to Restaurants, Shops, Attractions & Most Importantly - only steps to THE BEACH!! Large Community Outdoor Pool is on site. Many Toys, Games, Puzzles & a Bunk Bed perfect for children. Unit is No Smoking of Any Kind. Also No Pets, large groups (8 max.) or senior week rentals permitted. Book Today!

Guest favorite

Condo in Ocean City

4.97 out of 5 average rating, 226 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.

Guest favorite

Condo in Ocean City

4.85 out of 5 average rating, 99 reviews

Water Front Condo w/Pool Short Walk to Beach

FIRST FLOOR UNIT Bayside Condominium Sleeps 4 - 6 max Walking Distance to Northside Park Walk to the Ocean , don't worry about beach parking NON SMOKING 1 Bedroom 1 Bath condo, First floor unit with an outside deck This Air Conditioned, One Bedroom Condo has a fully equipped kitchen, washer/dryer, full refrigerator. There is a Queen bed and a full bed along with 1 Queen Sleep sofa in the living room *MUST BE 21 OR OVER* No Pets!

Superhost

Condo in Ocean City

4.89 out of 5 average rating, 164 reviews

🌊Oceanfront studio w/ amazing views & amenities🏖

Efficiency/studio condo oceanfront. Queen size Murphy bed, couch, loveseat, full kitchen, bathroom, washer & dryer, ac/heat, parking, awesome amenities. This building is beautiful with amazing views. We clean & stock this condo ourselves so you'll get the owners personal touch without the crazy extra fees that rental companies charge. I love to make everyone's stay as wonderful as possible. Please read entire listing.

Guest favorite

Condo in Ocean City

4.99 out of 5 average rating, 180 reviews

Cozy oceanfront condo with stunning ocean views

Fully updated 1 bed/1 bath oceanfront condo in a quiet, mid-rise building with a beachfront pool in uptown OC. The perfect unit for a quick romantic getaway, long weekend, or family vacation. ***Summer Season: Memorial Day - Labor Day *** -7 Nights, Fri-Fri or Mon-Mon -3 Nights, Fri-Mon -4 Nights, Mon-Fri ***Off Season: Labor Day - Memorial Day*** -Any 2 Nights