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Vacation rentals with a pool in Worcester County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Worcester County

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

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Home in Ocean City

4.89 out of 5 average rating, 114 reviews

Beautiful 4 BR 2 BA W/ shared pool & close 2 beach

"Beautifully decorated & completely renovated 4 BR 2 BA home only 2 blocks from the bay and a 20 minute walk to the beach! Enjoy this entire home in the coveted & quiet neighborhood of Montego Bay which boasts 2 pools, tennis courts, a fishing pier, a walking pond, mini golf and Northside Park. The kitchen is fully stocked and the house is kid-friendly. There are 2 parking spaces & tons of off-street parking. Finally, enjoy the sunset on the large deck complete with an area for al fresco dining.

Condo in Ocean Pines

4.97 out of 5 average rating, 149 reviews

Escape by the Bay

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

Home in Ocean Pines

4.98 out of 5 average rating, 115 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!

Townhouse in Ocean City

4.92 out of 5 average rating, 129 reviews

IslandCoveParadise: Luxury-NewlyBuilt/Brdwalk/Pool

We welcome you, your family and friends to stay at our luxury, Newly Built, beautifully furnished, & decorated 3 BA 3.5 BR w/ 2 parking garage spaces plus free street parking, and an outdoor pool on 25th street. Relax and enjoy the AMAZING VIEW on the water front from our triple balconies, just 2 blocks (3-4 minutes walk) from the boardwalk & the beach. Steps from Jolly Rogers Amusement Park and many miniature golf courses. Within walking distance are restaurants/, shopping, & nightlife.

Home in Ocean City

4.93 out of 5 average rating, 180 reviews

Right behind Alley Oops & Crab Bag. Walk to beach

Look no further! With Alley OOps in the backyard and a 5-minute walk to the beach, pool, tennis, and shopping, the fun is endless. This 3 bedroom, 2 bathroom house has high-end furniture, fast wifi, 4 flat screens and 2 free parking spots with street parking when available. Our Community offers all of these amenities included in your rental and free putt-putt too! Enjoy our natural wood-burning fireplace and large porch to take in the sunset through the trees. We do not rent to under 25.

Condo in Ocean City

4.89 out of 5 average rating, 179 reviews

Prime Condo North OC 2 Blocks to Beach w/ Pool

Pristine condo in North Ocean City with every amenity you need for a perfect stay. Rare end unit offers more space and views 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 suite in Ocean Pines

4.99 out of 5 average rating, 114 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.

Condo in Ocean City

4.89 out of 5 average rating, 159 reviews

Ocean Front Sea Terrace 209 Heated Pool

3 bedroom if you include the private den. Low Floor and Rare 2 Parking Passes (2nd spot may not be avaiable May -Sept) CONSTRUCTION OCT 2024-APRIL 2025 on pool deck - noise may occur from 7-5 daily. Enjoy your morning coffee on your private ocean front balcony or from the comfort of living room couch. Our ocean front retreat is an end unit (next to stairway) w/ ocean views, heated pool and tennis court. Conveniently located 88th Street walking distance of many OC's favorites.

Condo in Ocean City

4.97 out of 5 average rating, 254 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.

Condo in Ocean City

4.96 out of 5 average rating, 225 reviews

Caramar Couples Retreat

This cute little first floor efficiency condo is ocean front for a perfect vacation to the beach. It’s an older building but has been partially renovated and updated. You can get to the beach by a very short walk through a private walkway from the condo building. The view from the private balcony is perfect and relaxing. WiFi provided upon check in- xfinity, Netflix, and internet. Indoor and outdoor dining areas and a full kitchen. Closet and dresser for storage use.

Condo in Ocean City

4.88 out of 5 average rating, 188 reviews

🌊Oceanfront studio w/ amazing views & amenities🏖

Efficiency/studio condo oceanfront in Golden Sands. 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.

Condo in Ocean City

4.88 out of 5 average rating, 127 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!

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Popular amenities for Worcester County rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Berlin

4.96 out of 5 average rating, 71 reviews

Private pool, waterfront, kayaks, bikes, firepits!

Home in Ocean City

4.94 out of 5 average rating, 234 reviews

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

Home in Ocean City

5 out of 5 average rating, 18 reviews

Luxury OC Beach House w/ Deluxe Game Room & Pool!

Home in Ocean City

4.9 out of 5 average rating, 10 reviews

Welcome to Whitecaps!

Home in Salisbury

4.9 out of 5 average rating, 58 reviews

The Bury Oasis: Pool◈Hot Tub◈Master Suite◈PingPong

Home in Ocean Pines

4.76 out of 5 average rating, 33 reviews

Perfect Beach/Golf Getaway - 3BR Townhouse w/ View

Home in Ocean Pines

4.95 out of 5 average rating, 20 reviews

Tranquil Waters, OceanPines, 3 br, Dog Friendly

Home in Berlin

5 out of 5 average rating, 4 reviews

*Brand New* Bayside Breeze Townhome in West OC

Condo rentals with a pool

Condo in Ocean City

4.97 out of 5 average rating, 37 reviews

Relax, Unwind and Enjoy! Steps To The Beach!

Condo in Ocean City

4.96 out of 5 average rating, 152 reviews

Waterview, Steps from Beach, Linens Included!

Condo in Ocean City

4.96 out of 5 average rating, 27 reviews

2BR Waterfront | 1st Floor | Patio | Pool | W/D

Condo in Ocean City

5 out of 5 average rating, 54 reviews

Downtown, Large Deck, Walk everywhere

Condo in Ocean City

4.99 out of 5 average rating, 208 reviews

Cozy oceanfront condo with stunning ocean views

Condo in Ocean City

4.97 out of 5 average rating, 33 reviews

OCMD family vacation rental 2BR, 2BA, Pool.

Condo in Ocean City

4.89 out of 5 average rating, 123 reviews

2BR- St. Tropez Condominiums- Ocean City, MD!

Condo in Ocean City

4.92 out of 5 average rating, 258 reviews

Nice 2 BR Oceanfront, Year Round Fun & Amenities!

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