
Holiday rentals with a pool in West Ocean City
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in West Ocean City
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Bayside community for OCMD trip great rates
Welcome to MERMAID DREAMS where you can have FUN or just RELAX! We are ONLY 5 miles from OC, MD beaches/boardwalk & Assateague National Park/beaches. Our beach cottage provides you with all the essentials needed, including a washer/drier! Our gated community is bayside, has 2 awesome pools, big splash pool, rec center, a fishing/crabbing pier, pond with paddle boats, 2 playgrounds We are located next door to Frontier Town water slides , western shows, mini golf, a rope course, ice cream shop.

Vacation by the Bay: Condo with Marina View
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

Large beachy feel 4 Bedroom
Bring the whole family to this great place with lots of room for fun. 3 large family room areas for everyone to spread out if they want too! Great kitchen area with everything you need to feel at home including Keurig coffee maker! 3 full bathrooms makes getting ready with large groups easy & you will never run out of hot water with tankless on demand hot water heater! Pool steps from unit. Close to several restaurants & short ride to the beach! Linen package can be rented from 3rd party

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!

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.

Updated 3 Bedroom 2 Bathroom Home - Ocean Pines
Beautifully updated and recently renovated, rancher on a great street in Ocean Pines perfect for families and adults looking for a relaxing stay. We offer 3 bedrooms and 2 bathrooms on one level, with new large flat screen TV's, stainless appliances, and everything you'll need for your stay. We have a large driveway and a screened patio. Ocean Pines boasts over a dozen parks and walking trails, a public Yacht Club, 5 pools, 2 marinas, and a championship golf course - 10 min to the beach!

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.

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*

Our Little Cottage
Adorable 1940’s Bungalow remolded with all the modern conveniences of today. The backyard is equipped for fun with an inground pool and fire pit. The perfect location short walk to restaurants and shopping. Homer Gudelsky park located on the assawoman bay is in walking distance . Bring your boat the public boat ramp is just around the corner as well as the park and ride to take you to our world famous Boardwalk. We are also with in 15 minutes of Assagategue

Luxury Townhome close to OC beach & boardwalk!
Welcome to your ultimate getaway in our brand new luxury townhome! This stylish, three-story home offers over 2,500 sq. ft. of space and is perfect for families or groups, comfortably sleeping up to 11 guests. Just 3 miles from the Ocean City Boardwalk, you’ll have easy access to the beach, shops, restaurants, and endless fun. Enjoy resort-style living at Sea Oaks, ideally located between Ocean City and Assateague Island. Your perfect vacation spot awaits!

Mosaic Life Escapes -Bayfront Million Dollar Views
At Mosaic Life Escapes the BAYFRONT is our back yard! Safe gated community home. Water access for paddle boards & kayaks. Community fishing/crabbing pier 2 pools 3 ponds arcade room, playgrounds, paddle boats. 2 bd home w/a million dollar view. Minutes from Ocean City, Assateague Island & Casino. WiFi + 3 smart TVs We have implemented additional sanitizing procedures between guest stays to ensure a clean house! Perfect for a family or romantic get away!

Bayside Townhouse w/ amazing amenities
Vacation memories are made in the 3BR townhome situated in quiet private community. The property features an indoor and outdoor pool, clubhouse, basketball and tennis courts, kayak dock, crabbing fishing dock and much more! We are 10 minutes drive to OC and about 12 minutes to assateague island. Sleeps 8 Now includes an EV (J1772) charger!
Popular amenities for West Ocean City rentals with a pool
House rentals with a pool

Private pool, waterfront, kayaks, bikes, firepits!

NEW Beautiful Peaceful Costal Getaway

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

Peace in the Pines- 3BD, 2BA w/ Beach Club Pass

Ocean Pines, Waterfront Oasis

The Whale’s Tale Retreat w/ Beach Club Pass

Cozy 3 BR Pet Friendly Beach, Bay & Pond nearby.

OC Gateway: Modern 4BR/2.5BA home (dog friendly)
Apartment rentals with a pool

Lovely Condo Steps 2Beach+Pool Unlimited Parking

Boutique Moments OC • Pool • Walk to Boardwalk

OceanfrontStudio-Slps4-Pool-Pickleball-HBOMax-Dis+

Oceanfront Family Oasis: Pool, Beach & Parking!

PENTHOUSE 8th Floor- Boardwalk, Pool, Sundeck

Beautiful waterview 2B condo w/Dock&Close to Beach

The Jamaican Sand Turtle

Beachfront with a View and Amenities Galore
Other holiday rentals with a pool

Ocean City Waterfront Home with Skyline Views!

3BR/Den/3.5B/boat dock/2 blocks to beach/boardwalk

Bayside Bungalow - Waterfront

Bayside Condo in Midtown Ocean City MD

OceanPinesFamilyBeachRetreat~JettdTub~KingBed~Golf

Ocean Palms II - Renovated, Ocean Block, Midtown

Fenwick Island Sunset Retreat

Beach Paradise 1204 - New Luxury Townhouse w/Pool
Quick stats about holiday rentals with a pool in West Ocean City

Total holiday rentals
Explore 80 holiday rentals in West Ocean City

Nightly prices starting at
West Ocean City holiday rentals start at $114 SGD per night before taxes and fees

Verified guest reviews
Over 1,480 verified reviews to help you choose

Family-friendly holiday rentals
70 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
70 of West Ocean City holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across West Ocean City rentals

4.8 Average rating
West Ocean City stays are highly rated by guests – averaging 4.8 out of 5!
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- Rentals with pools Worcester County
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- Ocean City Beach
- Ocean City Boardwalk
- Chincoteague Island
- Cape May Beach NJ
- Wildwood Crest Beach New Jersey
- Broadkill Beach
- Assateague Island National Seashore
- Rehoboth Beach
- Willow Creek Winery & Farm
- Bayside Resort Golf Club
- Jolly Roger Amusement Park
- Northside Park
- Cape Henlopen State Park
- Assateague State Park
- Fenwick Island State Park Beach
- Delaware Seashore State Park
- Wildwoods Convention Center
- Roland E Powell Convention Center
- Mariner's Arcade
- Ocean City Boardwalk
- Hawk Haven Vineyard & Winery
- Bethany Beach Boardwalk
- Wildwood Boardwalk
- Trimper Rides of Ocean City




