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

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!

2BRCapri: Indoor Pool, Game Room, Massage Chair
ALL THE COMFORTS OF HOME AT THE BEACH! BRAND NEW RENOVATED BATHROOMS! -ALL LINENS INCLUDED -Comfortable electric-reclining sofas -65-in smart Roku TV with soundbar. -Massage chair in master bedroom -Balcony & Dining Area w/ Ocean +Bay Views -In-unit W/D -Many conventional & USB Outlets -Arcade level features b-ball hoop, pool tables, ping-pong, shuffleboard, air-hockey -Outdoor tennis court -Large heated indoor pools -can swim full laps -Sauna and Gym -Board games in unit -Fast Wifi

Oceanfront Studio Year round view and amenities!
Enjoy beach sunrise with coffee on balcony&wine w/ sunset on the bay. All w/out leaving the condo. Wall to wall, floor to ceiling window & balcony looking over the beach, & all the other activities. Indoor pool, sauna, gym, solarium, and game room. Summer time Tiki bar, beach volleyball,outdoor pool,private beach, pickle ball and shuffle board. HUGEcommon patio, & shops. Studio has queen murphy bed and sleeper sofa. See pics of beds open. Washer/dryer and full kitchen with dwasher in unit!

BEST SPOT IN OCEAN CITY
Beautiful spacious 3 bedroom 2.5 bath penthouse condo that offers it all. Tall ceilings, open floor plan, spectacular ocean view and gorgeous sunrise and sunsets. Rooftop pool, full kitchen access with a large bar and new appliances. Steps away from the beach. Enjoy great food from one of the many restaurants ocean city has to offer. Great for family vacation. Many activities to choose from including clubs, boardwalk, water park, mini golf, amusement park, indoor ice skating rink, and shopping,

Gone Coastal *Pool* Bayside with view* Top Floor
Welcome to Gone Coastal! Relax in this beautiful 2BR/2BA getaway featuring: 🛏 1 King (Master) | 1 Twin-over-Full Bunk | 1 Sleeper Sofa 🏊♂️ Outdoor Community Pools – Lap & Family Pool (Directly Across!) 🔑 Keyless, Contactless Check-in 🌅 Spacious Deck – Outdoor Dining + Bay & Pool Views 📺 Smart TVs + YouTube TV 🛒 1-Minute to Grocery Store 🍽 Fully Equipped Kitchen 📍 Prime Location – 120th St, Heron Harbor 🚗 Ample Free Onsite Parking A perfect retreat for families & beach lovers! 🌊☀️

DownByTheBay 4601-Midtown/Oversize Sleep 15 w/Pool
On the Bay, Beautifully Furnished 3BR/3BA located in the heart of Ocean City, MD Walking distance to everything you need for a fantastic vacation.. *1 block to beach- 2 min walk *Seacrets - 7 min walk *Dumser's Diaryland, Red Win Bar, 45th st House Bar and Grill- 5 min walk *OC Board walk-10-15 min walk *Jolly Roger Amusement Park- 10 min walk *Mini Market- 10 min walk *Mini golf- 2 min walk *This property DOES NOT provide linens/towels* ***Please contact host For current Promotion**

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

Beachfront 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 a breathtaking view of the beach and ocean.

Everything Under The Sun-Gorgeous Ocean&Bay Views!
FULLY RENOVATED!!! An efficient space in a GREAT location for your next beach getaway! Upon arrival, no need to get back in your car- walk to breakfast/lunch/dinner/late night hangouts, grocery, mini-golf, OC Center of the Arts, playground, beach or Assawoman Bay. Full kitchen for your convenience if you choose to dine-in. One reserved parking spot in the condo lot. Oceanfront pool with large concrete pool-deck! Fitness Center & coin operated laundry facility.

🌊Carousel Oceanfront 2 Bedroom Amazing Amenities
Welcome to our 2 bedroom 2 bath oceanfront condo at the Carousel. We take care of this condo ourselves to ensure you have a comfortable, clean & well stocked place to stay. This unit sleeps 6, 1 king bed, 1 queen bed & 1 queen sofa bed with washer/dryer. Ocean front balcony & a bay view balcony, an ice skating rink, indoor pool, outdoor pool, kiddie pool, 2 game rooms, restaurant & bar, fire pits, playground, hot tub, gift shop, gym & sauna & more!!!

Oceanfront & Amazing views! Time to book for 2026!
Great Mid-Town location! Direct Ocean front, 3 bedroom 2 full bath condo. Breathtaking views from very room. Natural light flows in from sliding glass doors and new windows, brightening the entire condo. When the surf gets too rough, go for a swim in the outdoor pool. 3 elevators and 2 assigned parking spaces. Make our home your home for vacation. Come stay at the Sandpiper Dunes and make wonderful memories that will last a lifetime!

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!
Popular amenities for Ocean City rentals with a pool
House rentals with a pool

Beach Paradise 2101-Downtown Luxury Condo Bay View

Ocean Pines Fun – Arcade, Pools & Near O.C. Beach

Bayside Townhome with Ample Parking

Bayside community near OCMD great rates

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

Welcome to Whitecaps!

Beautiful Cottage W/ shared pool & close 2 beach

Cozy 3 BR Pet Friendly Beach, Bay & Pond nearby.
Apartment rentals with a pool

Oceanfront Oasis: Sunrise Balcony, Pool and Beach!

Oceanfront Family Oasis: Pool, Beach & Parking!

Luxury Beachfront Condo, Ocean City MD

Bayside - Summer Winds Complex - 2 Bedroom, Pool

Beautiful 2BR 2BA oceanfront condo at the Atlantis

Love Above the Waves-Best Ocean View & Heated Pool

Ocean City New 2BR – Bayside Stay w/ Pool

DirectOceanFront on Boardwalk/Newly Remodeled/Pool
Other holiday rentals with a pool

Welcome to Splash Pad-pools, beach + private patio

Best Beach, Bay and OC views!

Direct ocean front 3 bedroom condo with pools

The Salty Tail @ Jamaica Bay 33rd Street - Midtown

4 BR/2.5 BA, Oceanblock w/pool & fantastic view!

Island Time 2E at Sunset Island

Luxurious Bayside Retreat

OC Beach Life
When is the best time to visit Ocean City?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $211 SGD | $207 SGD | $203 SGD | $217 SGD | $278 SGD | $358 SGD | $418 SGD | $405 SGD | $287 SGD | $241 SGD | $218 SGD | $204 SGD |
| Avg. temp | 3°C | 4°C | 7°C | 13°C | 18°C | 23°C | 26°C | 24°C | 21°C | 15°C | 9°C | 5°C |
Quick stats about holiday rentals with a pool in Ocean City

Total holiday rentals
Explore 3,110 holiday rentals in Ocean City

Nightly prices starting at
Ocean City holiday rentals start at $13 SGD per night before taxes and fees

Verified guest reviews
Over 61,810 verified reviews to help you choose

Family-friendly holiday rentals
2,420 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 130 rentals that welcome pets

Rentals with dedicated workspaces
1,580 properties have a dedicated workspace

Wifi availability
3,080 of Ocean City holiday rentals include wifi access

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

4.6 Average rating
Ocean City stays receive an average rating of 4.6 out of 5 from guests
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- Ocean City Beach
- Ocean City Boardwalk
- Broadkill Beach
- Wildwood Crest Beach New Jersey
- Cape May Beach NJ
- Chincoteague Island
- Assateague Island National Seashore
- Willow Creek Winery & Farm
- Jolly Roger Amusement Park
- Bayside Resort Golf Club
- Bear Trap Dunes
- Northside Park
- Cape Henlopen State Park
- Assateague State Park
- Fenwick Island State Park Beach
- Delaware Seashore State Park
- Lewes Public Beach
- Gordons Pond State Park Area
- Mariner's Arcade
- Funland
- Trimper Rides of Ocean City
- Hawk Haven Vineyard & Winery
- Roland E Powell Convention Center
- Wildwood Boardwalk




