
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

SeaGate Serenity | Oceanfront Condo with Balcony
Wake up to the sound of the waves crashing outside your window and finish your days relaxing on the private balcony as you watch the pastel skies over the ocean at sunset. Come find your serenity by the sea in our newly renovated oceanfront condo. Located in midtown, you can keep your car parked in our reserved spot and walk to many of the towns best restaurants, bars, and entertainment as well as the World Famous Ocean City Boardwalk. Morning beach strolls, pool days, and evening sips await :)

Spacious waterfront home & boat access!
Waterfront getaway with easy access to the beach (0.3 mile walk), pool, restaurants, and more. Linens & towels included! Bring your boat! Pier tie up available. Spacious 4 bedroom home with sleeping arrangements for 10. This well-maintained home is close to dining, shopping, NorthsidePark & all the fun activities Ocean City has to offer. Beach chairs, toys, kayaks & paddleboard available. A fireworks show at Northside Park can be viewed every Sunday summer night - right from the driveway!

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. We are happy to accommodate the dates and timeframes that meet the needs of our guests. If possible, please consider these recommended timeframes for your booking: Memorial Day - Labor Day -7 Nights, Fri-Fri or Mon-Mon -3 Nights, Fri-Mon -4 Nights, Mon-Fri Labor Day - Memorial Day -Any 2 Nights

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

Oceanfront Condo w/ Resort Amenities 3BDR &3pools
Sea Watch Condo's is an ideal family location with tons of amenities. The until is a recently updated 3 bedroom 2 bathroom condo that sleeps 6 people in 2 queen beds, 2 twin beds . The unit is ocean front with a large oceanfront balcony. The amenities Include, basketball court, tennis courts, playground, arcade, movie theater, billiard room, indoor pool and outdoor pool as well as a restaurant. The condo has 24 hour security and plenty of parking. Pools closed in off season

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.

Boutique Moments OC • Pool • Walk to Boardwalk
Absolutely no parties! Stylish, spotless boutique getaway just 2 blocks from the beach and minutes from the Boardwalk, downtown restaurants, and local attractions. Enjoy a beautiful pool, fast WiFi, cable TV, and a thoughtfully designed modern stay made for comfort and relaxation. Primary guest must be at least 21 to book. Adults-only stay, no parties, and no pets allowed. 🚪🚪 I’m here to help anytime—I live just 2 doors down.

Oceanfront Family Oasis: Pool, Beach & Parking!
Escape to your dream family vacation in this amazing 2-bedroom condo on the 8th floor! Enjoy incredible ocean views, direct beach access, and proximity to Ocean City's top attractions like the vibrant OC Boardwalk and thrilling amusement parks. This condo offers modern amenities, a refreshing seasonal outdoor pool, and the convenience of free parking. Perfect for families seeking fun and relaxation near the ocean.

Steps to Beach, Pool, Family Friendly with Linens
Welcome to Surf House at Island Cabana, a spacious 3-bedroom, 2-bath condo just steps from the beach in North Ocean City. This elevator building offers a pool, secure lobby, and easy beach access just steps away. Perfect for families, the condo includes beach gear, a fully stocked kitchen, organic bedding, and kid-friendly amenities—plus parking and in-unit laundry for a comfortable, stress-free stay.

Steps to Beach & Boardwalk
Modern 2BR/2BA bayside condo in Ocean City just 2 blocks to the beach, boardwalk & inlet events. Sleeps 6 with king & 2 queen beds, full kitchen, balcony, outdoor pool, smart TVs, WiFi & free parking (incl. guest pass). Walk to Springfest, Bike Week, air shows, rides & dining. Beach gear & onsite laundry included. Park once, walk everywhere — perfect for families, couples & event-goers year-round.
Popular amenities for Ocean City rentals with a pool
House rentals with a pool

2 BR Ocean Front Condo w/Pool, Expansive Views

Cozy beach home away from home!

Coastal Home - Outdoor Shower & 2 Pools

Bayside Oasis *In-Ground Pool*Hot Tub*Huge Yard*

Bayside Family Oasis - Perfect for Large Families

Oceanfront Penthouse - Ocean & Bay Views with Pool

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

Ocean Pines Retreat + Beach Club
Apartment rentals with a pool

Beach Paradise 202-Downtown Luxury Condo Bay View

Gorgeous oceanfront Capri Beach and Bay Views!!!!

Lovely Condo Steps 2Beach+Pool Unlimited Parking

Beach condo next to Seacrets

New Updated Direct Oceanfront Condo - Pool & Wifi!

Oceanfront Bldg.| 2 pools | Tennis | Game Room

OCEAN FRONT Gem w/Pools, Movie Theater, Gameroom

Love Above the Waves-OceanView/Rooftop Heated Pool
Other holiday rentals with a pool

Luxury Waterfront Beach Condo @ Coconut Malorie OC

Perfect Cozy Condo Retreat in OC

Beach House on the MD-DE Border of Ocean City!

Enjoy water view, 2 blocks from beach.

5-Min Walk to Beach | Pool | Sleeps 8 | 3BR/2BA

Bayside View | 3BR | Pool | Deck |Waterfront

Oceanfront•Sunrise View•Pool•Balcony•Elevator

Completely Renovated Luxury Bay Front Condo
When is the best time to visit Ocean City?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $206 SGD | $190 SGD | $190 SGD | $216 SGD | $277 SGD | $355 SGD | $415 SGD | $402 SGD | $286 SGD | $240 SGD | $217 SGD | $203 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 3,230 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 59,350 verified reviews to help you choose

Family-friendly holiday rentals
2,460 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 180 rentals that welcome pets

Rentals with dedicated workspaces
1,650 properties have a dedicated workspace

Wifi availability
3,170 of Ocean City holiday rentals include wifi access

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

4.7 Average rating
Ocean City stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Norfolk Holiday rentals
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- Rentals with lake access Ocean City
- Beachfront rentals Ocean City
- House rentals Ocean City
- Rentals with a sauna Ocean City
- Villa rentals Ocean City
- Rentals with an EV charger Ocean City
- Waterfront rentals Ocean City
- Rentals with a firepit Ocean City
- Rentals with a patio Ocean City
- Rentals with a washing machine and dryer Ocean City
- Rentals with a fireplace Ocean City
- Fitness-friendly rentals Ocean City
- Rentals with an accessible-height toilet Ocean City
- Apartment rentals Ocean City
- Rentals with an accessible-height bed Ocean City
- Hotel rooms Ocean City
- Rentals with outdoor seating Ocean City
- Rentals with a hot tub Ocean City
- Family-friendly rentals Ocean City
- Townhouse rentals Ocean City
- Pet-friendly rentals Ocean City
- Rentals with a cinema Ocean City
- Flat rentals Ocean City
- Beach house rentals Ocean City
- Beach apartment rentals Ocean City
- Rentals with a kayak Ocean City
- Rentals with beach access Ocean City
- Mansion rentals Ocean City
- Rentals with pools Worcester County
- Rentals with pools Maryland
- Rentals with pools United States
- Ocean City Beach
- Ocean City Boardwalk
- Cape May Beach NJ
- Ocean City Boardwalk
- Wildwood Crest Beach New Jersey
- Chincoteague Island
- Broadkill Beach
- Assateague Island National Seashore
- Rehoboth Beach
- Willow Creek Winery & Farm
- Bayside Resort Golf Club
- Northside Park
- Assateague State Park
- Jolly Roger Amusement Park
- Cape Henlopen State Park
- Fenwick Island State Park Beach
- Delaware Seashore State Park
- Bethany Beach Boardwalk
- Wildwoods Convention Center
- Ocean Pines Golf Club
- Roland E Powell Convention Center
- Wildwood Boardwalk
- Hawk Haven Vineyard & Winery
- Mariner's Arcade





