
Holiday rentals with a pool in Ocean City
Find and book unique homes with a pool on Airbnb
Quick stats about holiday rentals with a pool in Ocean City

Total holiday rentals
Explore 3,570 holiday rentals in Ocean City

Nightly prices starting at
Ocean City holiday rentals start at $51 SGD per night before taxes and fees

Verified guest reviews
Over 62,620 verified reviews to help you choose

Family-friendly holiday rentals
2,630 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 210 rentals that welcome pets

Rentals with dedicated workspaces
1,780 properties have a dedicated workspace

Wifi availability
3,270 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
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!
4.93 out of 5 average rating, 290 reviews
Beautiful waterview 2B condo w/Dock&Close to Beach
Welcome to the Canal Bungalow! A stylish 1000 sq. foot retreat to enjoy all the fun & relaxation of the coastal lifestyle in North Oc. Bring your boat with you and dock alongside your back porch, enjoy pool access in a private gated community, or bring your sports gear for Northside Park. We are tucked away on the quiet bayside of OC & only a few minutes walk to the beach. Unwind on our beautiful balcony while watching the boats go by & finally understand the true meaning of a coastal lifestyle!
5.0 out of 5 average rating, 122 reviews
Direct Oceanfront Newly Renovated W/ Pool 2 Bd
A slice of paradise on the 18th floor! This fully renovated beachfront condo boasts breathtaking views of the glistening ocean. With two bedrooms and two modern baths, this haven offers the perfect blend of luxury and comfort. Imagine waking up to the sound of waves crashing and sipping your morning coffee overlooking the endless horizon. Whether you're lounging by the shimmering pool or strolling along the pristine shoreline, every moment here is infused with the tranquility of coastal living.
4.99 out of 5 average rating, 107 reviews
3 BR Waterfront Home, Minutes to the Beach
Recently updated waterfront house located in the family-friendly Montego Bay community. Enjoy beautiful sunsets on the back deck or hop in one of the kayaks for a paddle around the wide-open canal. Try your hand at crabbing or fishing off the dock to catch your dinner. Within easy walking distance of the beach and Northside Park (about 10 minutes walk to both). Beach chairs, toys, boogie boards, and umbrellas are yours to use for fun in the sand and surf. The dock is available for boat tie-ups.
4.93 out of 5 average rating, 152 reviews
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
4.95 out of 5 average rating, 190 reviews
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
4.88 out of 5 average rating, 145 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.
4.94 out of 5 average rating, 338 reviews
Nice 2 BR Oceanfront, Year Round Fun & Amenities!
Gorgeous kitchen & main areas renovated 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, then daily by Memorial Day.
4.91 out of 5 average rating, 328 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.
4.96 out of 5 average rating, 327 reviews
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.
4.9 out of 5 average rating, 366 reviews
21st Floor Carousel - 2 BR Oceanfront & Bay View
NEW!! Welcome to our direct oceanfront 2 bedroom & 2 bath unit at the Carousel! Bringing the comfort of your home to the beach! Bring the whole family for lots of fun memories! We strive to take care of this condo to ensure you have a relaxing, comfortable, and clean stay! Our condo includes 2 DOUBLE SIZED balconies! An oceanfront balcony and a bay view balcony! You can enjoy both the sunrise and sunset!
4.96 out of 5 average rating, 118 reviews
Coastal 2 Bedroom Apartment w/pool
Have fun and enjoy a stylish experience at our two bedroom apartment located in a heart of Ocean City, only a few blocks away from the beach, Ocean City boardwalk and within a walking distance to many amazing restaurants and bars, convenience stores, amusement park, mini-golf, boutiques, playground.
4.99 out of 5 average rating, 108 reviewsPopular amenities for Ocean City rentals with a pool
House rentals with a pool

Stunning Bayview Home with Own Private Pool
4.98 out of 5 average rating, 162 reviews
Beachy Sunset Island Townhouse!
4.91 out of 5 average rating, 102 reviews
Cozy 3 BR Pet Friendly Beach, Bay & Pond nearby.
4.97 out of 5 average rating, 162 reviews
Ocean Pines Retreat with Beach Club
4.99 out of 5 average rating, 137 reviews
Camelot
4.97 out of 5 average rating, 153 reviews
The Big Chill at Bethany Beach
4.98 out of 5 average rating, 105 reviews
Point Break - 4BR Beach House Private Heated Pool
4.84 out of 5 average rating, 50 reviews
Ocean Palms II - Renovated, Ocean Block, Midtown
4.98 out of 5 average rating, 54 reviewsApartment rentals with a pool

Luxury Oceanfront Oasis!
4.95 out of 5 average rating, 107 reviews
Completely Renovated Luxury Bay Front Condo
4.97 out of 5 average rating, 108 reviews
DirectOceanFront on Boardwalk/Newly Remodeled/Pool
4.78 out of 5 average rating, 243 reviews
Beautiful 2BR 2BA oceanfront condo at the Atlantis
4.98 out of 5 average rating, 112 reviews
Ocean Block - Clean, cozy 1 Bedroom. Pool, Wifi
4.84 out of 5 average rating, 146 reviews
Spacious Bayside 2 BR Condo at Sunset Bay
4.95 out of 5 average rating, 118 reviews
OCEAN FRONT Gem w/Pools, Movie Theater, Gameroom
4.93 out of 5 average rating, 139 reviews
1st Floor Canal Front POOL 2 Blocks 2 Beach/Park
4.97 out of 5 average rating, 115 reviewsOther holiday rentals with a pool

Bayfront Cottage w/ Amazing Views
4.98 out of 5 average rating, 222 reviews
Luxury 3BR/4BA Condo: Indoor Pool, Walk to Beach
5.0 out of 5 average rating, 13 reviews
NEW: Oceanfront End-Unit Condo w/ 100ft Balcony
5.0 out of 5 average rating, 10 reviews
Beautiful Ocean Front Condo 2b/2ba with pool
4.98 out of 5 average rating, 92 reviews
2 Bedroom Private Condo Central Location OCMD
4.88 out of 5 average rating, 24 reviews
Oceanfront Balcony • Pool • North Ocean City
5.0 out of 5 average rating, 24 reviews
Sleeps26 Mins to Beach w. GameRoom-Pool-BBallCourt
4.92 out of 5 average rating, 37 reviews
Golden Sands Direct Beachfront/Oceanfront!
4.87 out of 5 average rating, 85 reviewsWhen is the best time to visit Ocean City?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $207 SGD | $191 SGD | $191 SGD | $209 SGD | $249 SGD | $352 SGD | $417 SGD | $404 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 |
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- Chincoteague Island
- Cape May Beach NJ
- Assateague Island National Seashore
- Wildwood Crest Beach New Jersey
- Ocean City Beach
- Broadkill Beach
- Rehoboth Beach
- Bethany Beach Boardwalk
- Assateague State Park
- Cape Henlopen State Park
- Willow Creek Winery & Farm
- Northside Park
- Wildwood Boardwalk
- Delaware Seashore State Park
- Jolly Roger Amusement Park
- Fenwick Island State Park Beach
- Roland E Powell Convention Center
- Wildwoods Convention Center
- Ocean Pines Golf Club
- Mariner's Arcade
- Ocean City Boardwalk
- Funland
- Bear Trap Dunes
- Hawk Haven Vineyard & Winery





