
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!

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!

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 :)

DirectOceanFront on Boardwalk/Newly Remodeled/Pool
Newly renovated and beautifully decorated direct oceanfront condo 1BR/1BA on the 4th floor, 12th St. on the center of the Boardwalk. Enjoy AMAZING VIEWS of the sunrises over the ocean and refreshing ocean breeze from the top floor. You can watch Ocean City’s best access to entertainment like the air show, fireworks, car shows and more on your private balcony. Within walking distance are great restaurants, shopping, nightlife, amusement parks, and plenty of water activities, and Pet Friendly.

Luxe Oceanfront 1BR | Pool, Hot Tub, Sun Deck
Wake up to breathtaking beach and ocean views from this beautifully renovated 3rd-floor oceanfront 1BR condo in North Ocean City. Enjoy direct beach access, one reserved parking space, elevators, linens and towels, a heated indoor pool and hot tub, and a stunning new 4,000 SF ocean-view sun deck completed for 2026. Inside, this stylish coastal retreat sleeps 4 with a king bedroom, queen sleeper sofa, 1.5 bathrooms, a renovated kitchen, private oceanfront balcony, and comfortable lounge space.

Luxury 3BR/4BA Condo: Indoor Pool, Walk to Beach
Spacious luxury condo on Harbour Island Marina, just two blocks from the beach and boardwalk . Relax and enjoy all Ocean City has to offer . Nearly 2,000 sq ft, 3 bedrooms, 3.5 baths, and a private balcony overlooking the marina . Enjoy luxury bedding, linens, bath & beach towels, beach chairs, and a beach wagon. Enjoy Indoor pool, fitness center, and private parking. Home of the White Marlin Open. Steps to fishing, boardwalk, watersports, and great restaurants. Sleeps 8 comfortably .

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

DownByTheBay 214-Sleeps 15/Downtown/Boardwalk/Pool
Come and enjoy this oasis, accommodates 15, this 3 BR 3.5 BA home is in the heart of Ocean City MD, minutes from the beach & located steps away from Ocean City most popular attraction, The BOARDWALK. There is everything you will need for a large group to retreat (fully equipped kitchen), 2 large balconies, 2 car parking plus community & street parking, outdoor pool *This property DOES NOT provide linens/towels* ***Please FIND us @ Down by the Bay OCMD For current Promotion**

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

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.

New Updated Direct Oceanfront Condo - Pool & Wifi!
Ocean Front, Just renovated, never rented unit is located in Mid-Town Ocean City on 58th St. and boasts incredible oceanfront and bay views! This is the perfect getaway for a couple or a small family looking to relax at the beach - there is a pool, a balcony perfect for watching the sunrise, a kitchen for making meals, a living room with flat screen TV, a private half bathroom in the bedroom, and a full bathroom off the hallway. Free wifi, washer/dryer

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

Cozy beach home away from home!

IdealSpotPoolGaragePingPongBikes2BlksBeach&BrdWlk!

Mi Casa at Bay Knolls

High Tide @ Lighthouse Bay

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

Peaceful place to escape.

Ocean Palms II - Renovated, Ocean Block, Midtown

Ocean Pines Retreat with Beach Club
Apartment rentals with a pool

Your Comfortable Beach Get-A-Way

Luxury Waterfront Beach Condo @ Coconut Malorie OC

1st Floor Canal Front POOL 2 Blocks 2 Beach/Park

Oceanfront Family Oasis: Pool, Beach & Parking!

Bayside Condo in Midtown Ocean City MD

Ocean Block - Clean, cozy 1 Bedroom. Pool, Wifi

Completely Renovated Luxury Bay Front Condo

Bright Oceanside Condo with Pool - Ocean City, MD
Other holiday rentals with a pool

Private pool, waterfront, kayaks, bikes, firepits!

Bayside Bungalow - Waterfront

Ocean Front Condo

Oceanfront 4 Bedroom Penthouse With Pool! FH1706

NEW: Oceanfront End-Unit Condo w/ 100ft Balcony

Townhome 90 steps to sand w Pool! New Beds!

Oceanfront Retreat | Pool | Deck | 2 Balconies

Bayside Family Oasis - Perfect for Large Families
When is the best time to visit Ocean City?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $208 SGD | $192 SGD | $192 SGD | $210 SGD | $250 SGD | $354 SGD | $419 SGD | $407 SGD | $289 SGD | $242 SGD | $219 SGD | $205 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
- Ocean City Beach
- Wildwood Crest Beach New Jersey
- Ocean City Boardwalk
- Broadkill Beach
- Rehoboth Beach
- Assateague State Park
- Cape Henlopen State Park
- Bethany Beach Boardwalk
- Willow Creek Winery & Farm
- Northside Park
- Ocean City Boardwalk
- Delaware Seashore State Park
- Jolly Roger Amusement Park
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- Wildwood Boardwalk
- Roland E Powell Convention Center
- Wildwoods Convention Center
- Mariner's Arcade
- Funland
- Dewey Beach Access
- Hawk Haven Vineyard & Winery





