
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!
LocationFamilyDecor

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!
FamilyLocationBiking

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
LocationFamilyBathroom

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.
FamilyValueNearby

Luxury Oceanfront Oasis!
Welcome to Marigot Beach, one of the most coveted building in OC. This stunning condo boasts 2 spacious bedrooms and 2 bathrooms, ideal for a large family or a large group up to 8 guests. The master bedroom features an en-suite bathroom, while the second bedroom offers two full-size beds. Included: free WiFi, smart TVs in every room, fully equipped kitchen, large-capacity washer/dryer, and elevator. PLUS, take advantage of TWO designated parking spots! Pool/hot tub are now OPEN!
LocationFamilyTV

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
ValueFamilyAmenities

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.
ValueLocationGetting around

Beachy Sunset Island Townhouse!
Located in the heart of Sunset Island, this 4 bed/4.5 bath townhouse is steps away from the clubhouse and bay. Beautifully decorated and suitable for families, this home even includes baby gear and a crib so you don't have to bring anything with you. Relax on Sunset Island's private beaches and never leave the community. Everything is available at your fingertips for an unforgettable stay. With 2,400 square feet of living space, there is room for everyone!
LocationFamilyIndoor spaces

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.
FamilyValueOutdoor spaces

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!
LocationFamilyHospitality

Oceanfront 2 Bedroom-Sleeps 6-Indoor/Outdoor Pool
Kick back and relax in this beautiful and modern newly remodeled condo in Golden Sands! This rare 2 bedroom, 1.5 bathroom unit has an amazing Master Suite with full-length windows providing panoramic views down the coastline, and direct access to the private patio. Renowned building amenities include outdoor pool, top floor indoor pool, gym, tiki bar, sun deck & more. Linens & towels included!
ValueFamilyKitchen

Boutique Style 2 Bedroom Apartment w/pool
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.
ValueLocationSleep quality
Popular amenities for Ocean City rentals with a pool
House rentals with a pool

Cozy beach home away from home!
FamilyLocationAccuracy

Sunshine Retreat and Free Mini Golf /Huge Pool
FamilyValueGrill

IdealSpotPoolGaragePingPongBikes2BlksBeach&BrdWlk!
FamilyLocationAmenities

Mi Casa at Bay Knolls
FamilyLocationAccuracy

High Tide @ Lighthouse Bay
LocationFamilyCondition

Cabin in the Pines I Luxury Touches + EV Charging
LocationFamilyNearby

Peaceful place to escape.
ValueLocationPool

Ocean Front Boardwalk Condo With Pool! EC204
ValueFamilyNearby
Apartment rentals with a pool

Your Comfortable Beach Get-A-Way
FamilyLocationSleep quality

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

Golden Sands Direct Beachfront/Oceanfront!
LocationValueNearby

Lovely Condo Steps 2Beach+Pool Unlimited Parking
ValueFamilyTV

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

Oceanfront•Pool•Private Balcony w/Sunrise Views
ValueLocationKitchen

Serene Bayfront Bliss 3 Bedroom Condo
LocationFamilyLaundry

Downtown Condo, Parking, Walk to Beach & Boardwalk
LocationValueBathroom
Other holiday rentals with a pool

Upscale Family Home in OC, Community Pool, Grill
FamilyLocationEV charging

Sun, Swim & Serenity
LocationFamilyHospitality

Bayside Bungalow - Waterfront
FamilyLocationLayout

Studio 1/2 block from the beach!
FamilyLocationSleep quality

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

Oceanfront Retreat | Pool | Deck | 2 Balconies
LocationFamilyParking

Bayside Family Oasis - Perfect for Large Families
FamilyLocationWalkability

2 Bedroom Private Condo Central Location OCMD
LocationFamilyQuiet
When 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 | $192 SGD | $192 SGD | $210 SGD | $250 SGD | $353 SGD | $418 SGD | $406 SGD | $288 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
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- Ocean City Beach
- Broadkill Beach
- Ocean City Boardwalk
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- Cape Henlopen State Park
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