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Holiday rentals with a pool in Ocean City

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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.

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Guest favourite
A light and airy deck features a rectangular dining table surrounded by aqua-colored chairs. A calm water view is visible beyond the railing, with flags gently waving in the breeze. Soft lighting is provided by string lights overhead, enhancing the inviting atmosphere.
Home in Ocean City

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!

LocationValueLaundry

4.94 out of 5 average rating, 288 reviews
Top guest favourite
The living area is spacious, featuring a light blue wall color and a large sectional sofa. Natural light floods through windows, illuminating the decorative rug. The outdoor porch includes dining furniture and offers views of the canal and neighboring buildings.
Apartment in Ocean City

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!

ValueLocationAmenities

5.0 out of 5 average rating, 120 reviews
Guest favourite
A back deck features a seating area composed of a sofa and ottoman with soft cushions, facing a calm canal. A wooden table is positioned nearby. A red umbrella is closed and stands beside the seating, while a sunset casts gentle hues across the water.
Home in Ocean City

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.

ValueFamilyDecor

4.93 out of 5 average rating, 150 reviews
Top guest favourite
An expansive view of a sandy beach stretches along the coastline under a clear blue sky. Colorful umbrellas dot the shore, and the calm ocean appears in vibrant shades of blue, merging with the horizon in the background.
Flat in Ocean City

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.

LocationFamilyParking

4.99 out of 5 average rating, 106 reviews
Guest favourite
A modern kitchen is complemented by a spacious dining area and cozy living room with ocean views. White cabinetry and stainless steel appliances enhance the kitchen, while large windows allow natural light to fill the space, highlighting the wood-paneled ceiling.
Apartment in Ocean City

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

LocationFamilyComfort

4.95 out of 5 average rating, 187 reviews
Guest favourite
A private balcony is showcased overlooking the ocean, featuring two comfortable chairs and a small table. The scene is framed by large sliding doors, allowing natural light to brighten the space. Green turf flooring complements the outdoor seating area.
Apartment in Ocean City

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!

LocationFamilyAccuracy

4.95 out of 5 average rating, 103 reviews
Top guest favourite
A panoramic view of the ocean is visible, with gentle waves lapping at the sandy beach. Below, an outdoor pool is surrounded by lounge chairs and clear pathways, providing a peaceful atmosphere. Skies are blue, enhancing the serene coastal setting.
Apartment in Ocean City

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

FamilyValueGetting around

4.88 out of 5 average rating, 142 reviews
Guest favourite
Apartment in Ocean City

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.

ValueLocationCleanliness

4.83 out of 5 average rating, 252 reviews
Top guest favourite
A cozy living area displays a light blue color scheme. A white sofa is positioned beside a coffee table on a patterned rug, while a dining table is set nearby. Floor-to-ceiling sliding doors open to a balcony, offering views of the ocean.
Apartment in Ocean City

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.

ValueLocationGetting around

4.96 out of 5 average rating, 322 reviews
Top guest favourite
A spacious balcony offers unobstructed ocean views, featuring two comfortable wooden chairs and a small circular table. The bright blue waters and clear sky create a serene backdrop, enhancing the feeling of open outdoor space.
Apartment in Ocean City

Beautiful 2BR 2BA oceanfront condo at the Atlantis

Beautiful ocean views from this 2BR, 2BA oceanfront condo. One of the few units in the Atlantis with an OPEN BALCONY. Located on the 14th floor in the Atlantis Building within midtown Ocean City. Equipped with elevator, wifi, outdoor pool, Direct TV streaming, washer/dryer, onsite Security, and much more. 1 parking spot for $60 registration fee paid at check-in. Food shopping, coffee shop, and restaurants are located across the street (walking distance).

ValueFamilyDecor

4.98 out of 5 average rating, 111 reviews
Top guest favourite
A bright living area features a blue sofa, a striped armchair, and a wooden coffee table. Natural light flows through sliding glass doors that lead to a balcony with ocean views. Light curtains frame the view, and a TV is mounted on a light-colored media console.
Apartment in Ocean City

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!

LocationFamilyCheck-in

4.96 out of 5 average rating, 115 reviews
Top guest favourite
A light-filled dining area features a long wooden table surrounded by several chairs. Soft curtains frame the windows, allowing natural light to enter. A cozy seating area includes a brown leather chair and a wooden side table, enhancing the space's inviting feel.
Flat in Ocean City

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.

LocationValueAir conditioning

4.99 out of 5 average rating, 103 reviews

Popular amenities for Ocean City rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Top guest favourite
The townhouse complex stands amidst vibrant trees, their leaves reflecting the colors of the season. The multicolored façades of the homes suggest a welcoming atmosphere, enhanced by the white railings of the porches. A clear blue sky frames the scene, creating a serene setting.
Home in Ocean City

Beachy Sunset Island Townhouse!

FamilyLocationNearby

4.91 out of 5 average rating, 102 reviews
Top guest favourite
A spacious living area features two sofas, one in dark leather and the other in a light fabric, arranged around a low wooden coffee table. A flat-screen TV is mounted on a light wall above a stone fireplace, adding a cozy touch to the room.
Home in Ocean City

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

LocationFamilyPool

4.97 out of 5 average rating, 160 reviews
Top guest favourite
The exterior of a single-story house is visible, featuring a spacious front porch with white railings. Large windows allow natural light to enter, while a driveway provides parking for two vehicles. A wooded area surrounds the property, enhancing its peaceful setting.
Home in Ocean Pines

Camelot

ValueLocationAir conditioning

4.97 out of 5 average rating, 152 reviews
Top guest favourite
A spacious living room features a comfortable dark sofa, two brown chairs, and a cozy fireplace. Natural light enters through large windows adorned with light blue drapes. A ceiling fan and recessed lighting contribute to a bright and airy atmosphere, complemented by modern decor.
Home in Ocean Pines

Ocean Pines Retreat with Beach Club

ValueFamilyParks

4.99 out of 5 average rating, 135 reviews
Guest favourite
A bright living area features a comfortable blue sofa and a cozy armchair, with a gas fireplace as the focal point. Natural light floods the space through large windows, while a dining table and chairs are visible in the background, creating an inviting atmosphere for gatherings.
Home in Ocean Pines

Tortuga Cottage: Your All- Season Getaway

LocationValueWalkability

4.88 out of 5 average rating, 168 reviews
Top guest favourite
A charming beach house is set on stilts, featuring a pink exterior with white shutters. The front porch offers a welcoming entry, surrounded by a landscaped yard with trees. Gravel driveway and a white picket fence enhance the appealing exterior in a tranquil neighborhood.
Home in Frankford

The Big Chill at Bethany Beach

ValueLocationTV

4.98 out of 5 average rating, 101 reviews
Top guest favourite
The exterior of a modern house is presented at dusk, featuring a welcoming porch with multiple seating areas. Illuminated windows reflect warm light, while a lamp post adds ambiance. A tidy driveway leads up to the home, framed by well-maintained landscaping.
Home in Ocean City

Upscale Family Home in North OC

FamilyLocationKitchen

5.0 out of 5 average rating, 66 reviews
Top guest favourite
A multi-story building features a light blue exterior with large balconies on each floor. The structure includes multiple levels, with a rooftop and decorative architectural elements. Surrounding landscaping includes trees and shrubs, providing a pleasant view from the street.
Home in Ocean City

Ocean Palms II - Renovated, Ocean Block, Midtown

ValueLocationAccuracy

4.98 out of 5 average rating, 52 reviews

Apartment rentals with a pool

Superhost
A light-filled living area features a soft, neutral-toned sectional sofa facing a wooden coffee table. Floor-to-ceiling windows showcase ocean views, with sunlight reflecting off the water. A flat-screen TV is mounted on a wooden entertainment unit, complementing the room's modern design.
Apartment in Ocean City

Oceanfront Family Oasis: Pool, Beach & Parking!

ValueFamilyCleanliness

4.9 out of 5 average rating, 365 reviews
Guest favourite
A three-story building with a light blue exterior is shown. Multiple balconies are visible, equipped with railings, and the entrance is marked by a sign. Underneath the structure, a private parking area is accessible, with a gate in the foreground.
Apartment in Ocean City

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

FamilyValueBathroom

4.84 out of 5 average rating, 144 reviews
Top guest favourite
An open kitchen-living area features modern black cabinetry and stainless steel appliances. A dining table is positioned near a large window, offering views of the ocean. Soft furnishings create a relaxed atmosphere, while natural light floods the space through the glass slider leading to the balcony.
Apartment in Ocean City

Nice 2 BR Oceanfront, Year Round Fun & Amenities!

LocationFamilyBathroom

4.91 out of 5 average rating, 328 reviews
Guest favourite
Apartment in Ocean City

Oceanfront Bldg.| 2 pools | Tennis | Game Room

ValueLocationHeating

4.96 out of 5 average rating, 125 reviews
Superhost
An open-concept living and dining area features a wooden dining table set for six, complemented by modern chairs. A comfortable seating arrangement with light-colored couches is situated near large windows, offering views of the surrounding area. A mounted TV and decorative elements enhance the space.
Apartment in Ocean City

OCEAN FRONT Gem w/Pools, Movie Theater, Gameroom

FamilyLocationSleep quality

4.93 out of 5 average rating, 138 reviews
Guest favourite
A view from the 14th floor balcony is presented, showcasing the ocean and sandy beach under clear blue skies. The sparkling water reflects sunlight, while a glass table and chairs provide a space for relaxation. Coastal vegetation can be seen along the shore.
Apartment in Ocean City

Oceanview Oasis with 2 private balconies

FamilyValueCleanliness

4.86 out of 5 average rating, 125 reviews
Superhost
A private balcony features two turquoise adirondack chairs facing the ocean. The oceanfront view showcases the sandy beach and rolling waves, inviting moments of relaxation and enjoyment. A decorative 'Seaside' sign is displayed on the wall, enhancing the coastal ambiance.
Apartment in Ocean City

DirectOceanFront on Boardwalk/Newly Remodeled/Pool

LocationValueHospitality

4.78 out of 5 average rating, 240 reviews
Guest favourite
A spacious living area features two light-colored sofas and a wooden coffee table at its center. A fireplace is positioned beneath a wall-mounted TV. Panoramic windows offer views of the bay, with access to a balcony visible in the background.
Apartment in Ocean City

Serene Bayfront Bliss 3 Bedroom Condo

LocationFamilyLaundry

4.91 out of 5 average rating, 35 reviews

Other holiday rentals with a pool

Guest favourite
Flat in Ocean City

Amazing oceanfront view 3 blocks from boardwalk

LocationValueHospitality

4.84 out of 5 average rating, 174 reviews
Top guest favourite
An open floor plan is showcased, featuring a modern kitchen with a central island and white cabinetry. Large sliding glass doors allow for natural light and ocean views. A cozy seating area includes a coffee table and comfortable blue couches, inviting relaxation in a bright environment.
Flat in Ocean City

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

FamilyLocationAmenities

5.0 out of 5 average rating, 10 reviews
Superhost
Flat in Ocean City

2 Bedroom Private Condo Central Location OCMD

LocationFamilySleep quality

4.91 out of 5 average rating, 22 reviews
Guest favourite
The living area is characterized by a light color palette, featuring a large blue sofa and a comfortable gray couch. A textured area rug anchors the seating around a round coffee table. Natural light enters through multiple windows, enhancing the open and airy feel of the space.
Townhouse in Ocean City

Beach Paradise 214-New Townhouse with Pool, Garage

LocationFamilyComfort

4.9 out of 5 average rating, 67 reviews
Guest favourite
An expansive view of the ocean is captured, showcasing the shimmering water reflecting sunlight. A stretch of sandy beach leads towards the horizon, bordered by a grassy area and wooden fencing. The serene landscape conveys a sense of tranquility and connection to nature.
Apartment in Ocean City

Luxury Beachfront Condo, Ocean City MD

FamilyLocationAir conditioning

4.91 out of 5 average rating, 33 reviews
Guest favourite
Flat in Ocean City

Oceanside Dream 2 BR midtown condo, steps to beach

LocationFamilyComfort

5.0 out of 5 average rating, 18 reviews
Top guest favourite
Home in Ocean City

Oceanfront Oasis Sunrise/Sunset balcony Beach/pool

LocationFamilyAccuracy

5.0 out of 5 average rating, 21 reviews
Superhost
A welcoming living area is characterized by a turquoise wall and features a light blue couch paired with a colorful patterned chair. A white coffee table sits centrally, and a lamp provides soft illumination. Natural light enters through multiple windows, enhancing the airy feel.
Bungalow in Ocean City

Riptide Beach House

ValueFamilyAccuracy

4.5 out of 5 average rating, 52 reviews

When is the best time to visit Ocean City?

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Avg. price$206 SGD$191 SGD$191 SGD$209 SGD$248 SGD$351 SGD$416 SGD$404 SGD$286 SGD$241 SGD$218 SGD$204 SGD
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