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Vacation rentals with a pool in Maryland Beach

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Top-rated rentals with a pool in Maryland Beach

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!

ValueFamilyCondition

4.93 out of 5 average rating, 290 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.
Condo 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!

LocationFamilyCondition

5.0 out of 5 average rating, 123 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.

ValueFamilyParking

4.93 out of 5 average rating, 152 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.
Apartment 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.

FamilyLocationLayout

4.99 out of 5 average rating, 107 reviews
Top guest favourite
A balcony is shown featuring two red Adirondack chairs and a small table, positioned to overlook the vast ocean. The horizon is visible in the distance, with a sandy beach below, inviting relaxation and scenic views.
Condo in Ocean City

Luxury Oceanfront Getaway!

Welcome to Marigot Beach, one of the most coveted buildings in OC. This newly renovated condo features a spacious one-bedroom with its own private 1/2 bath. Full bathroom located in the hallway. Sleeping arrangements can comfortably accommodate up to 4 guests, 2 can rest in the bedroom while 2 can enjoy the queen-size sofa in the living room. Included: free WiFi, smart TVs, fully equipped kitchen, washer/dryer, elevator. PLUS, a designated parking spot! Pool/hot tub closed are now OPEN!

LocationValueGetting around

4.96 out of 5 average rating, 104 reviews
Guest favourite
A comfortable living area features a gray sofa with blue accent pillows and a textured rug. Large sliding glass doors offer a view of the ocean and access to a private balcony with outdoor seating. Natural light fills the space, creating a welcoming atmosphere.
Condo in Ocean City

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

LocationFamilyAccuracy

4.98 out of 5 average rating, 271 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.
Condo 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

LocationFamilyParking

4.95 out of 5 average rating, 191 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.
Condo 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

LocationValueTV

4.88 out of 5 average rating, 147 reviews
Guest favourite
The living area features soft blue furnishings and a light wood coffee table. Floor-to-ceiling windows offer direct views of the ocean, while two lamps provide warm lighting. A coastal-themed artwork adorns the wall, enhancing the serene atmosphere of the space.
Condo in Ocean City

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.

FamilyValueBathroom

4.94 out of 5 average rating, 339 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.
Condo in Ocean City

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.

FamilyLocationCondition

4.91 out of 5 average rating, 330 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.
Condo in Ocean City

Oceanview Oasis with 2 private balconies

Relax with your closest friends & family in a serene 14th floor oceanfront condo with updated appliances, dining furniture, and floors! Watch the sun rise/set from 2 private balconies. Enjoy the pool/deck Memorial Day to September 30. Break a sweat on the private tennis & pickleball courts! Explore local restaurants, mini golf, amusement parks, & tax-free shopping in DE! Week long stays preferred during summer months but not mandatory. Minimum age 25.

ValueFamilyWalkability

4.86 out of 5 average rating, 127 reviews
Guest favourite
An open-plan kitchen and living area feature a light wooden counter with three stools. A fully equipped kitchen is visible, including a refrigerator, while a comfortable seating area with a cream-colored armchair and a coffee table is also present. Natural light enhances the inviting space.
Condo in Ocean City

Water Front Condo w/Pool Short Walk to Beach

FIRST FLOOR UNIT Bayside Condominium Sleeps 4 - 6 max Walking Distance to Northside Park Walk to the Ocean , don't worry about beach parking NON SMOKING 1 Bedroom 1 Bath condo, First floor unit with an outside deck This Air Conditioned, One Bedroom Condo has a fully equipped kitchen, washer/dryer, full refrigerator. There is a Queen bed and a full bed along with 1 Queen Sleep sofa in the living room *MUST BE 21 OR OVER* No Pets!

FamilyLocationView

4.89 out of 5 average rating, 187 reviews

Popular amenities for Maryland Beach rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

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.

LocationValueQuiet

4.97 out of 5 average rating, 162 reviews
Top guest favourite
A spacious living area features comfortable seating arrangements, including a large sectional sofa and recliners. A flat-screen television is positioned on an entertainment unit, and ample natural light is provided by multiple windows and a sliding door leading to the sunroom. Wooden flooring enhances the open atmosphere.
Home in Ocean City

Spacious waterfront home & boat access!

FamilyLocationParking

4.95 out of 5 average rating, 108 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

LocationFamilyLayout

4.99 out of 5 average rating, 140 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

ValueFamilyBiking

4.98 out of 5 average rating, 105 reviews
Top guest favourite
A wrap-around deck overlooks a tranquil waterfront view, featuring lush greenery and calm waters. A seating arrangement includes four chairs with cushioned backs, positioned for relaxation. The scene is punctuated by nearby trees, contributing to a serene atmosphere.
Home in Lewes

Beautiful Waterfront Home-Private, Clean, Relaxing

LocationFamilyAccuracy

4.99 out of 5 average rating, 238 reviews
Top guest favourite
The living area features a comfortable arrangement of seating including a gray sofa, an armchair with patterned upholstery, and a coffee table at the center. A television is mounted on the wall, and soft light is provided by a lamp on a side table. Large windows allow natural light to fill the space.
Home in Frankford

A Bethany Beach Gem 1.5 miles to Ocean Pickle Ball

ValueFamilyBathroom

4.94 out of 5 average rating, 218 reviews
Top guest favourite
The covered porch features a wooden floor and decorative string lights overhead. Two comfortable chairs are positioned for relaxation, offering views of the street and neighborhood. The warm glow of the sunset can be seen in the background, enhancing the inviting space.
Home in Ocean City

Coastal Home - Outdoor Shower & 2 Pools

ValueFamilyParks

4.98 out of 5 average rating, 122 reviews
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!

LocationValueKitchen

4.91 out of 5 average rating, 102 reviews

Condo rentals with a pool

Superhost
A spacious bedroom showcases a large window offering panoramic views of the ocean. The room features a king-sized bed with light, patterned bedding, complemented by a nightstand and a dresser. A cozy chair is positioned near the window, inviting relaxation.
Condo in Ocean City

Designer Oceanfront Condo | Pool, Hot Tub & Deck

ValueFamilyOutdoor spaces

4.94 out of 5 average rating, 106 reviews
Top guest favourite
An open living area is highlighted by large windows that offer views of the bay and pool. A comfortable sectional sofa is positioned adjacent to a smart TV, while a modern dining table for four is visible next to the kitchen. The space features light-colored walls and natural wood flooring.
Condo in Ocean City

Gone Coastal | Bay Views, Pool | Top Floor

FamilyLocationCondition

4.97 out of 5 average rating, 124 reviews
Top guest favourite
Condo in Ocean City

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

LocationValueGetting around

4.97 out of 5 average rating, 116 reviews
Top guest favourite
An open floor plan presents a well-lit living area featuring comfortable seating and light blue accents. A subtle sunburst mirror is mounted on the wall, while a patterned area rug adds texture to the space. Kitchen cabinetry and bar seating create an inviting atmosphere.
Condo in Ocean City

Entire beautifully updated Condo with Ocean Views!

LocationFamilySleep quality

4.93 out of 5 average rating, 107 reviews
Guest favourite
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.
Condo in Ocean City

Oceanfront Family Oasis: Pool, Beach & Parking!

FamilyLocationAmenities

4.9 out of 5 average rating, 366 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.
Condo in Ocean City

DirectOceanFront on Boardwalk/Newly Remodeled/Pool

FamilyValueBathroom

4.78 out of 5 average rating, 244 reviews
Guest favourite
Condo in Ocean City

Oceanfront Bldg.| 2 pools | Tennis | Game Room

LocationValueCondition

4.96 out of 5 average rating, 127 reviews
Guest favourite
Condo in Ocean City

Love Above the Waves-OceanView/Rooftop Heated Pool

FamilyValueWalkability

4.85 out of 5 average rating, 194 reviews

Other vacation rentals with a pool

Top guest favourite
A cozy living area is presented with two light-colored sofas, complemented by a woven coffee table at the center. A striped area rug lies beneath, and natural light filters through sheer curtains, enhancing the space's comfort. An indoor plant adds a touch of greenery.
Apartment in Ocean City

Little Paradise

ValueLocationQuiet

5.0 out of 5 average rating, 33 reviews
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.
Apartment in Ocean City

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

LocationFamilyCleanliness

5.0 out of 5 average rating, 10 reviews
Guest favourite
A light-filled living area features a comfortable sofa and a round coffee table. Sliding glass doors lead to a balcony with outdoor seating. Textured wall decor adds interest to the space, while the soft curtains diffuse natural light, creating a warm ambiance.
Apartment in Ocean City

Updated condo with pool & only two blocks to beach

FamilyLocationBeach

4.92 out of 5 average rating, 64 reviews
Top guest favourite
The living area features a spacious gray sectional sofa, complemented by decorative cushions. A wooden coffee table sits atop a vibrant patterned area rug. Light-colored walls and a framed nautical-themed artwork enhance the inviting atmosphere. The kitchen and dining area are visible in the background.
Townhouse in Ocean City

Beachside Luxe: Pool, Ensuite & Family Favorite

FamilyLocationCleanliness

5.0 out of 5 average rating, 33 reviews
Superhost
Condo in Ocean City

20th-Floor Oceanfront Family Escape @ Golden Sands

LocationValueComfort

5.0 out of 5 average rating, 3 reviews
Guest favourite
A welcoming living area features a modern sofa with soft cushions, flanked by two rocking chairs. A white coffee table is centrally placed on a textured area rug, while a colorful accent wall adds visual interest. Large sliding doors allow natural light to brighten the space.
Apartment in Ocean City

Beautiful Ocean City Escape w/ pool

FamilyValueGetting around

4.93 out of 5 average rating, 61 reviews
Guest favourite
A cozy bedroom features a bunk bed with a Twin bed above a Full bed, all adorned with striped bedding in shades of blue and green. Natural light entering through the window highlights the soft carpeted floor and simple furnishings.
Apartment in Ocean City

2 BR 2BA North Ocean City Condo

LocationFamilyAccess

4.93 out of 5 average rating, 59 reviews
Top guest favourite
A light-filled living area is complemented by a muted blue color scheme. A comfortable sofa with decorative pillows is positioned beside an ottoman. A dining table for four is visible, along with a large window offering views of the outdoors. A nautical-themed artwork adorns the wall.
Apartment in Ocean City

Steps to Ocean! North OC Retreat

FamilyLocationCheck-in

5.0 out of 5 average rating, 35 reviews

Destinations to explore