Holiday rentals with a pool in Ocean City

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.

4.94 out of 5 average rating, 279 reviews

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!

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.

4.96 out of 5 average rating, 125 reviews

OCEAN FRONT Gem w/Pools, Movie Theater, Gameroom

Launch your fabulous beach getaway at amenity-rich Sunset Cove at Sea Watch, part of an oceanfront condo complex offering 3 pools, complimentary movie theater, game room, gym, and much more. Enjoy spectacular ocean and bay views from 2 balconies, smart TVs in every bedroom and living room with provided satellite programming, fully equipped kitchen, comfortable living and bedroom spaces–and that’s just the beginning as your group has a blast at the beach and all of Ocean City’s fun attractions.

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.

4.98 out of 5 average rating, 244 reviews

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

4.84 out of 5 average rating, 178 reviews

Love Above the Waves-OceanView/Rooftop Heated Pool

🥂 Complimentary bottle of champagne on arrival, endless ocean views, private balcony, golden sunrises, rooftop heated pool, and direct beach access await at this romantic retreat. Celebrate your love from the 15th floor of Love Above the Waves - a romantic retreat for anniversaries, engagements, birthdays and peaceful escapes for two. Inside, a warm, inviting interior sets the mood—dine out nearby or enjoy a candlelit dinner on the balcony, often with dolphins playing in the waves.

4.82 out of 5 average rating, 114 reviews

Lovely beach-front condo with pool and views

Kick back and relax in this calm, stylish space. This one-bedroom condo is the perfect space for 1-2 couples, or a family. You have floor-to-ceiling beach views, plus amazing sunrises and sunsets from the two separate balconies. The kitchen is well equipped to cook every meal, or eat out at Ocean City's many restaurants. Your stay also comes with 4 pool passes for accessing the onsite seasonal outdoor pool (viewable from the unit) and access to the building’s tennis/pickleball courts!

4.87 out of 5 average rating, 112 reviews

A bright living room features a large sectional sofa and a decorative round coffee table on a colorful area rug. Natural light enters through a window adorned with light curtains, and a ceiling fan circulates air. A television setup is positioned on a media cabinet.

Townhouse in Ocean City

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**

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.

4.86 out of 5 average rating, 117 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

4.93 out of 5 average rating, 105 reviews

Boutique Moments OC • Pool • Walk to Boardwalk

Stylish, spotless getaway in an unbeatable location, just 2 blocks from the beach and minutes from the Boardwalk and downtown restaurants. Enjoy a beautiful pool, fast WiFi, cable TV, and a fully equipped, modern space. I personally care for the home to ensure exceptional cleanliness and comfort for every stay. The primary guest must be at least 21 years old to book, children are welcome with an adult present, and please note that no parties and no pets are allowed.

A balcony view reveals a vast ocean stretching toward the horizon, with golden sands lining the shore. Below, the sea meets a bustling beach town, with rows of buildings and palm trees lining the streets. A comfortable, dark wooden chair is positioned on the balcony.

4.95 out of 5 average rating, 197 reviews

Everything Under The Sun-Gorgeous Ocean&Bay Views!

FULLY RENOVATED!!! An efficient space in a GREAT location for your next beach getaway! Upon arrival, no need to get back in your car- walk to breakfast/lunch/dinner/late night hangouts, grocery, mini-golf, OC Center of the Arts, playground, beach or Assawoman Bay. Full kitchen for your convenience if you choose to dine-in. One reserved parking spot in the condo lot. Oceanfront pool with large concrete pool-deck! Fitness Center & coin operated laundry facility.

The living room features a large window providing stunning ocean views. Two turquoise chairs and a comfortable blue sofa are arranged around a wooden coffee table. A patterned rug adds visual interest to the space, while a flat-screen television is mounted on the wall.

4.92 out of 5 average rating, 142 reviews

Oceanfront 2 Bed/1.5 Bath, Balcony, Pools, Lounge

Wake up to breathtaking ocean views at Driftwood, a beautifully remodeled 2BR/1.5BA oceanfront condo in the amenity-rich Golden Sands Resort! Sleeps 6 with 2 queen beds + queen sleeper sofa. Enjoy your private balcony, indoor & outdoor pools, private beach, fitness center, game rooms, tennis, pickleball, volleyball, huge sun deck, and seasonal tiki bar. Steps to the sand and close to Northside Park, top restaurants, and the iconic Ocean City Boardwalk!

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.

4.91 out of 5 average rating, 346 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.

A serene ocean view is presented from a private balcony, featuring two teal chairs. The sandy beach stretches into the distance, with gentle waves lapping at the shore. A clear sky completes the tranquil coastal scene, creating a peaceful atmosphere.

4.92 out of 5 average rating, 270 reviews

Oceanfront Paradise | Pool | Hot Tub | Beach

-Oceanfront -Indoor pool & Hot tub -Walk to local dining and shopping -Elevator accessible plus luggage carts -Full kitchen for cooking meals -Fast Wifi and Streaming TVs -Fully Stocked Home: Clean linens, towels, toilet paper, paper towels & more! **2026 guests: Our pool and hot tub are in the process of being renovated and will be closed during your stay. They will re-open after Memorial Day**

Popular amenities for Ocean City rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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.

4.97 out of 5 average rating, 106 reviews

Coastal Oasis w/ Outdoor Shower + 2 Pools

The living room area features a comfortable sectional sofa, a large television mounted on the wall, and a media console. Natural light is provided by the sliding glass doors leading to the outdoor space, dressed with blue curtains that complement the neutral tones of the room.

5 out of 5 average rating, 12 reviews

Low Tide Hideaway

The exterior of a two-story house is showcased, featuring a modern design with blue shingles and white trim accents. Landscaping includes small shrubs and decorative gravel, while a pathway leads to the entrance. The mailbox is visible near the curb, adding to the welcoming appearance.

4.89 out of 5 average rating, 53 reviews

Welcome to the Pearl of the Oyster!

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.

4.97 out of 5 average rating, 140 reviews

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

4.98 out of 5 average rating, 43 reviews

A single-story home with a well-kept exterior is surrounded by trees, providing a serene setting. A covered porch with railings welcomes guests, while a gravel driveway leads to the entrance. The property features a reliable trash can and is nestled within a natural landscape.

Home in Ocean Pines

Tranquil Waters, OceanPines, 3 br, Dog Friendly

4.81 out of 5 average rating, 113 reviews

A serene view of Sinepuxent Bay stretches across the horizon, showcasing expansive grasslands and soft green vegetation. The sky transitions to warm hues of sunset, creating a calming atmosphere. A glimpse of the fishing pier is visible in the distance, enhancing the waterfront scenery.

Home in Berlin

Mosaic Life Escapes -Bayfront Million Dollar Views

The exterior of a multi-story building is displayed, featuring light gray siding and multiple windows. A landscaped area with flowering shrubs is visible in the foreground, and a paved pathway leads up to the entrance. Clear blue skies enhance the inviting atmosphere.

5 out of 5 average rating, 46 reviews

Large beachy feel 4 Bedroom

4.99 out of 5 average rating, 117 reviews

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

Updated 3 Bedroom 2 Bathroom Home - Ocean Pines

Apartment rentals with a pool

An outdoor courtyard features a round table surrounded by six mesh chairs under a blue umbrella. A patterned area rug adds color to the space. Wooden steps lead to the entrance of the unit, complemented by the blue siding of the building.

5 out of 5 average rating, 10 reviews

Welcome to Splash Pad-pools, beach + private patio

A dining area is visible, featuring a wooden table surrounded by four chairs. Large glass doors open to a balcony, revealing expansive views of the ocean and sandy beach. A comfortable seating area is seen nearby with a sofa and TV, creating a welcoming space.

5 out of 5 average rating, 14 reviews

9400 Building #1506| Great Location | Outdoor Pool

A vibrant sunset paints the sky in shades of pink, orange, and purple, with the sun descending towards the horizon over the bay. Silhouettes of nearby buildings and trees frame the scene, enhancing the serene waterfront view.

4.96 out of 5 average rating, 46 reviews

Amazing Bayside Views @Sunset309

5 out of 5 average rating, 21 reviews

The Salty Tail @ Jamaica Bay 33rd Street - Midtown

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.

5 out of 5 average rating, 103 reviews

Beautiful waterview 2B condo w/Dock&Close to Beach

A clear view of a swimming pool surrounded by a fenced area, providing access to the bay. Multiple boats are docked nearby, with calm waters visible in the background. The condo building's exterior is visible, showcasing a light grey finish.

4.89 out of 5 average rating, 84 reviews

UNIQUE Bay Front Sanctuary Condo

4.97 out of 5 average rating, 207 reviews

A serene waterfront scene is captured at sunset, with vibrant colors reflected in the calm water. A charming building with large windows is illuminated, surrounded by lush trees, and boats are docked along the waterfront, creating a peaceful atmosphere.

Apartment in Ocean Pines

Peaceful Marina Village Condo with Marina View

A modern dining area is seen, featuring a large dining table with seating for six. A stylish light fixture hangs overhead, while large windows offer expansive views of the beach and ocean. Comfortable lounge seating is visible in the background, enhancing the open concept design.

4.86 out of 5 average rating, 44 reviews

Extraordinary 3BR Oceanfront Escape | 2 Balconies

Other holiday rentals with a pool

The bedroom features a spacious bed adorned with layered pillows and a textured comforter. Neutral walls are complemented by earthy tones in the artwork above the bed. Natural light filters through the window, which is dressed with light-colored curtains.

4.89 out of 5 average rating, 27 reviews

Fabulous Ocean Block Condo!

A spacious balcony offers stunning water views, furnished with two comfortable chairs and a small table. The bright sky reflects off the water, enhancing the serene atmosphere. A grassy area is visible nearby, providing a contrast to the vibrant ocean hues.

5 out of 5 average rating, 19 reviews

Bella's Vista 306

A light-filled living area is shown with a comfortable sofa and a decorative lamp on a side table. Soft curtains frame the window, revealing a serene waterfront view. The dining area features a table surrounded by light-colored chairs, while the overall decor is bright and inviting.

5 out of 5 average rating, 25 reviews

Luxury Waterfront Beach Condo @ Coconut Malorie OC

4.97 out of 5 average rating, 39 reviews

A view of a serene waterway is captured, with various boats docked along the banks. Charming homes in soft colors line the waterfront, and the sky is clear with a few scattered clouds, creating a tranquil atmosphere.

Townhouse in Ocean City

3BR/Den/3.5B/boat dock/2 blocks to beach/boardwalk

5 out of 5 average rating, 4 reviews

Oceanfront Carousel Condo • Beach Access Resort

4.93 out of 5 average rating, 83 reviews

Two Bedroom/oceanside/boardwalk& Ocean view

4.88 out of 5 average rating, 43 reviews

Beachside Bliss- Steps 2 Sand-Indoor Pool, Game Rm

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.