Holiday rentals with a pool in Ocean City

The living area features comfortable electric reclining sofas facing a coffee table. Large windows provide views of the ocean, while a dining area and modern kitchen are visible in the background, creating a spacious and inviting atmosphere.

5 out of 5 average rating, 119 reviews

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

Superhost

A spacious open-plan living area is highlighted by hardwood flooring and large windows that allow natural light. A dining table with wooden chairs is set near the balcony. The kitchen features a breakfast bar with turquoise stools, adding a pop of color to the neutral decor.

Townhouse in Ocean City

4.84 out of 5 average rating, 206 reviews

DownByTheBay 115- Waterfront/4BR/Sleep 15/Pool

On The Bay, Beautifully furnished 4BR/3.5BR located in the heart of Midtown Ocean city, MD. * 1 block to beach- 5 min walk * Bonfire Buffet, Dough Roller, Ice cream Parlor - 2 min walk * Mini golf - 2 min walk * Bowling - 5 min walk * OC Boardwalk -7 minute by car * Seacrets - 5 minute by car * Convention Center - 5 minute by car * bus stop -1min walk * Market64- 2min drive *This property DOES NOT provide linens/towels* **Please FIND us at Down by the Bay OCMD For current Promotion**

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.

4.96 out of 5 average rating, 107 reviews

Gone Coastal *Pool* Bayside with view* Top Floor

Welcome to Gone Coastal! Relax in this beautiful 2BR/2BA getaway featuring: 🛏 1 King (Master) | 1 Twin-over-Full Bunk | 1 Sleeper Sofa 🏊‍♂️ Outdoor Community Pools – Lap & Family Pool (Directly Across!) 🔑 Keyless, Contactless Check-in 🌅 Spacious Deck – Outdoor Dining + Bay & Pool Views 📺 Smart TVs + YouTube TV 🛒 1-Minute to Grocery Store 🍽 Fully Equipped Kitchen 📍 Prime Location – 120th St, Heron Harbor 🚗 Ample Free Onsite Parking A perfect retreat for families & beach lovers! 🌊☀️

4.99 out of 5 average rating, 110 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

Beautifully updated and recently renovated, rancher on a great street in Ocean Pines perfect for families and adults looking for a relaxing stay. We offer 3 bedrooms and 2 bathrooms on one level, with new large flat screen TV's, stainless appliances, and everything you'll need for your stay. We have a large driveway and a screened patio. Ocean Pines boasts over a dozen parks and walking trails, a public Yacht Club, 5 pools, 2 marinas, and a championship golf course - 10 min to the beach!

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

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.

4.96 out of 5 average rating, 162 reviews

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

4.84 out of 5 average rating, 178 reviews

Love Above the Waves-Best Ocean View & Heated Pool

🥂 Complimentary champagne, endless ocean views, private balcony, breathtaking sunrises, warm swimming pool and beach strolls await you at this romantic retreat. Love Above the Waves is more than a stay—it’s an unforgettable celebration of love and romance, perfect for birthdays, anniversaries, engagements, or quiet escapes for two. Let the ocean be your witness, the champagne your spark, and the sunrise your reminder that some moments are meant to stay with you forever.

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.

4.95 out of 5 average rating, 310 reviews

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.

A spacious living area is displayed featuring comfortable navy blue sofas and patterned armchairs. A large coffee table rests on a textured rug, with a view of the ocean visible through floor-to-ceiling windows. An electric fireplace adds warmth, while a dining table invites gatherings.

4.86 out of 5 average rating, 229 reviews

PENTHOUSE 8th Floor- Boardwalk, Pool, Sundeck

Book 2 nights, get 1 night FREE stays thru March 10. inquire before booking This is a Ocbeachfrontrentals .com premier property 24/7 SUPPORT LINEN & TOWELS PROVIDED 8TH FLOOR PENTHOUSE! This stunning top floor 3 b 2.5 ba unit is the ULTIMATE friends & family beach trip, located in a premier building in Ocean City. Enjoy the ocean breeze and stunning views from over 150 square ft of private balcony. Wake up to ocean views from every room!

The living room features a comfortable seating area with gray sofas and a round coffee table. A flat-screen TV is mounted on the wall. Large sliding glass doors provide expansive views of the ocean, complemented by a blue area rug on the tiled floor.

4.9 out of 5 average rating, 157 reviews

Oceanfront & Amazing views! Time to book for 2026!

Great Mid-Town location! Direct Ocean front, 3 bedroom 2 full bath condo. Breathtaking views from very room. Natural light flows in from sliding glass doors and new windows, brightening the entire condo. When the surf gets too rough, go for a swim in the outdoor pool. 3 elevators and 2 assigned parking spaces. Make our home your home for vacation. Come stay at the Sandpiper Dunes and make wonderful memories that will last a lifetime!

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.

4.88 out of 5 average rating, 163 reviews

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!

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, 337 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.

Popular amenities for Ocean City rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.88 out of 5 average rating, 25 reviews

2 BR Ocean Front Condo w/Pool, Expansive Views

5 out of 5 average rating, 12 reviews

A charming house with a light blue exterior is surrounded by lush greenery. A spacious deck features potted plants and outdoor seating. Colorful Adirondack chairs in red and blue are placed around a small fire pit on a patterned stone patio, inviting relaxation.

Home in Ocean Pines

Cozy beach home away from home!

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, 275 reviews

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB

A light-filled living area features a comfortable blue sofa and two matching patterned armchairs. A woven coffee table sits in the center, while a television is positioned on a stand nearby. An outdoor balcony is accessible through sliding glass doors that enhance the open feel of the space.

4.85 out of 5 average rating, 39 reviews

Charming 2BR/2BA condo Oceanside, Midtown, Pool

5 out of 5 average rating, 106 reviews

The exterior of the single-family home is shown, featuring a welcoming entrance with a striped awning. A well-maintained front yard with shrubs and a tree provides shade, while the attached garage is visible on the left.

Home in Frankford

Quiet 3BR Coastal Home Minutes to Bethany Beach

The exterior of a modern three-story condo features a light grey façade with white trim. Three private balconies adorned with chairs are visible on the upper levels, providing outdoor seating. The entrance is marked by a door with a clear window and a large house number.

5 out of 5 average rating, 24 reviews

TwoBlockstoBeach&Boardwalk! Pool! PingPong! Bikes!

A bright living room features a blue sofa and an olive green chair, complemented by a blue coffee table. Large sliding glass doors provide views of the bay, while light-colored tile flooring adds to the airy atmosphere. Soft curtains frame the windows, enhancing natural light.

4.94 out of 5 average rating, 17 reviews

Bayside Retreat at Makai

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.

4.91 out of 5 average rating, 79 reviews

Beachy Sunset Island Townhouse!

Condo rentals with a pool

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

The living room features a spacious seating arrangement with a red armchair and a gray chair facing a wooden TV stand. Large sliding glass doors lead to the private oceanfront balcony, allowing natural light to fill the space and offering views of the ocean.

4.79 out of 5 average rating, 121 reviews

Spacious Direct Oceanfront 1BR Condo w/Balconies

Superhost

A comfortable living area features a light-colored table surrounded by ocean-themed upholstered seating. Large glass doors allow natural light to fill the space while offering a view of the balcony and ocean beyond. A flat-screen television is mounted on the wall.

4.89 out of 5 average rating, 118 reviews

Oceanfront Carousel building, Swimming Pools!

A spacious living area features a large sectional sofa in light beige fabric, complemented by a wooden coffee table with a rustic finish. A serene coastal photograph decorates the wall, while soft lighting from a nearby lamp creates a cozy ambiance.

4.95 out of 5 average rating, 60 reviews

Freshly renovated ! Steps to outdoor pool & beach

4.92 out of 5 average rating, 12 reviews

Island Time 2E at Sunset Island

A spacious living area is furnished with a large sectional sofa and two armchairs, creating a comfortable seating arrangement. A coffee table sits in the center, while a flat-screen TV is mounted on the wall. Large sliding glass doors open to a balcony with ocean views.

4.9 out of 5 average rating, 20 reviews

Fabulous Boardwalk Oceanfront w/ Pool

Three condominium buildings rise against a clear blue sky, showcasing varied architectural styles with prominent glass and concrete facades. A sandy path leads toward the beach, bordered by a wooden fence that adds a natural touch to the coastal view.

4.96 out of 5 average rating, 113 reviews

Oceanfront Bldg.| 2 pools | Tennis | Game Room

A furnished balcony offers a table and chairs, providing a perfect spot for enjoying meals with a view. Sunlight glints off the water's surface, while the shoreline features green grass and a pathway leading to the water.

5 out of 5 average rating, 11 reviews

Bayfront Condo 46th St *2 POOLS*Free Linens/Towels

Other holiday rentals with a pool

A panoramic view shows the sandy beach and ocean beyond, with colorful umbrellas dotting the shoreline. The pool area features lounge chairs arranged around a clear blue pool, with a wooden deck extending along the space. Pathways connect to the beach.

4.95 out of 5 average rating, 20 reviews

*New*- North OC Oceanfront 1+BR with Pool

5 out of 5 average rating, 21 reviews

The Salty Tail @ Jamaica Bay 33rd Street - Midtown

A spacious living area is furnished with a blue couch and two light-colored armchairs, set against a backdrop of large sliding glass doors. Natural light fills the room, highlighting the ocean view and access to the balcony. A decorative wall piece adds a touch of character.

4.98 out of 5 average rating, 42 reviews

Oceanfront condo with pool, sleeps 4, free Wi-Fi

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.

4.88 out of 5 average rating, 24 reviews

Luxury Beachfront Condo, Ocean City MD

4.89 out of 5 average rating, 62 reviews

A spacious deck is furnished with padded turquoise seating and a brown outdoor table, offering a relaxed setting for gatherings. The ocean is visible in the background, framed by the railing and complemented by a decorative area rug.

Townhouse in Ocean City

4 BR/2.5 BA, Oceanblock w/pool & fantastic view!

A bright and airy living area features a dining table surrounded by six white chairs. Natural light floods through sliding glass doors leading to a balcony with ocean views. Comfortable seating is provided by a woven chair and a small side table.

5 out of 5 average rating, 28 reviews

Belmont Towers #604 - A Magical Getaway Awaits!

4.9 out of 5 average rating, 21 reviews

The kitchen features wooden cabinets and a mosaic tiled backsplash. A center island with three rattan bar stools is present, alongside full-sized appliances, including a refrigerator and stove. A staircase is visible in the background, leading to the upper level.

Apartment in Ocean City

North OC- short walk 2 beaches and park