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, 278 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!

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

Spacious 1 bdr, 1bath direct oceanfront condo w/ private oceanfront balcony for sunrises and a private bayside balcony for sunsets! 15th floor. 1 min walk to beach. Outdoor pool. Fountainhead Towers Condo is located on 116th St off Coastal Hwy on the oceanfront. Food lion, CVS, DD, ice cream, wawa, convenient stores & restaurants all within close walking distance WEEKLY RENTALS ONLY: Sat to Sat GUESTS PROVIDE SHEETS & TOWELS Plus on arrival $50 CASH fee that includes parking for a week NO PETS

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, 124 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 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.

4.79 out of 5 average rating, 227 reviews

DirectOceanFront on Boardwalk/Newly Remodeled/Pool

Newly renovated and beautifully decorated direct oceanfront condo 1BR/1BA on the 4th floor, 12th St. on the center of the Boardwalk. Enjoy AMAZING VIEWS of the sunrises over the ocean and refreshing ocean breeze from the top floor. You can watch Ocean City’s best access to entertainment like the air show, fireworks, car shows and more on your private balcony. Within walking distance are great restaurants, shopping, nightlife, amusement parks, and plenty of water activities, and Pet Friendly.

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! 🌊☀️

4.82 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!

4.84 out of 5 average rating, 224 reviews

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.

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.

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.

4.86 out of 5 average rating, 101 reviews

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.

A modern living area features a spacious gray sofa and a wooden coffee table, complemented by a cozy area rug. Large glass doors open to a private oceanfront balcony, allowing natural light to fill the space. Decorative accents include a wall-mounted surfboard and a round mirror.

4.98 out of 5 average rating, 266 reviews

OceanFront-Fireplace-sleeps4-Balcony-King-Disney+

Welcome to Salty Shark - direct oceanfront studio! This remodeled studio sleeps 4 and is in North Ocean City near great restaurants, bars, and 58 acre North Side Park. The park has sports fields, a recreation center, a walking/biking path, crabbing pier, playground, and outdoor fitness area. Building has outdoor pool in summer too! The unit features a King Murphy bed, and a Queen sofa bed. There's also an outdoor pool open in summer months!

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, 344 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, 264 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

4.89 out of 5 average rating, 28 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!

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

A serene koi fish pond is framed by natural stone, with lush green lily pads floating on the water's surface. Various koi fish can be seen swimming in the clear water, adding a calming element to the outdoor space.

4.79 out of 5 average rating, 126 reviews

Welcome to our beach retreat!

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, 139 reviews

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

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.

4.98 out of 5 average rating, 45 reviews

Ocean Palms II - Renovated, Ocean Block, Midtown

A light-filled primary bedroom features a spacious bed with white linens and decorative pillows. Natural light enters through sliding glass doors leading to an outdoor area. Two lamps provide soft illumination beside the bed, and a potted plant adds a touch of greenery.

5 out of 5 average rating, 12 reviews

Spacious 3BD/2BA Condo Steps from the Beach

4.99 out of 5 average rating, 113 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

Condo rentals with a pool

4.97 out of 5 average rating, 63 reviews

Enjoy water view, 2 blocks from beach.

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

4.98 out of 5 average rating, 51 reviews

Steps to the Ocean & boardwalk/3bedroom/2bath

5 out of 5 average rating, 21 reviews

The Salty Tail @ Jamaica Bay 33rd Street - Midtown

4.93 out of 5 average rating, 83 reviews

Two Bedroom/oceanside/boardwalk& Ocean view

A modern kitchen is displayed with white cabinetry and granite countertops. An L-shaped island with four chrome swivel stools offers additional seating. Stainless steel appliances, including a microwave and refrigerator, complement the space. A window provides a view of the water outside.

4.97 out of 5 average rating, 98 reviews

Completely Renovated Luxury Bay Front Condo

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.

4.87 out of 5 average rating, 116 reviews

Oceanfront Condo w/ Resort Amenities 3BDR &3pools

An oceanfront studio features a full Murphy bed draped in a blue and white striped coverlet. A cozy seating area with a plush couch and coffee table is positioned near sliding glass doors, providing a view of the ocean and outdoor seating on the balcony.

4.96 out of 5 average rating, 56 reviews

Direct Oceanfront with Pool - Steps To The Beach

Other holiday rentals with a pool

A light-filled living room is furnished with a gray sectional couch and a low coffee table. A large artwork depicting a beach scene is displayed on one wall. A door leads to a patio area, while a window allows natural light to enhance the space.

4.91 out of 5 average rating, 46 reviews

Spacious, newly renovated

Superhost

A spacious living area presents comfortable seating with striped patterned sofas. A wooden coffee table centers the room, adorned with a decorative arrangement. The open floor plan transitions into a dining area that accommodates a large table, illuminated by natural light from overhead fixtures.

Townhouse in Ocean City

4.85 out of 5 average rating, 89 reviews

DBTB6-3BR Steps to Beach & Boardwalk+Pool/Parking

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

5 out of 5 average rating, 18 reviews

A bright living area features a comfortable blue sofa and an armchair, with a decorative lamp beside them. A white coffee table sits atop a patterned rug, which complements the room's light decor. Two windows, adorned with blinds, allow natural light to filter in.

Home in Ocean Pines

Stubbe's Beach House, Home in Ocean Pines, MD

5 out of 5 average rating, 43 reviews

The living area features a light-colored sofa adorned with decorative pillows, positioned beside a contemporary coffee table on a textured rug. A comfortable swivel chair and an accent table are nearby. Soft lighting is provided by a stylish floor lamp, enhancing the calm atmosphere.

Townhouse in Ocean City

Luxury Water Front 2 Bedroom Condo on Canal

The kitchen area features a wooden countertop with a modern sink and stylish faucet. Shelves hold various glassware and dinnerware, while a spacious dining area is visible in the background, showcasing a large table surrounded by natural lighting.

5 out of 5 average rating, 34 reviews

Bayside Bungalow - Waterfront

Superhost

4.62 out of 5 average rating, 34 reviews

Condo with Pool, Walk to the Beach