Home rentals with a pool near Assateague Island National Seashore

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, 287 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!

Superhost

A sunny deck features white lounge chairs beside an above-ground pool. Lush greenery lines the background, providing a natural setting. A tall umbrella offers shade, and a potted plant adds a touch of greenery to the space.

Holiday home in Berlin

Berlin Beach House, near Ocean City & Assateague!

Close to everything when you stay at this newly renovated vacation home in historic Berlin. Big yard, lots of parking, & walking distance to downtown Berlins restaurants, breweries, grocery, & more. 10 minutes to the beaches of Ocean City Maryland or Assateague Island wild horses. Arcade games and bikes added for 2025 season. Above ground pool open Mid May - Mid Sept. 2 washer & dryers. Locally owned managed and cleaned for a worry free stay. All linens and bath towels provided.License#2023-3

4.82 out of 5 average rating, 107 reviews

The inviting living area features a cozy couch and an armchair, adorned with decorative pillows. Bright blue walls complement the light streaming through multiple windows with white blinds. A coffee table with a boat decor piece rests on a patterned rug that evokes a beach theme.

4.82 out of 5 average rating, 234 reviews

Bayside community great fall rates & amenities

Welcome! Perfectly located for all your beach fun! Our gated community is amenity filled! Close drive to beaches (5 miles OC and Assateague) & to water parks, boardwalk, brewery, quaint town of Berlin, awesome restaurants and more! Short walk to our community pools, pier, rec center, playgrounds, paddle boats at no extra charge! Our beach cottage provides you with all essentials! We are located next door to Frontier Town where they have themed shows, water park, ice cream, and a big arcade!

4.97 out of 5 average rating, 224 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

Water view at Ocean Pines Yacht Club Condo

Steps to 2 pools, 2 marinas, tiki bar and OP Yacht Club. Live music Thursday-Sunday evenings from 6-10pm, (in season). Beach day? Ocean City 15 min drive or walk to the marina and hop on a boat with friends and head across the bay into OC. Assateague Island is a 20 min drive. Crabbing? Fishing? Walk to one of the many Ocean Pines canals or ponds. Golfing? The links are just across the Parkway. Wedding party? Be footsteps away from make lasting memories. Free beach parking on 49th included

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.

4.97 out of 5 average rating, 152 reviews

Camelot

HIGHEST RATED HOUSE IN OCEAN PINES! CHECK OUT OUR AMAZING GUEST REVIEWS :) Jumpstart your ultimate beach getaway at this impressive 3-bedroom, 2-bathroom retreat house! Complete with amenity-packed living spaces with vaulted ceilings and a serene location, you’ll never hunger for entertainment at this family friendly home. Grill out on the patio, roast marshmallows by the fire pit, tee off at a nearby golf course, or enjoy some retail therapy at Outlets Ocean City! A short drive to the beach!

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.

4.95 out of 5 average rating, 103 reviews

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!

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.

4.88 out of 5 average rating, 142 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

Farm stay in Princess Anne

A bright living area features wooden beams and large windows adorned with plaid curtains. A variety of cushions decorate a sectional sofa and a leather couch. A television offers a view of a sports event, while an area rug adds pattern to the wooden floor.

Farmhouse located on a horse farm

Farmhouse located just minutes off of Route 13 in Princess Anne, MD. Enjoy a peaceful farm experience while staying in a charming farmhouse with lots of character. You can walk the grounds of the farm, including a trail through the woods, or take a swim in the pool. We do not offer horseback riding lessons but you can interact with the horses. We are minutes to shopping, groceries, restaurants, UMES, and a short ride to Chincoteague (32 miles) and Ocean City (40 miles).

4.95 out of 5 average rating, 123 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.

4.81 out of 5 average rating, 122 reviews

Mosaic Life Escapes -Bayfront Million Dollar Views

At Mosaic Life Escapes the BAYFRONT is our back yard! Safe gated community home. Water access for paddle boards & kayaks. Community fishing/crabbing pier 2 pools 3 ponds arcade room, playgrounds, paddle boats. 2 bd home w/a million dollar view. Minutes from Ocean City, Assateague Island & Casino. WiFi + 3 smart TVs We have implemented additional sanitizing procedures between guest stays to ensure a clean house! Perfect for a family or romantic get away!

4.94 out of 5 average rating, 130 reviews

A modern kitchen is presented with white cabinetry and stainless-steel appliances, featuring a refrigerator, microwave, and coffee maker. A dining table is set for four, and a cozy seating area with a blue couch is visible. Natural light enters through a window, enhancing the space.

Cottage in Chincoteague

Key Lime Cottage

Escape to your own bayfront retreat in Chincoteague Island, Virginia. Our Key Lime Cottage at the Key West Cottages resort offers views of the Chincoteague Bay, giving you a front-row seat to the breathtaking sunsets that Chincoteague offers each night. This one-bedroom private cottage includes a master bedroom with two queen beds, a fully equipped kitchen, living and dining space, waterfront deck and access to many amenities!

4.97 out of 5 average rating, 137 reviews

A two-story farmhouse features a welcoming porch and elegant landscaping, including trimmed bushes and a stone pathway. The exterior showcases a mix of wood and shingle siding, with large windows reflecting the greenery surrounding the property. A well-maintained lawn is visible in the foreground.

Home in Fruitland

4bed/4.5bath Lux Farmhouse/Pool/Gym/5 min from SU

BEFORE BOOKING: Pool will be open 4/05/26 NO PARTIES/NO EVENTS/NO GATHERINGS, only the amount of guests in your reservation are allowed on the property. Fully restored top to bottom 1920s farm house. Every bedroom has its own full bathroom Full laundry room with extra refrigerator RH furniture All bedding/towels/paper towels/toilet paper/body wash/shampoo/conditioner/spices/laundry detergent included;Total turn key

4.91 out of 5 average rating, 133 reviews

A serene canal view captures waterfront homes reflecting in calm waters at sunset. Docked boats and lush trees frame the scene, showcasing the tranquil atmosphere of the eastern shore. The clear sky hints at the day's end, lending a peaceful ambiance to the surroundings.

Home in Greenbackville

Bayfront Modern Retreat • Dock, Kayaks, Views

Wake up to shimmering Chincoteague Bay views in this modern waterfront escape on Virginia’s Eastern Shore. Spend mornings on the water, afternoons by the fire pit, and evenings under glowing sunsets. Kayaks, bikes, pools, golf, pickleball, and trails are moments away, with beaches a short drive. Bring the dog, unplug, and settle in. Your coastal reset starts here.

Popular amenities for rentals with a pool near Assateague Island National Seashore

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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.

4.93 out of 5 average rating, 150 reviews

3 BR Waterfront Home, Minutes to the Beach

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.

4.99 out of 5 average rating, 135 reviews

Ocean Pines Retreat with Beach Club

4.98 out of 5 average rating, 101 reviews

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

A vibrant pot of red flowers is positioned in the foreground, with a wooden deck leading to a clear blue pool in the background. The pool area features a white fence and steps, surrounded by greenery and a cloudy sky above.

4.98 out of 5 average rating, 161 reviews

Stunning Bayview Home with Own Private Pool

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.

4.88 out of 5 average rating, 168 reviews

Tortuga Cottage: Your All- Season Getaway

A two-story blue house is framed by trees, with a well-maintained front yard. The home features black shutters and white steps leading to a central door. A porch flag and a welcoming bench are visible, enhancing the inviting exterior.

4.95 out of 5 average rating, 148 reviews

Little house in Berlin, Md.

4.94 out of 5 average rating, 218 reviews

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

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, 160 reviews

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

Apartment rentals with a pool

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, 290 reviews

Oceanfront Paradise | Pool | Hot Tub | Beach

4.83 out of 5 average rating, 252 reviews

Beachfront with a View and Amenities Galore

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.

4.96 out of 5 average rating, 322 reviews

Caramar Couples Retreat

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.

4.95 out of 5 average rating, 187 reviews

Oceanfront 1 Bedroom, Balcony, Sitting Room, Pool

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.

5.0 out of 5 average rating, 120 reviews

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

A spacious living area features a cozy arrangement of seating with patterned upholstery and soft textures. A circular coffee table is centered amidst the furniture, and a wall-mounted television is paired with a stone accent wall. Large sliding doors open to the private balcony.

4.9 out of 5 average rating, 198 reviews

Beach Paradise 202-Downtown Luxury Condo Bay View

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.

4.9 out of 5 average rating, 365 reviews

Oceanfront Family Oasis: Pool, Beach & Parking!

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.

4.98 out of 5 average rating, 111 reviews

Beautiful 2BR 2BA oceanfront condo at the Atlantis

Other holiday rentals with a pool

4.99 out of 5 average rating, 103 reviews

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

4.81 out of 5 average rating, 167 reviews

The image captures the exterior of a charming blue house surrounded by vibrant flower beds, primarily featuring red blooms. A yellow sign displaying the house name and address stands prominently in the foreground. Soft evening light enhances the welcoming atmosphere.

Bungalow in Horntown

Nature's retreat @ the Bug-a-Boo. Beaches nearby

Superhost

An aerial view of a marina with multiple boats docked along a well-maintained pathway. The surrounding residential community and parking area are visible, as sunlight reflects off the peaceful water, highlighting the scenic environment.

Townhouse in Ocean Pines

OceanPinesFamilyBeachRetreat~JettdTub~KingBed~Golf

4.87 out of 5 average rating, 109 reviews

4.91 out of 5 average rating, 69 reviews

Cottage in Chincoteague

Holiday Cottages -"Sea Star"~POOL~3 mi. to Beach

4.92 out of 5 average rating, 36 reviews

Sleeps26 Mins to Beach w. GameRoom-Pool-BBallCourt

5.0 out of 5 average rating, 63 reviews

A wooden walkway lined with lush greenery leads toward a tranquil water view, framed by trees. The sky is painted with hues of orange and pink, suggesting a beautiful sunset. A sign indicates safety regulations, enhancing awareness of the natural surroundings.

Townhouse in Selbyville

‘Dockside Retreat’ -pool, minutes to OC/beaches

A modern two-story home is portrayed, featuring a well-maintained front yard with lush green grass. An advanced golf simulator is set up outside, showcasing a virtual golf course on a large screen, with a golf club placed in front, inviting leisurely play.

4.92 out of 5 average rating, 48 reviews

Charming Getaway Golf Simulator