Waterfront vacation rentals in Henlopen Acres

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Henlopen Acres

Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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Superhost

A series of multi-story townhouses is presented, featuring white railings and balconies. The buildings exhibit a uniform architectural style with light-colored exteriors. Lush landscaping, including trees and shrubs, is visible in front of the homes, providing a well-maintained appearance.

Townhouse in Ocean City

4.85 out of 5 average rating, 194 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***

Guest favorite

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

4.96 out of 5 average rating, 102 reviews

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.

Guest favorite

A welcoming entrance is framed by a brick pathway lined with soft green grass and small white lights. Lush trees and vibrant shrubs provide a pleasant contrast to the exterior. Large windows invite natural light into the home, enhancing the overall charm.

Home in Millsboro

5 out of 5 average rating, 10 reviews

Bayfront Oasis Vacation Rental

Waterfront panoramic views with a crabbing dock and boat slip. 4 bedrooms (full/twin bunkbeds, 2 twin beds + full bath, queen bed + full bath, king bed + full bath, and sleeper sofa in living room); up to 14 guests. Additional features include ½ bath, sunroom, living room, kitchen, laundry room (washer/dryer), and gaming room. Outdoor space with dining table, outdoor kitchen, firepit, gazebo, cornhole. Resort amenities; swimming pool, bikes, playground, pickleball, dog park, marina, store.

Guest favorite

A serene view from the balcony captures the sun rising above Little Assawoman Bay, creating a soft blend of orange and pink hues in the sky. Silhouetted trees frame the landscape, while the water reflects the gentle morning light, enhancing the tranquil setting.

Home in Selbyville

5 out of 5 average rating, 5 reviews

Waterfront Luxury Vacation Home!

5 oversized bedrooms, large living space for family time with a direct view of Little Assawoman Bay. It is just a few minute drive to Fenwick Island, closed to grocery stores, restaurants and gas stations. It is the most desirable community in Delaware Beaches. Waking up in the primary bedroom with a view of sun rising from water will make your day start with smiles! Not in the primary? You can enjoy the same water view on the main level balcony. Also enjoy our spectacular community amenities

Top guest favorite

A night view showcases the tranquil canal, reflecting the illuminated houses lining its banks. Docked boats can be seen along the waterfront, while soft lights delineate the walkways. The skyline glows softly in the distance, providing a serene backdrop to the residential community.

Home in Selbyville

4.98 out of 5 average rating, 40 reviews

Waterfront, Bring your own boat! Huge canal home.

Look no further for your vacation rental at the beach, this house has it all! Extraordinary waterfront coastal home with amazing views of the Assawoman Bay and the Ocean City skyline. With 2 expansive living areas with open floor plans, there is plenty of space for multiple parties to unwind. Relax on the deck or in the yard and enjoy the canal breezes. Cook in the updated kitchen and enjoy panoramic water views! Enjoy the beach in Fenwick Island, DE/Ocean City, MD just over 2 miles away.

Guest favorite

A waterfront backyard features sandy areas lined with a white picket fence. A picnic table is positioned on the beach, facing the calm waterway. Houses are visible along the banks, framed by trees and distant structures under a soft evening sky.

Home in Ocean Pines

4.91 out of 5 average rating, 170 reviews

Waterfront Beach Home in the Ocean City, MD Area

There is room for 8 adults (plus 2 kids). Located in the premiere seaside community in the Ocean City area, Ocean Pines, this wonderful waterfront home provides amazing views both day and night. The open floor plan provides guests with lots of room to socialize and bond, but also has secluded bedrooms that provides needed privacy. The outdoor living area is to die for. Sit back and watch the sun set over the canal while you catch up with friends or loved one. Use our bikes!

Superhost

An A-frame cottage is framed by trees, showcasing a combination of blue siding and wooden accents. A wrap-around deck offers outdoor space, while large windows allow natural light to illuminate the interior. Leaves scatter on the ground, enhancing the natural setting.

Cottage in Lewes

4.75 out of 5 average rating, 20 reviews

Dock Holiday - Waterfront A-frame Cottage

Kick back and relax with family and friends in this comfy and stylish mid century modern waterfront cottage in Angola by the Bay, a gated community featuring community crab docks, trails, a pool, and tennis and pickleball. House has huge waterfront lawn for outdoor games. Minutes to the action and amenities nearby such as historic Lewes, Cape Henlopen State Park, Dewey Beach and the famous Rehoboth Beach boardwalk. Bring your own boat or kayaks and get out on the water!

Guest favorite

The serene canal view showcases a clear blue sky above a calm waterway lined with boats and boat slips. The waterfront buildings feature balconies overlooking the water, and manicured lawns extend along the bank, inviting a peaceful outdoor experience.

Townhouse in Ocean City

4.84 out of 5 average rating, 32 reviews

El Ancla

stunning bay sunsets and idyllic outdoor space at this peaceful waterfront home in prime 94th street location with amazing breeze. Recently rehabbed - new hardwood floors, bathroom, and brand new interior and exterior furniture. Bayfront deck with your own boat slip. Brand new casual comfort deck furniture. Remote work with a view! 10 min walk to beach, playground, community arts center, mini golf, bars. Beach chairs included. We can provide pack n play upon request

Guest favorite

A serene view of the bay is captured through large glass doors, showcasing water under a soft, colorful sky at sunset. In the foreground, a decorative mug sits on a quartz kitchen countertop, inviting relaxation.

Condo in Dewey Beach

4.85 out of 5 average rating, 195 reviews

On the Bay, Private Beach-Boat Slip

Enjoy your own piece of paradise! Walk out the door 10 steps to the water! Modern condo located on the bay with great views, a patio, a grill, a private beach, boat slip, and 2 blocks to the ocean. Perfect for couples and small families! This is a well-appointed 500 sqft open concept condo with 1 bedroom, office & 1 bath. We take great pride in our condo and keep everything updated. New living room furniture Spring 2021. Completely renovated in mid 2020.

Guest favorite

A waterfront home is showcased, featuring a light gray exterior with white accents. A small blue boat is moored beside the property, reflecting in calm waters. Lush greenery surrounds the area, enhancing the serene atmosphere. A porch with outdoor seating is visible.

Home in Berlin

5 out of 5 average rating, 10 reviews

Waterfront Home & Golf Getaway

Discover the perfect blend of tranquility and adventure at this one-of-a-kind waterfront escape. Nestled in a peaceful country setting just minutes from the beach, enjoy morning coffee with birdsong or sunset cocktails by the bay. Paddleboard, kayak, or grab fresh crabs from Elliott’s Seafood and dine at the water’s edge. Bring your own boat or rent one locally—this serene, scenic retreat offers everything you need for the ultimate coastal getaway.

Top guest favorite

A two-story house is situated amidst well-maintained landscaping, featuring a beige exterior with dark shutters and flower boxes. Two wooden garage doors complement the structure, while a paved driveway leads to the entrance. A bicycle is parked nearby, enhancing its welcoming feel.

Cottage in Wildwood Crest

4.99 out of 5 average rating, 284 reviews

Bayfront home on Sunset Lake.

We are a 5 star rated Airbnb. We worked hard to earn that and harder to keep it. Our goal is to provide the cleanest and most beautiful experience in the Wildwood's. Beautiful sunsets every evening. Amenities include full kitchen, sub-zero refrigerator, dishwasher and all utensils. Washer and dryer included. Master bedroom with Queen bed and private tile shower. Living room with dining area. Both tv’s are smart, Hulu, Netflix etc.

Superhost

An oversized balcony features comfortable seating with deep blue cushions. A glass-top table sits between the chairs. Below, the water view showcases boat traffic, while string lights add a gentle ambiance. The surrounding area includes other residential units and docks.

Condo in Ocean City

4.88 out of 5 average rating, 214 reviews

Bayside Retreat in the Heart of Ocean City!

Newly renovated condo!! -Water view. Watch the boat traffic. -Oversized balcony with comfortable seating. -Comfy LoveSac couch. -Walk to boardwalk or beach - 15 minutes. -Walk to Jolly Roger amusement park. -Fish off community dock down below unit. -Close to dining and shopping. -Kitchenette for cooking meals. -Fast Wifi and Streaming TVs. -Fully Stocked Home. Clean linens, towels, toilet paper, paper towels & more!