Beach house vacation rentals in Dewey Beach

A wooden deck with multiple sitting areas features stairs leading down to a sandy area with greenery. Sunlight illuminates the space, and a large umbrella provides shade atop the deck. The backdrop includes large windows of the house and a clear blue sky.

4.96 out of 5 average rating, 69 reviews

Relaxing Breezy Seaside 3bd/2ba/2decks King Bed

Wake up to stunning ocean views and the soothing sound of waves at this charming beachfront home. Relax on the breezy indoor and outdoor living decks. Enjoy recently updated stainless steel appliances, quartz countertops, and a fully tiled walk-in shower. The primary bedroom has direct access to the oceanfront deck, with ocean views in every bedroom. Nearby: Jolly Roger Amusement Park Boat Tours & Fishing Jetski & Parasailing Need more space? Rent the sister house next door! Message for details.

4.96 out of 5 average rating, 56 reviews

A scenic collage features various images: a tranquil beach sunset, a lush golf green with a white sand trap, a wooden pier stretching over gentle waves, wild horses running along the shore, and a charming screened porch nestled among tall trees.

Home in Ocean Pines

Ocean Pines-OCMD Bliss at the Beach- Sat. to Sat.

Welcome to Bliss at the Beach, our charming 3br, 2ba home nestled in the desirable, beloved Ocean Pines community. Loved for its safe, quaint, family friendly neighborhoods. Find yourself less than 15 minutes away from the beautiful beaches and vibrant shopping, dining and boardwalk district of Ocean City. Enjoy the ease of the prepaid parking at the Ocean Pines Beach club on 49th street, just unload the family and walk on the beach!! Summer months Bliss is a 7-night minimum to guests 25+old

The image displays a beachfront view from the penthouse balcony, showcasing the expansive ocean and sandy shoreline. Clear blue skies and gentle waves create a serene atmosphere. The balcony is furnished with chairs, offering a space to enjoy the coastal scenery.

4.89 out of 5 average rating, 28 reviews

Direct Oceanfront Penthouse

Come vacation at this direct oceanfront penthouse on 85th Street! This 3 bedroom, 3 bath two-story penthouse offers plenty of space for the entire group to stretch out and enjoy. Expansive bay and ocean views, the oversized balcony is the place you will want to be! The building offers a heated pool and is only a few small steps to the beach. For your convenience, this unit has a washer and dryer inside the property. In addition, games, beach chairs, and beach toys are available for your use!

A private balcony offers a clear view of the surrounding area, including nearby buildings and the ocean in the distance. Outdoor seating is visible, providing a space for relaxation. Bright blue skies and fluffy clouds enhance the scenic backdrop.

Ocean, Beach, Boardwalk, and Fun

Newly renovated throughout in 2025 with the Beach 😎 just 150 steps away and the quiet end of the boardwalk is a block away. Your family or friends will enjoy easy access to everything from this centrally located place. Whether it’s the beach, the boardwalk, or all the amenities you would need they are within a few steps. Plus you have a reserved parking spot!! And additional free street parking nearby If you are bringing the kids, Jolly Roger amusement park is right across the street..

4.93 out of 5 average rating, 46 reviews

An aerial view captures the serene coastline, with a spacious stretch of sandy beach lining the water's edge. The surrounding area features a mix of homes and vegetation, highlighting the peaceful neighborhood atmosphere and proximity to the beach.

Home in Milton

Pets Friendly Waterfront Large backyard with grill

Relax with the whole family or friends at this peaceful cottage. You will enjoy: proximity of the beach (waterfront - 2nd line from the beach, 345 feet to the high tide line, direct path to the beach), large backyard with campfire. Lower and upper levels decks. The large property lot also provides good level of privacy due to preserved vegetation. Porch is now screened - Jan 2025. This property underwent complete renovation in 2023/2024. You will enjoy clean looks and all modern amenities.

Top guest favorite

4.97 out of 5 average rating, 62 reviews

Hot Tub & Pool Table Waterfront Home | 4King Beds

Yes- Linens are included! (Bed sheets & bath towels) New pool table & jacuzzi!! Experience the ultimate Ocean City getaway this year, with unbelievable water views from every room & a private two-story wrap-around balcony. Enjoy 4 comfy king beds. The home is perfect for groups seeking relaxation & home away from home. Only 4.2 miles from the Ocean City Boardwalk! What else is included? Bonfire pit Parking area Shampoo-Conditioner-Body Wash Soaps Laundry Detergent Kayak Beach chairs

Top guest favorite

Home in Ocean Pines

4.99 out of 5 average rating, 96 reviews

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 serene ocean view stretches across the horizon, reflecting the sunlight on the calm water. Sandy beach lines the shore, complemented by natural dunes and sparse vegetation. The image captures the inviting atmosphere from a balcony railing, promoting relaxation and a connection with the surrounding environment.

4.74 out of 5 average rating, 42 reviews

“The Pelican’s Perch”

Spacious one bedroom condo with a great ocean view. Best ocean view in the building! Nice balcony to enjoy coffee & watch the waves & pelicans fly by. The building has an indoor pool and family game room. Large outdoor lounge area with picnic tables & view. Walking distance to north side park, great restaurants and entertainment. Beach is obviously right there to enjoy and parking is on location in private lot under cover. Dogs are permitted but only from Oct 1 thru April, off season

A bright living area features a spacious gray sectional sofa adorned with decorative pillows. A wooden coffee table sits in front, while large windows provide natural light and views of the balcony. The space is complemented by light-colored walls and soft hardwood flooring.

4.69 out of 5 average rating, 52 reviews

Golden Shores Penthouse

Elevate your Ocean City escape in our 3-bedroom, 2-bath penthouse condo, nestled in the heart of Mid-Town. This luxurious retreat offers stunning views, modern comforts, and stylish décor. The spacious living area, complete with a gourmet kitchen, is perfect for entertaining or relaxing. Each bedroom is a serene haven, promising restful nights. Steps away from the beach and close to popular dining and entertainment spots, our condo is your ideal base for a memorable vacation.

A modern kitchen is shown with grey cabinetry and sleek stainless steel appliances. A textured backsplash complements the countertops. Ample natural light enters through a window, enhancing the overall brightness of the space. A neutral area rug is positioned in front of the cooking area.

4.85 out of 5 average rating, 13 reviews

Relaxing Montego Bay/Fishing/2 Pools/Corner house

You will be welcomed by a large living room, dining room, and kitchen combination. 4 bedrooms all with cable TV and wifi, 2 sleeper sofas, and 2 bathrooms. Sit on the deck and enjoy the sun or eat crabs outside at picnic table. Great amenities 2 pools, walking blocks to the Ocean, walk along the bay, enjoy fishing, crabbing and the kids friendly park. Rent bicycles in the boardwalk early in the morning. Relax with the whole family at this wonderful place to stay.

Top guest favorite

A screened porch features ceiling fans for ventilation and is furnished with two lounge chairs and a set of light blue cushioned chairs and matching seating options. Large windows provide unobstructed views of the surrounding landscape and the bay.

Home in Milton

5 out of 5 average rating, 81 reviews

Beachcomber's Paradise is steps from the water

Welcome! Broadkill Beach is family friendly and offers lots of activities from fishing, golfing, biking, water sports and bonfires on the beach. Relax & enjoy the shabby chic decor in our home with all the modern conveniences. Our home is steps from the water with unlimited views of the dunes and Delaware Bay. Prime Hook Wildlife Refuge surrounding Broadkill has a family oriented hiking trail with an observation deck. Great views with lots of wildlife to see.

The beachfront property is depicted, featuring a two-story structure with multiple balconies. White railings line the expansive decks, overlooking the sandy beach. Sunlight brightens the scene, highlighting the natural surroundings and the wooden fencing that frames the pathway to the beach.