Beach house holiday rentals in Dewey Beach

5.0 out of 5 average rating, 21 reviews

Oceanfront Oasis Sunrise/Sunset balcony Beach/pool

Welcome to Oceanfront Oasis, Ocean City, Md. Rare Oceanfront & Bay Views from your 2 private balconies. Beachfront. Wake up to the sunrise, listen to the ocean waves, & sip your coffee on the Oversized ocean balcony(15 ft x 8 ft). Unwind at night on the bayside balcony watching the sunset. Walk out to the private heated pool, to the sand & the beach. Tennis court. Beach chairs, umbrellas , boogey boards & a lot more. Perfect for couples & families this cozy and well-situated condo is just right!

LocationFamilyView

Superhost

A spacious outdoor deck features cozy seating arrangements and a coffee table, with ocean views visible beyond. Relaxing chairs are positioned around, while the sparkling coastline and beach access paths are displayed in the background.

4.81 out of 5 average rating, 32 reviews

NEW! Oceanview Pool Sundeck Theater Game Room

Welcome to Your Elegant Oceanview Escape Home Experience the perfect blend of upscale comfort and family-friendly amenities in this spacious 5-bedroom retreat designed to host unforgettable getaways. Overlooking the sparkling coastline, steps from the beach, this home sleeps 16+ and offers everything you need to relax, recharge & reconnect. Highlights • Breathtaking ocean views from multiple decks • Pool and sundeck Pool Opens 05-23 to Sept 28th 2026 • Arcade/game room • Outdoor movie deck

ValueFamilyHospitality

4.9 out of 5 average rating, 79 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. Lower porch is screened. Large property lot also provides good level of privacy. Property underwent complete renovation in 2023/24. ***Mar 2026 update- construction of property on neighboring lot in front was completed end of 2025!***

LocationFamilyTV

Superhost

Home in Rehoboth Beach

Bright & Breezy Bayside Home | Sleeps 10

Experience the classic Dewey Beach vibe in this bright, two-story home just steps from the sand! Located on the bayside of town, tucked in on a charming side street, you’ll catch some bay views from the sitting room. Central & walkable, it’s easy to explore all Dewey has to offer. Expect a fun, lively atmosphere on summer weekends while having a comfortable retreat to come home to. And the best part? We’re pet-friendly, so your four-legged family members are welcome to join the beach getaway!

LocationFamilyLaundry

4.77 out of 5 average rating, 22 reviews

5.0 out of 5 average rating, 5 reviews

Home in Bethany Beach

Waterfront, Dock, Deck, Walk to the Beach!

Escape to Tern Drive in South Bethany Beach-a perfect vacation rental with spacious living areas, coastal comfort, and easy access to beach and bay! Enjoy relaxing outdoor waterfront space, plenty of room for family and friends, and a prime location near dining, shopping, attractions. 3 bedrooms; 1 King + 2 Queens. 2 full baths + outside shower. Grill, beach chairs, parking, WiFi, walk to the beach. New paint, flooring, furnishing, beds, mattresses. Large groups, rent the house next door too!

FamilyLocationWalkability

4.78 out of 5 average rating, 9 reviews

Home in Milton

Beach Haven waterfront house on Broadkill Beach DE

Relax with the whole family at this peaceful beachfront home located on the scenic Broadkill Beach in Delaware. The house has 4 spacious bedrooms and 2 and 1/2 baths with a full kitchen and a dining room with direct oceanviews. Lounge in the sunroom with panoramic views of the ocean and walk right over the dunes to the beach anytime. Primehook Refuge is a 5 minute drive, and a 15-20 min drive leads to Lewes beach, Cape Henlopen Park and Rehoboth boardwalk for restaurants and nightlife fun.

LocationFamilyWalkability

4.98 out of 5 average rating, 80 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

LocationValueBeach

A welcoming living area is featured, complete with a comfortable sofa adorned with blue throw pillows. Light wood beams enhance the ceiling, while a decorative surfboard adds a coastal touch. A dining table with wooden chairs complements the open kitchen space in the background.

4.95 out of 5 average rating, 56 reviews

The Blue Crush - 3BR Beachfront Family Retreat

Experience the magic of coastal living at 'The Blue Crush'. It's COMPLETELY REMODELED including 3 bedrooms and a deck to watch the sunrise over the ocean and sunset over the bay. If your family is looking for more space. Our sister beach house, Orange Crush is located next door, has 5 bedrooms and can accommodate up to 12 guests. Combining your stay at the Orange and Blue Crush, you accommodate up to 20 guests, in 8 bedrooms. Please reach out to us for special group pricing.

LocationValueAmenities

Two large windows frame the expansive ocean view, providing natural light to the living space. The scene features sandy beach dunes leading towards the water, where the calm blue ocean meets the clear sky.

4.89 out of 5 average rating, 155 reviews

Closest condo to the beach in OC! Dog Friendly!

Perfect getaway to the ocean in this updated, stylish home. Elevated ocean-front, with stunning views from every room and two private balconies. Amazing location - walk to great restaurants and still enjoy a private-feeling beach with lifeguard stand just steps away. No need to 'pack' for the beach -the house is just steps away. Enjoy coffee at the granite island overlooking the beach! There is a set of stairs up to the condo, and another set of stairs up to the main bedroom.

LocationFamilyDecor

5.0 out of 5 average rating, 12 reviews

Ocean Place 402 | Oceanfront Balcony Views

Welcome to Ocean Place 402, your modern oceanfront retreat in Ocean City, MD! This sleek 2-bedroom, 2-bath condo offers breathtaking views of the ocean right from your private balcony. Relax in style with coastal-chic décor, a fully equipped kitchen, and a comfy sleeper sofa for extra guests. Just steps from the sand, you can spend your days soaking up the sun, strolling the nearby Ocean City boardwalk, or dining at nearby favorites—all from this luxurious seaside escape.

FamilyLocationHospitality

4.94 out of 5 average rating, 103 reviews

The exterior of a rustic beachfront home is depicted, featuring weathered wood siding and multiple large windows. The structure is two stories, with a sloped roofline and steps leading to the entrance. A sandy path and grassy area are visible, creating a natural coastal setting.

Home in Milton

Beachfront Home with Unobstructed Water Views

Beachfront/Bayfront home with 4 bedrooms and 3 full bathrooms located in the quiet and relaxing community of Broadkill Beach. The property is just steps from the beach and features stunning, unobstructed water views from almost every room. The home has a coastal design with natural light, soft-tones and a clean aesthetic so that it feels like summer all year-round. We hope that you'll book your vacation with us and enjoy all that Broadkill Beach has to offer!

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