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Holiday rentals in Dewey Beach

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Top-rated holiday rentals in Dewey Beach

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Guest favourite
A serene outdoor area features a sparkling pool accompanied by a hot tub. Surrounding the space are several lounge chairs and a shaded patio with a large umbrella. Colorful flowers in planters add to the lush greenery and natural surroundings.
Home in Rehoboth Beach
4.98 out of 5 average rating, 53 reviews

Gorgeous 5BR, 4.5BA, in town, pool, hot tub, beach

In town Rehoboth, with Rise Up and the boardwalk just a quick walk away, you'll love this home with a POOL AND HOT TUB (April-Oct). There's a ton of natural light, plus comfy queen and king beds, nice new linens, and more. Please note there is a security camera on the pool and in the pool equipment area for your safety. Dogs are allowed for a $75 fee per stay for first pet, $25 per additional (additional pet fee after the first will be billed after your reservation is complete). Maximum 3 dogs.

Top guest favourite
A compact kitchen area is visible, featuring white cabinetry and modern appliances. Two bar stools are positioned at a small island. The cozy sitting area includes a light blue chair and a striped sofa, with light streaming in from the nearby window.
Apartment in Dewey Beach
4.97 out of 5 average rating, 334 reviews

Sweet getaway - beach block, steps from the beach!

Steps to beautiful, uncrowded beach in Rehoboth-by-the-Sea! Experience tiny house living in our quiet, sweet, light-filled beach getaway with king-sized bed. We provide sheets, towels! Easy check-in+out - no chore list! Dog-friendly! Free parking. Full kitchen, fast WiFi, Roku tv, outdoor dining space, outdoor shower, grill, fire pit - quiet beach block in Dewey, a short walk to the Rehoboth boardwalk. New windows, new HVAC! Great, beachy location for a wonderful, relaxing getaway!

Top guest favourite
A wooden gazebo overlooks the sandy beach, framing a sunset view across the water. Potted plants are situated on either side, while a pathway leads to the sand. Soft grassy areas feature low fencing, creating a serene outdoor environment.
Flat in Dewey Beach
4.91 out of 5 average rating, 44 reviews

Bayview Oasis-Pool/Free Parking

This cozy Bayside condo on the ground level of The Cove Complex offers a serene experience with stunning sunset views just steps away. The complex offers a pool, a tennis court and The Dewey post Restaurant for your convenience. Easy access to both the bay and beach. A free parking spot, walking distance to bars and restaurants in Dewey Beach. This Bayside condo is the perfect blend of comfort and style. Your family will be close to everything when you stay at this centrally-located place.

Top guest favourite
The living area features large sliding doors that open to a porch with stunning bay views during sunset. A neutral-colored couch and a cozy chair create a welcoming space. A wooden dining table complements the serene atmosphere, illuminated by the warm glow from the setting sun.
Townhouse in Ocean City
4.97 out of 5 average rating, 533 reviews

Edgewater Escape - Luxury Bayfront Loft with Porch

You've never seen waterfront like this. Welcome to Edgewater Escape, a luxury bayfront loft apartment that hangs entirely over the bay on 7th street in downtown Ocean City. Sit on the bay front porch or hang out inside and watch boats, dolphin, birds, and sometimes even seals swim by within feet of the porch. The loft has a roomy king sized bed and the downstairs couch pulls out into a comfy queen bed. Recently renovated, it comes fully equipped for your big trip or quiet staycation :)

Top guest favourite
A cozy living area features a teal sofa adorned with patterned pillows and a plush armchair. A decorative wall hanging adds texture above a glass coffee table, while soft light enters from a window dressed with sheer curtains. A stylish rug completes the inviting space.
Apartment in Dewey Beach
4.98 out of 5 average rating, 177 reviews

Ocean Block Boho Beach House

Welcome to my little boho inspired beach house located in the heart of Dewey Beach. 300 feet to the sand, you can hear and smell the ocean from the doorstep. This 2 bedroom 1 bath condo is perfect for small family getaway or with a few friends. Fully equipped little kitchen is available for light cooking, along with gas grills, outdoor showers, and outdoor seating in the condo common areas. I designed this space for me, but I hope you can love it too!Max 4 adults, no parties.

Guest favourite
A charming beach cottage in a vibrant blue hue is framed by a black gate and a wooden fence. Lush greenery and blooming azalea bushes add color to the entrance, leading to a pathway illuminated by natural light. A gentle slope of trees enhances the tranquil setting.
Cottage in Dewey Beach
4.91 out of 5 average rating, 117 reviews

Shady Shore Cottage in North Dewey Beach

Charming Mid-Century beach cottage located in north Dewey Beach. Relax and enjoy one of the original beach cottages built in Rehoboth by the Sea in the 1960s. Only two blocks to the ocean and a short walk to restaurants in downtown Dewey or take a trolley ride to Rehoboth Beach for more restaurants and shopping. No parking pass needed - there's room for 4 cars in the driveway. Feel free to borrow the 3 beach chairs and enjoy the outdoor shower when you get back from the beach.

Guest favourite
The cozy cottage showcases a welcoming exterior with wooden shingles and a front porch. An American flag is displayed, and two small shrubs frame the entrance. A clear pathway leads to the door, surrounded by a grassy area and trees in the background.
Tiny home in Ocean View
4.91 out of 5 average rating, 249 reviews

Tiny Cottage at Good Earth, near Bethany Beach

Welcome to the "Tiny Thyme Cottage" at Good Earth. The cottage is super cozy, perfect for a couple, with 1 queen bed, a kitchen & bathroom, and a small living area. You'll be staying on our 10-acre property, 4.7 miles from Bethany Beach. Convenient amenities include 2 on-site restaurants, market, theater, and ample parking. Our AIRBNB "Village" includes 2 tiny houses, a lofted apartment, and 2 cottages on the property. Staying at Good Earth is more than just a beach trip!

Top guest favourite
Apartment in Dewey Beach
4.98 out of 5 average rating, 94 reviews

Steps to Beach | 2 Balconies | Sleeps 8 | Parking

Welcome to your perfect getaway at our newly renovated condo in the heart of Dewey Beach! This spacious and stylish 3-bedroom, 3-bathroom retreat is less than a one minute walk to the beach and steps from everything beautiful Dewey Beach has to offer! This condo features: -Beach block -2 Car Reserved Parking -3 FULL Bathrooms -FAST 1gb Wifi -Fully Stocked Kitchen -Sleeping for 8 -Soothing white noise machines in all sleeping areas -Beach essentials -2 Outdoor Balconies

Top guest favourite
A duplex with a shingled exterior is displayed, featuring a rooftop deck accessible by an exterior spiral staircase. A fenced yard is visible, along with a gravel surface below. Large glass doors lead to the lower level, enhancing connection to the outdoors.
Townhouse in Dewey Beach
4.91 out of 5 average rating, 139 reviews

McKinley Duplex

Enjoy the Ocean and Bay Views from the roof top deck of this Pet Friendly duplex located in the ocean block in the heart of Dewey Beach! Just steps to the beach with a large enclosed porch, open living area, 6 bedrooms and 3.5 baths (2 King, 1 Queens, 6 Twins and a sofa bed), ample parking and much more. Walk to all the restaurants and nightlife - take the Jolly Trolley into Rehoboth to enjoy the beach, boardwalk and some of the finest dining in the area!

Guest favourite
A spacious corridor is shown, leading towards an open living area illuminated by natural light. The kitchen features an expansive island with seating and modern pendant lights overhead. A large window provides a view of the bay, creating a bright and airy atmosphere.
Apartment in Dewey Beach
4.98 out of 5 average rating, 42 reviews

Lovely two bedroom condo with stunning bay views

Your family will be close to everything when you stay at this centrally-located condo. Only 1 block from the beach. Enjoy spectacular views of the Rehoboth Bay and Rehoboth Bay Marina while relaxing on the large balcony. This luxury condominium is your ultimate vacation destination convenient to everything Dewey Beach has to offer. This coastal inspired space is perfect for gathering with family and friends.

Superhost
Apartment in Dewey Beach
4.83 out of 5 average rating, 12 reviews

Coastal | Private Balcony | 1 BR | Sleeps 4

Welcome to your relaxing coastal retreat just minutes from Dewey Beach. This stylish 1-bedroom getaway comfortably sleeps up to four guests and offers the perfect base for a beach escape. Whether you're planning sunny beach days, evening strolls along the shore, or exploring the nearby restaurants and attractions, this inviting space provides everything you need for a comfortable and memorable stay.

Top guest favourite
A round wooden dining table surrounded by eight woven chairs is positioned in a well-lit dining area. Soft natural light enters through large windows adorned with white blinds. A coastal-themed wall art piece enhances the serene ambiance, and a smaller table can be seen in the background.
Home in Rehoboth Beach
5 out of 5 average rating, 230 reviews

Beautiful Beach House in Rehoboth

Modern spacious house in Rehoboth Beach with a large open floor plan on a quiet street. Five bedrooms/3.5 baths. Walk to town/beach - four blocks from beach right off Rehoboth Ave. Private pool with two levels of decks, grill and table/umbrella on top deck. Big open kitchen/dining/living area, over 3000 square feet of space overall.

Popular amenities for Dewey Beach holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Dewey Beach's top sights

The Starboard

167 locals recommend

Dewey Beach Access

50 locals recommend

Northbeach

33 locals recommend

Dewey Beach Watersports

32 locals recommend

Towers Beach

23 locals recommend

Fifer's Farm Kitchen Dewey Beach

15 locals recommend

Other great holiday rentals in Dewey Beach

Top guest favourite
A spacious living area features high, white-beamed ceilings and a mix of cozy seating options, including a dark sofa and a striped armchair. A warm-hued ottoman is centrally located, with natural light streaming in through nearby windows adorned with light curtains.
Home in Rehoboth Beach
4.98 out of 5 average rating, 50 reviews

Storybook Cottage in DT Reho, Walk to Everything

Superhost
Home in Dewey Beach
5 out of 5 average rating, 3 reviews

Keys Cottage | Steps to Beach | Rooftop | Firepit

Top guest favourite
The exterior of the apartment shows a two-story building with a spacious deck above. Outdoor stairs lead to the entrance, while large windows provide ample natural light. Lush green grass and surrounding shrubs enhance the peaceful setting.
Guest suite in Rehoboth Beach
4.96 out of 5 average rating, 82 reviews

Winter or Summer - Quiet Studio Apt Near Beach

Top guest favourite
Townhouse in Dewey Beach
4.93 out of 5 average rating, 14 reviews

Bayfront Townhouse - Endless Views & Private Beach

Guest favourite
Apartment in Dewey Beach
4.93 out of 5 average rating, 81 reviews

Newly Updated OCEAN BLOCK 2 bed condo

Guest favourite
Apartment in Dewey Beach
4.94 out of 5 average rating, 98 reviews

Perfect Location in Dewey Beach!

Top guest favourite
A bright bedroom is presented with a spacious bed dressed in crisp white bedding. Natural light streams through several windows adorned with woven shades, revealing views of the lush outdoors. A large mirror and decorative tray add to the room's charming décor.
Home in Lewes
5 out of 5 average rating, 65 reviews

Lewes Carriage House-Hamptons Style Pool & Hot Tub

Top guest favourite
A sandy pathway leads to the beach, framed by tall grasses and wooden posts with rope fencing. The calm ocean is visible ahead, with a clear sky overhead, creating a serene view that invites relaxation.
Home in Dewey Beach
4.98 out of 5 average rating, 40 reviews

Dewey Beach Ocean Block 3 BR 2 BA Free Parking

Frequently Asked Questions

  • What are the best places to stay in Dewey Beach?

    Dewey Beach has a mix of beachfront rentals, family-friendly condos, and relaxed residential neighborhoods. Staying near the ocean or around the bay is often suggested for convenient access to water activities and local dining.

  • What are the best things to do in Dewey Beach with kids?

    Families often explore the wide sandy beach, paddle on the bay, or visit playgrounds and local parks. Seasonal events and nature programs also create engaging opportunities for children.

  • What are some of the best things to do in Dewey Beach?

    Dewey Beach has oceanfront spots perfect for swimming and sunbathing, as well as a bay area often recommended for water sports like paddleboarding or kayaking. Many visitors explore local eateries, enjoy live music venues, or stroll the sandy shoreline. The atmosphere is relaxed and welcoming.

  • How is the weather in Dewey Beach?

    Dewey Beach has cool winters around 28–48°F (-2–9°C) and warm, humid summers from 66–87°F (19–31°C), with rainfall spread throughout the year. Bring layers and sun protection for changing beach conditions.

  • What are the best places to visit in Dewey Beach?

    Explore the main beach, the bayside marina, and relaxed waterfront parks. Nearby, Rehoboth Beach has a nostalgic boardwalk and local shops, frequently suggested for day outings.

  • What are some hiking trails in Dewey Beach?

    Dewey Beach has access to sandy shoreline walks, coastal nature trails, and nearby state parks with looping paths. Trails often wind through dunes, marshes, and wildlife-rich habitats.

  • What are some family activities we can do in Dewey Beach?

    Spend time building sandcastles, join family-friendly bay cruises, or participate in beach games and seasonal festivals. Outdoor movie nights and interactive nature programs are frequently suggested for younger visitors.

  • What are some of the best day trip ideas from Dewey Beach?

    Consider exploring neighboring coastal towns, local wildlife refuges, or nature preserves around the Delaware shoreline. Rehoboth Beach and historic Lewes are popular day destinations for their shops, museums, and waterfront trails.

  • Are there any pet friendly accommodations available in Dewey Beach?

    Pet-friendly rentals are available in Dewey Beach, with some homes, condos, and oceanfront properties welcoming dogs. Many pets join their people on the sand during designated seasons and hours.

  • What are some local tips for visiting Dewey Beach?

    Pack a reusable water bottle, sun protection, and sandals for sandy walkways. Early mornings are quieter on the beach, and local eateries often feature live music or seasonal menus inspired by regional seafood.

  • What is Dewey Beach known for?

    Dewey Beach is known for its energetic surf culture, live music venues, and welcoming mix of family activities and nightlife. Its sandy shoreline attracts visitors seeking both relaxation and water sports.

  • What are the best hidden gems to explore in Dewey Beach?

    Look for quiet bayfront spots at sunset, tucked-away nature trails, or local art displays in small galleries. Neighborhood markets and low-key beach cafés are favored by those seeking a more local atmosphere.

  • What are the best foods to try in Dewey Beach?

    Fresh seafood is frequently suggested, including steamed crabs, oysters, and local fish. Classic boardwalk treats like fries, soft-serve ice cream, and saltwater taffy are also part of the Dewey Beach experience.

  • What should I bring for a trip to Dewey Beach?

    Pack beachwear, sunblock, and comfortable footwear for sandy and boardwalk areas. A lightweight jacket is helpful for cooler evenings, and reusable bags come in handy for shopping or carrying essentials.

  • What is the nightlife in Dewey Beach like?

    Dewey Beach has a lively nightlife scene with waterfront bars, live music performances, and dance venues. Many spots welcome a diverse crowd, especially during the summer season.

  • What are the most popular events or festivals in Dewey Beach?

    Dewey Beach is known for music festivals, sandcastle competitions, and community celebrations, often held in summer and around holiday weekends. Outdoor concerts and local fundraisers are recurring annual highlights.

  • Are there family friendly vacation rentals in Dewey Beach?

    Family-friendly vacation rentals are available throughout Dewey Beach, often featuring multiple bedrooms, full kitchens, and easy access to the ocean or bay. Look for listings highlighting family amenities and proximity to parks or playgrounds.

  • When is the best time to visit Dewey Beach?

    Late spring through early fall is often recommended for milder weather and lively seasonal events. Cooler months appeal to those seeking a quieter coastal experience.

Destinations to explore