Holiday rentals in Dewey Beach

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Top-rated holiday rentals in Dewey Beach

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Top guest favourite
An open-concept living area features a spacious gray sectional sofa arranged around a casual coffee table. Bar seating at the kitchen island is complemented by stylish stools. Natural light fills the room, highlighting the subtle décor and a wall adorned with decorative fish.
Apartment in Dewey Beach
4.98 out of 5 average rating, 105 reviews

Newly Renovated Modern 2 Bed/2 Bath Condo w/ Pool

Newly renovated and designer decorated 2 bedroom/2 bath beach condo with the most comfortable beds imaginable. Located in the heart of Dewey Beach with an outdoor pool and only 1 block to beach and bay. One bedroom includes a King sized bed with private bathroom. The 2nd bedroom includes a Queen and a Twin sized beds adjacent to the 2nd bathroom. The fully equipped kitchen features stainless steel appliances, granite countertops, an island w/ seating, and washer/dryer. 2 parking spots included.

Top guest favourite
A balcony view showcases the ocean, with serene waves and sandy shores. Large glass doors allow natural light to flood the interior, while outdoor seating and potted flowers add a charming touch to the space.
Apartment in Rehoboth Beach
4.96 out of 5 average rating, 168 reviews

Sunrise Studio - Ocean Front, on Boardwalk, Pool!

Our quiet ocean front studio has all the comforts of home with amazing views, a balcony hovering over a serene stretch of the Boardwalk, and is just steps away from restaurants, shops, arcades, rides and all of the best boardwalk foods! Walkable to everywhere in town! If you want to venture out further, a bike rental shop is just a few doors away! Enjoy a bike ride through town or to Dewey Beach. If you are looking for a scenic ride, enjoy the bike trails to Cape Henlopen State Park and Lewes.

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, 298 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 welcoming outdoor terrace features a round table surrounded by two wicker chairs with blue cushions. Hanging planters filled with greenery create a vibrant atmosphere, while a decorative pot adds a pop of color. Sunlight filters through lush trees, enhancing the serene environment.
Guest suite in Rehoboth Beach
4.99 out of 5 average rating, 210 reviews

Treetops beach getaway walkable to beach/boardwalk

East of Route 1, equidistant to both Rehoboth & Dewey beaches, about 1/2 mile easy bike/walk. Brand new for 2021, this fully equipped guest suite offers a private entrance, bedroom with a king bed on an adjustable frame, full bath, laundry, and a kitchenette. There is NO STOVE in this unit but we have provided a microwave and toaster convection oven/air fryer for easy beach meal prep. There is also a gas grill for barbecuing. Please note that this unit is strictly limited to 2 mature adults.

Guest favourite
The living area features a light gray sectional sofa with colorful accent pillows, situated within a bright space. A wooden console table is placed against the wall, and light fixtures illuminate the open kitchen area in the background.
Apartment in Dewey Beach
4.97 out of 5 average rating, 144 reviews

Luxury water-view condo with high-end finishes

Luxury 2-bedroom condo at The Residences at Lighthouse Cove located in the heart of Dewey Beach. This unit features great views of Rehoboth Bay and is only 1 block from the Atlantic Ocean. Easy walk to Dewey Beach’s shops, restaurants, and nightlife. This unit sleeps up to 6. There is a master bedroom with a king bed and ensuite bathroom. The second bedroom has a queen bed. There are 2 twin-size fold-away beds. Lounge at private rooftop pool, fire pits, & grills for Residences

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, 161 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.

Top guest favourite
A spacious living area features a sectional sofa adorned with red accent pillows. A wooden coffee table sits in front, contrasted by a patterned area rug. Natural light streams through large windows, highlighting a piece of wall art depicting a serene landscape.
Apartment in Lewes
4.99 out of 5 average rating, 346 reviews

Beach Sunrise: Walk Downtown & Beach

Explore Lewes (loo-iss) from our walkable in-town spot. ✔ Walk Downtown - Restaurants, shops, parks - 2 minute walk ✔ Walk or bike to Lewes Beach - Less than a half mile ✔ Bike Trails - Plenty of options at your fingertips ✔ Cape Henlopen State Park - Less than 2 miles ✔ Easy electronic keypad entry ✔ Fast Gigabit X2 Speed Wi-Fi (2100 Mbps) ✔ Roku Smart TV - includes free YouTube TV with cable channels ✔ Parking is plentiful *Bonus* Four complimentary bicycles provided

Top guest favourite
The living area features a large, L-shaped fabric sofa with soft cushions, positioned beside a wooden coffee table. A decorative wall art piece is displayed over the sofa, and sunlight filters through the window adorned with sheer curtains, creating a bright and cozy atmosphere.
Apartment in Dewey Beach
4.98 out of 5 average rating, 137 reviews

Dewey Beach Condo 2BR+sofa bed. Walk to the beach!

Located near the Town Hall & the Police Department, this charming 2-bedroom ground floor condo is a clean, safe, family-friendly coastal vacation environment! Only 1.5 blocks to the beach, 1 block to beautiful bayside dining, and 5 blocks from downtown Dewey. Fully furnished with 2 queen beds, comfortable sleeper sofa, full bath, washer & dryer, fully equipped kitchen, clean bed sheets & towels, fast WiFi, beach chairs & more. I'm a responsive, experienced SuperHost.

Top guest favourite
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.
Apartment in Ocean City
4.96 out of 5 average rating, 291 reviews

Caramar Couples Retreat

This cute little first floor efficiency condo is ocean front for a perfect vacation to the beach. It’s an older building but has been partially renovated and updated. You can get to the beach by a very short walk through a private walkway from the condo building. The view from the private balcony is perfect and relaxing. WiFi provided upon check in- xfinity, Netflix, and internet. Indoor and outdoor dining areas and a full kitchen. Closet and dresser for storage use.

Top guest favourite
The structure features a modern design with a wooden exterior and large glass windows. A spacious deck is accessible from the upper level, surrounded by lush greenery. The ground floor includes a stone facade with garage doors, creating a harmonious blend with the natural surroundings.
Guest house in Rehoboth Beach
4.87 out of 5 average rating, 343 reviews

The Winkler

The Winkler is a comfortable fully equipped 1BR / 1 BA apartment above our detached 3 garage @ The Tree House. Nestled in lush trees and landscaping in the Rehoboth Beach Country Club. Named after Henry Winkler who played the Fonz on Happy Days, (because he lived in the apt. over the Cunningham's garage). The apartment offers privacy and separation from the main house. Giving you an opportunity to make it your home away from home at the beach. Come Enjoy!!

Top guest favourite
A balcony view captures a wide expanse of lush green fields and dense trees, framed by a soft gray sky. The natural landscape offers a serene backdrop, highlighting a peaceful atmosphere. A railing can be seen in the foreground, providing a sense of depth.
Apartment in Lewes
4.99 out of 5 average rating, 165 reviews

Condo 2 Bedroom Waterfront Lewes/Rehoboth DE

2 Bedroom Condo Top Floor (3rd Floor) - Waterfront in Lewes/Rehoboth Beach DE Great Scenery Views - The Residence at Rehoboth Bay. *Community Pool available during in-season (8am-8pm) *No cleaning fee Nearby amenities and attractions include: Rehoboth Beach Boardwalk (6 Miles) Cape Henlopen State Park (8 Miles) Dewey Beach, DE (7 Miles) Bethany Beach, DE (18 Miles) Ocean City, MD (32 Miles) Shopping Outlets (4 Miles)

Top guest favourite
An in-ground pool is set within a stone patio, surrounded by a lush garden featuring various plants. Two lounge chairs are positioned beside the pool, and a tree provides natural shade, enhancing the backyard's inviting atmosphere.
Home in Rehoboth Beach
4.87 out of 5 average rating, 149 reviews

Hot Tub + Pool, Fire Pit, Cottage by Dogfish Head

This adorable beach cottage has it all, and it's bigger than it looks! With 3 full-size bedrooms, 2 full baths, and an enormous back yard with an IN-GROUND POOL, big back deck, huge HOT TUB, gas fire-pit, and dual charcoal and gas-burning BBQ, this home has everything you need for an unforgettable beach trip. You'll love the 3 KING SIZE BEDS, two of which are tempur-pedic, plus the two twin beds are great for kids.

Popular amenities for Dewey Beach holiday rentals

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.

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