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Holiday houses in Dewey Beach

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Top-rated holiday rentals in Dewey Beach

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Guest favourite
The exterior of the Izzy Plaza building is shown, featuring two levels of balconies with seating arrangements. A clear blue sky complements the contemporary design of the structure. The neighboring street and parking area are visible, providing a sense of the local atmosphere.
Condo in Dewey Beach
4.97 out of 5 average rating, 62 reviews

Izzy Plaza Penthouse | Oceanview, Walk to Beach

When you stay here, you and your guests will enjoy penthouse views of beautiful Dewey Beach. Steps from the beach and even closer to the night life, you will be centrally located for a fun adventure. You can enjoy happy hour sunsets on the patio, sunrise views with a cup of coffee in the morning, or late night adventures directly next to Starboard and Dewey Beer Company. Everything is walking distance or a short trolley ride to Rehoboth Beach. Park your car when you arrive and enjoy the ride.

Guest favourite
A black leather sofa is positioned against a neutral wall, flanked by two bedside tables with table lamps. Above the sofa, a decorative wall piece featuring wooden paddles is illuminated by soft lighting, adding texture to the space.
Apartment in Rehoboth Beach
4.89 out of 5 average rating, 54 reviews

Modern, compact w/ lake view & beach access

Location! Coastal convenience & tranquil waterfront enhancing your beach getaway. Located on the shoreline of Silver Lake, European styled kitchen, Ref/Freezer w/ a center island, open floorplan, smart TV, wifi, en-suite BR w/ queen bed & shower. Read & watch the wildlife attracted to the lake from the patio. Community pool just steps away. Walk across Turtle Bridge to the beach & boardwalk just 4 blocks away. Rehoboth Ave is approx. 7 blocks away. No smoking in or out. No Pets. Enjoy!

Top Guest favourite
The exterior of the cottage showcases a welcoming front porch adorned with turquoise seating. Lush green grass surrounds a clear walkway leading to the front door. Sunlight filters through the trees, highlighting the charming details of the home and its inviting atmosphere.
Home in Rehoboth Beach
5 out of 5 average rating, 39 reviews

Adorable beach cottage minutes to Rehoboth & Dewey

Adorably decorated, newly renovated cottage in charming Bay Vista. Close to downtown Rehoboth's fabulous restaurants and boutiques (see guidebook for recommendations). Enjoy quiet nights around the backyard fire pit or in the upstairs, screened sleep porch. Great neighborhood for walking/running/biking. Just bring yourselves -- all linens/towels, RB parking pass, beach chairs & towels included. 2 miles to downtown Rehoboth beach/boardwalk, and just over 2 miles to Dewey's famous Starboard.

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.
Condo in Dewey Beach
4.98 out of 5 average rating, 162 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
An aerial view captures a spacious rooftop pool adjacent to the bay, with sun loungers arranged around it. The nearby buildings are designed with large windows, reflecting the inviting waters of the bay and the clear sky above.
Apartment in Dewey Beach
4.89 out of 5 average rating, 19 reviews

Steps to the Beach | Bay View Condo + Rooftop Pool

The perfect Dewey Beach getaway to relax, recharge, and make memories. In The Residences top-floor of The Hyatt, 2-bedroom, 2-bath condo is steps from the beach, and blends family comfort with adult luxury. Enjoy a private outdoor rooftop pool, indoor pool, and gym. Families love the calm bayside beach—safe for kids to splash. While couples savor sunset views from the balcony and modern finishes inside. Walk to nearby restaurants, bars, and 5 minute drive to Rehoboth Beach.hey

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, 109 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
A cozy guest suite is presented, featuring a spacious bed covered with a vibrant blue blanket. Decorative elements include a light-colored rug and a plant next to the bed. A small bookshelf and artwork adorn the walls, contributing to the room's inviting decor.
Guest suite in Fenwick Island
4.8 out of 5 average rating, 115 reviews

Sea Dunes King Suite, Exclusive Private Beach - DOG FRIENDLY!

Unwind and chill in this boho coastal inspired guest suite on the ocean side. At Sea Dunes' private guest king suite, the surf and sand are steps away. Get ready to pack your cooler and enjoy a day in the sun on this beautiful, private dog-friendly beach. Sea Dunes is located in Fenwick Island, DE and nestled between protected state nature parks. Just a short trip in the car to a marina with watersports, kayak adventures on the bay, local dining, farm markets and shopping.

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
4.98 out of 5 average rating, 211 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 oven 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.

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.
Condo in Dewey Beach
4.98 out of 5 average rating, 140 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.

Guest favourite
The open-concept living area offers a view of the bay through large windows. A kitchen island with seating for four is visible, along with stainless steel appliances and light cabinetry. Natural light fills the space, showcasing a welcoming atmosphere by the water.
Condo in Dewey Beach
4.86 out of 5 average rating, 209 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. Refresh and update Fall 2025 with new living room and bedroom furniture.

Guest favourite
A deck area is featured, furnished with a table and black wrought-iron chairs, each adorned with red cushions. Potted plants add greenery, while a welcome mat is displayed at the entrance. Decorative items hang on the wall, creating an inviting atmosphere.
Home in Dewey Beach
4.84 out of 5 average rating, 45 reviews

Beach block dog-friendly Dewey gem!

Location, location, location! Half a block to the beach in one direction, and half a block to the Starboard in the other. Cute and cozy duplex perfect for small groups to enjoy all that Dewey has to offer. Walking distance to Rehoboth, too! Super close to all the action but still feels secluded thanks to greenery and being set back from the street. Enjoy coffee and drinks on the deck before a day at the beach or a night on the town.

Top Guest favourite
A bright dining area is illuminated by natural light from large glass doors that open to a scenic view of the Rehoboth Bay. A rectangular table with metal chairs is positioned near the windows, while a piece of framed artwork is displayed on the wall.
Townhouse in Dewey Beach
4.98 out of 5 average rating, 106 reviews

Bayfront 3-Bed Townhome W/Linens & Beach Gear.

Welcome to our Dewey Beach House! While staying here, you can expect a sun-filled, clean, relaxing space with an unbeatable location and an incredible view of the Rehoboth Bay. You are only: - 5 minute walk to the beach. - 5 minute walk to the Starboard, Bottle & Cork, and many other Restaurants and shops in town. - 2.5 miles to downtown Rehoboth Beach. Come experience what makes Dewey Beach & this stay so special!

Popular amenities for Dewey Beach holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Dewey Beach's top sights

Funland

244 locals recommend

The Starboard

160 locals recommend

Dewey Beach Watersports

32 locals recommend

Other great holiday rentals in Dewey Beach

Guest favourite
A single-story coastal cottage is presented with a light exterior and a welcoming front screen porch. The porch features seating options and is shaded by surrounding trees. A well-maintained garden area with decorative stone edging enhances the outdoor space, with greenery visible on the property.
Cottage in Dewey Beach
4.95 out of 5 average rating, 60 reviews

Walter's Coastal Cottage

Top Guest favourite
An aerial view of a sandy beachfront stretches alongside the Coastal Crush home, highlighting nearby beach access points. The image also includes a cozy living area with modern furnishings, a welcoming loft space featuring a wet bar, and a tastefully decorated bedroom with a spacious bed.
Townhouse in Bethany Beach
5 out of 5 average rating, 37 reviews

50 Steps to Beach! Rooftop & Modern Coastal Vibes!

Top Guest favourite
A serene deck area is visible through an open door, featuring a light-colored lounge chair and a large green umbrella providing shade. Lush greenery surrounds the space, creating a peaceful outdoor retreat.
Loft in Lewes
4.95 out of 5 average rating, 80 reviews

Country Loft. Private, comfy, special.

Guest favourite
The living area features a spacious sectional sofa in soft grey fabric positioned around a round coffee table with a glossy finish. A plush area rug covers the hardwood floor, and large windows allow natural light to fill the space. Nearby, a dining area is visible.
Home in Rehoboth Beach
4.96 out of 5 average rating, 68 reviews

Beach Zen 3BR Condo w/ Pool

Guest favourite
The modern condo building is set amid lush greenery and tranquil landscaping. A serene pond is visible in the foreground, complete with a gentle fountain. The building's exterior features a combination of white siding and dark accents, framed by manicured lawns and shrubbery.
Condo in Rehoboth Beach
4.94 out of 5 average rating, 62 reviews

Modern Condo w/Pool - Close to Beach

A two-story house features a light blue exterior with a charming green door. A balcony with two purple chairs overlooks the front yard, surrounded by trees and a wooden fence. The well-maintained landscaping adds to the overall inviting appearance.
Home in Dewey Beach
4.78 out of 5 average rating, 212 reviews

3 min walk to beach-Dewey Beach House-new updates!

Guest favourite
The cozy sleeping area is furnished with a queen-size bed draped in a light coverlet, accompanied by beach-themed throw pillows. A decorative painting of palm trees hangs above the bed while a surfboard is mounted above the doorway. Plants add a touch of greenery to the space.
Guesthouse in Ocean View
5 out of 5 average rating, 20 reviews

Guest house on the water

Guest favourite
The exterior of a spacious two-story vacation home is shown, featuring a wide porch with white railings and large windows. A well-maintained lawn with decorative plants lines the front, and gravel leads to the driveway. Clear blue skies complement the inviting atmosphere.
Home in Bethany Beach
4.95 out of 5 average rating, 57 reviews

Large waterfront home on South Bethany Canal

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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