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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.
Condo 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 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 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
A modern living area features a striped sofa adorned with colorful cushions and an adjacent neutral-toned loveseat. A wooden dining table is positioned in the foreground, while a well-equipped kitchen is visible in the background. Natural light fills the space through large windows.
Condo in Dewey Beach
4.94 out of 5 average rating, 101 reviews

Luxury at the Beach.

Luxury accommodations at the beach, walkout to the pool from your sliders to your gated private patio with poolview. Hardwood floors, fireplace, TV, WIFI, Enjoy the rooftop outdoor pool, fire pits & propane grills on the veranda for use only by The Residences at Lighthouse Cove tenants & owners. Access to indoor pool & fitness room along with the hotel guests. Breathe the salt air, bay views and one block to ocean. Restaurants walking distance too. Walking distance to ocean and bay.

Top Guest favourite
A spacious open-concept living area is visible, featuring large windows that allow ample natural light. The area includes a comfortable seating arrangement, a mounted TV, and a kitchen counter. A staircase leads to the upper level, while a surfboard decoration adds a beachy touch to the decor.
Home in Rehoboth Beach
5 out of 5 average rating, 44 reviews

Beach Loft - Sleeps 12/Rooftop/Bike to Reho Beach

The ultimate Rehoboth Beach getaway for 12. Walk to Rehoboth Ave, breweries, bars, restaurants and the outlets. An easy bike into downtown or take the trail to Lewes. Short Uber to Dewey. Watch the sunset from your private rooftop deck. Full kitchen, W/D, 4 br, 3 full baths, 2400 sq. feet of easy breezy open concept beach living. Fresh linens, towels, toiletries provided. In summer we provide bikes and beach towels, chairs and umbrellas. Designed by a local so you can live like a local!

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, 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.

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.

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.
Guesthouse in Rehoboth Beach
4.87 out of 5 average rating, 346 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!!

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.

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!

Guest favourite
The image shows a scenic waterfront view featuring a calm body of water reflecting nearby buildings and boats. Docks are visible, with a rustic structure and moored boats adding to the nautical atmosphere. Clear blue skies contribute to the serene setting.
Condo in Dewey Beach
4.86 out of 5 average rating, 211 reviews

Read Ave Dewey Condo - Bay Front, Private Beach

Escape to our waterfront Dewey Beach condo with stunning bay & marina views! This family-friendly retreat comfortably sleeps 6 and features a private dock, boat slip, and kayak. Enjoy spectacular sunsets from the porch, a fully equipped kitchen, and easy access to the beach just 2 blocks away. Perfect for a memorable family getaway with modern comforts and direct water access.

Top Guest favourite
A two-story beach house is depicted, featuring a spacious front porch with white railings and large deck areas. The structure is raised above a gravel driveway, with outdoor parking space visible below. The facade is painted in muted blue tones, complemented by wooden accents.
Home in Dewey Beach
4.97 out of 5 average rating, 182 reviews

McAvoy B & B

Enjoy the beautiful sunsets over the bay on our two huge decks! Relax by our fireplace. Our house is centrally located in Dewey near the Lion's playground, Sunset park on Read and all of the restaurants and bars. It's perfect for a large family or couples with two master bedrooms with king beds and their own bath.

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

157 locals recommend

Dewey Beach Watersports

31 locals recommend

Other great holiday rentals in Dewey Beach

Guest favourite
A sign for 'Oceans Reach' is prominently displayed in a natural setting. The colorful lettering features an orange sun setting over stylized waves and beach grass. Surrounding greenery and gravel pathways enhance the welcoming appeal of the entrance.
Townhouse in Dewey Beach
4.96 out of 5 average rating, 53 reviews

Oceans Reach # 3

Top Guest favourite
An elevated beach house stands gracefully by the canal, with a spacious upper deck visible under a colorful twilight sky. Lush trees frame the property, while a wooden dock provides direct access to the water, creating a serene and inviting coastal atmosphere.
Home in Ocean View
4.97 out of 5 average rating, 33 reviews

Waterfront Retreat with Kayaks, Deck, Views!

Top Guest favourite
The exterior of the home is framed by a bright blue façade, featuring a welcoming front door painted in coral. A white pergola extends over the porch, enhancing the entryway. Lush green shrubs line the pathway, complemented by a rustic picnic table situated in the front garden.
Home in Dewey Beach
4.95 out of 5 average rating, 226 reviews

Cozy Home at 109 Swedes St

Guest favourite
A comfortable living area is furnished with a large gray sectional sofa and an additional chair. A blue ottoman sits at the center, adorned with a decorative tray. Light pours in through large windows, highlighting a coastal-themed photograph on the wall.
Condo in Dewey Beach
4.92 out of 5 average rating, 79 reviews

Luxury Bay & Oceanview Condo in the Heart of Dewey

Guest favourite
The two-story cottage features a charming facade with light-colored siding and blue accents. Two front porches are equipped with white railings and seating for relaxation. Neatly landscaped greenery surrounds the entrance, enhancing the home's welcoming appearance.
Home in Rehoboth Beach
5 out of 5 average rating, 23 reviews

Suncatcher Cottage at Dewey Beach

Top Guest favourite
Aerial view of a private pool located in a fully-fenced backyard. The pool is surrounded by a stone patio, lounge chairs, and a shaded umbrella for outdoor comfort. Lush greenery and tall trees provide a natural backdrop, enhancing the outdoor space.
Home in Rehoboth Beach
5 out of 5 average rating, 67 reviews

Private Pool! Charming 4bdrm, BayVista Beach House

Top 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
5 out of 5 average rating, 38 reviews

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

Top Guest favourite
A charming two-story house features a large covered porch with seating and decorative lanterns. The soft green and white exterior is complemented by a manicured garden showcasing colorful flowers and lush greenery. Trees provide shade, creating a peaceful ambiance around the property.
Home in Rehoboth Beach
4.98 out of 5 average rating, 93 reviews

Modern Beach House | Walk to Beach & Town

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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