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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
A modern living area features a light-colored sectional sofa and a round dining table with four chairs. A flat-screen television is placed on a sideboard. The kitchen area includes white cabinetry and stainless steel appliances, while natural light enters through the nearby window.
Townhouse in Rehoboth Beach
5 out of 5 average rating, 132 reviews

THE STANLEY 1 BLOCK TO BEACH/BOARDS & DINE/IMBIBE

ONE BLOCK FROM THE BEACH/BOARD, ONE BLOCK FROM DINE AND IMBIBE. 1 SPOT OFF STREET IN-TOWN PARKING!! This loft-style townhome has been completely restored with full modern kitchen, two ensuite bathrooms, comfortable living space, office loft and private outdoor deck. Modern, clean and beautiful featuring exposed high ceilings, shiplap and sea grass through out. We provide everything you need for your beach getaway. Luxe linens, beach chairs and towels, bath and cleaning products. Just come enjoy!

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, 311 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!

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.
Apartment 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 living area is furnished with a large sectional sofa adorned with decorative pillows. Natural light enters through multiple windows, highlighting a round dining table nearby. A decorative mirror adds a touch of charm to the room, creating an inviting atmosphere.
Apartment in Dewey Beach
4.98 out of 5 average rating, 245 reviews

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

2 BR, ground floor condo on the south side of Dewey Beach! 1.5 blocks to the beach, 1 block south to beautiful bayside dining. Discounts for stays over 3 nights! The HOA maintains a relaxing, clean, family friendly atmosphere. Self check-in keypad code auto-sent upon booking. Professionally cleaned and beds made before your check in. Bed linens, shower towels/essentials, 2 Dewey Beach Street Parking Passes, and beach chairs are provided free of charge. Max occupancy of 6 at all times.

Guest favourite
A modern kitchen area features wooden cabinets, stainless steel appliances, and a stone accent wall. A circular glass dining table is surrounded by wicker chairs, providing a cozy space for meals. The overall layout is bright and inviting, with natural light highlighting the contemporary decor.
Apartment in Rehoboth Beach
4.94 out of 5 average rating, 122 reviews

Cozy Condo on Silver Lake - Walk to the beach!

Located in the middle of a nature preserve on Silver Lake, and walking distance to the beach this end unit condo boasts stunning views and cozy modern decor. Enjoy the pool just steps from your lakeside patio or take a short walk to the beach or town crossing the footbridge (known by locals as turtle bridge.) Lovely boutiques and fine dining in town plus numerous family friendly restaurants. 5 minute drive to Tanger Outlets. Rehoboth Beach parking pass provided with each rental.

Guest favourite
The exterior of Rosemary Cottage is displayed, featuring a welcoming entrance with a white path leading to the front door. The cottage showcases a warm wooden shingle façade, surrounded by landscaped grass and small shrubs, set against a backdrop of leafy trees.
Cottage in Ocean View
4.91 out of 5 average rating, 138 reviews

Rosemary Cottage at Good Earth, near Bethany Beach

Welcome to "Rosemary Cottage". It is the perfect size for a small family, with 2 bedrooms (1 queen bed, and 2 single beds) a kitchen, and a 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 another cottage just like this "Basil Cottage". Staying at Good Earth is more than just a beach trip!

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, 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
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
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, 130 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
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.
Apartment 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!

Top guest favourite
A comfortable seating area is presented with a light-colored sectional sofa adorned with blue accent pillows. A small black side table sits nearby, accompanied by a woven area rug. Natural light enters through two covered windows, while a floor lamp provides additional illumination.
Cottage in Sussex County
4.98 out of 5 average rating, 263 reviews

Classic Cottage for Two, Rehoboth Beach

Enjoy our sweet cottage that's close to the beach - it's less than a mile away! Our cottage is cozy and comfortable with all the amenities needed to make your stay relaxing and enjoyable. We're close to beaches, dining, shopping and outdoor activities. Our charming screened-in porch is the perfect spot to relax and enjoy reading a book, having dinner and cocktails, or doing nothing at all!

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

Top guest favourite
A spacious living area features a light gray sectional sofa adorned with decorative pillows. A striking world map art piece illuminated by blue lighting is mounted on the wall. Natural light fills the room, contributing to its inviting atmosphere, while an overhead lamp enhances the ambiance.
Apartment in Dewey Beach
4.96 out of 5 average rating, 54 reviews

Luxurious Penthouse, King beds. Dog & ADA Friendly

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
4.97 out of 5 average rating, 35 reviews

Storybook Cottage in DT Reho, Walk to Everything

Top guest favourite
Apartment in Dewey Beach
5 out of 5 average rating, 21 reviews

Spring Lake Escape | Dog-Friendly by Trail & Beach

Top guest favourite
A spacious oceanfront deck is featured, with two white Adirondack chairs positioned around a small table. The view showcases sandy dunes and the ocean in the background, while gentle waves can be seen under a clear blue sky.
Apartment in Ocean City
4.95 out of 5 average rating, 56 reviews

Direct oceanfront quiet getaway with large deck

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.
Flat in Dewey Beach
4.89 out of 5 average rating, 19 reviews

Steps to the Beach | Bay View Condo + Rooftop Pool

Top guest favourite
A light-filled living area features a comfortable gray sofa and two matching armchairs, complemented by a decorative coffee table. Soft-colored curtains frame the window, and a serene landscape painting adorns the wall. A patterned area rug adds warmth to the tile flooring.
Apartment in Dewey Beach
4.94 out of 5 average rating, 85 reviews

*Walk to the Beach* Ocean Block Condo - Pool

Top guest favourite
An all-season porch features large windows that allow natural light to fill the space. Two comfortable couches are arranged around a central coffee table adorned with fresh fruit and snacks, creating an inviting setting for relaxation. A neutral-striped rug complements the decor.
Townhouse in Rehoboth Beach
4.97 out of 5 average rating, 31 reviews

Clean Family Friendly Getaway w/ unbeatable value!

Top guest favourite
A two-story coastal home features a light blue exterior, elevated on stilts. A staircase leads to a spacious porch with railings. A sleek car is parked nearby, with tall grasses swaying in the foreground, and a soft evening light casts a warm glow over the scene.
Home in Milton
5 out of 5 average rating, 11 reviews

Broadkill Beach Bliss: Coastal Charm, Wild Beauty!

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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