Family-friendly holiday rentals in Dewey Beach

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Dewey Beach

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite

Home in Ocean View

4.9 out of 5 average rating, 583 reviews

Tiny House at Good Earth, near Bethany Beach

A custom 165 sq. ft. "Tiny House" located right between our theater and the garden dining area. True to the show "Tiny House Nation".. cool interior with custom woodwork, stairs to a lofted bed. Fully functioning kitchen. Spacious bathroom & shower. We provide TV and internet in the unit. We have 2 on-site restuarants, market, theater, and parking. Our AIRBNB village consists of 2 tiny houses, 2 cottages, tent sites, a loft appartment, and more! Staying at Good Earth is more than a beach trip!

Superhost

Home in Rehoboth Beach

4.8 out of 5 average rating, 696 reviews

Contemporary 1 Bedroom 2 level home

The unit has keyless entry system, A/C, brand new full size W/D, large patio w/grill, remote controlled open&close sky lights w/built in shades, new carpet, YoutubeTV/Netflix/Hulu/Amazon Prime Video & walk to the beach and attractions w/out crossing **pet friendly** **LOCATION** Intersection of Washington st & Jefferson St. supplied for guest: sheets blankets bath towels Shampoo/conditioner soap toilet paper paper towels trash bags Back pack type beach chairs (3) Beach umbrella Bikes (2)

Guest favourite

Apartment in Rehoboth Beach

4.83 out of 5 average rating, 384 reviews

2 Bedroom Condo Rehoboth Beach w/ No Chores

2 Bedrooms Condo. Great for families or couples. Walking distance to restaurants, beach, bars & other entertainment. Driving distance to 5 different golf courses within 15 minutes. Walking distance to water park & amusement park. Pool on site. Bike & running trail behind the condo. Roku on every TV with Xfinity app for local TV & a Spectrum app for premium channels. We have MGM +& you can add any of your own streaming services during your stay. Smoking area on deck. No chores for you to do!

Guest favourite

Townhouse in Ocean City

4.97 out of 5 average rating, 458 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 :)

Guest favourite

Townhouse in Rehoboth Beach

4.97 out of 5 average rating, 185 reviews

Walk to Beach, 3B/3B Dewey Beach Summer Rental

Welcome to our fully renovated 3 bed/3 bath end unit townhouse located in the quiet community of Ocean Dunes, ideally located just 2.5 blocks from the pristine shores of Carolina Street in Dewey. You're not just close to the beach, but also a mere 2 blocks from the Jolly Trolley stop. Hop on and enjoy a scenic ride directly to the Rehoboth Boardwalk. Other perks include: Screened-in front porch Dog Friendly (2 dog max per HOA) Short stays welcome (3 night minimum) Parking for 4 cars

Top guest favourite

Townhouse in Dewey Beach

4.9 out of 5 average rating, 122 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

Apartment in Dewey Beach

4.85 out of 5 average rating, 201 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. New living room furniture Spring 2021. Completely renovated in mid 2020.

Top guest favourite

Flat in Rehoboth Beach

4.99 out of 5 average rating, 227 reviews

The Sandy Starfish - Rehoboth Beach

Welcome to The Sandy Starfish! Your dream beach escape awaits in this stunning 3-bed, 2-bath top-floor condo, tucked inside the resort-style community of The Grande at Canal Pointe—just one mile from the sun, surf, and charm of Rehoboth Beach and its iconic boardwalk! Enjoy 2 saltwater pools, tennis/pickleball, gym, and playground. You’re minutes from Tanger Outlets and the beach— we’ve got your beach chairs & umbrella covered!

Superhost

Apartment in Dewey Beach

4.87 out of 5 average rating, 200 reviews

Read Ave Dewey Condo - Bay Front, Private Beach

Experience the Ultimate Family Getaway in Dewey Beach Perfectly situated in the heart of Dewey Beach: just 2 blocks from the beach with convenient walking access to bars and restaurants. Enjoy private beach access, a boat slip, and opportunities for fishing and crabbing. Ideal for families or professionals, this condo comfortably sleeps 6, with linens, towels, shampoo, and beach chairs included.

Guest favourite

Home in Dewey Beach

4.94 out of 5 average rating, 217 reviews

Cozy Home at 109 Swedes St

This home built in 2013, is a cozy and bright 3 bedroom 2 1/2 bath house. It is just 1 1/2 blocks to the beach, a walk to all of Dewey's nightlife and restaurants. Also a short drive or bike ride to Rehoboth Beach. Guests will need to bring your own sheets, towels and bath matts. Provided are 5/6 beach chairs and a beach cart. June 16 to September 15, 2025 Weekly Rental Friday to Friday

Top guest favourite

Home in Rehoboth Beach

5 out of 5 average rating, 200 reviews

Beautiful Beach House in Rehoboth

Last minute cancellation so July 20 week open! Gorgeous modern spacious house in Rehoboth Beach with large open floor plan on 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.

Top guest favourite

Apartment in Ocean City

4.98 out of 5 average rating, 229 reviews

Direct Oceanfront close to Northside Park!

Location, location, location! 2 bed, 2 bath direct oceanfront condo, with incredible ocean sunrise views from your private enclosed patio. Master bedroom features unbelievable views of the ocean, glass slider out to the patio & in suite full bath! Walking distance to Northside Park, restaurants & shopping. 2 assigned parking spaces. Elevator or steps - you pick. Washer/dryer in unit.