Family-friendly holiday rentals in Dewey Beach

Tiny home in Rehoboth Beach

4.94 out of 5 average rating, 284 reviews

Cutest-Quiet-bk rds-Bikes-Kayaks-Doorstep parking!

Beach Daze is a surprisingly spacious & bright “tiny house” nestled into a quiet zen-like hidden treasure of a neighborhood within the town of Rehoboth Beach, Delaware. It is walking or biking distance (on quiet, quaint streets) to so many delightful natural wonders including the beaches, the canal, the bay, and a nature preserve! Beach Daze is perfect as a couple's retreat or a family vacation! We provide PLENTY of TOYS… 2 kayaks, 2 bikes, 2 beach chairs & random array of games, toys & sporty.

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.

4.97 out of 5 average rating, 335 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!

4.97 out of 5 average rating, 100 reviews

An open-concept kitchen and living area features a large wooden island with a sink, surrounded by modern cabinetry. Natural light floods the space through wide windows, showcasing cozy seating and a vibrant dining area with a round table. Bookshelves line a portion of the wall.

Home in Rehoboth Beach

Modern Beach House w/ Private Pool

Modern eco-friendly retreat perfect year-round! This salt-box cottage is an open concept 3 bedroom, 2 bathroom filled with natural light. Huge yard with a pool house with dining table and grill, patio with lounge chairs, outdoor shower, and private pool (pool open May 15 - October 15). Located perfectly for Rehoboth Beach or Dewey Beach visitors. It is a 20 minute walk to the shops and restaurants on Rehoboth Ave or to the beach. Three parking spots, beach items, and all amenities included.

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.

4.95 out of 5 average rating, 154 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

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.

4.98 out of 5 average rating, 178 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.

4.91 out of 5 average rating, 117 reviews

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

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.

4.91 out of 5 average rating, 251 reviews

The cozy cottage showcases a welcoming exterior with wooden shingles and a front porch. An American flag is displayed, and two small shrubs frame the entrance. A clear pathway leads to the door, surrounded by a grassy area and trees in the background.

Tiny home in Ocean View

Tiny Cottage at Good Earth, near Bethany Beach

Welcome to the "Tiny Thyme Cottage" at Good Earth. The cottage is super cozy, perfect for a couple, with 1 queen bed, a kitchen & bathroom, and a small 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 2 cottages on the property. Staying at Good Earth is more than just a beach trip!

4.95 out of 5 average rating, 181 reviews

The interior of the bus features a cozy layout with wood paneling and large windows providing natural light. A comfortable seating area, equipped with pillows, is situated next to a compact kitchen with a stove and cabinets. A small dining table with two placemats is visible.

Bus in Frankford

Delightful Skoolie Near Bethany Beach

Try tiny living! Come to the Delaware beach for a unique glamping experience. The Coastal Cruiser is a 1985 Thomas School Bus turned tiny home. Spend your days exploring the Delaware Coast and come home to a rustic Skoolie with a full kitchen & outdoor area. You have access to fire pit, grill, and outdoor seating area. We’ve renovated- there is a bunk bed, and a full bathroom with toilet, shower, and sink. The bathroom is in a separate building about 20 ft from the bus.

4.91 out of 5 average rating, 139 reviews

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

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!

Holiday home in Dewey Beach

A modern dining area features a large white table surrounded by upholstered chairs. A vase with fresh flowers sits at the center, and sliding glass doors allow natural light to enter, providing a view of the outdoor space.

4.99 out of 5 average rating, 124 reviews

Luxury, Ocean Block 4B/3B Condo at Van Dyke Villas

Come stay at our stunning 4 bedroom, 3 full bathroom, ocean block condo with direct ocean views. This rental has every convenience for the perfect vacation. Located on the same block as the beach, you can have your feet in the warm sand within minutes. Newly renovated, this rental features modern amenities, including a fully upgraded kitchen and bathrooms, a gas fireplace, smart TVs throughout and an amazing, oversized screened-in porch with Ocean views.

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.

4.86 out of 5 average rating, 221 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.