Holiday rentals in Dewey Beach

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

In town Rehoboth, with Rise Up and the boardwalk just a quick walk away, you'll love this home with a POOL AND HOT TUB (April-Oct). There's a ton of natural light, plus comfy queen and king beds, nice new linens, and more. Please note there is a security camera on the pool and in the pool equipment area for your safety. Dogs are allowed for a $75 fee per stay for first pet, $25 per additional (additional pet fee after the first will be billed after your reservation is complete). Maximum 3 dogs.

Dewey Beach Ocean Block 3 BR 2 BA Free Parking

Unique Dewey Beach, DE Local Colliers Building saved from being taken down and turned into an extraordinary Ocean Block Beach Cottage. Indulge in the Ocean, Restaurants, Water Activities, and the Night Life of Dewey Beach, Delaware. Always a memorable visit when you stay in this town and our comfortable ocean block beach home. You will be steps to the Beach in this cozy, clean 3 BD Sleeper Queen Sofa and 2 BA, Private parking, Extra Secure Storage. Come escape to a little piece of paradise.

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!

Newly Updated OCEAN BLOCK 2 bed condo

Get ready for a fantastic stay at this adorable beach condo- steps from the beach in fabulous Dewey Beach. This 2 bedroom, 1 bath condo is on a quiet street in Dewey, but close enough to walk to all the action you need for a great getaway. Enjoy your morning coffee on the large screened porch, walk to the beach for the day, enjoy the sunset at the Rusty Rudder across the street or walk around the corner for dinner at Nalu. Everything you need for a great vacation is right at your fingertips!

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 :)

Clean & Comfy MCM Casita, Great Location, Fire-pit

Welcome to your cozy Bay Vista getaway, a private one-bedroom retreat just minutes from Rehoboth Beach. This charming home features vaulted ceilings, equipped kitchen, full bathroom, washer & dryer. Relax by the fire pit with complimentary firewood or head to the beach with the beach towels & chairs. Thoughtfully decorated in a mid-century modern style, the home includes an organic cotton mattress and high-end finishes throughout. A perfect blend of comfort, style, and location.

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!!

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.

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.

Luxurious Penthouse, King beds. Dog & ADA Friendly

Stunning Bayfront Penthouse w/ Ocean Views + Pools – Walk to Beach & Nightlife Stay in a luxurious top-floor 2BR/2BA condo at The Residences at Lighthouse Cove in Dewey Beach. Enjoy sunset views over the bay, partial ocean views, rooftop & indoor pools, and a private balcony overlooking live music at the Rusty Rudder. Walk to everything! Perfect for families, couples, or remote work—fully stocked kitchen, plush bedding, and garage parking included.

The Garden Apartment

Bubba & Banjo’s was built as a home for me and my husband before we bought our first house. And now we get to share it with others! Luxury garage apartment, barndominium, pole barn are a few words people have used when describing the spot. The garden view might be one of my favorite things but the spacious tile shower is a close runner up! It’s simple but checks all the boxes for what a great rental spot should be in our opinion.

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.