Dewey Beach Holiday Rentals

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Check prices for these dates

Tonight
25 Sept - 26 Sept
Tomorrow
26 Sept - 27 Sept
This weekend
26 Sept - 28 Sept
Next weekend
3 Oct - 5 Oct

Holiday Rentals in Dewey Beach

Our top choices for Dewey Beach holiday rentals

Sandy Paws Beach House. Pet Friendly! Completely renovated in 2024!
Outdoor dining

Sandy Paws Beach House. Pet Friendly! Completely renovated in 2024!

9.8 out of 10, Exceptional, (132)
"We had a great stay at this rental. Very clean and a perfect location right on the beach."
Sandy Paws Beach House. Pet Friendly! Completely renovated in 2024!
10 Chicago Street - 10 Bedrooms - 91/2 Path Ocean Block w/ pool
Beach

10 Chicago Street - 10 Bedrooms - 91/2 Path Ocean Block w/ pool

9.8 out of 10, Exceptional, (60)
"The location and amenities are amazing! Samanatha was "
10 Chicago Street - 10 Bedrooms - 91/2 Path Ocean Block w/ pool
Waterfront, spectacular sunsets, private beach, and Dock Sept wknds still avail
Smart TV, DVD player, music library, video library

Waterfront, spectacular sunsets, private beach, and Dock Sept wknds still avail

9.8 out of 10, Exceptional, (105)
"On the whole we love the place. Only negative if you have little ones the band noise is LOUD especially in the master bedroom you can hear it perfectly! Also if there is a lot of rain the street floods but it’s nothing against this place. It’s perfect for a safe little beach for our grandchildren ages 3 & 1. We would come again and stay here. "
Waterfront, spectacular sunsets, private beach, and Dock Sept wknds still avail
Serenity Amid it All. Dog friendly PET FEE, WiFi, outdoor shower, grill
Beach nearby

Serenity Amid it All. Dog friendly PET FEE, WiFi, outdoor shower, grill

9.8 out of 10, Exceptional, (287)
"Perfect location, quiet, easy access to everything "
Serenity Amid it All. Dog friendly PET FEE, WiFi, outdoor shower, grill
Charming 2-bedroom townhome with sweeping bay views in Dewey Beach
Beach

Charming 2-bedroom townhome with sweeping bay views in Dewey Beach

9.6 out of 10, Exceptional, (5)
"Location: Beautiful views of the bay and easy walk to restaurants and the beach. Perfect"
Charming 2-bedroom townhome with sweeping bay views in Dewey Beach
Breathtaking Ocean Front Condominium . Fall weekends with the dog.
Property grounds

Breathtaking Ocean Front Condominium . Fall weekends with the dog.

9.4 out of 10, Exceptional, (86)
"Location is perfect We had a wonderful week The place is very comfy and would Stay again Thank you Kerry"
Breathtaking Ocean Front Condominium . Fall weekends with the dog.
Ocean Block Dewey Beach Condo with Parking
Fridge, microwave, oven, stovetop

Ocean Block Dewey Beach Condo with Parking

3.0 out of 10, (2)
"We were very disappointed with this stay. Before I booked this place I messaged the owner / RE/Max regarding the property details and was given responses that ended up not being accurate. For example, the vrbo listing said one of the bedrooms had a daybed and 2 twin beds, but after I booked the non-refundable stay the owner said there are only 2 twin beds in that room. Another example, the vrbo listing said there is free wifii, but we were not provided any wifii info (username and password)...
Ocean Block Dewey Beach Condo with Parking
Bayfront Family Friendly 2BR on a Marina - Great Location & Beautiful Views!
Interior

Bayfront Family Friendly 2BR on a Marina - Great Location & Beautiful Views!

9.8 out of 10, Exceptional, (66)
"had fantastic time here!"
Bayfront Family Friendly 2BR on a Marina - Great Location & Beautiful Views!
Awesome 5 bedroom 4 bath with pool, hot tub & rooftop deck
Property grounds

Awesome 5 bedroom 4 bath with pool, hot tub & rooftop deck

9.6 out of 10, Exceptional, (28)
"This house was house"
Awesome 5 bedroom 4 bath with pool, hot tub & rooftop deck
Beautiful 2BR, 2BA Just Minutes from the Beach
Beach nearby

Beautiful 2BR, 2BA Just Minutes from the Beach

10.0 out of 10, Exceptional, (30)
"Great property"
Beautiful 2BR, 2BA Just Minutes from the Beach
Location, Location, Location! Immaculately Kept!
Exterior

Location, Location, Location! Immaculately Kept!

9.8 out of 10, Exceptional, (43)
"Really fun time playing golf, going to the beach and going out to the bars at night. Great location, can walk anywhere."
Location, Location, Location! Immaculately Kept!
Iconic A-Frame - Beach Block Dewey! Sleeps up to16! Walk Everywhere!
Outdoor dining

Iconic A-Frame - Beach Block Dewey! Sleeps up to16! Walk Everywhere!

10.0 out of 10, Exceptional, (31)
"Great outdoor spaces , Great location , Clean , so many bedrooms and bathrooms. Would recommend to anyone ! Comin back again !"
Iconic A-Frame - Beach Block Dewey! Sleeps up to16! Walk Everywhere!
Last minute opening!! Mini summer stay available!!
Fridge, microwave, oven, stovetop

Last minute opening!! Mini summer stay available!!

10.0 out of 10, Exceptional, (76)
"Great location and beautiful property. "
Last minute opening!! Mini summer stay available!!
Dewey Beach-Block Penthouse
Terrace/patio

Dewey Beach-Block Penthouse

10.0 out of 10, Exceptional, (3)
"Great Location! Lines provided. Clean and plenty of bathrooms and bedrooms."
Dewey Beach-Block Penthouse
Steps to Beach! California Vibe - Families, Groups, Reunions - Fun Property!
Fridge, microwave, oven, stovetop

Steps to Beach! California Vibe - Families, Groups, Reunions - Fun Property!

10.0 out of 10, Exceptional, (48)
"Beautiful house, well maintained. Excellent location - 2 blocks from Dewey Beach and the town is walkable. We also walked to Rehoboth Beach. Plenty of great amenities and an enormous amount of space. The owner, Todd, was helpful with recommendations and was responsive during our stay."
Steps to Beach! California Vibe - Families, Groups, Reunions - Fun Property!
Modern Condo On Beach Block in Dewey Beach
Fridge, microwave, oven, stovetop

Modern Condo On Beach Block in Dewey Beach

9.8 out of 10, Exceptional, (6)
"Great location. Steps from the beach. Beds were stained up but that’s what mattress protectors are for. A lot of flies hanging around outside that found there way in."
The price is HK$1,687
HK$3,240 total
includes taxes & fees
8 Oct - 9 Oct
Modern Condo On Beach Block in Dewey Beach
2 BR Dewey Beach Penthouse Paradise
Indoor pool, outdoor pool

2 BR Dewey Beach Penthouse Paradise

9.4 out of 10, Exceptional, (3)
"Our stay was great and I would highly recommend this property. Instructions were clear, the place was spacious, clean, modern, and in a great location. Gorgeous terrace views and pool and outdoor area were very nice. We would definitely stay here again. "
2 BR Dewey Beach Penthouse Paradise
CUTE OCEAN BLOCK CONDO - 21-1B Collins St, Dewey Beach, DE
Beach nearby

CUTE OCEAN BLOCK CONDO - 21-1B Collins St, Dewey Beach, DE

6.8 out of 10, (3)
"very nice "
CUTE OCEAN BLOCK CONDO - 21-1B Collins St, Dewey Beach, DE
Located on prime street in Dewey Beach walking to everything with brand new POOL
Fridge, microwave, oven, stovetop

Located on prime street in Dewey Beach walking to everything with brand new POOL

10.0 out of 10, Exceptional, (35)
"Great place to stay in the heart of Dewey. Check-In was easy, place was clean, and landlord was very responsive."
Located on prime street in Dewey Beach walking to everything with brand new POOL
70 STEPS TO THE OCEAN No streets to cross to get to the Beach. Walk to everythin
Property grounds

70 STEPS TO THE OCEAN No streets to cross to get to the Beach. Walk to everythin

9.6 out of 10, Exceptional, (66)
"Convenient Location in the middle of all the excitement Dewy beach has to offer. Owner was very responsive and helpful. Must rent or bring your own towels (bath & kitchen) and linens for beds. "
70 STEPS TO THE OCEAN No streets to cross to get to the Beach. Walk to everythin
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Dewey Beach Hotel Reviews

The Surf Shanty Motel

The Surf Shanty Motel

10/10 Excellent
"Very accommodating manager. Extremely well kept property! Excellent mattresses!!!"
Norma 2-night trip
Posted 1 day ago
The Surf Shanty Motel

Find out more about Dewey Beach

Find out more about Dewey Beach

Search for holiday rentals in Dewey Beach on Expedia! You can easily find your home rentals, villas, holiday apartments in Dewey Beach using one of the methods below:

  • View our selection of featured holiday rentals in Dewey Beach
  • Use the map to find apartments and other holiday homes in the Dewey Beach neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Dewey Beach while they last

Look no further and take a look at our great range of rental properties in Dewey Beach!

Frequently asked questions

Can I find a holiday rental in Dewey Beach?

Yes, there are holiday rentals in Dewey Beach close to Dewey Beach Parasail, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Dewey Beach speak positively about the popular beaches and top-notch restaurants in this destination. Give yourself some extra time to check out the shops and bars during your trip.

What are some of the best holiday rentals that Dewey Beach has to offer?

10 Chicago Street - 10 Bedrooms - 91/2 Path Ocean Block w/ pool: This highly rated holiday home rental in Dewey Beach offers a fireplace, a balcony and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 10 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a pool table.

How many holiday rentals are there in Dewey Beach?

Expedia has 288 holiday rentals for your stay in Dewey Beach.

What can I see and do in Dewey Beach?

Family-friendly attractions include Dewey Beach Parasail and East of Maui, whereas Dewey Beach and Indian Beach are a couple of great spots to enjoy the outdoors. While here, Delaware Seashore State Park and Bottle & Cork are other places worth a visit.

What are holiday rentals like in Dewey Beach?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Dewey Beach. Holiday rentals provide amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitised environment, holiday rentals can provide a sense of safety away from shared hotel lifts and busy front desks while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for a family trip.