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Dog Friendly Private Pool Dewey Beach 2nd Ocean Block Home

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Fridge, microwave, oven, stovetop
5 bedrooms, iron/ironing board, free WiFi
Fridge, microwave, oven, stovetop
Interior
Interior

Reviews

9.8 out of 10
Exceptional

Entire home

5 bedrooms3 bathroomsSleeps 12204 sq m

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Free Wi-Fi

Explore the area

View in a map
Dewey Beach, DE
  • Place, Fifer Orchards Local-Fresh Market - Dewey Beach
    ‪1 min walk‬
  • Place, Dewey Beach
    ‪5 min walk‬
  • Place, Rehoboth Beach Boardwalk
    ‪3 min drive‬
  • Airport, Georgetown, DE (GED-Sussex County)
    ‪27 min drive‬

Room options

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About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Dog Friendly Private Pool Dewey Beach 2nd Ocean Block Home

Welcome to 118 Chicago Street, a charming single-family home nestled in the Rehoboth By the Sea community, just 1.5 blocks from the heart of Dewey Beach. This coastal retreat offers the ideal blend of comfort and convenience, placing you within walking distance of Dewey's vibrant nightlife, exciting water sports, and the Jolly Trolley, which provides easy access to the boardwalk, shops, and dining in nearby Rehoboth Beach.
Recently upgraded, the home features a private heated pool, a spacious rear patio with ample seating, a fire pit, a gas grill, and an outdoor shower with a private changing room. Comfortably accommodating 12 guests, the main level features a cozy living room, a kitchen overlooking the pool area, one bedroom, a hall bath, and a dining space ideal for family meals. The second floor features four generously sized bedrooms and two additional bathrooms, offering ample space for everyone.
Set on a quiet, family-friendly street lined with mature trees and lush landscaping, the home also includes off-street parking for six vehicles and a Universal 220/240 EV cable stored in the laundry room for guest use. The private pool is open from May through October. Additional amenities include ceiling fans, Wi-Fi, a washer and dryer, and accommodations for two dogs with a pet fee (no cats permitted). Linens are not supplied, but rental packages are available for your convenience.
For a memorable beach getaway in the heart of Dewey Beach, this home offers an unbeatable combination of location, comfort, and amenities. Damage Waiver Information
Your reservation includes a nightly Damage Waiver fee (plus tax, if applicable), which covers accidental damage to the property or its contents—such as furniture, appliances, or fixtures—up to $3,000, as long as the incident is reported to the host before checkout.
This fee replaces a traditional security deposit and offers additional peace of mind during your stay. Guests can choose to opt out of the Damage Waiver and instead provide a refundable security deposit if they prefer. The $249.99 processing fee is non-refundable if you need to cancel your reservation. Delaware Accommodations Intermediary #2024713094
During your stay at this vacation home, you're just a quick walk from Fifer Orchards Local-Fresh Market - Dewey Beach. Enjoy features like a water park and laundry facilities. The vacation home offers free WiFi and a private pool.
  • Air-conditioned home with private pool, kitchen, and washing machine
  • Free WiFi
  • Splash around at the water park
  • Amenities include laundry facilities and a car charging station
  • Steps from Fifer Orchards Local-Fresh Market - Dewey Beach and East of Maui
This vacation home offers its guests a water park. This vacation home also features barbecue grills and laundry facilities.

Property amenities

Beach

  • Beach nearby

Pool/Spa

  • Heated pool
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Electric car charging station on site
  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 5 bedrooms

Bathroom

  • 3 bathrooms
  • Bathtub or shower
  • Shower

Living spaces

  • Dining table
  • Living room

Entertainment

  • Smart TV with cable/satellite channels

Outdoor areas

  • Barbecue grill
  • Fenced yard
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the city centre
  • Near a health/beauty spa
  • Near a hospital
  • Near an outlet shopping centre
  • Near the bay
  • Near the sea

Things to do

  • Heated pool
  • Optional golf privileges
  • Water park
  • Basketball nearby
  • Birdwatching nearby
  • Casino nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Ice skating nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Parasailing nearby
  • Surfing/bodyboarding nearby
  • Swimming nearby
  • Theme park nearby
  • Whale watching nearby
  • Wildlife walks nearby
  • Windsurfing nearby
  • Winery tours nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • Electric car charging station
  • Unit size: 2,200 square feet

Policies

Check-in

Check-in time starts at 3:00 PM
Contactless check-in available
Minimum check-in age: 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Rules

High-risk rentals and special events are strictly prohibited at this property. This includes bachelor parties, senior weeks, and large groups.

Pets

  • Pets are welcome
  • Service animals are exempt from fees

Children and extra beds

  • Children are welcome.

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
You will receive an email from the host with check-in and check-out instructions. You will also receive an email from Vrbo with a link to a Vrbo account which will enable you to manage your booking.
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with EU regulations about consumer rights, property booking services are not subject to the right of withdrawal.

Property is also known as

849621

Dog Friendly Private Pool Dewey Beach 2nd Ocean Block Home Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 9 out of 10 reviews
Rating 8 - Good. 1 out of 10 reviews
Rating 6 - Okay. 0 out of 10 reviews
Rating 4 - Poor. 0 out of 10 reviews
Rating 2 - Terrible. 0 out of 10 reviews

9.8/10

Cleanliness

Reviews

10/10 Excellent

Elizabeth R.

Liked: Cleanliness
Stayed 7 nights in Sep 2025

10/10 Excellent

John T.

Liked: Cleanliness
Clean and comfortable with great pool and close proximity to Dewey Beach and restaurants.
Stayed 7 nights in Jul 2025

10/10 Excellent

Rick J.

Liked: Cleanliness
great for family vacation at beach.Couple comments:1. Linen package didn’t include one of the beds.2. Description said EV charging cable available upon request. It took some back and forth to get cable, and we were told owner was gonna change the description about cable availability. Personally, I think the charging cable is a selling point. We had two EV’s, and it was a selling point for us.
Stayed 7 nights in Jul 2025

10/10 Excellent

Allison M.

Liked: Cleanliness

Great location! Excellent for families with kids!!

We stayed here with 8 adults and 4 children and everyone had a great time! We loved the proximity to the beach and Rehoboth!! The house was well-maintained and the perfect fit for our group. We would definitely stay here again!!
Stayed 7 nights in Jun 2025

10/10 Excellent

Marilyn S., Beaver Dam

Liked: Cleanliness

Location, location, location!

Fantastic location, walking distance to everything. Property mgr was exceptionally responsive to our needs. Pool was a hit sunce it was so hot and humid. We wete in it twice a day! Bedroooms comfortable and kitchen had all we needed for mesl prep.
Stayed 7 nights in Jun 2025

10/10 Excellent

Patricia D.

Liked: Cleanliness
It was such a wonderful stay with our family. We loved the easy access to downtown Dewey or rehobeth. The pool was such a bonus for two little girls age 4 and 7. The house had anything and everything that we could have imagined. It was nicely decorated as well. Highly recommend!!
Stayed 4 nights in Jun 2025

10/10 Excellent

Dale B., Chambersburg, USA

Liked: Cleanliness

Family Vacation

Calm, peaceful location convenient to many activities. Space met the needs for all ages.
Stayed 7 nights in Sep 2024

10/10 Excellent

Janet K., Huntingdon Valley, Pennsylvania

Liked: Cleanliness

We had a wonderful time!

Thank you for sharing your lovely home with us! We all enjoyed the casual and relaxed spirit of this home. It was clean, well-equipped, spacious, and welcoming. Close to the beach and an adorable farm market with everything we needed. Lovely vacation!!
Stayed 7 nights in Aug 2024

10/10 Excellent

Bridget M.

Liked: Cleanliness

Super

We stay at the beach every summer, first time with a pool. I was surprised at how wonderful it was to have a pool. Fun for the kids in the evening while we made dinner. There was plenty of sleeping space but it didn’t feel crowded. The house was very clean the the kitchen well stocked and the location could not have been better.
Stayed 7 nights in Aug 2024

8/10 Good

Thomas R., New York

Liked: Cleanliness

Lovely & Peaceful!

The home is a perfect blend of beach cozy w/modern day comforts, convenience of location and your own pool! Really Love the location and easy walk to Fifer’s, the beach and into Dewey for lunches and dinners too. The only constructive feedback I’d give is to update the listing to properly reflect the home doesn’t have a Primary Bedroom w/En Suite. None of the five bedrooms has a bathroom directly or privately attached. For this Renter, w/Family and Friends invited, that distinction is very important prior to booking. It felt purposely misleading and having that prior knowledge would certainly help to avoid confusion and any arrival disappointments of future renters. Other than that PR mistake we loved the home. Thank You!
Stayed 7 nights in Jun 2024