Set on the Atlantic Coast, Dewey Beach is a small town with all the charm and beauty of a beach vacation destination. This vibrant city is full of friendly faces, great restaurants, and many attractions to explore. Some of the must-visit destinations include Delaware Seashore State Park, John Waples Memorial Playground and Sunset Park. Travellers flock to Dewey Beach each year for the beautiful sunsets and relaxing atmosphere. The crashing surf lures surfers, parasailers enjoy spectacular vistas as they sail across the waters, anglers cast out in the hope of a deep-sea catch, and party-goers dance until dawn at some of the best beach bars. Dewey Beach rentals are also world-class, offering first-class amenities and luxurious furnishings. If you really want to feel at some during your trip, stay in any of the best vacation rentals with private pool in Dewey Beach, Delaware, listed below.
We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to private pool. The image galleries get refreshed with the latest updates regularly. They were last updated on February 22, 2025.
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1. Luxurious villa minutes away from the beach (from USD 1300)
This luxurious beachside villa sits in the heart of Dewey Beach, Delaware. This massive beachside villa boasts fifteen bedrooms equipped with three beds and a crib. Moreover, the villa has 10 complete bathrooms, all featuring bath essentials. The villa has a fully furnished kitchen and a dining room that can seat 32 people, perfect for family gatherings or weddings.
For relaxation, you will find a heated rooftop pool, two hot tubs, and a golfing area in the garden. The pool can also double up as a hot tub, thanks to the jets. A 24/7 concierge service is available to assist with anything from tours to catering in the villa.
9.47 km (5.9 mi) from Cape Henlopen State ParkAccommodates: 32
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 60 days before check-in.
Top guest reviews
Host:
just have to say that the owner was very kind and made us feel very welcomedgary was a wonderful host and we all very much enjoyed the staythis place worked out great to host our small company's retreatthe owner was attentive and kept the place clean and amenableLocation:
loved the location great farm stand within walking distancethis house was the perfect location to get a 25 person weekend getawaygreat location - 5 houses from the beach and walking distance to restaurants mini golfsuper close to town as well which is a treat 100% walking distance to everythingwe loved the spacious house and location it was perfect for our large groupCleanliness:
was a great time house was beautiful clean and near everything we wanted to doRead more reviewsAmenities & Room:
we loved the great room with the giant table and beautiful kitchen
2. Charming mid-century cottage
Situated just a few blocks from the beach, this spacious five-bedroom cottage is perfect for your next vacation. This newly renovated cottage includes many modern amenities such as an outdoor heated pool that is open between April to November.
There’s an outside shower to clean up after a beach excursion equipped with a washboard sink and sprayer station. The property also features outdoor lounge chairs and dining table. The front of the home boasts a spacious deck with potted plants.
9.34 km (5.8 mi) from Cape Henlopen State ParkAccommodates: 13
Minimum Nights: 2
Refund Policy :
Top guest reviews
Host:
the owner is very responsive and easy to work withlyn was very responsivethe host was extremely responsive answering every question we asked usually in just a few minuteswould definitely recommend lyn was very responsive and a great hostthe owners lyn and brett are great to work with and couldn’t be more accommodatingLocation:
everything was easy and location was very convenientit was an excellent location close to the beach and many restaurantsthe house was so cute and walking distance to just about anywhere you would want to goCleanliness:
the property was clean upon arrival and had many personal touches that made it feel cozythe house is charming (my kids loved all the little design details) exceptionally clean and very well stockedthis property is perfect exceptionally clean beautifully decorated lovely patio with fenced yard and a great locationthe house is perfect for the beach - clean cool and a one block walk to the beachRead more reviewsAmenities & Room:
the pool in the backyard was perfect with all the kidsthe backyard and pool were the real highlight of our staymodernized kitchen is great for cooking
3. Plush luxury home close to Lake Comegy (from USD 893)
Slip into a state of relaxed elegance with this gorgeous eight-bedroom villa. This property is breathtakingly beautiful featuring rich greenery and offering a relaxing getaway for a large group. The outdoor living space is equipped with an in-ground pool that is open from early Spring through late Autumn. The pool can be heated on request. The outdoor space also boasts fountains and a lush garden.
Inside, the airy contemporary living space has high ceilings, wooden flooring, and a floor-to-ceiling door made of glass that leads to a screened porch with views of the in-ground pool and Lake Comegy, which is just across the street.
Dewey Beach, DE, US
4. Newly built luxurious villa with a hot tub and a rooftop deck (from USD 1071)
This incredible five-bedroom four-bathroom rental features a rooftop deck and a stunning private pool on a fenced patio. Guests get to enjoy expansive beach and ocean views from the comfort of their own rooftop. This recently built house comfortably accommodates 17 people. The rental also has a fully equipped kitchen for preparing homemade meals, a well-appointed living area, and a dining area.
10.32 km (6.5 mi) from Cape Henlopen State ParkAccommodates: 17
Minimum Nights: 7
Refund Policy :
Top guest reviews
Host:
the owner was helpful when i spoke to her by phoneLocation:
great location with plenty of restaurants and shops close byeasy walk to beach restaurants and playgroundalso really nice park right across the streetrehobeth was close enough to go back-and-forth for great shopping and diningvery nice house with prime location to the beach and other parts of dewey beachCleanliness:
very clean and well stockedthe home was clean when we arrivedthe grill was pretty gross - looked like it hadn't been cleaned in quite a whilethis home was very clean not to mention plenty of bathrooms and showersthis was an excellent property absolutely beautiful and very cleanRead more reviewsAmenities & Room:
hot tub wonderful pool nice but not heated and coldthe kids loved the pool and the decks are very nice with gorgeous sunset views over the bayenjoyable pool hot tub large kitchen and dining tableit was so nice having a pool
5. Beautifully decorated luxury home
This luxurious beachside home, just a few minutes of walk away from Dewey Beach, comes with a stunning enclosed pool ideal for cooling off during hot days. The private pool is open between the months of June and September. The property has a well-furnished kitchen, a comfortable living area with a swing, an enclosed outdoor hot tub, and an outdoor shower. The front and back porches are perfect for relaxing after a day at the beach.
Dewey Beach, Delaware, United States
9.52 km (6.0 mi) from Cape Henlopen State ParkAccommodates: 14
Top guest reviews
Host:
dawn’s place is amazing and she was the perfect host in every waydawn is an amazingly responsive host and lovely to deal withthank you dawn for everything- you are a wonderful hostdawn was attentive to our needs and promptly communicated with us and made sure our stay was perfectdawn is a great host and we would definitely come back againRead more reviewsLocation:
location is also perfectlocation was ideal for daily lounging on dewey beachit is close to the beach with easy access to restaurants and storesthe house is in a perfect locationit is a quick 4 minute walk to the beautiful beach
Escape to Dewey Beach
Staying in vacation rentals with a private pool is a one-of-a-kind experience. You will get to enjoy unlimited time in the pool having fun or just keeping cool in the summer heat. Plan your next vacation to Dewey Beach and stay in one of the best rentals with a pool, here.
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