6 Best Vacation Rentals With Private Pool In Dewey Beach, Delaware - Updated 2024

| 3 min read

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 April 12, 2024.

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.

Stayed at this property?

9.47 km (5.9 mi) from Cape Henlopen State Park
81 reviews   Wifi Available
villa 32 Guests 15 Bedrooms 10 Bathrooms

Accommodates: 32
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
we loved the great room with the giant table and beautiful kitchen
was a great time house was beautiful clean and near everything we wanted to do
just have to say that the owner was very kind and made us feel very welcomed
gary was a wonderful host and we all very much enjoyed the stay
this place worked out great to host our small company's retreat
the owner was attentive and kept the place clean and amenable
loved the location great farm stand within walking distance
this house was the perfect location to get a 25 person weekend getaway
great location - 5 houses from the beach and walking distance to restaurants mini golf
super close to town as well which is a treat 100% walking distance to everything
we loved the spacious house and location it was perfect for our large group
Read more reviews
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2. Charming mid-century cottage (from USD 875)

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.

Stayed at this property?

9.34 km (5.8 mi) from Cape Henlopen State Park
70 reviews   Wifi Available
House 13 Guests 5 Bedrooms 3 Bathrooms

Accommodates: 13
Minimum Nights: 2
Refund Policy :

Top guest reviews
Amenities & Room:
the pool in the backyard was perfect with all the kids
the backyard and pool were the real highlight of our stay
modernized kitchen is great for cooking
the property was clean upon arrival and had many personal touches that made it feel cozy
the house is charming (my kids loved all the little design details) exceptionally clean and very well stocked
this property is perfect exceptionally clean beautifully decorated lovely patio with fenced yard and a great location
the house is perfect for the beach - clean cool and a one block walk to the beach
the owner is very responsive and easy to work with
lyn was very responsive
the host was extremely responsive answering every question we asked usually in just a few minutes
would definitely recommend lyn was very responsive and a great host
the owners lyn and brett are great to work with and couldn’t be more accommodating
everything was easy and location was very convenient
it was an excellent location close to the beach and many restaurants
the house was so cute and walking distance to just about anywhere you would want to go
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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.

Stayed at this property?
Dewey Beach, DE, US
18 Guests 8 Bedrooms 6 Bathrooms
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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.

Stayed at this property?

10.32 km (6.5 mi) from Cape Henlopen State Park
14 reviews   Wifi Available
House 17 Guests 5 Bedrooms 4 Bathrooms

Accommodates: 17
Minimum Nights: 7
Refund Policy :

Top guest reviews
Amenities & Room:
hot tub wonderful pool nice but not heated and cold
the kids loved the pool and the decks are very nice with gorgeous sunset views over the bay
enjoyable pool hot tub large kitchen and dining table
it was so nice having a pool
very clean and well stocked
the home was clean when we arrived
the grill was pretty gross - looked like it hadn't been cleaned in quite a while
this home was very clean not to mention plenty of bathrooms and showers
this was an excellent property absolutely beautiful and very clean
the owner was helpful when i spoke to her by phone
great location with plenty of restaurants and shops close by
easy walk to beach restaurants and playground
also really nice park right across the street
rehobeth was close enough to go back-and-forth for great shopping and dining
very nice house with prime location to the beach and other parts of dewey beach
Read more reviews
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5. Beautifully decorated luxury home (from USD 2164)

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.

Stayed at this property?
Dewey Beach, Delaware, United States
9.52 km (6.0 mi) from Cape Henlopen State Park
23 reviews   Wifi Available
ENTIRE HOME 6 Beds 14 Guests 6 Bedrooms 6 Bathrooms

Accommodates: 14

Top guest reviews
dawn’s place is amazing and she was the perfect host in every way
dawn is an amazingly responsive host and lovely to deal with
thank you dawn for everything- you are a wonderful host
dawn was attentive to our needs and promptly communicated with us and made sure our stay was perfect
dawn is a great host and we would definitely come back again
location is also perfect
location was ideal for daily lounging on dewey beach
it is close to the beach with easy access to restaurants and stores
the house is in a perfect location
it is a quick 4 minute walk to the beautiful beach
Read more reviews

6. Pet-friendly cottage with a heated pool

This classic cottage boasts bright colours and modern furnishings that will make you feel at home. It boasts three bedrooms, two with king-size beds and each with its own en-suite bath. The third bedroom comes with a queen-size bed fitted with luxurious linens. The enclosed backyard with an outdoor dining space and an in-ground pool is ideal for family bonding activities. The pool features a small cascade and can be heated for a fee.

Stayed at this property?

9.2 km (5.8 mi) from Cape Henlopen State Park
7 reviews   Wifi Available
House 6 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 6
Minimum Nights: 3
Refund Policy :

Top guest reviews
the property manager was extremely helpful when we needed to call them
great location with close beach access and beautiful pool area
enjoyed the close proximity to the lake & the ocean
charming cozy cottage fantastic location beautiful pool and surroundings
Read more reviews
Oops, this listing is currently inactive. Check out these alternative properties in the same location.
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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.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.


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Hannah an avid traveller who enjoys research, writing and making presentations. She has a passion for graphics design and photography. Learning new things is her daily goal.

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