10 Best Vacation Rentals With Private Pool In Delaware, USA

Heyleena
Heyleena 
Updated

Escape the daily grind and rejoice with your family for an intimate holiday in some of the best places in Delaware, where you can relax in the coastal hamlets of Bethany Beach, Lewes Beach, or Rehoboth Beach, close to white sand beaches. You can spend a wonderful family reunion or celebrate a birthday with friends here in your preferred vacation rental, outfitted with a private pool. Unwind with refreshing cocktail glasses at the pool, or explore colonial villages, museums, like Hagley Museum and Library and Winterthur Museum, Garden and Library, rustic countryside, and bustling towns when holidaying in Delaware. After a long, tiring day exploring the neighborhood, ensconce yourself comfortably in a swanky bedroom, where you can enjoy a good night slumber. For an epic holiday, read on for our list of the best vacation rentals with private pool in Delaware, USA.

1. Swanky family house with a private pool in Fenwick Island (from USD 775)

For the ultimate luxury stay, choose this swanky family house, nestled close to the beach. Right in a quiet neighborhood, this five-bedroom house is perfect for discerning guests who are looking for comfort and a luxury interior. Styled with whitewashed walls, rustic hardwood floors, and sleek furniture, every little corner of this property has been aesthetically designed.

Apart from its beautiful interior, this bolthole has a stunning master bedroom which has extra closets, a heated floor, and a bespoke shower. Other amenities to consider are the private covered balcony, gas grill, private pool, and sunroom, where you can chat over a cup of coffee.

Congratulations! You have found one of the Best Vacation Homes in Fenwick
51 reviews  Wifi Available
House 12 Guests 5 Bedrooms 6 Bathrooms

Accommodates: 12
Minimum Nights: 4
Refund Policy :

Top guest reviews
Amenities & Room:
this property is fantastic from head to toe every room is impeccably decorated it's bright and homey
it is so spacious and comfortably fit 10 people with room to spare
Cleanliness:
clean and comfortable beds
house was clean and had easy parking
the house is neat clean and has an upscale decor
the house was clean and the linen service was a nice plus
Host:
owner is responsive and available
the owner is particular about keeping the house in great shape and i appreciate that
frank- the owner- was easy to get ahold of with any questions
frank was very helpful and always quick to respond
Location:
very easy walk to the beach
very spacious great location within a block of the beach
beautiful place to stay for family
Read more reviews

2. Large guesthouse with an outdoor swimming pool in Dewey Beach (from USD 375)

If you are planning for a big family reunion, then this large guesthouse might just be your best bet. Located close to the beach in a quiet neighborhood, this deluxe property can cater up to 20 people thanks, to the 6 spacious bedrooms and 2 large living areas.

With total privacy, spend quality time with your loved ones in the inviting swimming pool. Other amenities to consider when booking this place are the hot tub, fully equipped kitchen, stylish bedrooms, and immaculate bathrooms.

Dodd House - Pool/Hot Tub, pet friendly, isolate in style if you choose!
42 reviews  Wifi Available
House 24 Guests 6 Bedrooms 6 Bathrooms

Accommodates: 24
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Amenities & Room:
there were board games and a great living room space
we were a huge group of 21 and we had enough room for everyone
the house is massive and easily accommodated all 15 of us with plenty of room to spare
the pool and hot tub made it easy for us to stay safe during the pandemic
the outside area was absolutely superb with the pool hot tub and bar area with surrounding music speakers
Cleanliness:
house was professionally cleaned and all fresh linens and towels and the house was in immaculate condition
the place was extremely clean with having all linens towels and kitchen items available that we needed
the place is clean spacious fun and the pool area is a blast for families
the backyard is beautiful and the home is spacious and sparkling clean
Host:
the owners were very responsive though to solving issues
the owners were very friendly and responsive to any questions or issues that came up
owners are very responsive and excellent to work with
the hosts are very responsive and a pleasure to work with
first the hosts lynn and brian were extremely welcoming and inviting into their home
Location:
3 blocks from the beach the location was great and bike friendly town
i love this house and location
the house is fantastic and it’s a great location
enjoyed our stay - great for groups we enjoyed the pool and close proximity to the beach
overall we had a great time and the house is in a great location
Read more reviews

3. Luxurious house with a heated pool in Bethany Beach (from USD 1506)

Located close to Bethany Beach and the gated community of Gulls Nest, this luxurious house is second to none when it comes to amenities. Outfitted with eight well-appointed bedrooms, including master suites with balconies and full private bathrooms, this property is ideal for a large family holiday in Delaware.

Its best features consist of a heated private pool, a gourmet kitchen, and a game room, which has billiard and foosball tables. The best part of staying here is the free access to thrilling outdoor activities such as paddleboarding, golfing, wine tasting, yoga, and playing in water parks.

Spectacular 8BR w/Elevator! Sleeps 16 w/Heated Pool, Elevator, 1 House to Ocean w/ Free Activities
35 reviews
House 16 Guests 8 Bedrooms 8 Bathrooms

Accommodates: 16
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
the kitchen is well-stocked with nice cooking equipment and incidentals
the beds were comfortable and the kitchen very well supplied only a crockpot was not available
our favorite spot was probably the heated pool for the adults and the pool table for the children
Cleanliness:
the house has 8 nice sized bedrooms all of which are clean and comfortable
the beach is just steps away and is clean and beautiful
Host:
the people in neighboring houses were so friendly we had many community games of soccer and volleyball
kitchen was well equipped and was very helpful since we cooked all of our meals there
bethany is a beautiful town as well quiet and family friendly
Location:
nice location great house for large groups
the location is great and beach is not crowded
it is easy to walk in and cook for a family of 18 without difficulty
Read more reviews

4. Six-bedroom house in a secluded area in Rehoboth Beach (from USD 289)

Tucked away from the bustling downtown, this six-bedroom house is in a secluded area. Its six bedrooms are styled in pastel colors, exuding a cozy vibe. Some of its features include a kitchen with a large pantry and a living area fitted with comfy upholstered sofas.

One of the best places to unwind in summer is the pool area, which has a small patio to sunbathe on. The pool is designed in a unique circular design. Check out the cozy fire pit area, where guests can enjoy quality time together.

Lots Of Room--Main House And Cottage With Pool (Sleeps 12)
46 reviews  Wifi Available
House 12 Guests 6 Bedrooms 4 Bathrooms

Accommodates: 12
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
we enjoyed the comfortable living room for movie watching nights and played cards at the dining room table
our group of 14 plus two small children really enjoyed this house and pool
there was plenty of space for everyone to feel comfortable
Cleanliness:
everything was very clean and very spacious
the pool was very clean and everyone thoroughly enjoyed it
very clean and location is nice and peaceful
they are spotless good quality and not too expensive
the swimming pool is large and clean and the patio is large as well
Host:
owner was great in addressing our questions and needs
jim was a great host with and very helpful
home was clean and owner was responsive
Location:
the location and pool were ideal for us given covid
the house was the perfect place to stay while we celebrated my friend's birthday week
Read more reviews

5. Quaint cottage with saltwater pool in Dewey Beach (from USD 712)

For your vacation, bring your family to spend some fun time in this quaint cottage, located not too far from Jolly Trolley. The property is composed of five spacious bedrooms, a gourmet kitchen, and a living room, awash with natural light. The interior has a great combination of vintage charm and sleek contemporary decor. Some of its key highlights are the saltwater pool and fire pit area - ideal places to hang out with your loved ones.

NEWLY LISTED, character, charm & fully renovated, pet friendly.
40 reviews  Wifi Available
House 14 Guests 5 Bedrooms 4 Bathrooms

Accommodates: 14
Minimum Nights: 3
Refund Policy :

Top guest reviews
Amenities & Room:
the pool was heated and warm which was great as the weather was a little cool
Cleanliness:
house itself is modern clean and spacious
every bit of the the house was perfectly clean and inviting
open floor plan completely updated beautiful decor comfy beds extremely clean and a relaxing pool
Host:
lyn was perfect host
owner was very helpful before and during the trip
very comfy and lots of seating options - clearly it could host a much bigger family than ours
communication with the property manager was timely helpful and thorough
thanks so much lynn for being an amazing and very communicative host
Location:
the location is great too
convenient to all the beach attractions water sports biking trails shopping fishing boating cape henlopen park etc
great location and responsive hosts
location was perfect easy walk to the beach and quick drive into town
quiet street in the beautiful and unique rehoboth by the sea neighborhood
Read more reviews

6. Deluxe house with a gorgeous sunroom in Bethany Beach (from USD 486)

Nestled in the tranquil neighborhood of Bethany Beach, this deluxe guest house beckons weary souls to rejuvenate in a private setting. The best part of this property is no doubt the gorgeous sunroom, an ideal place to unwind with family after lunch. Just nearby is the pool area, equipped with sun loungers, where you can spend a fun time, with some refreshing cocktail drinks.

Another unit that you can’t miss is the sleek living area, kitted out with a rattan sofa and a fireplace. Whipped up some scrumptious dishes at the fully equipped kitchen, which consists of gorgeous granite counters, cabinets, electronic appliances, and utensils.

Tropical Beach House With In-Ground Pool
41 reviews  Wifi Available
House 9 Guests 3 Bedrooms 4 Bathrooms

Accommodates: 9
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Cleanliness:
very clean nice and plenty of relaxing areas
nice property very clean we spent a lot of time in the sunroom
property was in fabulous location extremely clean great home amazing pool etc
Host:
carol and bob were very helpful with any questions we had
owners are great they delivered us extra blankets hope to visit another time
carol was fantastic and attentive host
the owner is very responsive and we can easily recommend staying here for couples and families
we can't think of a single suggestion to the owners for making it better
Location:
close enough to everything but far enough away to relax
the location is in an upscale quiet neighborhood in easy driving distance to the beaches
beautiful house & location on the bay great for walking & biking
lovely neighborhood for bike rides and walks
a great quiet neighborhood for morning walks and relaxing by the pool
Read more reviews

7. Upscale guesthouse with a gorgeous deck in Rehoboth Beach (from USD 750)

Discerning guests will want to bed down in this upscale guesthouse, situated close to the beach and Rehoboth Avenue. Apart from its convenient location, the property elevates your vacation experience through its quality amenities and stunning interior.

Styled with a lavish look (think modern furnishings, sleek hardwood floor, and contemporary pendant lamps), every little corner of the place has been carefully designed to meet expectations. Its key features are the beautiful deck, where guests can kick off their shoes and relax, and, just beside it, the private outdoor pool, where the whole family can have fun.

2 1/2 Blocks to Beach, Saltwater Pool.
49 reviews  Wifi Available
House 10 Guests 4 Bedrooms 4 Bathrooms

Accommodates: 10
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

8. Five-bedroom house with a private pool in Bethany Beach (from USD 399)

If you’re looking for an amazing swimming pool surrounded by lofty green trees, then this five-bedroom house is a good option to consider. Spend your summer vacation unwinding at the pool area with a glass of mojito and enjoy sunbathing on the comfy sun loungers in all privacy with your family.

The property has five spacious bedrooms, perfect for a large family with children. The interior of the house is immaculate and modern. Some of the facilities consist of a fully stocked kitchen, a large living room, clean bathrooms equipped with bathing products, and a large backyard for children to play. Nearby attractions include the beach and the Indian River Inlet.

Fall Rates Family home sleeps 12 , 1.5 Miles from Town and Beaches
50 reviews  Wifi Available
House 12 Guests 5 Bedrooms 4 Bathrooms

Accommodates: 12
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
many things are well past their time like the coffee maker carpets and bedding
having the downstairs kitchen was great too
Cleanliness:
the house is clean and spacious
it is very dated and could use an extra deep clean
it’s spacious and clean
Host:
lovely hosts as well
)the owner was very helpful
john and alex were great host
owners were a pleasure to work with
house is very well maintained and the owners were super responsive and organized
Location:
great location nice bike ride to beach very close to town shopping and restaurants
the house is in a great location
great location with great outdoor space
plenty of space with a comfortable layout the pool is wonderful and the location is convenient to everything
Read more reviews

9. Quaint house with backyard in Bethany Beach (from USD 489)

Families looking for a quiet neighborhood in Delaware will find this quaint house with five bedrooms one of the best options for a family holiday. With total seclusion and privacy, you can rejuvenate in this relaxing sanctuary without being disturbed. Its amenities, such as the inviting swimming pool, include features that you would not want to miss.

Whether you wish to sunbathe or read a good magazine on the comfy sun loungers, the poolside is ideal. The backyard is another feature that you while appreciate when you book this place. Other facilities include the large, open kitchen, the dining room, and the living area.

Private Salt-Water Pool-Close to Ocean!Kayaks provided-Crabbing Dock-sleeps 14+
51 reviews  Wifi Available
House 14 Guests 5 Bedrooms 4 Bathrooms

Accommodates: 14
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
house and pool were perfect for our multi-generational family stay
Cleanliness:
very clean and comfortable with plenty of room for the 10 of us
we had a very relaxing stay at this spacious and clean home
the house was clean spacious and the location was great
Host:
owner is also accommodating and responsive to requests
the owner is very responsive and friendly
host was always available and very helpful
owner is on site but unobtrusive and respectful of privacy
Location:
great property in a great location made a lot of family memories
house was in a good location easy to get to the beach
we would recommend to others looking for a place close to the beach
great place to enjoy and get away
location in quiet nice neighborhood and within easy drive from everything you need owner was helpful and responsive
Read more reviews

10. Mid-century cottage with an enchanting outdoor area in Dewey Beach (from USD 600)

Relax in an enchanting outdoor area, kitted out with an inviting swimming pool, when staying in this mid-century cottage. This place is one of the most recommended homes to bed down when it comes to luxury interior, privacy, and comfort. Surrounded by luxuriant trees, wake up to the soothing songs of birds in the morning when staying in this property.

The cottage is composed of five swanky bedrooms, equipped with comfy beds and crisp linens. Make delicious breakfasts in the modern kitchen and relax on the large deck area, studded with beautiful pots of flowers. There is even a porch swing to relax in the afternoon. Additionally, a large car parking area is available.

Charming, 5BR, heated pool, firepit, pet friendly.
66 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
Cleanliness:
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
Host:
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
Location:
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
Read more reviews

Spend an intimate vacation in Delaware

Whether you wish to bond with loved ones or plan a private event for this summer holiday, Delaware offers a wonderful setting. For a refreshing stay, consider our list of the best vacation rentals with private pool in Delaware, USA, mentioned above.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Heyleena is a passionate Mauritian blogger who enjoys writing outdoor adventure and travel articles for people who seek to explore new places in a more conscious way. She has spent a year among the...Read more

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