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.
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 March 13, 2023.
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.
Top guest reviews
Amenities & Room:
this property is fantastic from head to toe every room is impeccably decorated it's bright and homeyit is so spacious and comfortably fit 10 people with room to spareCleanliness:
clean and comfortable bedshouse was clean and had easy parkingthe house is neat clean and has an upscale decorthe house was clean and the linen service was a nice plusHost:
owner is responsive and availablethe owner is particular about keeping the house in great shape and i appreciate thatfrank- the owner- was easy to get ahold of with any questionsfrank was very helpful and always quick to respondRead more reviewsLocation:
very easy walk to the beachvery spacious great location within a block of the beachbeautiful place to stay for family
2. Large guesthouse with an outdoor swimming pool in Dewey Beach (from USD 781)
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.
Top guest reviews
Amenities & Room:
there were board games and a great living room spacewe were a huge group of 21 and we had enough room for everyonethe house is massive and easily accommodated all 15 of us with plenty of room to sparethe pool and hot tub made it easy for us to stay safe during the pandemicthe outside area was absolutely superb with the pool hot tub and bar area with surrounding music speakersCleanliness:
house was professionally cleaned and all fresh linens and towels and the house was in immaculate conditionthe place was extremely clean with having all linens towels and kitchen items available that we neededthe place is clean spacious fun and the pool area is a blast for familiesthe backyard is beautiful and the home is spacious and sparkling cleanHost:
the owners were very responsive though to solving issuesthe owners were very friendly and responsive to any questions or issues that came upowners are very responsive and excellent to work withthe hosts are very responsive and a pleasure to work withfirst the hosts lynn and brian were extremely welcoming and inviting into their homeRead more reviewsLocation:
3 blocks from the beach the location was great and bike friendly towni love this house and locationthe house is fantastic and it’s a great locationenjoyed our stay - great for groups we enjoyed the pool and close proximity to the beachoverall we had a great time and the house is in a great location
3. Luxurious house with a heated pool in Bethany Beach (from USD 2506)
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.
Top guest reviews
Amenities & Room:
the kitchen is well-stocked with nice cooking equipment and incidentalsthe beds were comfortable and the kitchen very well supplied only a crockpot was not availableour favorite spot was probably the heated pool for the adults and the pool table for the childrenCleanliness:
the house has 8 nice sized bedrooms all of which are clean and comfortablethe beach is just steps away and is clean and beautifulHost:
the people in neighboring houses were so friendly we had many community games of soccer and volleyballkitchen was well equipped and was very helpful since we cooked all of our meals therebethany is a beautiful town as well quiet and family friendlyRead more reviewsLocation:
nice location great house for large groupsthe location is great and beach is not crowdedit is easy to walk in and cook for a family of 18 without difficulty
4. Six-bedroom house in a secluded area in Rehoboth Beach (from USD 435)
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.
Top guest reviews
Amenities & Room:
we enjoyed the comfortable living room for movie watching nights and played cards at the dining room tableour group of 14 plus two small children really enjoyed this house and poolthere was plenty of space for everyone to feel comfortableCleanliness:
everything was very clean and very spaciousthe pool was very clean and everyone thoroughly enjoyed itvery clean and location is nice and peacefulthey are spotless good quality and not too expensivethe swimming pool is large and clean and the patio is large as wellHost:
owner was great in addressing our questions and needsjim was a great host with and very helpfulhome was clean and owner was responsiveRead more reviewsLocation:
the location and pool were ideal for us given covidthe house was the perfect place to stay while we celebrated my friend's birthday week
5. Quaint cottage with saltwater pool in Dewey Beach (from USD 898)
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.
Top guest reviews
Amenities & Room:
the pool was heated and warm which was great as the weather was a little coolCleanliness:
house itself is modern clean and spaciousevery bit of the the house was perfectly clean and invitingopen floor plan completely updated beautiful decor comfy beds extremely clean and a relaxing poolHost:
lyn was perfect hostowner was very helpful before and during the tripvery comfy and lots of seating options - clearly it could host a much bigger family than ourscommunication with the property manager was timely helpful and thoroughthanks so much lynn for being an amazing and very communicative hostRead more reviewsLocation:
the location is great tooconvenient to all the beach attractions water sports biking trails shopping fishing boating cape henlopen park etcgreat location and responsive hostslocation was perfect easy walk to the beach and quick drive into townquiet street in the beautiful and unique rehoboth by the sea neighborhood
6. Deluxe house with a gorgeous sunroom in Bethany Beach (from USD 457)
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.
Top guest reviews
Cleanliness:
very clean nice and plenty of relaxing areasnice property very clean we spent a lot of time in the sunroomproperty was in fabulous location extremely clean great home amazing pool etcHost:
carol and bob were very helpful with any questions we hadowners are great they delivered us extra blankets hope to visit another timecarol was fantastic and attentive hostthe owner is very responsive and we can easily recommend staying here for couples and familieswe can't think of a single suggestion to the owners for making it betterRead more reviewsLocation:
close enough to everything but far enough away to relaxthe location is in an upscale quiet neighborhood in easy driving distance to the beachesbeautiful house & location on the bay great for walking & bikinglovely neighborhood for bike rides and walksa great quiet neighborhood for morning walks and relaxing by the pool
7. 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.
Top guest reviews
Amenities & Room:
house and pool were perfect for our multi-generational family stayCleanliness:
very clean and comfortable with plenty of room for the 10 of uswe had a very relaxing stay at this spacious and clean homethe house was clean spacious and the location was greatHost:
owner is also accommodating and responsive to requeststhe owner is very responsive and friendlyhost was always available and very helpfulowner is on site but unobtrusive and respectful of privacyRead more reviewsLocation:
great property in a great location made a lot of family memorieshouse was in a good location easy to get to the beachwe would recommend to others looking for a place close to the beachgreat place to enjoy and get awaylocation in quiet nice neighborhood and within easy drive from everything you need owner was helpful and responsive
8. Mid-century cottage with an enchanting outdoor area in Dewey Beach (from USD 875)
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.
Top guest reviews
Amenities & 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 cookingCleanliness:
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 beachHost:
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 accommodatingRead more reviewsLocation:
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 go
9. Five-bedroom house with a private pool in Bethany Beach
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.
2.91 km (1.9 mi) from Bethany Beach BoardwalkAccommodates: 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 beddinghaving the downstairs kitchen was great tooCleanliness:
the house is clean and spaciousit is very dated and could use an extra deep cleanit’s spacious and cleanHost:
lovely hosts as well)the owner was very helpfuljohn and alex were great hostowners were a pleasure to work withhouse is very well maintained and the owners were super responsive and organizedRead more reviewsLocation:
great location nice bike ride to beach very close to town shopping and restaurantsthe house is in a great locationgreat location with great outdoor spaceplenty of space with a comfortable layout the pool is wonderful and the location is convenient to everything
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.
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