10 Best Vacation Rentals With Private Pool In Kailua, Hawaii - Updated 2024

Alyssandra Raiza
Alyssandra Raiza 
Updated
| 5 min read

Located about 19.3 km (12 mi) from Honolulu, Kailua is an idyllic coastal town on the island of Oʻahu. It is known for its sandy beaches, turquoise waters, and stunning marine life. Kailua boasts a laid-back vibe, perfect for those seeking a respite from city life. Its two beaches, Lanikai and Kailua, each offer picture-perfect views as well as opportunities to go kayaking, swimming, and diving. Besides its stunning shores, there is plenty to see and enjoy right within the town. A selection of local stores, restaurants, and even dive shops where you can get supplies are all easily accessible. Eager to plan your next getaway to this tropical paradise? We can help you find your ideal abode. Read on to see our pick of the best vacation rentals with private pool in Kailua, Hawaii.

We handpicked these listings carefully, considering (wherever possible) Superhost status. recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on February 09, 2024.

1. Family-friendly house with a private lanai (from USD 1123)

With enough space to accommodate 10 guests, you can bring the entire family to this lovely house for some fun in the sun. If you’re traveling with children, they’re sure to love the boogie boards and pool toys available for use. The house also features a walkway leading directly to the shore. You can hit the beach and swim, dive, windsurf, and play to your heart’s content.

On days you feel like staying indoors, you can spend some “me” time on the private courtyard lanai with your favorite beverage in hand, take a relaxing dip in the solar-heated pool, or luxuriate in the separate spa whirlpool. The swimming pool also comes with an automatic safety cover, which is a nice touch that keeps everyone protected.

Stayed at this property?
39 reviews   Wifi Available
House 10 Guests 5 Bedrooms 4 Bathrooms

Accommodates: 10
Minimum Nights: 30
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
the highlight of the property is its outdoor living space and especially its swimming pool
ac kept us cool and comfortable during the hot summer weather
the kids just adored the pool and spent hours in it every day
Cleanliness:
clean and well kept
the house is dated but clean great size and very comfortable for a large family
can't say the property was clean
Host:
the property care taker was also on site in the adjacent property frequently
Location:
the location and living space was ideal
amazing location on a beautiful beach
great location property well equipped
unbeatable location—maybe 75 yards sandy walkway to the beautiful beach; big private pool for family fun
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2. Kailua Bliss Beach House (from USD 2500)

This chic beach house is ideal for a friends’ reunion or family getaway, as it can easily host as many as 10 guests. Families with young kids will also find this house baby-friendly, with childcare essentials available on site, such as a pack-and-play, a baby gate, and an infant bathtub.

Guests staying here can easily walk to the beach for a day in the sun. However, days spent at the beach house are sure to be just as fun-filled. Kids can stay entertained in the game room. Almost every room in the house also comes with a flat-screen TV with access to cable and streaming services. There’s also a large outdoor pool surrounded by chaise lounge chairs, a perfect spot for lazing. Pool toys are available for kids, and fencing can be done for added safety.

Stayed at this property?
27 reviews   Wifi Available
House 10 Guests 4 Bedrooms 4 Bathrooms

Accommodates: 10
Minimum Nights: 14
Refund Policy :

Top guest reviews
Amenities & Room:
bedroom a/c units were quiet and efficient
great cross breeze comes through - sleeping: very comfortable beds with quality linens pillows
the outdoor space is awesome including the private walled-in pool and fire-pit patio
the beds were very comfortable with high quality pillows and bedding
the trade winds blow nicely through the house keeping it cool and comfortable
Cleanliness:
the pool is great and the home was spotless and well organized
the amazing kailua beach house is clean comfortable spacious and has everything you could need and thensome
Host:
the vacation / the home / the owner are all fantastic and as advertised in the pictures
sasha exceeded our expectations she was very responsive and great to work with
misty the property manager was fantastic responsive to all our needs
Location:
-location: great location to grocery stores drugstores banks coffee shops shopping restaurants etc
we loved the pool and only a short walk to the beach
an incredible place to relax on your vacation
the beach path is a few moment's walk to the most amazing stretch of oceanfront we've ever experienced
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3. Newly remodeled house with an outdoor shower (from USD 750)

This bright and beautiful house feels as good as new, having recently been remodeled. Up to eight guests are welcome to stay here, with plenty of comforts to help them feel at ease. Each of the four bedrooms is fitted with a plush bed and air conditioning or fan to keep guests feeling cool. The kitchen and dining areas are spacious and well-equipped so that guests can prepare and enjoy meals together.

After a day at the beach, which is just a three-minute walk from the property, guests can rinse off in the outdoor shower. The yard and outdoor pool are enclosed and private. There is also a heated spa whirlpool, where guests can soak and unwind.

Stayed at this property?
75 reviews   Wifi Available
House 8 Guests 4 Bedrooms 3 Bathrooms

Accommodates: 8
Minimum Nights: 30
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
my 82 year old father even enjoyed doing laps in the pool
inside we enjoyed the cool air conditioning comfortable beds and the clean and fully stocked kitchen
very comfortable for the 7 of us and close to shops restaurants grocery store etc
Cleanliness:
pool clean and maintained
warm clean water and sand
the pool was very clean and the grounds well kept
this home made our stay in kailua so wonderful it was spacious clean and comfortable
Host:
everyone we interacted with was pleasant and helpful
john the property manager was very helpful and responsive and the house was very clean
Location:
great location in kailua 5-10 minute walk to beach
great location close to the beach
the property location was amazing
the house is in a great location: very quiet but near everything
unsurpassable location best stocked rental house we’ve ever had
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4. Well-furnished house with a garden (from USD 575)

If you want to be real close to the beach, this house is just a minute’s walk away from it. With three bedrooms and three bathrooms, this house can easily host up to six people. When hunger pangs strike, whip up something delectable in the fully equipped kitchen or make use of the barbecue grill and enjoy it in the dining area or on the furnished patio outside.

You can also enjoy your morning cuppa in your private garden after a swim in the outdoor pool, which is kept clean throughout the year.

Stayed at this property?
Kailua, Hawaii, United States
27 reviews   Superhost Wifi Available
ENTIRE HOME 4 Beds 6 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
the garden space in the backyard is deceptively large and the pool and grill are great features
Cleanliness:
the beach was clean and quite and not crowded at all
clean quiet nice pool close to the beach and fully equipped kitchen
Host:
the host was very helpful and considering
check in and out were easy as there was not much interaction with the host
the host responded very quickly to inquiries and we would definitely work with her again
we even hosted our local family for a nye dinner party of 10 people in the yard
Location:
great place and location for a family
great location by the beach
great place and a great location
perfect location and very nice house to live in
super close to the beach and kailua is not a far drive
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5. Lakefront house with a spacious deck (from USD 585)

Overlooking the Ka'elepulu Pond, this lovely three-bedroom house can comfortably accommodate six guests. As you enter the property, you’ll immediately notice the open-plan layout. Lots of natural light, modern kitchen appliances, and a full sofa make the space feel spacious and inviting. Each of the bedrooms comes with an air conditioning unit and a closet for your convenience.

At the back of the property, you’ll find the beautiful infinity pool, offering clear views of the lake as you swim. There’s also a deck with seating for eating outdoors and lounging.

Stayed at this property?
Kailua, Hawaii, United States
125 reviews   Superhost Wifi Available
ENTIRE HOME 5 Beds 8 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
the pool and the deck are fantastic
amazing how breezy and windy no air conditioning used or needed for the week
the view was good the home in good condition and it had a/c in all the rooms
the view is beautiful and we had plenty of room for 6 of us
the home was nice and the pool and deck space were very nice to have
Cleanliness:
everything was great very spacious great location and very clean
Host:
the host was amazing & very easy to communicate with
hosts are very attentive and responsive
jessica is kind and very responsive and quick to reply to questions or issues & offer help
jessica is a very gracious and attentive host
jessica was very responsive when we contacted her
Location:
the house is located in a good location
good location near kailua town and 7min drive to the beach
close to town close to the beaches and pretty quiet
this place is in a very good location in kailua
it’s a beautiful location that captures the sunrise perfectly
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6. Stylish house with a covered patio (from USD 252)

This newly renovated family house boasts an open and warm atmosphere that reflects the best of Hawaii. It has clean white interiors and large windows that welcome bags of natural light. The kitchen has granite countertops and stainless steel appliances, ideal for home cooking. The guest room has a Hawaiian-print futon sofa and TV that sets the scene for movie nights in.

Outside, the pool surrounded by lush greenery is a definite eye-catcher. There’s also a covered patio with outdoor seating for relaxing and enjoying your meals. You can even pick some of the fruits here if they are in season, including papayas and avocados. Note that monthly rentals are encouraged.

Stayed at this property?
Kailua, Hawaii, United States
26 reviews   Wifi Available
ENTIRE HOME 3 Beds 4 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 4

Top guest reviews
Amenities & Room:
the pool is lovely (not heated though and no railing for older people)
Cleanliness:
very clean and in person the place looks even better than the pictures
very quite and clean we love virginia house hope next time
the backyard is beautiful and the rooms are decorated beautifully and very clean
it is as (website hidden by airbnb) is sparkling clean great location and in a quiet/safe area
Host:
aralie was a great host very quick to respond to any questions
host was informative helpful and responsive
virginias home is one of the coolest we have stayed in great host as well :)
lee was super responsive and very sweet
Location:
was a nice house location and experience
staying in such a wonderful location made it the perfect holiday
fantastic location and a great host
great place if you don’t want the crazy busy tourist area
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7. Cozy home near the beach (from USD 250)

Ideal for couples on vacation, this one-bedroom apartment is just a five-minute walk away from Kailua Town and Kailua Beach. After a day of sightseeing, cool off in the private pool. When feeling peckish, you can fire up the grill in the lanai area for a barbecue lunch.

There’s also a full kitchen where you can cook up a storm. Note that your stay has to be at least 30 days and that you can’t bring kids under 12 years of age.

Stayed at this property?
Kailua, Hawaii, United States
17 reviews   Wifi Available
Entire guest suite 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
pool was awesome; kitchen spectacular
very comfortable living area comfy bed new large flat screen tv with all the channels dvd player
loved the pool and outside sitting area in the back yard
Cleanliness:
wonderful clean and peaceful place
the unit itself is quite large with a well stocked kitchen with use of a clean bbq too
otherwise a very nice clean large apartment very close to everything you need whist on holidays
Host:
her response to the inquiry was so quick and needless to say she was friendly and kind
the hosts thought of everything to make our visit enjoyable
the owner cheryl was very nice
cheryl was a great host
cheryl and john are awesome host responsive and attentive
Location:
the location is great
location is also perfect
this location is in the most beautiful neighborhood in kailua
the neighborhood is also very nice with a whole foods close by
so awesome close to everything we wanted/needed
Read more reviews

8. Palione Papalani (from USD 2662)

Palione Papalani is a gorgeous house, steps away from the pristine shores of Kailua Beach. With floor-to-ceiling windows and an open-plan design, the home is bright and breezy and boasts a fantastic view of the ocean.

A large group or family of up to eight people can feel right at home here, with six bedrooms to ensure guests sleep comfortably and five full baths for everyone’s privacy. There are communal areas where guests can gather and enjoy each other’s company. Guests are welcome to sunbathe on the deck, swim some refreshing laps in the gorgeous landscaped pool or enjoy a long soak in the hot tub.

Stayed at this property?
49 reviews  
House 14 Guests 6 Bedrooms 6 Bathrooms

Accommodates: 14
Minimum Nights: 0
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
it had plenty of space for everybody and the grounds and pool were gorgeous
otherwise the pool/hot tub/back yard are fantastic
kitchen was very well stocked and knives were sharp which is a nice surprise for a rental
it had a well stocked kitchen and nicely furnished - very casual and comfortable
Cleanliness:
the house was clean
the house was perfectly clean and the landscaping is great
the water was clean
the vacation rental was very clean
Host:
mitchell and steven were so helpful
rating details: the property manager was very helpful
rating details: the property manager was very helpful
rating details: the property manager was very helpful
rating details: the property manager was very helpful
Location:
the house location and property were all amazing
the beach is walking distance and amazing
i was very happy with the location
i was very happy with the location
i was very happy with the location
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9. Helen's Beach House

Located just four houses away from the beach and minutes away from shops and restaurants, this five-bedroom property is the perfect home base for those eager to explore the town. This beach home also offers some much-needed rest after a fun day out. You can relax on the spacious patio with a drink in hand or swim some laps in the outdoor pool.

If you feel like barbecuing, there’s a private gas grill outside. But if indoor cooking is more your thing, a kitchen with a refrigerator and oven is at your disposal. At the end of the night, you’ll be happy to retire to one of the inviting bedrooms equipped with air conditioning and an en-suite bath for absolute comfort and privacy.

Stayed at this property?
41 reviews   Wifi Available
House 12 Guests 5 Bedrooms 6 Bathrooms

Accommodates: 12
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
the two kitchens and one being with ac was a blessing
the two kitchens were great to prepare large lunch/dinner spreads
a little cool for the pool but some brave members used it
Cleanliness:
the vacation rental was very clean
the vacation rental was very clean
Host:
rating details: the property manager was adequately helpful
richard was a great attentive host
rating details: the property manager was very helpful
rating details: the property manager was very helpful
rating details: the property manager was very helpful
Location:
reviewer comments: beautiful location
but by far the best feature is its location
still we love the house and the location and would return
reviewer comments: wonderful location wonderful house wonderful help
a two minute walk to the beach and a great pool satisfied all of our vacation dreams
Read more reviews
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10. Luxurious house in a quiet residential community

There is no expense spared in this eight-person house, which boasts a large swimming pool with waterfalls for extra flair. There is even a spa pool if you want a more therapeutic experience. It can be accessed from the master bedroom as well, so a quick dip is always an option.

Inside, the living room and kitchen share an open plan design and feature beautiful tiled floors. A seamless transition from the pool to the living room is made possible by the large glass dividers. It also has four spacious bathrooms with a hairdryer and large closet.

Stayed at this property?
Kailua, Hawaii, United States
21 reviews   Superhost Wifi Available
ENTIRE HOME 5 Beds 8 Guests 4 Bedrooms 4 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
and enjoy the sunsets from the pool deck facing the mountains
need new light bulbs for most areas ( especially the fan lights )
the back patio pool and hot tub are a calming oasis for relaxing
Host:
the host was very responsive and helpful
katy was rapidly responsive to any needs or questions
katy was responsive when we needed info
Location:
great location close to kailua beach
the location is fabulous just a short walk to the beach and hiking trails
good place can’t beat the location
excellent location with nice swimming pool and hot tub
great location and beautiful home with an open floor plan
Read more reviews

Soak up Kailua's laid-back vibe

With the sun shining bright on this side of Oahu island, there is much beauty to discover in Kailua. The Kailua and Kalama beaches are the main draw here, and if you want to go further, Honolulu is just 12 mi (19 km) southwest. For an unforgettable experience, book any of the above listed vacation rentals with private pool in Kailua, Hawaii.

Stayed at this property?
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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Aly is an ever-curious wanderer who enjoys constantly learning and exploring the world. With more than five years of experience as a travel writer based in Manila, she enjoys writing about her...Read more

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