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

Stephen
Stephen 
Updated
| 4 min read

Located on the west coast of Hawaii Island, Kailua-Kona is a lovely travel destination known for its wonderful tropical climate and stunning coastline. Nature lovers can explore ancient rock art and sea turtles at Kaloko-Honokohau National Historical Park. If you wish to learn about the history of the place, you can visit Hulihe’e Palace and check out its wide collection of artifacts. Outdoor enthusiasts can indulge in a nature hike at Hualalai. Other top attractions include Moku’aikaua Church, which is the oldest Christian church in Hawaii. Scroll down for a list of the best vacation rentals with private pool in Kailua-Kona, Hawaii.

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. Breathtaking oceanfront home with a hot tub (from USD 1023)

Nestled only an arm’s stretch away from the ocean, this stunning Airbnb vacation rental in Kona is an ideal choice for your most awaited Hawaiian getaway. It boasts a gorgeous compound with a wrap-around driveway and a water feature.

When the afternoon temperatures start rising, you can enjoy refreshing laps in the lovely outdoor pool with sweeping views of the ocean. There is a hot tub right next to the pool where you can unwind at night while admiring the star-speckled sky. You can also get a suntan while relaxing on one of the poolside sun loungers.

Stayed at this property?
Kailua-Kona, Hawaii, United States
15 reviews   Superhost Wifi Available
ENTIRE HOME 6 Beds 10 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 10

Top guest reviews
Location:
a walking distance to a sand beach with a good spot for surfing just around the corner
Read more reviews

2. Splendid home in a gated community (from USD 1691)

Enjoy peace and tranquility in this magnificent Vrbo vacation rental nestled in a gated community in Kailua-Kona. There’s a cozy gazebo where you can have your breakfast as you admire dolphins playing on the shore.

Guests will have unfettered access to a private beach with hammocks, a saltwater pool, and a swimming lagoon that’s connected to the open sea. There are sun loungers and a sandpit in the pool area that will give you ultimate beach vibes.

Stayed at this property?
Kailua Kona, Hawaii, United States
PRIVATE VACATION HOME 10 Guests 5 Bedrooms 6 Bathrooms

Top guest reviews
Amenities & Room:
beds are comfortable and there was plenty of space for our extended family of 9
Cleanliness:
the house is very spacious and generous in space 8 adults had plenty of room
Host:
security was very helpful with parking and directions
Location:
sunset from this location is amazing too
good location on the island
it was a beautiful and well located home close to town but felt far away from everything
perfect location and very nice house to stay in
very happy with the house and location
Read more reviews
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3. Amazing vacation home best for families (from USD 510)

Families will enjoy a memorable holiday in this amazing vacation home. Featuring an outdoor pool, the property allows you to have fun swimming and sunbathing while on a vacation. It comes with two covered lanais where you can hang out and dine al fresco.

Going inside the house, a spacious living area will greet you. It has comfy sofas and a flat-screen TV, so everyone can watch movies together. Just a few steps away is the fully equipped kitchen. Make use of modern appliances to prepare your meals or you can use the grill outdoors to cook barbecues and kebabs.

Stayed at this property?
Kailua-Kona, Hawaii, United States
PRIVATE VACATION HOME 8 Guests 4 Bedrooms 4 Bathrooms

Top guest reviews
Amenities & Room:
there is definitely plenty of room in this house for multiple families
the kitchen is huge and had everything we needed to cook multiple meals
Cleanliness:
pool was clean and worked great
great location and very clean
Host:
rachel was super responsive when we had questions
rachel is wonderful and very responsive
communication with the owner was easy and quick
we will go back loved this trip thanks to the wonderful host
Location:
the location is great convenient yet in a quiet neighborhood
Read more reviews
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4. Beautiful home with nature views (from USD 395)

Enjoy stunning views of Kona’s coast when you book a stay in this beautiful home. It boasts a lap pool that sits by the edge of the property, offering 180-degree nature views. There is also a covered lanai with outdoor furniture beside the pool for you to relax after swimming. In case you get hungry while having fun outdoors, you can cook tasty meat at the barbecue area.

Additionally, the property has a kitchen that lets you prepare delicious home-cooked meals and its roomy living area is cozy enough for a late-night movie marathon.

Stayed at this property?
Holualoa, Hawaii, United States
Wheelchair accessible Visual Aid: Braille
PRIVATE VACATION HOME 2 Guests 1 Bedroom 1 Bathroom

Top guest reviews
Amenities & Room:
a comfortable house with a wonderful view of the ocean
and birds would come to the pool for a drink of fresh water
Host:
one of a kind property nestled above kona
Location:
this was such a great place to unwind
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5. Kini Kini Pua (from USD 395)

Stay in this adorable paradise with beautiful décor throughout the place during your Kailua-Kona getaway. The living room is bright and spacious, offering a peaceful ambiance for relaxing. There is a nice family room furnished with a cozy sofa and a large flat-screen TV.

This house rental with a pool in Kona boasts a sleek kitchen with up-to-date appliances. Guests can enjoy al fresco dining on the tiled porch. You’ll have access to a solar-heated outdoor pool with pool stairs and pool deck seating. It is open throughout the year.

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

Accommodates: 4

Top guest reviews
Amenities & Room:
it was like showering in a jungle hideaway
the pool was perfect and the view of downtown kona in the evenings was superb
richard's place was wonderful the outdoor gardens pool and patio were meticulously maintained and beautiful
beds were very comfortable
there is all beach and swimming pool gear along with a nice new pack and play
Cleanliness:
clean super comfortable and well decorated
the beds are amazing and clean
super clean and the champagne was a nice touch
richards’s house was amazing very clean decorated beautifully
great place so clean and the outside space wasso nice
Host:
richard was the perfect host and had fast responses to any questions that we had
he was a fantastic host he was very responsive and answered any questions we had
top notch house and excellent host
the owner communicates timely professionally and quick is very easy to work with
it truly made our trip special and richard was a great host
Location:
it’s located in a very nice quiet neighborhood yet it is close to restaurants and shopping
the house is conveniently located 15 minutes from the airport in a very quiet and safe neighborhood
the location is also great - 20 minutes from beaches 10 minutes from the city center
the neighborhood was quiet and within a few minutes of many great restaurants and activities
this is a very well maintained home in an excellent location on the big island
Read more reviews

6. Romantic paradise with a fire pit (from USD 1199)

Tucked away in an exclusive area, this is a gorgeous house that offers incredible ocean views. It comes with a private heated saltwater infinity pool where guests cool down from the scorching sun. The volcano fire pit is also a welcome addition to the pool area during a cozy night swim. During your free time, you can teach your kids golfing skills on the golf course within 20 minutes from the property.

The interior of the rental is beautifully decorated and furnished with top-notch amenities.

Stayed at this property?
Kona, Hawaii, United States
PRIVATE VACATION HOME 6 Guests 3 Bedrooms 3 Bathrooms

Top guest reviews
Amenities & Room:
badminton and a few pools toys were fun to have
loved the house and the gorgeous views from the pool
enjoyed the home view pool
the pool is very private and sunny with flotation devices designed to enhance relaxation
we loved that the pool is salt water soft to the touch a nice change from chlorinated pools
Host:
great information from the owners
the owners have taken care of every detail leaving you wanting for nothing
thanks to shannon who was readily available (although we didn't need much) and quite accommodating for our requests
outstanding attention to detail and communication from the owner
Location:
a great central location from which to plan day trips
collessie was a great place to spend a week with the family
clean everything works views are grand and close to town
Read more reviews
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7. Beachfront home with a fully equipped kitchen (from USD 1002)

Wake up to the sound of rolling waves crashing on the shore when you stay at this wonderful rental set a few steps from the beach. It comes with three bedrooms that can sleep up to eight guests, making it perfect for family vacations. The property comes with a beautiful backyard with a barbecue grill, a swimming pool, and sun loungers.

Guests can play pool table on the covered porch as they watch kids splash water in the pool. The kitchen is spacious and fitted with marble countertops.

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

Accommodates: 8
Minimum Nights: 0
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Amenities & Room:
fan on ac ran all night so was kind of loud
views are great all around - cottage was comfortable and very well stocked and supplied
bed was very comfortable only working ac was in the 4 bedrooms
the lanai off the informal dining room was a great place to relax
we loved being able to cook our own meals in the fully furnished kitchen
Cleanliness:
very clean and well maintained
reviewer comments: house was great clean and beautiful setting
the house was clean as described comfortable and well maintained
need to clean this up for the price we paid should not have to deal with 911 calls
it had everything we needed very clean and beautifully furnished
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
rating details: the property manager was very helpful
rating details: the property manager was very helpful
Location:
location was very good
the location was good - 15 min
we would recommend this location
the house is magnificent perfectly equiped and in the best location on the island
easy walk to local restaurants
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8. Gorgeous haven overlooking the beach (from USD 1574)

Have a slice of paradise when you stay in this magnificent home with stunning vistas of the beach and the sea. There is a stylish outdoor infinity pool where guests can swim as they admire the blue waters of the sea. With a barbecue and a sink by the poolside, guests can enjoy cookouts and al fresco dining.

The floating pedestal is an amazing spot to eat your breakfast or enjoy a romantic moment with your better half.

Stayed at this property?
Kailua-Kona, Hawaii, United States
Wheelchair accessible Visual Aid: Braille
PRIVATE VACATION HOME 12 Guests 4 Bedrooms 5 Bathrooms

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9. Mermaid Cove (from USD 2592)

Experience a laid-back stay at Mermaid Cove, a gorgeous vacation rental set a few yards from the beach. There is a furnished porch where you can chill out as you listen to the sweet melodies from the birds. Featuring exposed wooden beam ceilings, the house boasts an extravagant living room that offers expansive ocean views. The kitchen comes equipped with a wine fridge and a gas range.

There’s a magical outdoor pool with a bar area, a barbecue area, and a shaded seating area.

Stayed at this property?
60 reviews  
House 13 Guests 4 Bedrooms 4 Bathrooms

Accommodates: 13
Minimum Nights: 5
Refund Policy :

Top guest reviews
Amenities & Room:
one ceiling fan turns backwards and 2 of the standing fans (white) do not work
reviewer comments: house view location and everything about it was fantastic only improvement would be air conditioning
the kitchen and dining area has gorgeous views of the ocean
the beach and tide pools was perfect for the little ones
several calls to management and one pool light was restored with the spa heater
Cleanliness:
super clean and comfortable
very clean and well furnished
the washer and dryer was really quite nice and clean no musty smell
the vacation rental was very clean
the vacation rental was very clean
Host:
rating details: the property manager was adequately 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:
location was perfect
the location was wonderful
perfect location for a family with children
luxury in a perfect location
outstanding location with ease to farmers market and town
Read more reviews
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10. Pet-friendly home with internet (from USD 1654)

Indulge in a wonderful tropical vibe when you book accommodation in this fabulous home with awe-striking ocean views. Enjoy romantic sunsets as you sip wine while relaxing on the chairs in the backyard. The circular outdoor pool ensures that you get to feast your eyes on sweeping ocean vistas while you swim.

With five bedrooms plus three-and-a-half bathrooms, this home can easily host twelve people. It is pet-friendly and features free wireless internet connectivity and free on-site parking.

Stayed at this property?
Kailua-Kona, Hawaii, United States
31 reviews   Wifi Available
ENTIRE HOME 7 Beds 12 Guests 5 Bedrooms 3 Bathrooms

Accommodates: 12

Top guest reviews
Amenities & Room:
the air conditioning was really nice for the evenings
beautiful home perfect for large groups we really enjoyed the pool and views from the back yard
the house the view and the pool are great we loved watching the sunset each evening while swimming
the pool has a beautiful view of the ocean it is a great place to spend time
Cleanliness:
very clean with homey touches
the house was clean and well stocked
Host:
our hosts were very communicative and responsive
Location:
great location just minutes from the beach/anything you need
a beautiful house in an incredible location
beautiful home in a beautiful location
breathtaking views and amazing location
this is a great place for a large family
Read more reviews

11. Hale Pahukoa (from USD 100)

Enjoy a thrilling water adventure in Kailua-Kona when you spend your holiday in this romantic home located a few yards from the beach. From here, you’ll be within a walking distance to attractions, such as Kailua Pier, restaurants, and shopping outlets.

It has an elegant outdoor pool with stunning ocean views. Poolside loungers are provided, so you can have a suntan before you take a refreshing dip in the pool. If you don’t want to dive, you can use the pool stairs to get into the pool.

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

Accommodates: 8

Top guest reviews
Amenities & Room:
the pool was amazing and the included floaties were a nice touch
beds were very comfortable
besides who needs ac when you have a pool hosts were very communicative professional and kind
Location:
very good price for the location
we loved staying at this house it was the perfect location for our trip
Read more reviews

12. Chic guesthouse close to the airport (from USD 120)

Looking for a place to stay that’s near the airport and Kailua town? You can rent this guesthouse, which is a great option. It has one bedroom and a bathroom, making it perfect for couples and solo adventurers. There is a fully functional kitchen for those who prefer to eat home-made meals. The house comes with a 55-inch TV to keep you entertained and free WiFi to keep you connected.

There’s an oversized outdoor pool where you can enjoy refreshing laps during the day.

Stayed at this property?
150 reviews   Wifi Available
guest house 2 Guests 1 Bedroom 1 Bathroom

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

Top guest reviews
Amenities & Room:
location is great it’s comfortable and has a beautiful backyard view of the ocean
the room featured a queen bed and large bathroom with an adjacent room with entertainment area and kitchen
Cleanliness:
it was clean and cozy
the rooms were clean and comfortable
rooms were clean and cute
this place was beautiful clean and peaceful
the room was clean tastefully decorated and safe
Host:
great hosts great directions
host was very friendly
the host was very accommodating and pleasant
very welcoming owners feels like home
owners very friendly and helpful
Location:
the location was very good
convenient super close to everything
cute place nice people close to town
it was in a great location
their place was convenient to our point of interest 10-15 mins
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

Relax and rejuvenate in Kailua-Kona

Kailua-Kona is a fantastic place for those who wish to have a nice breath of fresh air and explore its breathtaking landscape. Book one of the best vacation rentals with a private pool that we’ve listed above for a chance to rest and rejuvenate in Kailua-Kona.

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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Stephen is an avid content writer with a passion for adventure. He enjoys traveling and has visited several countries around the world. So far, South Africa stands out as his most exciting...Read more

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