Vacation Rentals with Pool in Historic Kailua Village, HI: Compare 10+ Sites & Save

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  2. Vacation Rentals with Pool
  3.  USA

  4.  Hawaii

  5.  Kailua-Kona

  6.  Historic Kailua Village

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1519 Best Vacation Rentals with Pool in Historic Kailua Village (Starting from $141)

Alii Villas 307
Alii Villas 307
Apartment
Historic Kailua Village, Kailua-Kona, Hawaii, USA
0.1k from Historic Kailua Village center

Apartments, Cheap, Accommodations, Lodgings, Places to stay, Family, Accessible hotels

2 Bedrooms4 Guests
8.8

Fabulous

16 reviews

$382
Average price / night
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Luxury Beachfront Gated retreat in-town SPA/AC/BBQ accessible to the public pool
Luxury Beachfront Gated retreat in-town SPA/AC/BBQ accessible to the public pool
House
Kailua-Kona, HI, 96740, United States
0.1k from Historic Kailua Village center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Hot Tub, Internet, Kitchen

4 Bedrooms12 Guests
8.6

Fabulous

7 reviews

$1388
Average price / night
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Holiday Inn Express & Suites Kailua-Kona by IHG
Holiday Inn Express & Suites Kailua-Kona by IHG
Resort
Kailua-Kona, HI, USA
0.1k from Historic Kailua Village center

Accommodations, Pools, Resorts, Parking, Holiday inn , 3-star, Lodgings, Hot tubs, Places to stay

61 Bedrooms56 Guests
8.1

Very Good

405 reviews

$244
Average price / night
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Outstanding Oceanfront Studio - Kona Islander Inn Condos Condo by RedAwning
Outstanding Oceanfront Studio - Kona Islander Inn Condos Condo by RedAwning
Condo
75-5776 Kuakini Highway, Kailua-Kona, HI, 96740, United States
0.1k from Historic Kailua Village center

Barbecue, Dryer, Internet, No Smoking, Pool, TV, Washer

4.0

Review score

1 reviews

$685
Average price / night
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Kona Plaza#218
Kona Plaza#218
House
Kailua-Kona, HI, USA
0.2k from Historic Kailua Village center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$172
Average price / night
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Condo in the center of Kona, 2-unit AC, Washer/Dryer, Full Kitchen, Free Parking
Condo in the center of Kona, 2-unit AC, Washer/Dryer, Full Kitchen, Free Parking
Condo
Kailua-Kona, HI, 96740, United States
0.2k from Historic Kailua Village center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Internet, Kitchen, Laundry

1 Bedroom4 Guests
9.0

Fabulous

4 reviews

$198
Average price / night
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Kona Plaza#203
Kona Plaza#203
House
Kailua-Kona, HI, USA
0.2k from Historic Kailua Village center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom4 Guests
6.5

Good

2 reviews

$254
Average price / night
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Paradise Heart of Kona Town
Paradise Heart of Kona Town
Condo
Kailua-Kona, HI, 96740, United States
0.2k from Historic Kailua Village center

AC, Balcony, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

1 Bedroom4 Guests
10.0

Exceptional

2 reviews

$206
Average price / night
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Kona Plaza#411
Kona Plaza#411
House
Kailua-Kona, HI, USA
0.2k from Historic Kailua Village center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$251
Average price / night
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Top-Floor Condo in Kona Plaza – 1 Bedroom Gem in the Heart of Kailua-Kona!
Top-Floor Condo in Kona Plaza – 1 Bedroom Gem in the Heart of Kailua-Kona!
Condo
Kailua-Kona, HI, 96740, United States
0.2k from Historic Kailua Village center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

1 Bedroom4 Guests
9.6

Exceptional

4 reviews

$240
Average price / night
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Kona Plaza#221
Kona Plaza#221
House
Kailua-Kona, HI, USA
0.2k from Historic Kailua Village center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

1 Bedroom4 Guests
10.0

Exceptional

1 reviews

$261
Average price / night
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New Discount Weekly,Monthly,Daily,OceanviewSteps to Town,Beach,Pier,Ocean access
New Discount Weekly,Monthly,Daily,OceanviewSteps to Town,Beach,Pier,Ocean access
Condo
Kailua-Kona, HI, 96740, United States
0.2k from Historic Kailua Village center

AC, Balcony, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry

1 Bedroom2 Guests
9.2

Superb

52 reviews

$141
Average price / night
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Kalanikai #319
Kalanikai #319
Apartment
Kailua-Kona, HI, USA
0.2k from Historic Kailua Village center

Apartments, Accommodations, Pools, Lodgings, Places to stay

1 Bedroom4 Guests
5.0

Review score

1 reviews

$240
Average price / night
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Heart of Kona Ocean View Condo w/ Pool, Oversized Lanai, Incredible Location
Heart of Kona Ocean View Condo w/ Pool, Oversized Lanai, Incredible Location
Condo
Kailua-Kona, HI, 96740, United States
0.2k from Historic Kailua Village center

AC, Barbecue, Crib, Dryer, Elevator, Extra Bed, Free Parking, Internet, Kitchen

2 Bedrooms4 Guests
9.6

Exceptional

37 reviews

$419
Average price / night
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Kona Plaza#302
Kona Plaza#302
House
Kailua-Kona, HI, USA
0.2k from Historic Kailua Village center

Cheap, Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

1 Bedroom4 Guests
10.0

Exceptional

1 reviews

$245
Average price / night
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Walk to the Beach | Downtown Kona Condo with Pool Access
Walk to the Beach | Downtown Kona Condo with Pool Access
Condo
Kailua-Kona, HI, 96740, United States
0.2k from Historic Kailua Village center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area

1 Bedroom2 Guests
9.4

Superb

36 reviews

$210
Average price / night
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Kalanikai 118 - Highly Walkable
Kalanikai 118 - Highly Walkable
House
Kailua-Kona, HI, USA
0.2k from Historic Kailua Village center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$237
Average price / night
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Garden View Studio - Kona Islander Inn Condos Condo by RedAwning
Garden View Studio - Kona Islander Inn Condos Condo by RedAwning
Condo
75-5776 Kuakini Highway, Kailua-Kona, HI, 96740, United States
0.2k from Historic Kailua Village center

Barbecue, Dryer, Free Parking, Internet, No Smoking, Outdoor Space, Pool, TV, Washer

6.0

Review score

1 reviews

$557
Average price / night
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Kona Plaza#414
Kona Plaza#414
House
Kailua-Kona, HI, USA
0.2k from Historic Kailua Village center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$294
Average price / night
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Updated condo with air conditioning in the heart of downtown Kona.
Updated condo with air conditioning in the heart of downtown Kona.
Condo
Kailua-Kona, HI, 96740, United States
0.2k from Historic Kailua Village center

AC, Balcony, Barbecue, Dryer, Elevator, Free Parking, Internet, Kitchen, Laundry

1 Bedroom6 Guests
9.8

Exceptional

31 reviews

$232
Average price / night
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Kona Plaza#409
Kona Plaza#409
House
Kailua-Kona, HI, USA
0.2k from Historic Kailua Village center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom8 Guests
New to Booking
$942
Average price / night
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Beautifully Furnished Downtown Kailua-Kona Hawaii Condo.
Beautifully Furnished Downtown Kailua-Kona Hawaii Condo.
Condo
Kailua-Kona, HI, 96740, United States
0.2k from Historic Kailua Village center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave

1 Bedroom4 Guests
9.8

Exceptional

13 reviews

$401
Average price / night
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Peaceful Retreat • 5 min Walk to Town, Pier & Beach • Free Parking
Peaceful Retreat • 5 min Walk to Town, Pier & Beach • Free Parking
Condo
Kailua-Kona, HI, 96740, United States
0.2k from Historic Kailua Village center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Internet, Kitchen, Laundry

1 Bedroom4 Guests
9.6

Exceptional

5 reviews

$253
Average price / night
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Closed to public
Closed to public
Condo
Kailua-Kona, HI, 96740, United States
0.3k from Historic Kailua Village center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Kitchen, Laundry, Living Area, Microwave

1 Bedroom3 Guests
10.0

Exceptional

1 reviews

$168
Average price / night
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Kona Hawaii 2 bedroom Condo Sleeps 6
Kona Hawaii 2 bedroom Condo Sleeps 6
Resort
Kailua-Kona, HI, 96740, United States
0.3k from Historic Kailua Village center

AC, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms6 Guests
New to Booking
$879
Average price / night
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Oceanfront -Waterview 1 BedroomCondo Heart of Town at Kona Plaza walk to Ironman
Oceanfront -Waterview 1 BedroomCondo Heart of Town at Kona Plaza walk to Ironman
Condo
Kailua Kona, HI, 96740, United States
0.3k from Historic Kailua Village center

AC, Balcony, Barbecue, Dryer, Elevator, Free Parking, Internet, Laundry, Living Area

1 Bedroom4 Guests
9.4

Superb

29 reviews

$446
Average price / night
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 Completely redecorated Aug. 2019 1 block to beach, free wi-fi, parking, and AC
Completely redecorated Aug. 2019 1 block to beach, free wi-fi, parking, and AC
Condo
Kailua-Kona, HI, 96740, United States
0.3k from Historic Kailua Village center

AC, Balcony, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms5 Guests
9.2

Superb

98 reviews

$320
Average price / night
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Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals with Pool in Historic Kailua Village.

Stay Near Historic Kailua Village's Top Attractions

VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

Historic Kailua Village Vacation Rentals with Pool on the Map

Frequently Asked Questions

You can explore 1519 verified vacation rentals with a pool in Historic Kailua Village. These include a wide range of private homes, villas, and condos that offer on-site swimming facilities for a more relaxing stay.

Prices for vacation rentals with a pool in Historic Kailua Village vary depending on the season, property size, and whether the pool is private or shared. Rates typically start from around $141 per night, with private pool homes and peak travel periods often costing more.

Many rentals in Historic Kailua Village offer private pools for exclusive use, while others provide access to shared or community pools. You can use filters to specifically find properties with private pools if that is your preference.

Yes, some vacation rentals with pools in Historic Kailua Village welcome pets. Currently, 4 listings allow pets, although policies may vary by property. It’s a good idea to review any rules related to pets around pool areas before booking.

Properties with pools are often in high demand, especially during warmer months and holidays, so booking 90 to 120 days in advance is recommended for the best selection. During off-peak seasons, you may still find availability closer to your travel dates.

Vacation rentals with pools in Historic Kailua Village often include additional outdoor features such as Pool, View, and Laundry. These amenities enhance comfort and make it easier to enjoy outdoor living during your stay.

Some vacation rentals in Historic Kailua Village offer heated pools, which can be especially useful during cooler months. In certain cases, pool heating may be available for an additional fee, so it’s best to check the property details before booking.