Explore Kahakuloa Vacation Rentals
Condo
10.0Exceptional
(184 Reviews)
3 Bedrooms
2 Baths
9 Guests
Parking
Pool
Ocean View
Balcony/Terrace
US $1,329/Night
7 Nights - US $9,306
House
- Lahaina
- ·
- Historic Lahaina Front Street
- 1.10 mi to center
3 Bedrooms
3 Baths
12 Guests
3003.13 ft²
Private Beach- Parking
- Pool
- Ocean View
US $980/Night
7 Nights - US $6,860
Bed & Breakfast
- Wailuku
- ·
- Wailuku Heights
- 0.75 mi to center
10.0Exceptional
(56 Reviews)
1 Bedroom
1 Bath
Breakfast- Parking
- Balcony/Terrace
Kitchen
US $275/Night
7 Nights - US $1,925
Condo
10.0Exceptional
(174 Reviews)
1 Bedroom
1 Bath
3 Guests
540 ft²
Hot Tub- Parking
- Pool
- Ocean View
US $197/Night
7 Nights - US $1,377
Apartment
1 Bedroom
1 Bath
6 Guests
43.06 ft²
- Pool
Child Friendly
US $350/Night
7 Nights - US $2,450
Condo
10.0Exceptional
(167 Reviews)
1 Bedroom
1 Bath
2 Guests
938 ft²
Private Pool
Oceanfront- Hot Tub
- Parking
US $611/Night
7 Nights - US $4,278
Condo
10.0Exceptional
(167 Reviews)
1 Bedroom
1 Bath
4 Guests
938 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $450/Night
7 Nights - US $3,148
Condo
10.0Exceptional
(162 Reviews)
3 Bedrooms
3 Baths
8 Guests
2700 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $994/Night
7 Nights - US $6,956
Condo
10.0Exceptional
(157 Reviews)
1 Bedroom
1 Bath
2 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $488/Night
7 Nights - US $3,419
Luxury Places to Stay in Kahakuloa
Over 10000+ Luxury Places to Stay in or Near Kahakuloa
Condo
11 Bedrooms
1 Bath
28 Guests
- Balcony/Terrace
- Kitchen
Internet- Child Friendly
Unlock the Best Price
Condo
8 Bedrooms
1 Bath
22 Guests
- Balcony/Terrace
- Kitchen
- Internet
- Child Friendly
Unlock the Best Price
Condo
8 Bedrooms
1 Bath
22 Guests
- Balcony/Terrace
- Kitchen
- Internet
- Child Friendly
Unlock the Best Price
Condo
9 Bedrooms
1 Bath
28 Guests
- Balcony/Terrace
- Kitchen
- Internet
- Child Friendly
Unlock the Best Price
Condo
7 Bedrooms
1 Bath
22 Guests
- Balcony/Terrace
- Kitchen
- Internet
- Child Friendly
Unlock the Best Price
Condo
Honua Kai | 3 FREE CARS | KBM Resorts | Extra Large Corner Suite! | 3 Units, 7 Bedrooms | HK ML-3577
7 Bedrooms
1 Bath
22 Guests
- Balcony/Terrace
- Kitchen
- Internet
- Child Friendly
Unlock the Best Price
Condo
7 Bedrooms
7 Baths
22 Guests
- Balcony/Terrace
- Kitchen
- Internet
- Child Friendly
Unlock the Best Price
Hotel
2 Baths
- Breakfast
- Pool
- Balcony/Terrace
- Kitchen
Unlock the Best Price
House
- Lahaina
- ·
- Historic Lahaina Front Street
- 0.52 mi to center
1 Bedroom
4 Baths
10 Guests
3993.41 ft²
- Oceanfront
- Breakfast
- Ocean View
View
Unlock the Best Price
Top-Rated Vacation Rentals with a Pool in Kahakuloa
Over 9378+ Top-Rated Vacation Rentals with a Pool in or Near Kahakuloa
Condo
10.0Exceptional
(457 Reviews)
1 Bedroom
1 Bath
4 Guests
400 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $370/Night
7 Nights - US $2,587
Condo
10.0Exceptional
(318 Reviews)
2 Bedrooms
2 Baths
6 Guests
1240 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $750/Night
7 Nights - US $5,250
Condo
10.0Exceptional
(286 Reviews)
1 Bedroom
1 Bath
2 Guests
938 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $866/Night
7 Nights - US $6,059
Apartment
10.0Exceptional
(247 Reviews)
1 Bedroom
1 Bath
3 Guests
400 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $359/Night
7 Nights - US $2,515
Condo
10.0Exceptional
(234 Reviews)
2 Bedrooms
2 Baths
6 Guests
1100 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $756/Night
7 Nights - US $5,295
Condo
10.0Exceptional
(233 Reviews)
2 Bedrooms
2 Baths
4 Guests
700 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $499/Night
7 Nights - US $3,493
Condo
10.0Exceptional
(228 Reviews)
3 Bedrooms
2 Baths
6 Guests
1140 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $984/Night
7 Nights - US $6,888
Condo
10.0Exceptional
(227 Reviews)
2 Bedrooms
2 Baths
5 Guests
1400 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $921/Night
7 Nights - US $6,446
Condo
10.0Exceptional
(222 Reviews)
4 Bedrooms
3 Baths
10 Guests
1600 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $1,156/Night
7 Nights - US $8,094
Pet-Friendly Vacation Rentals in Kahakuloa
Over 82+ Pet-Friendly Vacation Rentals in or Near Kahakuloa
Condo
10.0Exceptional
(31 Reviews)
1 Bedroom
1 Bath
4 Guests
777 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $334/Night
7 Nights - US $2,338
Apartment
1 Bedroom
1 Bath
4 Guests
990.28 ft²
- Breakfast
- Pool
- Balcony/Terrace
Air Conditioner
US $4,812/Night
7 Nights - US $33,684
Apartment
- Lahaina
- ·
- Historic Lahaina Front Street
- 0.81 mi to center
8.0Excellent
(17 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Breakfast
- Parking
- Pool
US $457/Night
7 Nights - US $3,196
Condo
10.0Exceptional
(11 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $814/Night
7 Nights - US $5,695
Apartment
1 Bedroom
1 Bath
3 Guests
538.2 ft²
- Breakfast
- Air Conditioner
- Internet
Pet Friendly
US $5,572/Night
7 Nights - US $39,004
Condo
9.8Exceptional
(54 Reviews)
1 Bedroom
1 Bath
6 Guests
1000 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $790/Night
7 Nights - US $5,528
Villa
1 Bedroom
2 Baths
4 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $534/Night
7 Nights - US $3,739
House
1 Bedroom
1 Bath
2 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $358/Night
7 Nights - US $2,505
House
5 Bedrooms
5 Baths
8 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $897/Night
7 Nights - US $6,279
Large Vacation Homes & Villas in Kahakuloa
Over 2313+ Large Vacation Homes & Villas in or Near Kahakuloa
Villa
- Lahaina
- ·
- Montage Kapalua Bay
- 0.06 mi to center
10.0Exceptional
(29 Reviews)
4 Bedrooms
3 Baths
8 Guests
3532 ft²
- Oceanfront
- Hot Tub
- Breakfast
- Parking
US $3,372/Night
7 Nights - US $23,605
Bed & Breakfast
- Lahaina
- ·
- Historic Lahaina Front Street
- 3.24 mi to center
10.0Exceptional
(3 Reviews)
6 Bedrooms
6 Baths
12 Guests
301.39 ft²
- Oceanfront
- Parking
- Pool
Spa
US $499/Night
7 Nights - US $3,493
Villa
8.0Excellent
(1 Review)
1 Bedroom
1 Bath
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $1,567/Night
7 Nights - US $10,966
House
10.0Exceptional
(91 Reviews)
4 Bedrooms
2 Baths
10 Guests
2250 ft²
- Pool
- Kitchen
- Air Conditioner
- Internet
US $1,867/Night
7 Nights - US $13,072
Apartment
10.0Exceptional
(2 Reviews)
12 Bedrooms
11 Baths
38 Guests
1048.01 ft²
- Private Beach
- Oceanfront
- Hot Tub
- Breakfast
US $495/Night
7 Nights - US $3,468
House
10.0Exceptional
(110 Reviews)
7 Bedrooms
7 Baths
28 Guests
6000 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $3,634/Night
7 Nights - US $25,440
House
10.0Exceptional
(65 Reviews)
6 Bedrooms
3 Baths
12 Guests
3500 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $1,981/Night
7 Nights - US $13,864
Condo
10.0Exceptional
(43 Reviews)
3 Bedrooms
1 Bath
10 Guests
1940 ft²
- Balcony/Terrace
- Kitchen
- Internet
- Child Friendly
US $2,013/Night
7 Nights - US $14,091
Villa
9.8Exceptional
(59 Reviews)
2 Bedrooms
2 Baths
8 Guests
1200 ft²
- Hot Tub
- Parking
- Pool
- Spa
US $1,533/Night
7 Nights - US $10,732
Wheelchair Accessible Vacation Homes in Kahakuloa
Over 4996+ Wheelchair Accessible Vacation Homes in or Near Kahakuloa
Condo
10.0Exceptional
(150 Reviews)
2 Bedrooms
2 Baths
4 Guests
1150 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $754/Night
7 Nights - US $5,275
Bed & Breakfast
- Lahaina
- ·
- Historic Lahaina Front Street
- 1.48 mi to center
9.5Exceptional
(192 Reviews)
1 Bedroom
1 Bath
2 Guests
258.33 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $129/Night
7 Nights - US $903
Condo
10.0Exceptional
(16 Reviews)
1 Bedroom
1 Bath
- Hot Tub
- Parking
- Pool
- Spa
US $575/Night
7 Nights - US $4,025
Condo
10.0Exceptional
(147 Reviews)
2 Bedrooms
2 Baths
6 Guests
1100 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $1,389/Night
7 Nights - US $9,724
Hotel
8.8Fabulous
(11 Reviews)
4 Baths
1006.43 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $157/Night
7 Nights - US $1,099
Condo
10.0Exceptional
(144 Reviews)
2 Bedrooms
1 Bath
5 Guests
851 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $503/Night
7 Nights - US $3,524
Condo
10.0Exceptional
(112 Reviews)
3 Bedrooms
3 Baths
9 Guests
2050 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $1,200/Night
7 Nights - US $8,400
Condo
10.0Exceptional
(95 Reviews)
2 Bedrooms
2 Baths
4 Guests
1400 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $719/Night
7 Nights - US $5,035
Condo
10.0Exceptional
(92 Reviews)
3 Bedrooms
3 Baths
8 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $1,054/Night
7 Nights - US $7,380
Kahakuloa Villas and Airbnb Homes Under $200
Over 253+ Kahakuloa Villas and Airbnb Homes Under $200
Condo
10.0Exceptional
(11 Reviews)
1 Bedroom
1 Bath
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $190/Night
7 Nights - US $1,329
House
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
10.76 ft²
- Parking
- Pool
- Internet
- Child Friendly
US $193/Night
7 Nights - US $1,351
Condo
9.4Exceptional
(8 Reviews)
1 Bedroom
1 Bath
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $106/Night
7 Nights - US $745
House
10.0Exceptional
(9 Reviews)
2 Bedrooms
1 Bath
3 Guests
- Child Friendly
US $161/Night
7 Nights - US $1,125
House
- Wailuku
- ·
- Waihee-Waiehu
- 1.02 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
3 Baths
8 Guests
2002.09 ft²
- Parking
- Internet
- Child Friendly
Barbecue/Outdoor Cooking
US $111/Night
7 Nights - US $777
House
10.0Exceptional
(5 Reviews)
1 Bedroom
1 Bath
3 Guests
- Child Friendly
US $178/Night
7 Nights - US $1,247
House
10.0Exceptional
(5 Reviews)
1 Bedroom
2 Baths
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $177/Night
7 Nights - US $1,237
House
9.6Exceptional
(4 Reviews)
1 Bedroom
1 Bath
1 Guest
- Air Conditioner
- Child Friendly
Security/Safety
US $186/Night
7 Nights - US $1,304
Condo
9.2Exceptional
(51 Reviews)
1 Bedroom
1 Bath
3 Guests
560 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $187/Night
7 Nights - US $1,309
Instantly Bookable Vacation Homes in Kahakuloa
Over 7591+ Instantly Bookable Vacation Homes in or Near Kahakuloa
Cottage
10.0Exceptional
(149 Reviews)
2 Bedrooms
2 Baths
4 Guests
1700 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $452/Night
7 Nights - US $3,162
Condo
- Lahaina
- ·
- Historic Lahaina Front Street
- 0.72 mi to center
10.0Exceptional
(161 Reviews)
1 Bedroom
1 Bath
5 Guests
1100 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $414/Night
7 Nights - US $2,899
Condo
10.0Exceptional
(131 Reviews)
2 Bedrooms
2 Baths
8 Guests
2100 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $939/Night
7 Nights - US $6,574
Condo
10.0Exceptional
(86 Reviews)
1 Bedroom
2 Baths
4 Guests
938 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $484/Night
7 Nights - US $3,387
House
- Paia
- ·
- Spreckelsville
- 0.10 mi to center
10.0Exceptional
(77 Reviews)
3 Bedrooms
3 Baths
6 Guests
2350 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $1,776/Night
7 Nights - US $12,433
Condo
10.0Exceptional
(75 Reviews)
1 Bedroom
2 Baths
4 Guests
1100 ft²
- Parking
- Pool
- Spa
- Ocean View
US $744/Night
7 Nights - US $5,206
Condo
10.0Exceptional
(67 Reviews)
2 Bedrooms
1 Bath
6 Guests
915 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $545/Night
7 Nights - US $3,815
Condo
10.0Exceptional
(62 Reviews)
1 Bedroom
1 Bath
2 Guests
600 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $593/Night
7 Nights - US $4,153
Condo
9.8Exceptional
(397 Reviews)
1 Bedroom
1 Bath
3 Guests
400 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $310/Night
7 Nights - US $2,171
Book a Last Minute Place to Stay in Kahakuloa
About Kahakuloa Vacation Rentals
Explore more than 12634 vacation rentals available in Kahakuloa. These accommodations, including vacation homes and HawaiiVillas properties, boast excellent amenities and exceptional value, blending comfort and luxury. Enjoy spaciousness and convenience at a HawaiiVillas property in Kahakuloa.
Looking for last-minute deals or the best available offers on cottages, condos, private villas, and large vacation homes? With HawaiiVillas in Kahakuloa, you can effortlessly compare various options with a simple click. Whether you seek properties with swimming pools, hot tubs, pet-friendly policies, or expansive master suites with large screen TVs, you'll find vacation rentals by owner (RBOs) and other popular Airbnb-style accommodations near Kahakuloa. The average room size in accommodations near Kahakuloa is 839.57 ft². Prices average US $1,305 per night.
HawaiiVillas streamlines and secures your search for vacation rentals in Kahakuloa, often offering savings of 30-40% compared to hotel prices. Start your search today and book with confidence.
Show more
Show less
Top Rental Accommodation Types in Kahakuloa
| Type | Count |
|---|---|
| Holiday Apartments | 2131 |
| Vacation Homes | 1183 |
| Villas | 557 |
| Cottages | 27 |
Use these Quick Filters to Find a Vacation Rental in Kahakuloa
★ Pro Tip: HawaiiVillas simplifies comparison of top listings across various online vacation rental platforms like Booking.com and others. Use the Advanced Filter feature to switch effortlessly between HawaiiVillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, property types, cancellation policies, prices, and more. These tools streamline the search for your ideal accommodation for your next vacation in Kahakuloa.
Weather in Kahakuloa, HI
View the weather forecast for Kahakuloa before booking your Kahakuloa Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Kahakuloa, HI
HawaiiVillas offers a wide selection of top attractions nearby Kahakuloa . Research things to do on your vacation before you visit Kahakuloa.
Frequently Asked Questions About Kahakuloa?
What are the top vacation rentals in Kahakuloa?
Currently, HawaiiVillas lists over 12634 properties in the Kahakuloa area for 2026, with more being added continuously. By consolidating listings from various websites, HawaiiVillas provides a wide selection of top properties in Kahakuloa.
- DISCOUNT Sept/Oct/Nov/Dec - Oceanfront Studio!
- HOKULANI 436-CORNER UNIT 2BD/2BA w/OCEAN & MOUNTAIN VIEWS,505SQFT LANAI BALCONY
- Mahana at Kaanapali, Spectacular Oceanfront, Amazing Sunsets & Sea Life Unit1014
- Direct Oceanfront Maui Studio,Romantic,Breathtaking View from Huge Private Lanai
- Maui Resort Rentals: Hokulani 605 – Premier 6th-Floor Oceanview Penthouse | Closest 2BR Column to the Ocean!
- Our home burned down - NOT our VACATION RENTAL! It's our income! Come and enjoy!
- The Ultimate Oceanfront Experience. Tropical Luxury And Spectacular View
- Breathtaking Oceanfront/Beachfront Corner View Luxury on Kaanapali Beach 2B 2B
- 3BD Oceanfront Retreat w/Lanai, Floor-to-Ceiling Views & Modern Kitchen - Honua Kai 825
- On Top of Water View-5 Stars-Pohailani 303
How many vacation rentals have private pools in Kahakuloa?
Discover 402 vacation rentals featuring private pools near Kahakuloa. Highly-rated HawaiiVillas properties with swimming pool access include:
- 6th Floor Ocean Front, king bed, partial kitchen Sleeps 3, newly remodeled
- Lahaina-2bd/2bath at Aina Nalu next to Pool
- Ocean View Suite at Royal Kahana
- Lahaina Baby Beach House/Pool. 1 Minute walk to beach. Grand Re-Opening
Which vacation homes in Kahakuloa are best for families?
If you're searching for a family-friendly vacation residence in Kahakuloa, explore one of these highly-rated properties, all praised for their excellent reviews among families or groups visiting Kahakuloa:
- Kuleana 407 Ground Oceanfront - No Additional Owner Fees and Discounts Available
- Kapalua Golf Villa 14T Villa
- Puunoa - CoralTree Residence Collection
How many Hawaii.Villas vacation rentals are available in Kahakuloa?
At present, HawaiiVillas showcases more than 12634 properties available in the Kahakuloa area for 2026, with new listings added regularly. By aggregating listings from multiple sources, HawaiiVillas offers a diverse range of premier properties in Kahakuloa.
People Also Ask
Map
