Kahakuloa Vacation Rentals from $239: Search Short-Term Rentals

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Our top choices for Kahakuloa vacation rentals

A beach with clear blue water, palm trees, and a resort in the background.

1. Napili Village Hotel

Lahaina

Alysson E

$202 nightly

Oct 19 - Oct 20

Total with taxes and fees

A tropical garden with a waterfall, lush greenery, and a gazebo.

2. Aston Kaanapali Shores

Lahaina

Roopa Rani

$216 nightly

Sep 24 - Sep 25

Total with taxes and fees

A beach with clear turquoise water, sandy shore, palm trees, and a resort building in the background.

3. Napili Shores Maui by OUTRIGGER

Lahaina

Diana

$295 nightly

Sep 24 - Sep 25

Total with taxes and fees

A beach view with lounge chairs and a clear sky.

4. Napili Sunset on the Beach

Lahaina

Beverly

$281 nightly

Sep 24 - Sep 25

Total with taxes and fees

A beach with clear turquoise water, a sandy shore, and some greenery.

5. Unit 23 Waena Inn - Maui Private Suite

Wailuku

Suzan F.

$280 nightly

Sep 24 - Sep 25

Total with taxes and fees

A wooden deck with a chair, surrounded by lush tropical vegetation and a clear blue sky.

6. Yonegan Maui Getaways - Haiku

Haiku

Matt

$283 nightly

Oct 4 - Oct 5

Total with taxes and fees

A staircase leading to a stone wall with a 'WELCOME' sign, a framed mirror, and potted plants.

7. Unit 22 Waena Inn - Maui Private Suite

Wailuku

Claire R.

$273 nightly

Sep 28 - Sep 29

Total with taxes and fees

An aerial view of a resort with multiple buildings, solar panels, a swimming pool, and a view of the ocean.

8. Updated Studio, AC, steps to beach

Lahaina

MeMe C.

$348 nightly

Oct 6 - Oct 7

Total with taxes and fees

A swimming pool with lounge chairs and umbrellas, surrounded by palm trees.

9. Napili Shores 1BR Condo – 2-Min Walk to Beach, Pools, AC & No Resort Fees

Lahaina

Shannon D.

$451 nightly

Sep 29 - Sep 30

Total with taxes and fees

A tropical garden with a waterfall, a gazebo, and lush vegetation.

10. Charming Studio at Oceanfront Ka’anapali Shores | Pools, Beach Access, AC

Lahaina

Michael

$682 nightly

Sep 26 - Sep 27

Total with taxes and fees

A beach with clear blue water, rocky shore, and palm trees.

11. Condo w/ Lanai at Beginning of Road to Hana!

Paia

Kiana C.

$359 nightly

Oct 5 - Oct 6

Total with taxes and fees

A balcony table with a decorative centerpiece, overlooking a beach with palm trees and a clear sky.

12. Beautiful Ocean and Outer Island Views! See Whales in season!

Lahaina

Jasdeep Singh

$350 nightly

Oct 6 - Oct 7

Total with taxes and fees

A tropical garden with palm trees and a view of the ocean.

13. Aloha Hale Ocean View Maui Condo In Ocean Front/Beach Resort Swim with Turtles!

Lahaina

Eric L.

$417 nightly

Sep 27 - Sep 28

Total with taxes and fees

A beach with clear turquoise waters, rocky shoreline, and distant mountains under a clear sky.

14. Hale Nihi - Paia, Maui

Paia

Chameil H.

$399 nightly

Sep 24 - Sep 25

Total with taxes and fees

A beachfront hotel with clear turquoise waters, lush greenery, and palm trees.

15. Direct Oceanfront ground floor - Kuleana 706

Lahaina

Margarita R.

$771 nightly

Sep 24 - Sep 25

Total with taxes and fees

A balcony with a glass table, a blue chair, and a view of the ocean and palm trees.

16. Top floor! Direct view! Sleeps 6! Highly Desirable! #213

Lahaina

"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Aloha, we had the most amazing experience all around as a family of 5. Valerie went above and beyond in the front office and was so friendly and kind. She suggested many places to eat and snorkel. David kept the property looking great and was...

Ryan T.

$525 nightly

Sep 24 - Sep 25

Total with taxes and fees

A beachside hotel with lounge chairs and umbrellas, a pool, and a rocky shoreline.

17. Cute and Cozy Ground Floor! Beach access! Great Location! #113

Lahaina

Kiele P.

$413 nightly

Oct 4 - Oct 5

Total with taxes and fees

A round table with two chairs on a balcony overlooking a clear blue sea and a distant mountain.

18. Direct Ocean Front~Kaanapali Beach~West Maui Paradise Welcomes You!

Lahaina

Anthony P.

$355 nightly

Sep 24 - Sep 25

Total with taxes and fees

A two-story house with a balcony, surrounded by well-maintained lawns and tropical vegetation.

19. Yonegan Maui Getaways - Haiku - Unit 6

Haiku-Pauwela

Bryan

$310 nightly

Sep 29 - Sep 30

Total with taxes and fees

A view of a beach with palm trees and a sailboat on the water.

20. The Whaler Resort Kaanapali Beach

Kannapali Beach Area

Sam

$561 nightly

Oct 5 - Oct 6

Total with taxes and fees

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Top Kahakuloa Hotel Reviews

The Ritz-Carlton Maui, Kapalua

10/10 Excellent

"This hotel is very nice and the scenery is beautiful. It’s a little tucked-away, so it is very quiet and peaceful. The staff was mostly great- ironically the one person that was kind of rude was at the concierge desk. The wait staff and housekeeping staff was great. We would stay here again. If I were to nitpick something it would be that some of the room service food was disappointing. It seemed to have sat a while prior to delivery. Overall, this was expensive, but probably worth the expense given how nice the property was."

Sheraton Maui Resort & Spa

10/10 Excellent

"Beautiful well maintained property on the best part of Kanapali beach. Very nice pool and beach. Very friendly staff. Would highly recommend an ocean front room. It is worth the extra money. Very close to Whalers Village with shops and some great dining options. There is a free shuttle from the hotel. Car rental available at the hotel. Dining options are good but pricy. Try other options for breakfast as it was good but not worth $100.00 for 2. Would recommend this hotel while in Maui"

Hilton Vacation Club Ka'anapali Beach Maui

8/10 Good

"I asked for late check out on 16 Sep but was told they could not because they already had the maids scheduled. The day before I was in the lobby and I heard the person at the front desk asking if they wanted a late checkout. We just wanted to checkout by noon since our flight was at 5pm. That is a long time to wait at the airport. Also, I think it would be a plus to offer breakfast. Thank you"

Hyatt Regency Maui Resort & Spa

10/10 Excellent

"We had an amazing stay at the Hyatt in Maui and would absolutely come back. The hotel is beautiful, modern, very clean, and surrounded by gorgeous tropical gardens. The lobby is stunning, and the staff was extremely kind and welcoming from the moment we arrived. We were even greeted with a Hawaiian kukui nut necklace. We traveled with our 1-year-old and found the resort very family-friendly. We used the kids’ pools constantly, and there are also several other pools and a lazy river. We added the breakfast buffet to our stay, which was worth it because we did not have to pay separately every morning. There was a great variety, everything was clean and fresh, and our baby ate so well because there were many options. A few things to know: self-parking is about $50 per day and valet is about $55. Cocktails and drinks are around $20 each, so be prepared for a larger resort bill at the end of your stay. The location is beautiful, but many attractions are far away. Most places required at least 30 minutes of driving, the airport was around 50 minutes away, and Road to Hana took us close to 3 hours each way. A rental car is definitely necessary. Overall, we loved the hotel, the staff, the amenities, and how family-friendly it was. We would absolutely stay here again."

The Whaler Resort Kaanapali Beach

8/10 Good

"Good condo but refrigerator and faucet maintenance issues. Property misrepresented housekeeping. No bedding change in 12 days. Was told they would give us extra sheets for a cost but would not make the bed. (We washed and remade the bed ourselves). Also was told on site that “housekeeping” every fourth day to change towels, sweep and run dishwasher but they only came in once in 12 day stay. Luckily we requested extra towels and the condo had a washer/dryer. Our idea of “housekeeping” certainly differed from that of the property. Great location. I just wish they had been true to their word and their Expedia posting."

Find out more about Kahakuloa

Everything you need to know about Kahakuloa vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Kahakuloa vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Kahakuloa vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Kahakuloa vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Kahakuloa. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Kahakuloa in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $239 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Kahakuloa rentals

At Expedia, we put the best Kahakuloa vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Kahakuloa rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Kahakuloa vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Kahakuloa. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Frequently asked questions

Can I find a vacation rental in Kahakuloa?

Yes, you can find vacation rentals near well known local attractions in Kahakuloa, or you can choose a more secluded option if you'd like a relaxing place to stay. Kahakuloa is known for its beaches and restaurants. Make sure you have time to check out the sporting events while you're in the area.

What's the top vacation rental that Kahakuloa has to offer?

Yonegan Maui Getaways - Haiku : This vacation home rental outside of Kahakuloa is located near the beach and has a hot tub, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a microwave, a coffee maker, and kitchenware.

What’s there to see and do in Kahakuloa?

Explore the area and family-friendly sights such as Hawaii Nature Center of Iao Valley, or get out into nature at a spot like Kahakuloa Beach. You’ll find favorite places to visit like Kaanapali Beach and Napili Bay in the larger area.

What’s a vacation rental in Kahakuloa like?

A vacation rental is a private property where you can stay for a couple of days or more in Kahakuloa. Vacation rentals offer extras such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for a family getaway.

Kahakuloa Vacation Rentals

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Check prices for these dates

Our top choices for Kahakuloa vacation rentals

1. Napili Village Hotel

2. Aston Kaanapali Shores

3. Napili Shores Maui by OUTRIGGER

4. Napili Sunset on the Beach

5. Unit 23 Waena Inn - Maui Private Suite

6. Yonegan Maui Getaways - Haiku

7. Unit 22 Waena Inn - Maui Private Suite

8. Updated Studio, AC, steps to beach

9. Napili Shores 1BR Condo – 2-Min Walk to Beach, Pools, AC & No Resort Fees

10. Charming Studio at Oceanfront Ka’anapali Shores | Pools, Beach Access, AC

11. Condo w/ Lanai at Beginning of Road to Hana!

12. Beautiful Ocean and Outer Island Views! See Whales in season!

13. Aloha Hale Ocean View Maui Condo In Ocean Front/Beach Resort Swim with Turtles!

14. Hale Nihi - Paia, Maui

15. Direct Oceanfront ground floor - Kuleana 706

16. Top floor! Direct view! Sleeps 6! Highly Desirable! #213

17. Cute and Cozy Ground Floor! Beach access! Great Location! #113

18. Direct Ocean Front~Kaanapali Beach~West Maui Paradise Welcomes You!

19. Yonegan Maui Getaways - Haiku - Unit 6

20. The Whaler Resort Kaanapali Beach

Find vacation rentals that suit your style

Top Kahakuloa Hotel Reviews

The Ritz-Carlton Maui, Kapalua

Find out more about Kahakuloa

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