Kalawao County Holiday Rentals: Short-Term Accommodations for Rent

A coastal landscape with steep cliffs and a calm sea.

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Our top choices for Kalawao County holiday rentals

A coastal landscape with a sandy beach, clear turquoise waters, and green hills in the background.

1. sweet escape - Moloka'i living

Kaunakakai

Frank

HK$2,948 total

includes taxes & fees

9 Sept - 10 Sept

A well-maintained lawn with palm trees and outdoor seating areas, overlooking a body of water.

2. COCONUT COVE CONDO–Molokai Shores 303

Kaunakakai

Mary C.

HK$2,893 total

includes taxes & fees

9 Sept - 10 Sept

A tropical view with a table set with a fruit plate, a dragon fruit, and a mug.

3. September Sale! Molokai Island Retreat

Kaunakakai

PATRICK C.

HK$2,571 total

includes taxes & fees

21 Sept - 22 Sept

A resort with multiple buildings, a swimming pool, and a view of the ocean.

4. 2BR Ocean View w/Lanai and Kitchen - Molokai Shores 217

Kaunakakai

Ryan

HK$5,448 total

includes taxes & fees

3 Oct - 4 Oct

A resort with a pool, palm trees, and a view of the ocean.

5. Modern Oceanfront W/Lanai and WiFi–Molokai Shores

KAUNAKAKAI

Kevin

HK$4,579 total

includes taxes & fees

9 Sept - 10 Sept

A coastal view with a rocky shoreline, palm trees, and a clear sky.

6. Efficiency

Maunaloa

Sabina B.

HK$2,158 total

includes taxes & fees

9 Sept - 10 Sept

7. Ocean Front-Unobstructed Views- Beautiful Upgraded Condo

Maunaloa

Tristan

HK$2,669 total

includes taxes & fees

9 Sept - 10 Sept

A coastal beach with rocky shoreline, sandy beach, and houses in the background.

8. Ke Nani Kai Unit 156- More Molokai

Maunaloa

Lisa W.

HK$3,213 total

includes taxes & fees

9 Sept - 10 Sept

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

9. Napili Shores Maui by OUTRIGGER

Lahaina

Diana

HK$2,296 total

includes taxes & fees

11 Sept - 12 Sept

A cozy living room with a sofa, chairs, and a dining area.

10. Rustic retreat with panoramic views at Pu'u O Hoku Ranch

Kaunakakai

"The Sunrise Cottage, and indeed the entire Pu'u o Hoku Ranch is a hidden gem. We may be biased since we held our wedding celebration here back in 2016, but to return ten years later and find it even more lovely was a delight. Molokai isn't for everyone, but to those drawn to it a wonderful adventure awaits. We'll return as often as they'll have us. Mahalo to all those who made our stay so wonderful."

Scott J.

HK$6,254 total

includes taxes & fees

19 Sept - 20 Sept

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

11. Napili Village Hotel

Lahaina

Alysson E

HK$1,757 total

includes taxes & fees

15 Sept - 16 Sept

A beachfront hotel with multiple buildings, a sandy beach, and palm trees.

12. Garden View Second Floor Studio at Napili Shores – Steps to Napili Bay D229

Lahaina

Lynda M.

HK$5,994 total

includes taxes & fees

20 Sept - 21 Sept

A resort pool area with palm trees, lounge chairs, and a view of the ocean.

13. Royal Kahana Resort Unit 218 - Oceanview Studio near Beach, Pool. A/C

Lahaina

Michelle R.

HK$3,090 total

includes taxes & fees

11 Sept - 12 Sept

A balcony with a table set for two, overlooking a beach with palm trees and a view of the ocean.

14. Luxury Oceanfront Studio at Napili Shores A203 View of Lanai and Molokai

Lahaina

Bob D.

HK$6,755 total

includes taxes & fees

20 Sept - 21 Sept

A tropical beach with palm trees and clear turquoise water.

15. Fabulous Oceanfront Retreat at Kuleana 622 3rd Floor Condo A/C

Lahaina

Bob E.

HK$6,138 total

includes taxes & fees

10 Sept - 11 Sept

A tropical resort with palm trees, a beach view, and a thatched-roof building.

16. Gorgeous Napili Shores G258 Newly remodeled Studio Condo

lahaina

Elaine E.

HK$6,090 total

includes taxes & fees

14 Sept - 15 Sept

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

17. Aston Kaanapali Shores

Lahaina

Shad

HK$1,977 total

includes taxes & fees

30 Sept - 1 Oct

A resort with multiple buildings, a swimming pool, and a rocky shoreline with clear blue water.

18. Ultra Modern/Coastal-Remodel, Oceanview, AC - Napili Shores G154

Lahaina

Stephen T.

HK$6,090 total

includes taxes & fees

22 Sept - 23 Sept

A beach with palm trees and rocky outcrops at sunset.

19. 🐬Whales and The Waves | Discount | Beachfront | Oceanview | Pool | AC🐬

Lahaina

Simona M.

HK$2,791 total

includes taxes & fees

30 Sept - 1 Oct

A beach view with lounge chairs and a clear sky.

20. Napili Sunset on the Beach

Lahaina

Chris

HK$2,617 total

includes taxes & fees

9 Sept - 10 Sept

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Top Kalawao County Hotel Reviews

Aston Kaanapali Shores

10/10 Excellent

"The staff were very helpful, hotel very clean!"

Napili Shores Maui by OUTRIGGER

8/10 Good

"A no frills stay but excellent location. Grounds are pretty, rooms and buildings don’t do much for aesthetics but they’re clean (when you arrive...) I really hated that they only clean rooms in between guests. We needed to go to the front desk for towels regularly, and wished our sheets were changed within our 5 day stay. The staff on deck for activities was friendly and knowledgeable, which was super convenient. The location is FANTASTIC. The beach is calm, very relaxing. Great for snorkeling, easy to walk to a nicer resort for dinner. We visited lots of different beaches but nothing beat our little walk from the hotel at sunset."

Hilton Vacation Club Ka'anapali Beach Maui

10/10 Excellent

"Great property! Beautiful grounds with lots of areas to explore. Easy beach access with a beautiful beach area for taking a short dip or snorkeling to see al the amazing fish. Turtles in the surf outside the windows. The snack bar has really amazing food too! One of the best things is there are sooo many great food options within a very short walk. And the grocery store has great Poke & Sushi! We also love the music on the patio with the beautiful Hawaiian sunsets! Bring a lots of sunscreen and a container for pool water/beverages. You can also bring blow up pool toys."

Napili Kai Beach Resort

8/10 Good

"We stayed in Unit 202 from August 29 through September 5. While the property is approximately 65 years old, the furniture in the unit appeared just as dated. I understand that this is a timeshare, but at nearly $1,000 per night, the owner should seriously consider updating the furnishings. At that price, guests should expect a more modern and comfortable interior. On a positive note, the bed was very comfortable, the property’s location was excellent, and the staff was wonderful. A special thank-you to Kim, the concierge, who was absolutely incredible and made our experience much better. Would I stay here again? Probably not, mainly because the price does not reflect the condition and age of the furnishings."

The Ritz-Carlton Maui, Kapalua

10/10 Excellent

"Stay was comfortable staff very attentive & accomodating, We stayed in the fire lanai deluxe room (ocen-view) it was amazing. Be prepared to get your steps in going from your room to the main lobby if you’re staying over there, but you will have easy access to the pool and the exclusion will be very much appreciated. Def worth it!!"

Sands of Kahana

10/10 Excellent

"Very clean and spacious room. We asked for an ocean view and got not only a room with an amazing view of the ocean, but also a penthouse suite. The room had an incredible view of the beach from the living room, kitchen, master bedroom, not to forget the main balcony. The second balcony had a nice view of the mountains. The property was clean, quiet, and very accommodating. We really enjoyed our stay."

Room 1

Change your mind

Treat yourself

Be picky

Our top choices for Kalawao County holiday rentals

1. sweet escape - Moloka'i living

2. COCONUT COVE CONDO–Molokai Shores 303

3. September Sale! Molokai Island Retreat

4. 2BR Ocean View w/Lanai and Kitchen - Molokai Shores 217

5. Modern Oceanfront W/Lanai and WiFi–Molokai Shores

6. Efficiency

7. Ocean Front-Unobstructed Views- Beautiful Upgraded Condo

8. Ke Nani Kai Unit 156- More Molokai

9. Napili Shores Maui by OUTRIGGER

10. Rustic retreat with panoramic views at Pu'u O Hoku Ranch

11. Napili Village Hotel

12. Garden View Second Floor Studio at Napili Shores – Steps to Napili Bay D229

13. Royal Kahana Resort Unit 218 - Oceanview Studio near Beach, Pool. A/C

14. Luxury Oceanfront Studio at Napili Shores A203 View of Lanai and Molokai

15. Fabulous Oceanfront Retreat at Kuleana 622 3rd Floor Condo A/C

16. Gorgeous Napili Shores G258 Newly remodeled Studio Condo

17. Aston Kaanapali Shores

18. Ultra Modern/Coastal-Remodel, Oceanview, AC - Napili Shores G154

19. 🐬Whales and The Waves | Discount | Beachfront | Oceanview | Pool | AC🐬

20. Napili Sunset on the Beach

Find holiday rentals that suit your style

Top Kalawao County Hotel Reviews

Aston Kaanapali Shores

Napili Shores Maui by OUTRIGGER

Hilton Vacation Club Ka'anapali Beach Maui

Napili Kai Beach Resort

The Mauian - Boutique Beach Studios on Napili Bay

Kahana Beach Vacation Club

The Ritz-Carlton Maui, Kapalua

Napili Village Hotel

Sands of Kahana