Halena Holiday Rentals

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Halena

Castle at Moloka'i Shores

3.0 star property
7.0 out of 10, Good, (156)
"I arrived at night and didn’t realize there wasn’t a front desk. My phone had no signal, so I couldn’t make a call. A guy who lived there was outside and let me borrow his phone, so I was then able to call and get instructions. There was apparently a key box, and they gave me the code. However, I couldn’t figure out how to open the key box, so I went back to that same guy, and, between the two of us, we figured it out. It was very frustrating getting inside, but once I did, I really liked...
Castle at Moloka'i Shores

ALOHA OceanFront Condo w.A/C, Molokai, Hawaii Watch whales Dec-April.

9.4 out of 10, Exceptional, (86)
"Great location and we really enjoyed having the A/C. The property manager was very nice and responsive. Would recommend!"
ALOHA OceanFront Condo w.A/C, Molokai, Hawaii Watch whales Dec-April.

Exceptional Molokai vacation condo - Steps from Hawaii's longest beach

9.0 out of 10, Wonderful, (53)
"From the helpfulness of both Melissa and Matthew the condo mgmt. to all the fellow guest and owners we were wonderfully welcomed like family. Beautiful pool and hot tub area in a well maintained and meticulously landscaped and that was laid out to have ultimate privacy to all units. We felt the safest of all places that we ever stayed and everyone on entire island was friendly and helpful wherever we visited!"
Exceptional Molokai vacation condo - Steps from Hawaii's longest beach

Peaceful retreat, ocean view, desired 2nd floor, WIFI

9.2 out of 10, Wonderful, (127)
"Berit is the most wonderful host that I have ever had the pleasure of meeting and working with for my 11 day stay. This condo, its stunning property, and it breathtaking view are definitely a vacationers absolutel dream! Thank you for sharing your paradise Brit! "
Peaceful retreat, ocean view, desired 2nd floor, WIFI

Kepuhi Beach Resort Condo! Relax at a family condo that sleeps 4 w/ ocean view..

9.2 out of 10, Wonderful, (13)
"This condo was perfect! Absolutely beautiful. Kitchen was well equipped, had everything we needed. Very comfortable. Host was exceptionally helpful, very easy to communicate with. Absolutely will stay here again. Perfect way to enjoy the relaxing Molokai! "
Kepuhi Beach Resort Condo! Relax at a family condo that sleeps 4 w/ ocean view..

Beautiful oceanfront condo with lanai, pool, beach access, & washer/dryer

9.8 out of 10, Exceptional, (23)
"Loved staying here. It doesn’t get much more peaceful than this. The wrap around lanai was where we spent most of our time. The property manager went out of her way to ensure we’d be comfortable. I’ll definitely book again. "
Beautiful oceanfront condo with lanai, pool, beach access, & washer/dryer

The Ultimate Oceanfront Penthouse - 'Hale No Ka Oi'

9.8 out of 10, Exceptional, (80)
"All was great except that I should have asked if there was air conditioning in the unit. The heat and humidity made it uncomfortable other than early in the mornings. But overall, the unit was great."
The Ultimate Oceanfront Penthouse - 'Hale No Ka Oi'

Kepuhi Beachfront Lofted Studio w/pool & BBQ. Remote and Private. Hawaii's best.

8.8 out of 10, Excellent, (11)
"The pTio needed some cleaning, but everything wlse was great!"
Kepuhi Beachfront Lofted Studio w/pool & BBQ. Remote and Private. Hawaii's best.

Lovely 2 bdr 2 bath condo in prestigious Paniolo Hale, 4min walk to Kepuhi Beach

9.4 out of 10, Exceptional, (53)
"We loved this place! The screened in porch was incredible and the place was perfect for our family to have time to be together and play games. There were four large beds and the place was tropical and minutes from the beach. We will stay there again. Highly recommended!"
Lovely 2 bdr 2 bath condo in prestigious Paniolo Hale, 4min walk to Kepuhi Beach

Kaunakakai Vacation Rental w/ Pool Access & A/C!

10.0 out of 10, Exceptional, (3)
"The property is very close to town (one mile), the interior of the unit was clean, new and with modern appliances. I would definitely stay again. I liked the fridge/freezer, and dishwasher. There are many quirky features to adjust to. Needlessly complex for a rental unit, motion sensitive on/off for the kitchen faucet, and the lighting with dimmer that was more complex than on/off dim. Table lamp upstairs required tapping the base to control on/off/light level. Previous user had loosened the...
Kaunakakai Vacation Rental w/ Pool Access & A/C!

Laid back Molokai beach-hideaway

10.0 out of 10, Exceptional, (50)
"Lovely vacation spot, tranquil, quiet, clean and well appointed."
Laid back Molokai beach-hideaway

Molokai Oceanfront large beautiful home - Gorgeous secluded beaches out front!

10.0 out of 10, Exceptional, (13)
"A perfectly located home just minutes walk to the beach. Beautiful indoor/outdoor living, with ceiling fans in every room. A fully equipped kitchen with coffee provided. Everything we needed for a wonderful relaxing vacation. "
Molokai Oceanfront large beautiful home - Gorgeous secluded beaches out front!

Secluded Corner Condo w/Nature Views, Wrap-Around Lanai, Free WiFi, Shared Pool

8.8 out of 10, Excellent, (23)
"Location was amazing. Beautiful area. Jungle style. Love it"
Secluded Corner Condo w/Nature Views, Wrap-Around Lanai, Free WiFi, Shared Pool

Kepuhi Beach Resort

3.0 star property
6.2 out of 10, (26)
"Just peaceful, wonderful people on Molokai. Beautiful place. Mahalo "
Kepuhi Beach Resort

Ke Nani Kai Unit 156- More Molokai

9.4 out of 10, Exceptional, (45)
"This is a beautiful condo. Clean, safe and updated. It has all amenities stated in the listing so you can hang out all day or enjoy the island. Highly recommend this unit!"
Ke Nani Kai Unit 156- More Molokai

Beautiful Ocean-View unit with easy beach access. Ask about vehicle option.

10.0 out of 10, Exceptional, (1)
"Well stocked and clean. Very comfortable and relaxing. Easy access to walking, biking, hiking. Had a good stay."
Beautiful Ocean-View unit with easy beach access. Ask about vehicle option.

Maunaloa Vacation Rental Studio - Walk to Beach!

8.0 out of 10, Very good, (2)
"I was surprised to this unit had an ocean view. Lots of staff keeping up the grounds. Very safe. The place could easily sleep 3. Parking was easy. Use front row. Back row is for employees. They have a bbq onsite. I used mine and they asked me not to. Showed me the location about 200 feet in front of the unit in bushes"
Maunaloa Vacation Rental Studio - Walk to Beach!

sweet escape - Moloka'i living

9.4 out of 10, Exceptional, (22)
"The location of the condo and how it was stocked was really nice. The description of it having air conditioning was not clear. Only the bedroom has air, leaving the rest of the condo uninhabitable and unusable for the evening hours. Being on the 3rd floor, the heat was unbearable - impossible for the loft area in the afternoons/evenings. The weather was mid 80s while we were there, but the condo stayed well into the 90s until late. I got this condo because I enjoy cooking. I was only able to do...
sweet escape - Moloka'i living

Kepuhi Beachfront Lofted Studio w/pool & BBQ. Remote and Private. Hawaii's best.

9.6 out of 10, Exceptional, (10)
"We love the quiet of Molokai and so staying there is always a pleasure. This condo has been remodeled and is pleasantly appointed in Hawaiian theme. The loft king bed is very comfortable. The stairs are spiral so one needs to be agile to manage them. "
Kepuhi Beachfront Lofted Studio w/pool & BBQ. Remote and Private. Hawaii's best.

Newly Upgraded- One Bedroom Ocean Front Condo/Spectacular Sunset View

9.4 out of 10, Exceptional, (119)
"Sweet little condo with all you could need! Clean, and comfy! The grounds are beautifully kept and the view and pool are unmatched! We chatted with so many welcoming islanders and made friends with all the unexpected wildlife! Thank you Dorothy for a great stay! "
Newly Upgraded- One Bedroom Ocean Front Condo/Spectacular Sunset View
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Halena
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Halena you may be interested in

Castle at Moloka'i Shores

3.0 star property
7.0 out of 10, Good, (156)
"I arrived at night and didn’t realize there wasn’t a front desk. My phone had no signal, so I couldn’t make a call. A guy who lived there was outside and let me borrow his phone, so I was then able to call and get instructions. There was apparently a key box, and they gave me the code. However, I couldn’t figure out how to open the key box, so I went back to that same guy, and, between the two of us, we figured it out. It was very frustrating getting inside, but once I did, I really liked...
Castle at Moloka'i Shores

Hotel Moloka'i

3.0 star property
8.2 out of 10, Very good, (605)
"Excellent hotel with great restaurant and bar beautiful views"
The price is AU$485
includes taxes & fees
30 Nov - 1 Dec
Hotel Moloka'i

ALOHA OceanFront Condo w.A/C, Molokai, Hawaii Watch whales Dec-April.

9.4 out of 10, Exceptional, (86)
"Great location and we really enjoyed having the A/C. The property manager was very nice and responsive. Would recommend!"
ALOHA OceanFront Condo w.A/C, Molokai, Hawaii Watch whales Dec-April.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find a holiday rental in Halena?

Yes, there are holiday rentals close to the most popular sights in Halena, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Halena has to offer?

Beautiful oceanfront condo with lanai, pool, beach access, & washer/dryer: This holiday home rental outside of Halena is located on the beach, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What’s there to see and do in Halena?

Explore the area and family-friendly sights such as Coffees of Hawaii Plantation Store, or get out into nature at a spot like Moloka'i Beaches. In the wider area, you’ll find Papohaku Beach and Kepuhi Beach.

What’s a holiday rental in Halena like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Halena. Holiday rentals offer amenities such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about a clean environment, a holiday rental can provide a sense of security away from public hotel lifts and lobbies packed with people while still allowing you to travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for a family trip.