The bedroom has its own air conditioner. Kahana catches the trade winds most evenings, but not every night — and plenty of older West Maui condos still don't have bedroom A/C. Yours does.
This is why we love Kahana. The big resort beaches down in Kāʻanapali are beautiful, but they're busy — here you can walk down with a chair from the closet and have a stretch of sand mostly to yourself. Molokaʻi sits out on the horizon, and in winter you'll see whales from right where those chairs are.
No towel-on-the-chair at 6am. Our pool is small and quiet, and the BBQ grills are right there when you'd rather grill than pay resort prices.
This is where the day winds down. The sectional seats the whole group, the dining table fits four, and there's a 55" TV with a Google device for streaming or music. It's the part of a condo you don't get in a hotel room — somewhere to actually sit together after the beach instead of perching on the end of a bed.
A dining table for four, right inside the door. It sounds small, but it's the thing people miss most in a hotel room — somewhere to sit down together with fish you grilled downstairs, or coffee before anyone's ready to leave. Eating out every meal on Maui adds up fast. Here you don't have to.

Maui Makai Condo

1 bedroom·1 bath
Napili-Honokowai • Hawaii
4.92(114 reviews)

$917.64 USD total for 3 nights

Sep 21 – 24, 2026

View of Island of Lanai from Whaler 1063
King Bed
Whaler Grounds
You have arrived!
View of Island of Lanai from Whaler 1063

Whaler 1063 on Ka'anapali Beach, Maui, Hawaii

1 bedroom·1 bath
Kaanapali • Hawaii
4.98(165 reviews)

$1,406.74 USD total for 3 nights

Sep 27 – 30, 2026

Luxury Oceanfront Turtles Sunsets - Maui, Hawaii
Luxury Oceanfront Turtles Sunsets - Maui, Hawaii
Luxury Oceanfront Turtles Sunsets - Maui, Hawaii
Luxury Oceanfront Turtles Sunsets - Maui, Hawaii
Luxury Oceanfront Turtles Sunsets - Maui, Hawaii

Luxury Oceanfront Turtles Sunsets - Maui, Hawaii

1 bedroom·1 bath
Napili-Honokowai • Hawaii
4.9(302 reviews)

$1,256.76 USD total for 3 nights

Nov 11 – 14, 2026

Sit, Relax, and Enjoy our very comfortable Living Room
Sit, Relax, and Enjoy our very comfortable Living Room
Sit, Relax, and Enjoy our very comfortable Living Room
Your kids will sleep comfortably on our queen-size pull-out couch.
Sit, Relax, and Enjoy your private deck

Cozy Tropical Retreat Guest House with AC

1 bedroom·1 bath
Hilo • Hawaii
4.98(300 reviews)

$656.02 USD total for 3 nights

Oct 10 – 13, 2026

Fairways resort pool & Keiki pool
Lava rock hot tub and water falls
Mauna Lani Beach Club (Makaiwa Bay) w/ free-to-use shade canopy lounge chairs
Beach at Makaiwa Bay, aka, Mauna Lani Beach Club
Villa Lava Floor plan and topographical view to pool from lanai

Villa Lava

2 bedrooms·2½ baths
Puako • Hawaii
5(75 reviews)

$2,303.01 USD total for 5 nights

Sep 25 – 30, 2026

The Kings view at twilight is one of our favorites. Don't let the ocean side spectacular sunset side detract you from this view with pink clouds and frequeent rainbows.
View from the dining area table, or work station if needed.
Resort pool for morning swims before creative work or exploration begins. Peaceful early hours, social when you want it. Most guests here are digital nomads, writers, and remote workers.
Vintage style glass knobbed doors provide privacy between the toilet and shower room and the sink and mirror area to provide "together but separate" privacy. Bath gel, Shampoo and conditioner are provided.
Privacy when it matters. A full wood door between the shower and toilet space and the the sink, cabinet and vanity area.

Beachfront Guest Favorite | Turtles, Seals & Surf

1 bedroom·1 bath
Lahaina • Hawaii
5(15 reviews)

$828.00 USD total for 3 nights

Sep 29 – Oct 2, 2026

Ocean Escape
Ocean Escape
Ocean Escape
Ocean Escape
Ocean Escape

Ocean Escape

0 bedrooms·1 bath
Kihei • Hawaii
5(92 reviews)

$848.99 USD total for 3 nights

Sep 26 – 29, 2026

Kiahuna Plantation 248 sits on an amazing beach, perfect for surfing, boogie boards, swimming or catching a few rays. A quick 2 minute walk down the grass from our unit
Wake up and enjoy breakfast on the lanai and soak in the ocean view and palm trees
Upgraded, A/C, Ocean View, In Unit W/D, KP 248
Upgraded, A/C, Ocean View, In Unit W/D, KP 248
California King Bed in bedroom Dresser, Ceiling Fan and TV

Upgraded, A/C, Ocean View, In Unit W/D, KP 248

1 bedroom·1 bath
Koloa • Hawaii

$1,185.24 USD total for 3 nights

Sep 21 – 24, 2026

Tropical Hawaiian Oceanfront - Maui, Hawaii
Tropical Hawaiian Oceanfront - Maui, Hawaii
Tropical Hawaiian Oceanfront - Maui, Hawaii
Tropical Hawaiian Oceanfront - Maui, Hawaii
Tropical Hawaiian Oceanfront - Maui, Hawaii

Tropical Hawaiian Oceanfront - Maui, Hawaii

1 bedroom·1 bath
Napili-Honokowai • Hawaii
4.85(215 reviews)

$882.32 USD total for 3 nights

Sep 23 – 26, 2026

View of the living room, kitchen and patio from the bedroom.
View of living room and bedroom with large sliding barn door for privacy.
North Shore Cottage Guest House | AirbnbOahu.com
North Shore Cottage Guest House | AirbnbOahu.com
Bedroom has a queen size bed, ceiling fan, mirror and closet.

North Shore Cottage Guest House | AirbnbOahu.com

1 bedroom·1 bath
Waialua • Hawaii
4.98(291 reviews)
$280/ night(excl. fees & taxes)
Entire home in Koloa, Hawaii, United States
Entire home in Koloa, Hawaii, United States
Entire home in Koloa, Hawaii, United States
Entire home in Koloa, Hawaii, United States
Entire home in Koloa, Hawaii, United States

Entire home in Koloa, Hawaii, United States

4 bedrooms·4 baths
Koloa • Hawaii
5(29 reviews)

$8,014.68 USD $7,295.12 USD total for 4 nights

Oct 10 – 14, 2026

Remodeled throughout in 2023 including all new decor, furniture (including sofa sleeper), windows and more!
Kamaole II is literally across the street! One of the best beaches in Maui! Kihei Akahi is so conveniently located!
Brand NEW high-end KING size Mattress and Platform Bed! New Tommy Bahama Beach Chairs in the closet.
Dine, read, relax or work from this convenient, quiet 'D' building, ground floor lanai.
Two pools on property: Upper Pool just steps to our DG 06 condo!

Kihei Akahi (2531 S. Kihei Road), #DG06

1 bedroom·1 bath
Kihei • Hawaii
4.97(120 reviews)

$905.57 USD total for 3 nights

Sep 21 – 24, 2026

View from right outside bedroom door.
Sunrise!
Hotel Room w/in beautiful Oceanfront Condo.
Hotel Room w/in beautiful Oceanfront Condo.
Hotel Room w/in beautiful Oceanfront Condo.

Hotel Room w/in beautiful Oceanfront Condo.

1 bedroom·1 bath
Kapaa • Hawaii
4.84(99 reviews)

$1,035.37 USD total for 3 nights

Oct 9 – 12, 2026

Oceanfront Turtle Cove Maui Pole House Estate image 2
Oceanfront Turtle Cove Maui Pole House Estate image 3
Oceanfront Turtle Cove Maui Pole House Estate image 1
Room for the entire family to enjoy intimate outdoor dining with literally one of the Very Best oceanviews in all of Maui.
Panoramic "Wow" views great you the moment you walk in the front door.

Oceanfront Turtle Cove Maui Home - 5BR, 4BA, A/C

5 bedrooms·4 baths
Lahaina • Hawaii
4.78(148 reviews)

$5,955.00 USD total for 3 nights

Sep 27 – 30, 2026

Amazing Sunsets Oceanfront Views - Maui, Hawaii
Amazing Sunsets Oceanfront Views - Maui, Hawaii
Amazing Sunsets Oceanfront Views - Maui, Hawaii
Amazing Sunsets Oceanfront Views - Maui, Hawaii
Amazing Sunsets Oceanfront Views - Maui, Hawaii

Amazing Sunsets Oceanfront Views - Maui, Hawaii

1 bedroom·1 bath
Napili-Honokowai • Hawaii
4.81(194 reviews)

$832.86 USD total for 3 nights

Oct 3 – 6, 2026

KAUAI | OCEANVIEW PENTHOUSE ON POIPU BEACH | A/C
KAUAI | OCEANVIEW PENTHOUSE ON POIPU BEACH | A/C
KAUAI | OCEANVIEW PENTHOUSE ON POIPU BEACH | A/C
KAUAI | OCEANVIEW PENTHOUSE ON POIPU BEACH | A/C
KAUAI | OCEANVIEW PENTHOUSE ON POIPU BEACH | A/C

KAUAI | OCEANVIEW PENTHOUSE ON POIPU BEACH | A/C

1 bedroom·1 bath
Koloa • Hawaii
4.75(8 reviews)

$1,255.52 USD total for 3 nights

Oct 26 – 29, 2026

KAUAI | PARADISE GARDEN VIEW | STEPS FROM BEACH!
KAUAI | PARADISE GARDEN VIEW | STEPS FROM BEACH!
KAUAI | PARADISE GARDEN VIEW | STEPS FROM BEACH!
KAUAI | PARADISE GARDEN VIEW | STEPS FROM BEACH!
KAUAI | PARADISE GARDEN VIEW | STEPS FROM BEACH!

KAUAI | PARADISE GARDEN VIEW | STEPS FROM BEACH!

1 bedroom·1 bath
Koloa • Hawaii
4.86(29 reviews)

$1,241.36 USD total for 3 nights

Oct 29 – Nov 1, 2026

Private Patio with Whitewater Views
Lush Backyard Surrounds the Infinity Edge Pool
Terraced Property to the End of the Point
Privacy on a Peninsula
Watch the Sunset from the End of the Point

Kauai Vacation Rental at Honu Point

3 bedrooms·4 baths
Princeville • Hawaii
5(144 reviews)

$10,085.58 USD total for 4 nights

Sep 23 – 27, 2026

Island Glow Kailua Village downtown/freeparking/AC
Island Glow Kailua Village downtown/freeparking/AC
Island Glow Kailua Village downtown/freeparking/AC
Island Glow Kailua Village downtown/freeparking/AC
Island Glow Kailua Village downtown/freeparking/AC

Island Glow Kailua Village downtown/freeparking/AC

1 bedroom·1 bath
Kailua-Kona • Hawaii
5(53 reviews)

$825.72 USD total for 3 nights

Sep 21 – 24, 2026

Kauai Oasis Luxe Ocean View Pool SPA AC Sleep22
Kauai Oasis Luxe Ocean View Pool SPA AC Sleep22
Kauai Oasis Luxe Ocean View Pool SPA AC Sleep22
Kauai Oasis Luxe Ocean View Pool SPA AC Sleep22
Kauai Oasis Luxe Ocean View Pool SPA AC Sleep22

Kauai Oasis Luxe Ocean View Pool SPA AC Sleep22

6 bedrooms·6 baths
Koloa • Hawaii
5(18 reviews)

$14,564.34 USD $13,377.70 USD total for 3 nights

Sep 27 – 30, 2026

Breathtaking 180 Ocean Views with Pool, Hot Tub
Breathtaking 180 Ocean Views with Pool, Hot Tub
Breathtaking 180 Ocean Views with Pool, Hot Tub
Breathtaking 180 Ocean Views with Pool, Hot Tub
Breathtaking 180 Ocean Views with Pool, Hot Tub

Breathtaking 180 Ocean Views with Pool, Hot Tub

4 bedrooms·4½ baths
Kailua-Kona • Hawaii
4.73(86 reviews)

$4,348.61 USD total for 5 nights

Sep 21 – 26, 2026

Aloha and welcome to your dream Maui vacation!
A comfortable Queen size sofa bed easily sleeps 2 guests.
Make yourself at home! Inside you'll find 1 bedroom, 1 bathroom and an open space living room.
Want to take some rest and spend a day at home? No problem! Enjoy 55' Smart TV, DVD, high-speed Internet (up to 300Mbps), upgraded Wi-FI (up to 5334 Mbps) as well as our collection of books, board gam
Let the ceiling fans and split AC system make your stay comfortable.

Convenient 1BD/1BA in South Kihei, Maui

1 bedroom·1 bath
Kihei • Hawaii
4.94(79 reviews)

$1,749.61 USD total for 5 nights

Sep 26 – Oct 1, 2026

Aloha! Welcome to the Tranquil Turtle Retreat studio!
Relax and watch your favorite TV show on the comfortable California King bed. If needed our beautiful light blocking bamboo drapes will provide extra privacy.
On entrance there is a built in closet to store all your clothes.
Woke up early? Cook your morning breakfast in the convenient kitchenette. Check out other photos to see our recently remodeled bathroom!
There is some extra storage under the sink to store all your essentials.

Cozy Studio in South Kihei, Maui

0 bedrooms·1 bath
Kihei • Hawaii
4.98(95 reviews)

$1,207.73 USD total for 4 nights

Oct 9 – 13, 2026

A beach view right from the living room!
A picture-perfect setting for your morning coffee! We are facing East so you will see some amazing sunrises.
Custom made Hawaiian furniture.
Another view of the living and dining area. Hallway to the right leads to the bedrooms and bathrooms.
Spacious kitchen and dining area for you to enjoy.

Exquisite Oceanfront home, 4Bed/2B, Sleeps 8, A/C

4 bedrooms·2 baths
Kapaa • Hawaii
4.85(13 reviews)

$4,124.10 USD total for 4 nights

Sep 21 – 25, 2026