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

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

Coconut Coast Studio
Coconut Coast Studio, Kauai
Coconut Coast Studio, Kauai
Coconut Coast Studio, Kauai
Coconut Coast Studio, Kauai

Coconut Coast Studio, Kauai

0 bedrooms·1 bath
Kapaa • Hawaii
4.74(54 reviews)

$759.73 USD total for 3 nights

Oct 23 – 26, 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

Breezy Pool Oasis 5BR AC Ocean Views 5min to Beach
Breezy Pool Oasis 5BR AC Ocean Views 5min to Beach
Breezy Pool Oasis 5BR AC Ocean Views 5min to Beach
Beautiful front yard with pool, hot tub, and mountain views!
Breezy Pool Oasis 5BR AC Ocean Views 5min to Beach

Breezy Pool Oasis 5BR AC Ocean Views 5min to Beach

5 bedrooms·3 baths
Kailua-Kona • Hawaii
5(33 reviews)

$3,022.00 USD total for 3 nights

Oct 19 – 22, 2026

Mahana 919
Mahana 919
photo shows added ceiling fan
Mahana 919
Mahana 919

Mahana 919

2 bedrooms·2 baths
Lahaina • Hawaii
5(193 reviews)

$5,668.40 USD total for 5 nights

Oct 1 – 6, 2026

Our house is set up perfectly for outdoor living. Lounge seating for 8. New outdoor furniture Feb 2025.
Giant 77-inch OLED 4K Smart TV, 450 cable channels, 160 DVD movies, 120 books, Infinity electronic game table
Read, have a cocktail, take a nap
Secluded 6-person hot tub with a hot water outdoor shower
Stocked with every imaginable kitchen tool to make cooking a breeze.

Kihei Garden Oasis

4 bedrooms·2 baths
Kihei • Hawaii
5(161 reviews)

$3,610.70 USD $2,958.95 USD total for 5 nights

Oct 1 – 6, 2026

Kona Paradise with Oceanfront views!
Ocean View from Pool Patio
Front Entrance to condo
Kitchen/Living Open Floor plan
Kitchen Bar or table seating

Kona Paradise with Oceanfront views!

2 bedrooms·2 baths
Kailua-Kona • Hawaii
4.8(166 reviews)

$1,589.30 USD total for 5 nights

Sep 27 – Oct 2, 2026