Big Island. Kona Bay View Condo. Pool+Lanai. AC.
Main bedroom
Main bedroom
Main bedroom
Main bedroom

Big Island. Kona Bay View Condo. Pool+Lanai. AC.

2 bedrooms·1½ baths
Kailua-Kona • Hawaii
4.66(116 reviews)

$970.62 USD $834.34 USD total for 3 nights

Sep 26 – 29, 2026

Kauai. Pool Ocean View. 4 Star Beachfront Resort
Kauai. Pool Ocean View. 4 Star Beachfront Resort
Kauai. Pool Ocean View. 4 Star Beachfront Resort
Kauai. Pool Ocean View. 4 Star Beachfront Resort
Kauai. Pool Ocean View. 4 Star Beachfront Resort

Kauai. Pool Ocean View. 4 Star Beachfront Resort

1 bedroom·1 bath
Lihue • Hawaii
4.9(87 reviews)

$1,059.65 USD $873.57 USD total for 3 nights

Oct 1 – 4, 2026

Oahu. Ocean Views. Walk to Waikiki Beach. AC.
Oahu. Ocean Views. Walk to Waikiki Beach. AC.
Oahu. Ocean Views. Walk to Waikiki Beach. AC.
Oahu. Ocean Views. Walk to Waikiki Beach. AC.
Oahu. Ocean Views. Walk to Waikiki Beach. AC.

Oahu. Ocean Views. Walk to Waikiki Beach. AC.

1 bedroom·1 bath
Honolulu • Hawaii
5(20 reviews)

$1,142.75 USD $920.16 USD total for 3 nights

Sep 28 – Oct 1, 2026

KAUAI | OCEANVIEW | POIPU BEACH IS YOUR BACKYARD
KAUAI | OCEANVIEW | POIPU BEACH IS YOUR BACKYARD
Soak in the ocean view and the sound of the waves on your private lanai.
This condo is fully renovated with luxury finishings like travertine tiles, granite countertops and a marble shower.
Enjoy Kiahuna Beach as if it were your backyard! Be steps away from the beautiful white sand beach.

KAUAI | OCEANVIEW | POIPU BEACH IS YOUR BACKYARD

1 bedroom·1 bath
Koloa • Hawaii
4.93(60 reviews)

$1,228.38 USD total for 3 nights

Sep 29 – Oct 2, 2026

Ocean Views- Beachfront- Steps to a Sandy Beach!
Ocean Views- Beachfront- Steps to a Sandy Beach!
Ocean Views- Beachfront- Steps to a Sandy Beach!
Ocean Views- Beachfront- Steps to a Sandy Beach!
Ocean Views- Beachfront- Steps to a Sandy Beach!

Ocean Views- Beachfront- Steps to a Sandy Beach!

1 bedroom·1 bath
Lahaina • Hawaii
4.95(151 reviews)

$1,557.60 USD total for 3 nights

Oct 18 – 21, 2026

Welcome to your home away from home at the Aloha Lani condo #A208. This panorama view shows you the kitchen and living room with our newly updated flooring and granite counters.
💖Relaxing & Well Appointed Kona HI Getaway w/ AC
💖Relaxing & Well Appointed Kona HI Getaway w/ AC
💖Relaxing & Well Appointed Kona HI Getaway w/ AC
Our fully stocked kitchen is filled to the brim with everything including rice cooker, sharp knifes, Ninja blender and so much more.

💖Relaxing & Well Appointed Kona HI Getaway w/ AC

1 bedroom·1 bath
Kailua-Kona • Hawaii
5(11 reviews)

$1,042.09 USD total for 4 nights

Nov 1 – 5, 2026

sunrise!
enjoy your meals and relax on the lanai
Open the sliding doors to enjoy the Kauai air
view of living from from the lanai
Listing image 5

Oceanfront Aloha @ tropical vacation paradise.

2 bedrooms·1 bath
Kapaa • Hawaii
5(55 reviews)

$1,965.19 USD total for 4 nights

Oct 9 – 13, 2026

Living area with pull out sleeper couch
Living Area with pull out sleeper couch
Open kitchen
New Microwave and Solid Surface Range Installed March 2026
New Ninja Dual (Drip and Pods) Coffee Maker installed June 2026

Serenity awaits - located just steps from beautiful Poipu beach with A/C

1 bedroom·1 bath
Koloa • Hawaii
5(117 reviews)

$1,990.62 USD $1,695.03 USD total for 4 nights

Oct 26 – 30, 2026

Private saltwater pool (warm 82-85F).
Bird of Paradise home is located on the rim of a dormant crater. This house sits high and is positioned perfectly to take advantage of the panoramic views of Pu'u Wanawana crater and Ha'upu mountain range, Pacific, rainbows and sunrises.
BreathtakingViews•Sleeps12•Private Pool•BeachWalk image 3
Outdoor dining area
Second King master suite (Bungalow suite) great view, ac, private, coffee maker/microwave/small fridges

BIRD OF PARADISE

4 bedrooms·3½ baths
Koloa • Hawaii
5(238 reviews)

$3,184.57 USD $2,845.51 USD total for 2 nights

Nov 6 – 8, 2026

Oceanfront in beautiful Coconut Coast#paradise
Oceanfront in beautiful Coconut Coast#paradise
Oceanfront in beautiful Coconut Coast#paradise
Oceanfront in beautiful Coconut Coast#paradise
Oceanfront in beautiful Coconut Coast#paradise

Oceanfront in beautiful Coconut Coast#paradise

2 bedrooms·1½ baths
Kapaa • Hawaii
4.94(129 reviews)

$1,965.19 USD total for 4 nights

Sep 27 – Oct 1, 2026

Aloha Kiahuna 247, A/C Top Floor, w/Ocean Views
Aloha - welcome to Kauai. Queen Sleeper Sofa and Twin Sleeper Sofa in the living room
Aloha Kiahuna 247, A/C Top Floor, w/Ocean Views
Aloha Kiahuna 247, A/C Top Floor, w/Ocean Views
Dining Room featuring seating for 5 and Kauai vintage art by a local artist

Aloha Kiahuna 247, A/C Top Floor, w/Ocean Views

1 bedroom·1 bath
Koloa • Hawaii

$1,270.71 USD total for 3 nights

Oct 7 – 10, 2026

Kauai. Mountain View Room.4 Star Beachfront Resort
Kauai. Mountain View Room.4 Star Beachfront Resort
Kauai. Mountain View Room.4 Star Beachfront Resort
Kauai. Mountain View Room.4 Star Beachfront Resort
Kauai. Mountain View Room.4 Star Beachfront Resort

Kauai. Mountain View Room.4 Star Beachfront Resort

1 bedroom·1 bath
Lihue • Hawaii
5(36 reviews)

$1,040.65 USD total for 3 nights

Oct 26 – 29, 2026

Living room, open floorplan with panoramic ocean views, sunrise, moonrise, whale watching here. The whole house has wifi speaker playing your musics
Luxe Oceanview Villa-As Seen on TV,Heated Pool,AC image 2
Luxe Oceanview Villa-As Seen on TV,Heated Pool,AC image 3
Elegant dining table set before wide glass doors, framing palm trees and a deep blue ocean. Warm wood accents, tropical-patterned chairs, and bright daylight create a relaxed, resort-style atmosphere
Breathtaking sunrise views over the Pacific Ocean, enjoyed right from the living room, dining, kitchen and bedrooms!

Orchid House: Poipu Koloa Luxury with Ocean Views & Pool, Sleeps 12

4 bedrooms·4½ baths
Koloa • Hawaii
5(186 reviews)

$8,715.30 USD total for 5 nights

Sep 21 – 26, 2026

Kauai. Garden View Room. 4 Star Beachfront Resort
Kauai. Garden View Room. 4 Star Beachfront Resort
Kauai. Garden View Room. 4 Star Beachfront Resort
Kauai. Garden View Room. 4 Star Beachfront Resort
Kauai. Garden View Room. 4 Star Beachfront Resort

Kauai. Garden View Room. 4 Star Beachfront Resort

1 bedroom·1 bath
Lihue • Hawaii
4.84(37 reviews)

$1,559.42 USD $1,119.42 USD total for 3 nights

Sep 21 – 24, 2026

Kauai.Beachfront Resort. Oceanview Lanai. King Bed
New! Beachfront Resort. Oceanview Lanai. King Bed image 1
New! Beachfront Resort. Oceanview Lanai. King Bed image 4
New! Beachfront Resort. Oceanview Lanai. King Bed image 5
New! Beachfront Resort. Oceanview Lanai. King Bed image 9

Kauai.Beachfront Resort. Oceanview Lanai. King Bed

1 bedroom·1 bath
Lihue • Hawaii
4.76(17 reviews)

$1,038.28 USD $777.77 USD total for 3 nights

Sep 21 – 24, 2026

Welcome to Sea and Sky Condo in Kapa'a! Our oceanfront condo with direct access to beach on property.
Living room with ocean and pool view
Relax comfortably and enjoy the view of ocean from living room
Living room with AC
Living room

Sea and Sky Beachfront Condo, Kauai

2 bedrooms·1½ baths
Kapaa • Hawaii
5(72 reviews)

$1,560.19 USD total for 4 nights

Sep 27 – Oct 1, 2026

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

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

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