Location

Dates

Guests

Vacation rentals in Hawaii

Wailea Studio image 1

Maui Banyan Studio T204A

Maui Banyan Studio T204A

Maui Banyan Studio T204A

Maui Banyan Studio T204A

Maui Banyan Studio T204A

0 bedrooms·1 bath

Kihei • Hawaii

4.72(130 reviews)

$566.03 USD total for 3 nights

Oct 12 – 15, 2026

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

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

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

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 room looking at to the lanai

Kitchen dining area with pantry

Looking out the front door no stairs to block your view and barbecue right out front.

Kihei Kai Nani, Sandy Beaches, Free Parking, Wi-Fi

1 bedroom·1 bath

Kihei • Hawaii

5(33 reviews)

$684.20 USD total for 3 nights

Sep 21 – 24, 2026

Keauhou Resort - Entire Ocean & Sunset View Condo, 2 Lanais, AC

"Serene, peaceful, beautiful home to nurture one's soul."-Robynne, California

Have breakfast with an Ocean View

Two Salt water pools to choose from.

TV cabinet pulls out into a queen Murphy bed.

"The upstairs balcony with ocean view is absolutely stunning." - Kelly, Seattle

Keauhou Resort - Entire Ocean & Sunset View Condo, 2 Lanais, AC

1 bedroom·1 bath

Kailua-Kona • Hawaii

4.99(95 reviews)

$1,011.00 USD total for 3 nights

Nov 4 – 7, 2026

Living area with pull out sleeper couch

Living Area with pull out sleeper couch

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

Ka Hale Nani o Wainani

Ka Hale Nani o Wainani

Ka Hale Nani o Wainani

Ka Hale Nani o Wainani

Ka Hale Nani o Wainani

Ka Hale Nani o Wainani

4 bedrooms·3½ baths

Koloa • Hawaii

5(70 reviews)

$6,274.00 USD total for 5 nights

Oct 3 – 8, 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

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

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