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

Comfortable updated furnishings and remote controlled ceiling fans

Ocean views from the Lanai

Smart TV with Netflix provided

Queen sized fold out couch with mattress topper for extra comfort

Molokai Island Retreat

1 bedroom·1 bath

Kaunakakai • Hawaii

4.98(58 reviews)

$522.06 USD total for 3 nights

Sep 21 – 24, 2026

View of the ocean and Prince Kuhio Park from the lanai

Remodeled kitchen

Prince Kuhio Resort

Prince Kuhio Resort

Prince Kuhio Resort

Prince Kuhio Resort

1 bedroom·1 bath

Koloa • Hawaii

4.77(203 reviews)

$1,257.40 USD total for 4 nights

Dec 3 – 7, 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

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

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

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

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

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!

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.

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

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