Location

Dates

Guests

Vacation rentals in Kihei

Wailea Grand Champions Villa

Local Island Decor

Wailea Grand Champions Villa

Wailea Grand Champions Villa

2 bedrooms·2 baths

Wailea-Makena • Hawaii

4.94(145 reviews)

$1,236.98 USD total for 3 nights

Nov 14 – 17, 2026

Wailea Surf Shack: Beaches, Shops & Golf!

Wailea Surf Shack: Beaches, Shops & Golf!

Wailea Surf Shack: Beaches, Shops & Golf!

Wailea Surf Shack: Beaches, Shops & Golf!

Wailea Surf Shack: Beaches, Shops & Golf! image 5

Wailea Surf Shack: Beaches, Shops & Golf!

1 bedroom·2 baths

Kihei • Hawaii

5(134 reviews)

$1,401.99 USD total for 3 nights

Oct 21 – 24, 2026

Privacy guaranteed on the lanai! No golfers yelling fore or pool noise.

Fully stocked eat-in kitchen with pots and pans, spices, and all the essentials.

Cook if you want to or don't since you're on vacation. Monkeypod is two minutes away.

A bright and airy open plan makes it easy to spend time with friends and family.

Turn on the AC on, put your feet up, and relax after a hard day at the beach.

Wailea Oasis

2 bedrooms·2 baths

Wailea-Makena • Hawaii

$1,593.30 USD total for 4 nights

Oct 25 – 29, 2026

Spacious Ground Floor Maui Retreat, Grand Champion

Spacious Ground Floor Maui Retreat, Grand Champion

Spacious Ground Floor Maui Retreat, Grand Champion

Spacious Ground Floor Maui Retreat, Grand Champion

Spacious Ground Floor Maui Retreat, Grand Champion

Spacious Ground Floor Maui Retreat, Grand Champion

2 bedrooms·2 baths

Wailea-Makena • Hawaii

$1,638.50 USD total for 3 nights

Oct 29 – Nov 1, 2026

Dine with the Best Views

View from the Bar

Nothing but Ocean!

Front Lanai with BBQ

Oceanfront Maui Penthouse

3 bedrooms·3 baths

Wailea-Makena • Hawaii

5(106 reviews)

$8,512.71 USD total for 5 nights

Dec 11 – 16, 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

Oct 20 – 23, 2026

Exceptional Oceanfront Location One Bed Condo image 1

Exceptional Oceanfront Location One Bed Condo image 2

Exceptional Oceanfront Location One Bed Condo image 3

The pool located right on the ocean.

Welcome to Lahaina Roads Suite 212

1 bedroom Oceanfront Maui Vacation Condo

1 bedroom·1 bath

Lahaina • Hawaii

4.67(45 reviews)

$1,043.12 USD total for 3 nights

Oct 20 – 23, 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

Oct 29 – Nov 1, 2026

Whaler 552

2 bedrooms·2 baths

Lahaina • Hawaii

5(74 reviews)

$7,508.41 USD total for 5 nights

Oct 20 – 25, 2026

Honua Kai - Hokulani 746

Kaanapali Beach

Honua Kai - Hokulani 746

Honua Kai - Hokulani 746

Honua Kai - Hokulani 746

2 bedrooms·2 baths

Lahaina • Hawaii

$2,223.60 USD total for 3 nights

Nov 1 – 4, 2026

Perfect for Whale Watching!

Kids shallow pool area with waterfall and waterslide in the background.

Honua Kai - Hokulani 749

2 bedrooms·2 baths

Lahaina • Hawaii

5(10 reviews)

$349 – $799/ night(excl. fees & taxes)

Lounge chairs and table with Champagne Ice Bucket

View from Lanai

Honua Kai - Konea 218

2 bedrooms·2 baths

Lahaina • Hawaii

5(13 reviews)

$229 – $954/ night(excl. fees & taxes)

Honua Kai - Konea 512

2 bedrooms·1 bath

Lahaina • Hawaii

5(6 reviews)

$1,625.19 USD total for 3 nights

Oct 21 – 24, 2026

Famous Kaanapali Beach - Just steps away from the condo!

Property grounds

Honua Kai - Konea 830

1 bedroom·1 bath

Lahaina • Hawaii

5(3 reviews)

$1,253.10 USD total for 3 nights

Dec 3 – 6, 2026

This is your view! You come to Maui for the Ocean - stay oceanfront.

Maui - Papakea F307

Maui - Papakea F307

Maui - Papakea F307

Maui - Papakea F307

Maui - Papakea F307

1 bedroom·1 bath

Lahaina • Hawaii

4.81(32 reviews)

$838.16 USD total for 3 nights

Oct 26 – 29, 2026

photo shows added ceiling fan

Mahana 919

2 bedrooms·2 baths

Lahaina • Hawaii

5(193 reviews)

$5,668.40 USD total for 5 nights

Oct 26 – 31, 2026

Papakea B108

1 bedroom·1 bath

Lahaina • Hawaii

$607.81 USD total for 3 nights

Nov 3 – 6, 2026

Maui - Mahana 607

Dining Area at The Maui Condos

Maui - Mahana 607

High End Kitchen Remodel:

Maui - Mahana 607

Maui - Mahana 607

1 bedroom·1 bath

Kaanapali • Hawaii

4.93(30 reviews)

$1,484.00 USD total for 4 nights

Oct 31 – Nov 4, 2026

These are the views from the Lanai

Maui - Mahana 507

Maui - Mahana 507

Maui - Mahana 507

Maui - Mahana 507

Maui - Mahana 507

1 bedroom·1 bath

Kaanapali • Hawaii

$1,868.65 USD total for 4 nights

Nov 25 – 29, 2026

Beautiful view from the Lanai of the ocean and grounds.

Kitchen at Papakea H304

Maui - Papakea H304

Maui - Papakea H304

Maui - Papakea H304

Maui - Papakea H304

2 bedrooms·2 baths

Lahaina • Hawaii

4.94(34 reviews)

$1,129.03 USD total for 3 nights

Oct 20 – 23, 2026

Paki Maui

1 bedroom·1 bath

Lahaina • Hawaii

$491.47 USD total for 3 nights

Oct 20 – 23, 2026

Updated PM 216

1 bedroom·1 bath

Lahaina • Hawaii

$549.64 USD total for 3 nights

Oct 25 – 28, 2026

Maui - Papakea F205

Maui - Papakea F205

Maui - Papakea F205

Oceanfront Views

Maui - Papakea F205

Maui - Papakea F205

1 bedroom·1 bath

Lahaina • Hawaii

4.87(15 reviews)

$1,081.54 USD total for 3 nights

Oct 27 – 30, 2026

Kahana Villa

2 bedrooms·2 baths

Lahaina • Hawaii

$717.02 USD total for 3 nights

Oct 22 – 25, 2026