Dine with the Best Views
View from the Bar
Nothing but Ocean!
Front Lanai
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

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

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

Living Room
Living Room
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

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

Wailea Luxury Retreat | Walk to Beach & Shops
Wailea Luxury Retreat | Walk to Beach & Shops
Wailea Luxury Retreat | Walk to Beach & Shops
Wailea Luxury Retreat | Walk to Beach & Shops
Wailea Luxury Retreat | Walk to Beach & Shops

Wailea Luxury Retreat | Walk to Beach & Shops

1 bedroom·1 bath
Wailea-Makena • Hawaii

$1,364.50 USD total for 3 nights

Oct 28 – 31, 2026

Serene Maui Retreat | Walk to Beach & Shops
Serene Maui Retreat | Walk to Beach & Shops
Serene Maui Retreat | Walk to Beach & Shops
Serene Maui Retreat | Walk to Beach & Shops
Serene Maui Retreat | Walk to Beach & Shops

Serene Maui Retreat | Walk to Beach & Shops

1 bedroom·1 bath
Wailea-Makena • Hawaii

$1,033.00 USD total for 3 nights

Oct 20 – 23, 2026

Palms at Wailea 2204 - ocen views from all rooms and lanais
Gem near Keawakapu Beach - Privacy and Ocean Views image 2
Gem near Keawakapu Beach - Privacy and Ocean Views image 3
Gem near Keawakapu Beach - Privacy and Ocean Views image 4
A built-in storage for all your beach needs.

Gem near Keawakapu Beach - Privacy and Ocean Views

1 bedroom·2 baths
Kihei • Hawaii
4.96(76 reviews)

$2,387.55 USD total for 6 nights

Oct 31 – Nov 6, 2026

Newly Redesigned Condo Featuring Hawai'i Art
Living Room
Condo Information for Guests
Dining
Keawakapu Ocean View Condo

Keawakapu Ocean View Condo

2 bedrooms·1 bath
Kihei • Hawaii
4.94(149 reviews)

$1,198.99 USD total for 4 nights

Nov 5 – 9, 2026

Luxury Maui Condo | Ocean Views + Resort Perks
Luxury Maui Condo | Ocean Views + Resort Perks
Luxury Maui Condo | Ocean Views + Resort Perks
Luxury Maui Condo | Ocean Views + Resort Perks
Luxury Maui Condo | Ocean Views + Resort Perks

Luxury Maui Condo | Ocean Views + Resort Perks

1 bedroom·2 baths
Wailea-Makena • Hawaii

$1,124.50 USD total for 3 nights

Oct 22 – 25, 2026

Beachfront Bliss | Walk to Sand, Pool, Restaurants
Beachfront Bliss | Walk to Sand, Pool, Restaurants
Beachfront Bliss | Walk to Sand, Pool, Restaurants
Beachfront Bliss | Walk to Sand, Pool, Restaurants
Beachfront Bliss | Walk to Sand, Pool, Restaurants

Beachfront Bliss | Walk to Sand, Pool, Restaurants

1 bedroom·2 baths
Wailea-Makena • Hawaii

$1,432.00 USD total for 3 nights

Oct 28 – 31, 2026

Oceanfront, Resort-Style Condos w/ Pool & Private Lanai
Oceanfront, Resort-Style Condos w/ Pool & Private Lanai
Oceanfront, Resort-Style Condos w/ Pool & Private Lanai
Oceanfront, Resort-Style Condos w/ Pool & Private Lanai
Oceanfront, Resort-Style Condos w/ Pool & Private Lanai

Oceanfront, Resort-Style Condos w/ Pool & Private Lanai

2 bedrooms·2 baths
Wailea-Makena • Hawaii

$2,247.50 USD total for 3 nights

Oct 31 – Nov 3, 2026

Steps to Beach! Chic 2BR at Maui Banyan Resort
Steps to Beach! Chic 2BR at Maui Banyan Resort
Steps to Beach! Chic 2BR at Maui Banyan Resort
Steps to Beach! Chic 2BR at Maui Banyan Resort
Steps to Beach! Chic 2BR at Maui Banyan Resort

Steps to Beach! Chic 2BR at Maui Banyan Resort

2 bedrooms·2 baths
Wailea-Makena • Hawaii

$959.00 USD total for 3 nights

Oct 28 – 31, 2026

Steps to Beach | Hot Tub | Luxe Maui Retreat
Steps to Beach | Hot Tub | Luxe Maui Retreat
Steps to Beach | Hot Tub | Luxe Maui Retreat
Steps to Beach | Hot Tub | Luxe Maui Retreat
Steps to Beach | Hot Tub | Luxe Maui Retreat

Steps to Beach | Hot Tub | Luxe Maui Retreat

0 bedrooms·1 bath
Kihei • Hawaii

$740.50 USD total for 3 nights

Oct 28 – 31, 2026

Luxe Maui Beach Retreat | Walk to Kamaole Beach
Luxe Maui Beach Retreat | Walk to Kamaole Beach
Luxe Maui Beach Retreat | Walk to Kamaole Beach
Luxe Maui Beach Retreat | Walk to Kamaole Beach
Luxe Maui Beach Retreat | Walk to Kamaole Beach

Luxe Maui Beach Retreat | Walk to Kamaole Beach

1 bedroom·1 bath
Wailea-Makena • Hawaii

$1,207.00 USD total for 3 nights

Oct 28 – 31, 2026

Beachside Retreat | Walk to Shops & Dining
Beachside Retreat | Walk to Shops & Dining
Beachside Retreat | Walk to Shops & Dining
Beachside Retreat | Walk to Shops & Dining
Beachside Retreat | Walk to Shops & Dining

Beachside Retreat | Walk to Shops & Dining

1 bedroom·1 bath
Wailea-Makena • Hawaii

$1,036.00 USD total for 3 nights

Oct 31 – Nov 3, 2026

Oceanview Retreat | Walk to Beach & Restaurants
Oceanview Retreat | Walk to Beach & Restaurants
Oceanview Retreat | Walk to Beach & Restaurants
Oceanview Retreat | Walk to Beach & Restaurants
Oceanview Retreat | Walk to Beach & Restaurants

Oceanview Retreat | Walk to Beach & Restaurants

1 bedroom·1 bath
Wailea-Makena • Hawaii

$1,667.50 USD total for 3 nights

Oct 20 – 23, 2026

Beachfront Studio | Walk to Kamaole Beach + Pools
Beachfront Studio | Walk to Kamaole Beach + Pools
Beachfront Studio | Walk to Kamaole Beach + Pools
Beachfront Studio | Walk to Kamaole Beach + Pools
Beachfront Studio | Walk to Kamaole Beach + Pools

Beachfront Studio | Walk to Kamaole Beach + Pools

1 bedroom·1 bath
Wailea-Makena • Hawaii

$971.50 USD total for 3 nights

Oct 28 – 31, 2026

5-Min Walk Beach Condo w/Pool, Hot Tub, Free Parking
5-Min Walk Beach Condo w/Pool, Hot Tub, Free Parking
5-Min Walk Beach Condo w/Pool, Hot Tub, Free Parking
5-Min Walk Beach Condo w/Pool, Hot Tub, Free Parking
5-Min Walk Beach Condo w/Pool, Hot Tub, Free Parking

5-Min Walk Beach Condo w/Pool, Hot Tub, Free Parking

1 bedroom·1 bath
Wailea-Makena • Hawaii

$1,312.00 USD total for 3 nights

Oct 26 – 29, 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)

$1,757.07 USD total for 5 nights

Oct 29 – Nov 3, 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 27 – 31, 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 2 bedrooms, 2 bathrooms 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 ceiling fans and a split AC system make your stay comfortable.

Comfortable 2BR/2BA in South Kihei, Maui

2 bedrooms·2 baths
Kihei • Hawaii
5(44 reviews)

$2,549.40 USD total for 4 nights

Oct 29 – Nov 2, 2026

Aloha and welcome to your dream Maui vacation!
We have fully stocked kitchen so that you can easily prepare your favorite meal.
Stock the fridge with your favorite food and drinks.
Enjoy your meal at the table with enough room for 4 people.
Nice seating area to spend an evening.

Tranquil 1BD/2BA in South Kihei, Maui

1 bedroom·2 baths
Kihei • Hawaii
5(82 reviews)

$2,341.32 USD total for 5 nights

Oct 29 – Nov 3, 2026

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Chic Condo steps from White Sandy Beach Fast Wi-Fi

1 bedroom·1 bath
Kihei • Hawaii

$3,198.00 USD total for 3 nights

Oct 20 – 23, 2026