Kaanapali vacation rentals

We found 6,653 vacation rentals — enter your dates for availability

Holiday rentals with weekly discounts - Kaanapali

Showing deals for:Jan 1 - Jan 8

Pool
Terrace/patio
Room
Property grounds
Exceptional
(24 reviews)

NEW LISTING! The Luxurious Bella Mare at Puamana Lahaina Maui

Lahaina

9% off
$1,633
$11,432 for 7 nights
All fees included
NEW LISTING! The Luxurious Bella Mare at Puamana Lahaina Maui
Huge master bedroom with king size bed and 42 inch flat-screen TV.
Evening Bliss.
Open kitchen with stainless steel Bosch appliances and granite counter tops.
Enjoy home cooked meals on the lanai with family and the West Maui Mountains!
Exceptional
(151 reviews)

GREAT VALUE! Huge Upgraded 765 Sqft 1 Bed TOP FLOOR Penthouse! 5 star AVG RATING

Lahaina

8% off
$438
$3,065 for 7 nights
All fees included
GREAT VALUE! Huge Upgraded 765 Sqft 1 Bed TOP FLOOR Penthouse! 5 star AVG RATING
Lobby feature
Direct oceanfront views from the 10th floor.
Lobby window where you register to receive your free parking pass.
Well equipped kitchen
Exceptional
(109 reviews)

Direct OCEANFRONT STUDIO CONDO

Lahaina

8% off
$369
$2,581 for 7 nights
All fees included
Direct OCEANFRONT STUDIO CONDO
Dining
Terrace/patio
Interior
Whaler's beautiful inner courtyard
Exceptional
(101 reviews)

LOVE DA, THE WHALER # 1018, BLACK ROCK OCEAN VIEW STUDIO! Feb - Mar 2027 Avail.

Lahaina

7% off
$444
$3,109 for 7 nights
All fees included
LOVE DA, THE WHALER # 1018, BLACK ROCK OCEAN VIEW STUDIO! Feb - Mar 2027 Avail.
Entry - Tile Floor through-out.
Sunset View
Security Gates to the Beach
Open Parking
Exceptional
(81 reviews)

The Napili Bay Resort - Ocean View #114 - Voted Most Beautiful Bay on Maui

Lahaina

8% off
$300
$2,100 for 7 nights
All fees included
The Napili Bay Resort - Ocean View #114 - Voted Most Beautiful Bay on Maui
Heated Pool
Property grounds
Tropically landscaped grounds
Looking in from the lanai - 32" flat panel TV with cable.
Exceptional
(55 reviews)

Direct Oceanfront Studio With Private Lanai

Lahaina

8% off
$255
$1,783 for 7 nights
All fees included
Direct Oceanfront Studio With Private Lanai
Tropically Landscaped Grounds
Relax on our lanai and enjoy the view
Condo 1009 lanai is 3rd down and 3rd over from upper right corner
Heated Pool
Exceptional
(23 reviews)

Direct Oceanfront Valley Isle Resort 1009

Lahaina

9% off
$325
$2,277 for 7 nights
All fees included
Direct Oceanfront Valley Isle Resort 1009
parking lot of the complex
Room
Outdoor dining with a view of the ocean.
Dining
Exceptional
(41 reviews)

The Napili Bay, Steps to Sand, Studio, King bed, Remodeled in June of 2023

Lahaina

6% off
$385
$2,694 for 7 nights
All fees included
The Napili Bay, Steps to Sand, Studio, King bed, Remodeled in June of 2023
Oceanfront Royal Kahana Resort view from water
Property grounds
Pool
Living area
Exceptional
(7 reviews)

Last Minute Open! Ocean & Mountain View’s 2 Bd/2Ba ! Hotel zoned Safe 2 Book!

Lahaina

8% off
$533
$3,732 for 7 nights
All fees included
Last Minute Open! Ocean & Mountain View’s 2 Bd/2Ba ! Hotel zoned Safe 2 Book!
Dining area.
Rainbows love to show up in Napili. Photo taken from the condo’s lanai.
Dining and living area.
Wide-angle view of the studio.
Wonderful
(8 reviews)

Beach View Condo - Few Steps from Napili Beach - The Napili Bay Resort #111

Lahain

8% off
$441
$3,086 for 7 nights
All fees included
Beach View Condo - Few Steps from Napili Beach - The Napili Bay Resort #111
Sitting area of #101
Lush exterior of the resort
Interior of #101
Nothing between the unit and the ocean but sand and swaying palms.
Exceptional
(60 reviews)

Spectacular Oceanfront Studio Condo on Napili Bay,Maui

Lahaina

8% off
$349
$2,443 for 7 nights
All fees included
Spectacular Oceanfront Studio Condo on Napili Bay,Maui
Private kitchen
Outdoor dining
Beach
Bright, open living space that flows seamlessly to the lanai, bringing the beauty of the outdoors inside
Excellent
(35 reviews)

Sunlit 2BR Island Haven Plantation Style

Lahaina

7% off
$563
$3,942 for 7 nights
All fees included
Sunlit 2BR Island Haven Plantation Style
Queen bed with ocean view
Kaimana at Pohailani
Oceanfront Studio
Queen bed with ocean view
Exceptional
(403 reviews)

On top of the Ocean Hideaway - Oceanfront Condo with Views on Maui

Lahaina

22% off
$250
$1,747 for 7 nights
All fees included
On top of the Ocean Hideaway - Oceanfront Condo with Views on Maui
Breathtaking aerial view of the oceanfront resort complex, showcasing the vibrant blue waters, lush tropical canopy, and sweeping panoramic views of the neighboring island of Molokai in the distance
Outdoor dining
Sparkling heated oceanfront resort pool BBQ grills, lounge seating, and stunning ocean views
Entry - Ocean views throughout the main living space
Exceptional
(5 reviews)

Oceanfront Escape | Molokai Views & Cool Tropical Breezes

Lahaina

8% off
$669
$4,680 for 7 nights
All fees included
Oceanfront Escape | Molokai Views & Cool Tropical Breezes
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Frequently asked questions

What is the best area to stay in Kaanapali, Hawaii, United States of America when booking a vacation rental?
When considering a vacation rental in Kaanapali, Hawaii, a popular area to stay is near the beachfront along Kaanapali Beach itself. This vibrant neighborhood is known for its stunning views, golden sands, and crystal-clear waters, making it a superb spot for beach lovers and outdoor enthusiasts. Here, you can find a variety of vacation rentals, ranging from luxurious condos to cozy beachfront homes, providing plenty of options for different tastes and budgets.In close proximity, you'll find top attractions such as the Whalers Village, which offers an array of shopping, dining, and entertainment options. Additionally, the scenic Black Rock is nearby, where visitors can enjoy snorkeling, cliff diving, or simply relaxing by the water.
How much does it cost to rent a vacation home in Kaanapali?
Prices for vacation rentals in Kaanapali vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Kaanapali to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Kaanapali vacation house rentals?
You can find great discounts on house rentals in Kaanapali on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I find long-stay vacation rentals in Kaanapali?
A long-stay vacation rental in Kaanapali is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search. *Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there any Kaanapali vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Kaanapali with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
When is the best time to visit Kaanapali for a vacation rental?
The peak season for visiting Kaanapali typically spans from March to May, making it an ideal time for travelers seeking warm weather and vibrant beach activities. During these months, you can expect average temperatures to hover in the pleasant range of the mid-70s to low 80s Fahrenheit, great for lounging on the beach, snorkeling in crystal-clear waters, or enjoying a round of golf at one of the stunning coastal courses.If you're planning to experience the beauty of Kaanapali while avoiding the crowds, consider visiting in October. This month offers a tranquil atmosphere, with comfortable temperatures in the low 70s Fahrenheit, making it an excellent time for exploring the lush landscapes and beautiful beaches without the hustle and bustle of peak tourist activity. You can indulge in leisurely hikes along the coastline or partake in local cultural events, all while enjoying more affordable vacation rental options.Ultimately, whether you prefer the lively option of peak season with endless outdoor adventures or the serene charm of the shoulder months, Kaanapali has something to offer every traveler.
How early should I book a Kaanapali vacation rental?
Book your Kaanapali vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Kaanapali, Hawaii, United States of America?
In Kaanapali, visitors can enjoy a variety of attractions that showcase the beauty of Maui. The famous Kaanapali Beach is a major highlight, offering pristine sands and clear waters great for swimming, snorkeling, and sunbathing. Nearby, the historic Whalers Village provides shopping, dining, and cultural experiences, including exhibits on the whaling history of the area.For those interested in outdoor activities, the Black Rock is a great spot for diving and cliff jumping, and it's easily accessible from the beach. The scenic backdrop of the West Maui Mountains adds to the area's charm, making it ideal for hiking and exploring lush trails.Additionally, the nearby Kaanapali Golf Courses attract golf enthusiasts with their stunning ocean views and challenging layouts.
Can I change or cancel my Kaanapali home rental booking on Vrbo?
To find Kaanapali vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Kaanapali vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively. Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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