Best Vacation Homes in Kaanapali
New
Condo
10.0(1 Review)
1 Bedroom
2 Baths
4 Guests
1150 ft²
Hot Tub
Pool
Ocean View
View
US $368/Night
7 Nights - US $2,577
Apartment
10.0(4 Reviews)
1 Bedroom
1 Bath
3 Guests
538.2 ft²
Oceanfront- Hot Tub
Spa- Pool
US $679/Night
7 Nights - US $4,754
Condo
10.0(4 Reviews)
1 Bedroom
1 Bath
4 Guests
- Spa
Fireplace/Heating- Pool
- Ocean View
US $2,166/Night
7 Nights - US $15,165
Condo
10 Bedrooms
10 Baths
28 Guests
Balcony/Terrace
Kitchen
Internet
Child Friendly
US $7,624/Night
7 Nights - US $53,370
Bed & Breakfast
10.0(4 Reviews)
2 Bedrooms
2 Baths
4 Guests
398.26 ft²
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
US $439/Night
7 Nights - US $3,073
Condo
8 Bedrooms
8 Baths
22 Guests
- Balcony/Terrace
- Kitchen
- Internet
- Child Friendly
US $6,787/Night
7 Nights - US $47,508
New
Condo
9 Bedrooms
9 Baths
26 Guests
- Balcony/Terrace
- Kitchen
- Internet
- Child Friendly
US $6,723/Night
7 Nights - US $47,062
Condo
7 Bedrooms
7 Baths
20 Guests
4990 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $4,759/Night
7 Nights - US $33,312
Kaanapali Luxury Rentals
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Hotel
6 Baths
- Pool
- Balcony/Terrace
Breakfast- Kitchen
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Hotel
2 Baths
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
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House
10.0(21 Reviews)
11 Bedrooms
9 Baths
26 Guests
Private Pool- Oceanfront
- Fireplace/Heating
- Pool
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Condo
10.0(7 Reviews)
9 Bedrooms
9 Baths
22 Guests
11076 ft²
- Private Pool
- Hot Tub
- Pool
- Ocean View
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Condo
9 Bedrooms
9 Baths
30 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
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House
10.0(1 Review)
1 Bedroom
1 Bath
4 Guests
570.49 ft²
- Pool
- View
- Child Friendly
Accessibility
US $9,848/Night
7 Nights - US $68,936
Resort
Oceanfront - 2 Bedroom - Marriott's Maui Ocean Club: Molokai, Lanai, Maui Towers - Full Resort Acces
9.6(17 Reviews)
3 Baths
8 Guests
1305 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $9,830/Night
7 Nights - US $68,808
Kaanapali Pet Friendly Vacation Rentals
New
Villa
1 Bedroom
2 Baths
4 Guests
- Fireplace/Heating
Pet Friendly
Air Conditioner- Internet
US $534/Night
7 Nights - US $3,739
Resort
9.0(258 Reviews)
20 Baths
80 Guests
487.06 ft²
- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
US $537/Night
7 Nights - US $3,758
Villa
10.0(1 Review)
2 Bedrooms
2 Baths
6 Guests
- Ocean View
- View
- Pet Friendly
- Child Friendly
US $909/Night
7 Nights - US $6,365
Apartment
9.0(1 Review)
1 Bedroom
2 Baths
4 Guests
904.17 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Spa
US $519/Night
7 Nights - US $3,633
Apartment
1 Bedroom
1 Bath
4 Guests
500 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $342/Night
7 Nights - US $2,395
Condo
2 Bedrooms
1 Bath
4 Guests
613 ft²
- Private Pool
- Hot Tub
- Spa
- Pool
US $1,344/Night
7 Nights - US $9,405
House
2 Bedrooms
2 Baths
8 Guests
700 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $936/Night
7 Nights - US $6,549
House
2 Bedrooms
2 Baths
8 Guests
740 ft²
- Ocean View
- Balcony/Terrace
- View
- Pet Friendly
US $796/Night
7 Nights - US $5,572
Kaanapali Large Vacation Homes
Condo
8 Bedrooms
8 Baths
24 Guests
- Balcony/Terrace
- Kitchen
- Internet
- Child Friendly
US $4,730/Night
7 Nights - US $33,109
Apartment
10.0(2 Reviews)
12 Bedrooms
11 Baths
38 Guests
1048.01 ft²
Private Beach- Oceanfront
- Hot Tub
- Pool
US $495/Night
7 Nights - US $3,468
House
9.8(147 Reviews)
6 Bedrooms
7 Baths
16 Guests
6500 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $2,495/Night
7 Nights - US $17,468
New
Condo
7 Bedrooms
7 Baths
20 Guests
- Balcony/Terrace
- Kitchen
- Internet
- Child Friendly
US $4,160/Night
7 Nights - US $29,122
House
10.0(1 Review)
17 Bedrooms
34 Baths
78 Guests
1572.16 ft²
Parking- Internet
- Child Friendly
Security/Safety
US $704/Night
7 Nights - US $4,928
Condo
6 Bedrooms
6 Baths
18 Guests
- Balcony/Terrace
- Kitchen
- Internet
- Child Friendly
US $3,879/Night
7 Nights - US $27,154
New
Condo
4 Bedrooms
4 Baths
12 Guests
- Balcony/Terrace
- Kitchen
- Internet
- Child Friendly
US $3,242/Night
7 Nights - US $22,694
New
Condo
6 Bedrooms
6 Baths
18 Guests
- Balcony/Terrace
- Kitchen
- Internet
- Child Friendly
US $3,162/Night
7 Nights - US $22,137
Why Choose Rent By Owner for your Kaanapali Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Kaanapali
When should you plan your Vacation Rentals stay?
Choosing the ideal time to vacation here ensures you enjoy optimal weather and fewer crowds, making your stay in this popular Hawaiian destination truly memorable.
Peak Season Highlights
Winter (December to February)
During the winter months, this destination experiences its peak tourist season due to warmer weather and favorable ocean conditions, making it ideal for beach activities and sightseeing.
Average Temperature Daytime: around 80°F (27°C) - Nighttime: about 65°F (18°C)
Summer (June to August)
The summer season attracts many visitors seeking sunny days and vibrant local festivities, ensuring lively atmospheres and excellent weather for outdoor adventures.
Average Temperature Daytime: approximately 85°F (29°C) - Nighttime: roughly 70°F (21°C)
Off-Season Highlights
Spring (March to May)
In spring, fewer travelers visit, providing a quieter experience while still enjoying pleasant temperatures and clear skies.
Average Temperature Daytime: about 78°F (26°C) - Nighttime: around 63°F (17°C)
Fall (September to November)
Autumn offers a more relaxed atmosphere as the crowds thin out, with mild weather perfect for exploring the area at your own pace.
Average Temperature Daytime: near 81°F (27°C) - Nighttime: approximately 66°F (19°C)
Weekly Weather Forecast for Kaanapali
How to Book Your Kaanapali Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Kaanapali
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy access to a swimming pool for relaxing swims on your vacation in the area.
- Take advantage of outdoor barbecue grills to host memorable cookouts with family and friends.
- Make the most of lush landscaped gardens and outdoor sitting areas to unwind in the fresh Hawaiian air.
- Benefit from convenient parking facilities, ensuring easy access to this popular destination.
- Access tennis courts or other sports facilities to stay active during your stay here.
- Use shaded outdoor lounge areas perfect for soaking up the sun or enjoying ocean views.
- Participate in organized outdoor activities or community events offered at some properties for a more immersive experience.
Top Attractions Around Kaanapali
What attractions are nearby?
In this vibrant area, you can enjoy a variety of activities including relaxing on pristine beaches, exploring scenic oceanfront walks, and discovering local shops and dining options just steps from your vacation rentals in Lahaina, Hawaii.
Family Activities
- Snorkeling at Black Rock: Discover vibrant marine life while exploring the calm waters just off the coast, an activity perfect for families seeking adventure in this seaside region.
- Whale Watching Tours: Take a family-friendly boat tour to see majestic whales during their annual migration, offering an unforgettable experience here in the region's waters.
- Kahekili Beach Park: Relax and unwind on this sandy beach with calm waters ideal for swimming, picnicking, and building sandcastles with children.
- Maui Ocean Center: Explore Hawaii’s largest showcase of marine life, providing an engaging educational outing for families wanting to learn about local ocean ecosystems.
Adult Activities
- Sailing and Sunset Cruises: Embark on a scenic cruise along the coast to enjoy breathtaking views of the ocean during sunset, offering a relaxing and memorable experience in this popular destination.
- Golfing at Premier Courses: Play a round on some of Hawaii’s top golf courses, where the stunning landscape enhances your game, making it a must-do activity for golf enthusiasts visiting here.
- Snorkeling and Diving Adventures: Explore the vibrant marine life beneath the waves with snorkeling or diving excursions that highlight the region’s rich underwater ecosystem.
- Nightlife and Luau Experiences: Immerse yourself in local culture through lively luaus and vibrant nightlife spots that showcase traditional Hawaiian entertainment right here in the area.
Other Places to Stay in Kaanapali, HI
Kaanapali Hillside
Keka'a Beach
Kahekili Beach
May's Beach
Skyline Eco Adventure
Black Rock
Whalers Village Museum
Whalers Village
Kaanapali Kai Course at Kaanapali Golf Resort
Kaanapali Beach
Kaanapali Golf Courses
Hanakaoo Beach Park
Kaanapali Travel Tips
How Can You Make the Most of Your Stay?
- Plan your outdoor activities: Take advantage of the area's renowned beaches and scenic coastline by scheduling early morning walks or sunset views to enjoy the best weather and tranquility.
- Explore local dining options: Discover authentic flavors at nearby eateries to fully experience the region’s vibrant culinary scene and support local businesses.
- Utilize strategic transportation: Rent a scooter or bicycle to explore the area comfortably and maximize your time enjoying picturesque spots without the hassle of parking.
- Book accommodations in prime locations: Choose vacation rentals close to popular beaches and attractions for easy access and an immersive stay in this sought-after destination.
Transportation Options
- Rental Car Services: Renting a car here offers the greatest flexibility to explore the surrounding beaches, golf courses, and iconic sights at your own pace.
- Public Transportation: The local bus system provides an affordable and convenient way to navigate the area without the hassle of parking or traffic.
- Taxi and Ride-Sharing Services: Taxis and ride-sharing options like Uber and Lyft are readily available for quick, reliable transportation across this popular Hawaiian destination.
- Bicycle Rentals: Cycling here is a scenic and eco-friendly choice, allowing you to enjoy the coastal beauty and explore the region's charming neighborhoods comfortably.
Local Customs Options
- Respect for the Aloha Spirit: You’ll find that embracing the Aloha Spirit is essential, emphasizing kindness and harmony in interactions with locals here.
- Traditional Hawaiian Blessings: Participating in or observing Hawaiian blessings and ceremonies shows appreciation for the region’s spiritual heritage.
- Reverence for Nature and Land: Maintaining a respectful attitude towards beaches, parks, and natural sites is customary to preserve this destination’s pristine environment.
- Handling Cultural Artifacts with Care: When engaging with local art and historical items, it’s important to do so respectfully and with permission, honoring the area's cultural significance.
Kaanapali Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Kaanapali?
There are a lot of options in Kaanapali. If you plan on staying in the Kaanapali area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Kaanapali:
- HOKULANI 436-CORNER UNIT 2BD/2BA w/OCEAN & MOUNTAIN VIEWS,505SQFT LANAI BALCONY
- SLEEP NUMBER BED! #759 1bdrm-A Guest Favorite-Ocean/Beach View w/XBOX & ROKU!
- The Whaler! ~Beautifully remodeled ground floor courtyard studio~
- Maui Resort Rentals: Hokulani 605 – Premier 6th-Floor Oceanview Penthouse | Closest 2BR Column to the Ocean!
- Honua Kai 825 3BD Oceanfront Retreat w/Lanai, Floor-to-Ceiling Views & Modern Kitchen
- Maui is calling you back! Enjoy our Ocean View Cottage- 200+ Rave Reviews Await!
- The Whaler 814, Black Rock, All 5 Stars. Ocean and Beachfront Views
- Modern Renovated Kaanapali Studio! We have the Best Reviews for a Reason!
- Maui Resort Rentals: The Whaler 1015 - Gorgeously Remodeled 10th Floor Interior Courtyard Studio, Spectacular Ocean and Mountain Views!
- +BEACHFRONT RESORT+OCEAN VIEW STUDIO A-317+CENTRAL A/C+FULLY EQUIPPED KITCHEN+
2. How many vacation rentals have private pools in Kaanapali?
There are 99 vacation rentals with private pools near Kaanapali. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Kaanapali are best for families?
If you are looking for a family-friendly vacation home in Kaanapali, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Kaanapali:
4. How many Rentbyowner vacation rentals are available in Kaanapali?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 3944 in the Kaanapali area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Kaanapali.
5. What is the cancellation policy for a vacation rental in this region?
Cancellation policies vary depending on the individual listing. It is recommended that you review the specific policy outlined in the booking details or contact the property owner directly to understand the terms and any potential fees.
6. Are there any additional fees I should be aware of when booking a rental here?
Additional fees such as cleaning fees, service charges, or local taxes may apply. Please check the listing details or reach out to the host for a comprehensive breakdown of all applicable charges before finalizing your reservation.
7. What amenities are typically included in these rentals?
Most properties offer essential amenities like Wi-Fi, fully equipped kitchens, air conditioning, and laundry facilities. To ensure the rental meets your needs, review the amenities list provided in the listing description or contact the owner for more information.
8. How do I find the best vacation rental deals in this area?
To secure the best rates, consider booking well in advance and comparing listings with similar features. Reading reviews and communicating with hosts can also help you find a property that offers good value for your stay.
9. What should I do if I encounter issues during my stay?
If you experience any problems during your visit, contact the property owner or host promptly through the contact information provided. Many listings also include support options to assist with resolving concerns efficiently.
Kaanapali Top Rated Vacation Rentals
Condo
10.0(312 Reviews)
2 Bedrooms
2 Baths
6 Guests
1240 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
US $796/Night
7 Nights - US $5,574
Condo
10.0(255 Reviews)
1 Bedroom
1 Bath
4 Guests
901 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Spa
US $526/Night
7 Nights - US $3,685
Apartment
10.0(246 Reviews)
1 Bedroom
1 Bath
4 Guests
523 ft²
- Hot Tub
- Spa
- Pool
- Ocean View
US $379/Night
7 Nights - US $2,653
Condo
10.0(234 Reviews)
2 Bedrooms
2 Baths
6 Guests
1100 ft²
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
US $1,213/Night
7 Nights - US $8,488
Condo
10.0(222 Reviews)
4 Bedrooms
3 Baths
10 Guests
1600 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $1,284/Night
7 Nights - US $8,985
Cottage
10.0(206 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $508/Night
7 Nights - US $3,558
Apartment
10.0(200 Reviews)
1 Bedroom
1 Bath
4 Guests
585 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
US $477/Night
7 Nights - US $3,342
Condo
10.0(197 Reviews)
1 Bedroom
1 Bath
4 Guests
570 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
US $336/Night
7 Nights - US $2,352
