303+ Vacation Rentals Near Kaanapali |
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Wine Country Villas - Vacation Rentals in Kaanapali

Maui Resort Rentals: Marriott's Maui Ocean Club 2 Bedroom Oceanfront Villa From US $1,561
         

9.8 (57 Reviews)
Villa
Maui Resort Rentals: Marriott's Maui Ocean Club 2 Bedroom Oceanfront Villa
  • Air Conditioner
  • Parking
  • Pool

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Maui Kaanapali Villas B225 From US $448
         

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8.0 (9 Reviews)
Apartment
Maui Kaanapali Villas B225
  • Air Conditioner
  • Parking
  • Pool

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THANKSGIVING WEEK - Maui Resort - Westin Nanea Villas 3BR Oceanfront Villa From US $2,583
         

New
Villa
THANKSGIVING WEEK - Maui Resort - Westin Nanea Villas 3BR Oceanfront Villa
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

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Ocean Front Sunset & Whale-Watching Views at Hyatt Vacation Club From US $1,454
         

10.0 (11 Reviews)
Villa
Ocean Front Sunset & Whale-Watching Views at Hyatt Vacation Club
  • Air Conditioner
  • Parking
  • Pool

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Maui Resort Rentals: Penthouse 3BR Oceanfront Villa @ Marriott's Maui Ocean Club! From US $2,385
         

9.2 (7 Reviews)
Villa
Maui Resort Rentals: Penthouse 3BR Oceanfront Villa @ Marriott's Maui Ocean Club!
  • Air Conditioner
  • Parking
  • Pool

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Maui Resort Rentals: Marriott's Maui Ocean Club 1BR Oceanfront Villa - New Lahaina and Napili Towers From US $1,301
         

10.0 (2 Reviews)
Villa
Maui Resort Rentals: Marriott's Maui Ocean Club 1BR Oceanfront Villa - New Lahaina and Napili Towers
  • Air Conditioner
  • Parking
  • Pool

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MRR Presents - Hyatt Residence Club 1BR Oceanfront Lower Villa From US $762
         

8.0 (3 Reviews)
Villa
MRR Presents - Hyatt Residence Club 1BR Oceanfront Lower Villa
  • Air Conditioner
  • Parking
  • Pool

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Maui Resort Rentals - Exclusive Hyatt Residence Club 1BR Oceanfront Upper Floor Viilla From US $1,117
         

10.0 (4 Reviews)
Villa
Maui Resort Rentals - Exclusive Hyatt Residence Club 1BR Oceanfront Upper Floor Viilla
  • Air Conditioner
  • Parking
  • Pool

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Luxury Places to Stay in Kaanapali

Over 3716+ Luxury Places to Stay in or Near Kaanapali
Private Beach House + Backyard, Patio, and Hot Tub From US $38,294
         

New
Hotel
Private Beach House + Backyard, Patio, and Hot Tub
  • Air Conditioner
  • Pool
  • TV

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Oceanfront - 2 Bedroom - Westin Kaanapali Ocean Resort Villas - Full Resort Access From US $24,183
         

9.8 (32 Reviews)
Resort
Oceanfront - 2 Bedroom - Westin Kaanapali Ocean Resort Villas - Full Resort Access
  • Air Conditioner
  • Parking
  • Pool

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Honua Kai Ocean Front 4 FREE Rental Cars KBM Resorts Ocean Front 4 Units 11 Bedrooms HK ML-2648 From US $22,085
         

New
Apartment
Honua Kai Ocean Front 4 FREE Rental Cars KBM Resorts Ocean Front 4 Units 11 Bedrooms HK ML-2648
  • Air Conditioner
  • Parking
  • Pool

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Bungalow with Garden View + Kitchen + Pool Access From US $21,938
         

New
Hotel
Bungalow with Garden View + Kitchen + Pool Access
  • Air Conditioner
  • Pool
  • TV

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Honua Kai Ocean Front 4 FREE Rental Car KBM Resorts Ocean Front 4 Units 10 Bedrooms HK ML-2642 From US $21,192
         

New
Apartment
Honua Kai Ocean Front 4 FREE Rental Car KBM Resorts Ocean Front 4 Units 10 Bedrooms HK ML-2642
  • Air Conditioner
  • Parking
  • Pool

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Kaanapali Plantation 32 · KPL 32 3BD w/Sweeping Ocean Views, Ne From US $17,883
         

New
House
Kaanapali Plantation 32 · KPL 32 3BD w/Sweeping Ocean Views, Ne
  • Parking
  • Security/Safety
  • Barbecue/Outdoor Cooking

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Near Kāʻanapali Golf Course + Pools. Tennis. Spa. From US $17,140
         

New
Hotel
Near Kāʻanapali Golf Course + Pools. Tennis. Spa.
  • Air Conditioner
  • Pool
  • TV

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Honua Kai Ocean Front 4 FREE Rental Cars KBM Resorts Ocean Front 4 Units 11 Bedrooms HK ML-2639 From US $16,710
         

New
Apartment
Honua Kai Ocean Front 4 FREE Rental Cars KBM Resorts Ocean Front 4 Units 11 Bedrooms HK ML-2639
  • Air Conditioner
  • Parking
  • Pool

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Find More Kaanapali Villas, Resorts, & Rentals on BedroomVillas

Top-Rated Vacation Rentals with a Pool in Kaanapali

Over 3105+ Top-Rated Vacation Rentals with a Pool in or Near Kaanapali
HOKULANI 436-CORNER UNIT 2BD/2BA w/OCEAN & MOUNTAIN VIEWS,505SQFT LANAI BALCONY From US $1,001
         

10.0 (309 Reviews)
Condo
HOKULANI 436-CORNER UNIT 2BD/2BA w/OCEAN & MOUNTAIN VIEWS,505SQFT LANAI BALCONY
  • Air Conditioner
  • Parking
  • Pool

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SLEEP NUMBER BED! #759 1bdrm-A Guest Favorite-Ocean/Beach View w/XBOX & ROKU! From US $586
         

10.0 (246 Reviews)
Condo
SLEEP NUMBER BED! #759 1bdrm-A Guest Favorite-Ocean/Beach View w/XBOX & ROKU!
  • Air Conditioner
  • Parking
  • Pool

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The Whaler! ~Beautifully remodeled ground floor courtyard studio~ From US $461
         

10.0 (245 Reviews)
Apartment
The Whaler! ~Beautifully remodeled ground floor courtyard studio~
  • Air Conditioner
  • Parking
  • Pool

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Maui Resort Rentals: Hokulani 605 – Premier 6th-Floor Oceanview Penthouse | Closest 2BR Column to the Ocean! From US $829
         

10.0 (234 Reviews)
Condo
Maui Resort Rentals: Hokulani 605 – Premier 6th-Floor Oceanview Penthouse | Closest 2BR Column to the Ocean!
  • Air Conditioner
  • Parking
  • Pool

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Honua Kai 825 3BD Oceanfront Retreat w/Lanai, Floor-to-Ceiling Views & Modern Kitchen From US $1,326
         

10.0 (222 Reviews)
Condo
Honua Kai 825 3BD Oceanfront Retreat w/Lanai, Floor-to-Ceiling Views & Modern Kitchen
  • Air Conditioner
  • Pool
  • TV

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Maui is calling you back! Enjoy our Ocean View Cottage- 200+ Rave Reviews Await! From US $480
         

10.0 (205 Reviews)
Cottage
Maui is calling you back! Enjoy our Ocean View Cottage- 200+ Rave Reviews Await!
  • Parking
  • Pool
  • TV

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Modern Renovated Kaanapali Studio! We have the Best Reviews for a Reason! From US $683
         

10.0 (192 Reviews)
Condo
Modern Renovated Kaanapali Studio! We have the Best Reviews for a Reason!
  • Air Conditioner
  • Parking
  • Pool

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Maui Resort Rentals: The Whaler 1015 - Gorgeously Remodeled 10th Floor Interior Courtyard Studio, Spectacular Ocean and Mountain Views! From US $548
         

10.0 (183 Reviews)
Condo
Maui Resort Rentals: The Whaler 1015 - Gorgeously Remodeled 10th Floor Interior Courtyard Studio, Spectacular Ocean and Mountain Views!
  • Air Conditioner
  • Parking
  • Pool

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Pet-Friendly Vacation Rentals in Kaanapali

Over 18+ Pet-Friendly Vacation Rentals in or Near Kaanapali
Ocean View Studio at Westin Ka’anapali North From US $1,005
         

New
Apartment
Ocean View Studio at Westin Ka’anapali North
  • Air Conditioner
  • Pet Friendly
  • Pool

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K B M Resorts- WH1-1218 Stunning Studio, whale watching, big ocean views, steps to beach From US $5,572
         

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New
Apartment
K B M Resorts- WH1-1218 Stunning Studio, whale watching, big ocean views, steps to beach
  • Air Conditioner
  • Pet Friendly
  • Breakfast

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Island View Studio at Westin Ka’anapali North From US $769
         

New
Apartment
Island View Studio at Westin Ka’anapali North
  • Air Conditioner
  • Pet Friendly
  • Pool

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Ocean View Studio at Westin Ka’anapali North From US $756
         

New
Apartment
Ocean View Studio at Westin Ka’anapali North
  • Air Conditioner
  • Pet Friendly
  • Pool

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Westin Kaanapali Ocean Resorts/Studio Villa From US $715
         

New
Apartment
Westin Kaanapali Ocean Resorts/Studio Villa
  • Air Conditioner
  • Parking
  • Pet Friendly

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Luxury 2 BR Villa, sleeps 6, on Maui's World Famous Kaanapali Beach From US $909
         

10.0 (1 Review)
Villa
Luxury 2 BR Villa, sleeps 6, on Maui's World Famous Kaanapali Beach
  • Pet Friendly
  • View
  • Ocean View

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KBM Resorts: Konea HKK-930, Expansive Mountain Views, Includes Free Rental Car! From US $1,344
         

New
Condo
KBM Resorts: Konea HKK-930, Expansive Mountain Views, Includes Free Rental Car!
  • Parking
  • Pet Friendly
  • Pool

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Dive Into Your Summer Vacation! 2 Units with Ocean View, Beachfront Location! From US $936
         

New
House
Dive Into Your Summer Vacation! 2 Units with Ocean View, Beachfront Location!
  • Air Conditioner
  • Parking
  • Pet Friendly

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See More Pet-Friendly Vacation Rentals in Kaanapali on PetFriendly.io

Large Vacation Homes & Villas in Kaanapali

Over 481+ Large Vacation Homes & Villas in or Near Kaanapali
Hale Holokai at KAANAPALI VISTA~LUXURY Golf Course Ocean View Home 6 bedroom 3 bathroom~ From US $2,034
         

10.0 (62 Reviews)
House
Hale Holokai at KAANAPALI VISTA~LUXURY Golf Course Ocean View Home 6 bedroom 3 bathroom~
  • Air Conditioner
  • Parking
  • Pool

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Kaanapali Maui at the Eldorado by OUTRIGGER - Select Your Unit From US $495
         

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10.0 (2 Reviews)
Apartment
Kaanapali Maui at the Eldorado by OUTRIGGER - Select Your Unit
  • Air Conditioner
  • Parking
  • Pool

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Spectacular Sunset and Ocean Views with Pool & Hotbub near Kaanapali Beach From US $2,495
         

9.8 (147 Reviews)
House
Spectacular Sunset and Ocean Views with Pool & Hotbub near Kaanapali Beach
  • Air Conditioner
  • Parking
  • Pool

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KBM Resorts | FREE CAR | Honua Kai Hokulani | Ocean view | Deluxe 3-Bedroom Condo includes Beach Gear! HKH-504 From US $1,812
         

10.0 (41 Reviews)
Condo
KBM Resorts | FREE CAR | Honua Kai Hokulani | Ocean view | Deluxe 3-Bedroom Condo includes Beach Gear! HKH-504
  • Air Conditioner
  • Parking
  • Pool

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Maui Resort Rentals: Honua Kai - 4 Total Bedrooms, 5th floor Ocean AND West Maui Mountain Views From US $2,242
         

9.6 (22 Reviews)
Condo
Maui Resort Rentals: Honua Kai - 4 Total Bedrooms, 5th floor Ocean AND West Maui Mountain Views
  • Air Conditioner
  • Parking
  • Pool

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Hyatt Residence Club, Lahaina, Hawaii, United States of America 3 bed & 3 bath From US $3,087
         

9.8 (6 Reviews)
Condo
Hyatt Residence Club, Lahaina, Hawaii, United States of America 3 bed & 3 bath
  • Air Conditioner
  • Parking
  • Pool

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Maui Resort Rentals: Westin Kaanapali Ocean Resort North 1BR Oceanview Villa From US $795
         

New
Villa
Maui Resort Rentals: Westin Kaanapali Ocean Resort North 1BR Oceanview Villa
  • Air Conditioner
  • Parking
  • Pool

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HYATT RES. CLUB KA'ANAPALI BCH, OCEAN FRT -MAY23-MAY 30 AND MAY30th-JUNE6, 2026 From US $1,662
         

10.0 (1 Review)
Condo
HYATT RES. CLUB KA'ANAPALI BCH, OCEAN FRT -MAY23-MAY 30 AND MAY30th-JUNE6, 2026
  • Air Conditioner
  • Parking
  • Pool

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Wheelchair Accessible Vacation Homes in Kaanapali

Over 1632+ Wheelchair Accessible Vacation Homes in or Near Kaanapali
Sea, beach and courtyard views - prime location From US $649
         

10.0 (72 Reviews)
Condo
Sea, beach and courtyard views - prime location
  • Air Conditioner
  • Parking
  • Pool

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Kaanapali Royal F303 From US $346
         

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10.0 (2 Reviews)
Apartment
Kaanapali Royal F303
  • Pool
  • View
  • Wheelchair Accessible

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The Whaler Resort Kaanapali Beach From US $747
         

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9.6 (346 Reviews)
Condo
The Whaler Resort Kaanapali Beach
  • Air Conditioner
  • Parking
  • Pool

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Oceanfront Corner Unit - #201 - Panoramic Ocean View - Over 170 "5" star reviews From US $666
         

10.0 (174 Reviews)
Condo
Oceanfront Corner Unit - #201 - Panoramic Ocean View - Over 170 "5" star reviews
  • Air Conditioner
  • Parking
  • Pool

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Spacious Corner Location with Wrap Around Lanai -BEST VALUE! From US $498
         

9.8 (72 Reviews)
Condo
Spacious Corner Location with Wrap Around Lanai -BEST VALUE!
  • Air Conditioner
  • Parking
  • Pool

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KBM Resorts | FREE CAR | Honua Kai Hokulani | Ocean view | 3-Bedroom Condo with Sweeping views! HKH-503 From US $1,314
         

9.8 (43 Reviews)
Condo
KBM Resorts | FREE CAR | Honua Kai Hokulani | Ocean view | 3-Bedroom Condo with Sweeping views! HKH-503
  • Air Conditioner
  • Parking
  • Pool

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KBM Resorts | FREE CAR | Honua Kai Hokulani | Ocean view | 2-Bedroom Corner Condo with Huge Lanai! HKH-620 From US $764
         

9.8 (41 Reviews)
Condo
KBM Resorts | FREE CAR | Honua Kai Hokulani | Ocean view | 2-Bedroom Corner Condo with Huge Lanai! HKH-620
  • Air Conditioner
  • Parking
  • Pool

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Hawaii Life Presents "Kahua Kai" Whaler 102- Direct Oceanfront 2BR/2BA From US $1,070
         

9.6 (116 Reviews)
Condo
Hawaii Life Presents "Kahua Kai" Whaler 102- Direct Oceanfront 2BR/2BA
  • Air Conditioner
  • Parking
  • Pool

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Kaanapali Vacation Rentals and Airbnb Places to Stay Under $200

Over 5+ Kaanapali Vacation Rentals and Airbnb Places to Stay Under $200
Ka’anapali Studio at Westin – Resort Pools, Beach Access & Island Comfor From US $186
         

New
Resort
Ka’anapali Studio at Westin – Resort Pools, Beach Access & Island Comfor
  • Air Conditioner
  • Parking
  • Pool

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Maui Kaanapali Villas Ocean View Studio in Emerald Bldg Sleeps 3 guests From US $148
         

9.2 (37 Reviews)
Condo
Maui Kaanapali Villas Ocean View Studio in Emerald Bldg Sleeps 3 guests
  • Air Conditioner
  • Parking
  • Pool

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My Perfect Stays: Was $229 - Now $149 till Nov 21 From US $169
         

3.9 (14 Reviews)
Condo
My Perfect Stays: Was $229 - Now $149 till Nov 21
  • Air Conditioner
  • Bedding/Linens
  • Child Friendly

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Serenity...Low-Low Rate - Kaanapali Beach Cabana 7 minute walk From US $165
         

9.4 (98 Reviews)
Condo
Serenity...Low-Low Rate - Kaanapali Beach Cabana 7 minute walk
  • Air Conditioner
  • Pool
  • Balcony/Terrace

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Island Serenity Awaits: Studio Premium Villa at Westin Ka’anapali North From US $184
         

New
Resort
Island Serenity Awaits: Studio Premium Villa at Westin Ka’anapali North
  • Air Conditioner
  • Parking
  • Pool

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Instantly Bookable Vacation Homes in Kaanapali

Over 2065+ Instantly Bookable Vacation Homes in or Near Kaanapali
Exquisite Condo with an Awesome Ocean View Emerald 289 From US $421
         

10.0 (155 Reviews)
Condo
Exquisite Condo with an Awesome Ocean View Emerald 289
  • Air Conditioner
  • Parking
  • Pool

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KBM Resorts | Spacious 3-Bedroom Honua Kai Collection | Multi Unit Listing | Same Floor | Ocean Views + 2 Free Rental Cars! HKH-516/20 From US $2,757
         

New
Condo
KBM Resorts | Spacious 3-Bedroom Honua Kai Collection | Multi Unit Listing | Same Floor | Ocean Views + 2 Free Rental Cars! HKH-516/20
  • Air Conditioner
  • Parking
  • TV

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Paradise Found: Spacious, Comfortable, Private Hawaiian Cottage From US $423
         

10.0 (143 Reviews)
Cottage
Paradise Found: Spacious, Comfortable, Private Hawaiian Cottage
  • Parking
  • Pool
  • TV

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KBM Resorts | Spacious 3-Bedroom Honua Kai Collection | Multi Unit Listing | Same Floor | Ocean Views + 2 Free Rental Cars! HKH-516/20/24 From US $1,720
         

New
Condo
KBM Resorts | Spacious 3-Bedroom Honua Kai Collection | Multi Unit Listing | Same Floor | Ocean Views + 2 Free Rental Cars! HKH-516/20/24
  • Air Conditioner
  • Parking
  • TV

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Kaanapali Villas, Oceanfront Luxury Maui Condo #180 From US $887
         

9.8 (132 Reviews)
Condo
Kaanapali Villas, Oceanfront Luxury Maui Condo #180
  • Air Conditioner
  • Parking
  • Pool

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Maui Eldorado K203 2BD Condo w AC Pool Beach Cabana From US $442
         

9.6 (67 Reviews)
Condo
Maui Eldorado K203 2BD Condo w AC Pool Beach Cabana
  • Air Conditioner
  • Parking
  • Pool

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4BR Oceanview Estate | Infinity Pool + Pickleball Ct. From US $2,079
         

10.0 (85 Reviews)
House
4BR Oceanview Estate | Infinity Pool + Pickleball Ct.
  • Air Conditioner
  • Parking
  • Pool

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Maui Resort Rentals: Kaanapali Ali'i 362 - Elegantly Remodeled 6th Floor 2BR w/Ocean AND Mountain Views! From US $1,067
         

10.0 (54 Reviews)
Condo
Maui Resort Rentals: Kaanapali Ali'i 362 - Elegantly Remodeled 6th Floor 2BR w/Ocean AND Mountain Views!
  • Air Conditioner
  • Parking
  • Pool

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About Kaanapali Vacation Rentals

With more than 303 Kaanapali vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Winecountryvillas and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Kaanapali.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Winecountryvillas Kaanapali, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Kaanapali. Places to stay near Kaanapali are 636.67 ft² on average, with prices averaging $921 a night.

Winecountryvillas makes it easy and safe to find and compare vacation rentals in Kaanapali with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Kaanapali

Type Count
Villas 265
Holiday Apartments 30
Vacation Homes 4
Hotels with Suites 3
Resorts 1

Use these Quick Filters to Find a Vacation Rental in Kaanapali

★ Pro Tip: Winecountryvillas makes it easy to compare the best listings on Winecountryvillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Winecountryvillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Kaanapali.

Weather in Kaanapali

View the weather forecast for Kaanapali before booking your Kaanapali Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Kaanapali, HI

Winecountryvillas offers a large selection of top attractions around Kaanapali. Research things to do on your vacation before you visit Kaanapali.


Kaanapali Beach Whalers Village Black Rock Kaanapali Golf Courses Kahekili Beach Kaanapali Kai Course at Kaanapali Golf Resort West Maui Parasail Hanakaoo Beach Park Skyline Eco Adventure Drums of the Pacific Lu au May's Beach Shoreline Snuba Keka'a Beach Whalers Village Museum Napili Bay Lahaina Harbor Maui Ocean Center Kapalua Beach Kapalua Golf Club Plantation Course Maalaea Harbor

Other Places to Stay Near Kaanapali, HI


Keka'a Beach 8,522 Properties Kahekili Beach 8,421 Properties May's Beach 8,188 Properties Kaanapali Hillside 8,174 Properties Skyline Eco Adventure 7,505 Properties Black Rock 7,364 Properties Whalers Village Museum 7,225 Properties Whalers Village 7,211 Properties Kaanapali Kai Course at Kaanapali Golf Resort 7,154 Properties Kaanapali Beach 7,120 Properties Kaanapali Golf Courses 7,090 Properties Hanakaoo Beach Park 6,914 Properties

Complexes around Kaanapali, HI


Honua Kai Lahaina 426 Properties Hyatt Residence Club 11 Properties The Westin Maui Resort 3 Properties Klvr Presents Luana Villa Resort 2 Properties Villa At The Westin Resort 2 Properties

Kaanapali Vacation Rental Frequently Asked Questions

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:

How many vacation rentals have private pools in Kaanapali?

There are 187 vacation rentals with private pools near Kaanapali. Top-rated homes that have access to a swimming pool include:

How many vacation rentals are available in Kaanapali?

Currently, the total number of properties listed in 2026 is over 303 in the Kaanapali area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Kaanapali.