Travel The Horizon - Vacation Rentals in Kahoolawe

Breathtaking Oceanfront Boutique From US $405
         

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8.5 (2 Reviews)
House
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Modern & Polished Oceanfront Vistas From US $524
         

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10.0 (21 Reviews)
Condo
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Hawaiian Cottage and Personal Paradise/BBKM 2013/0004 From US $1,136
         

10.0 (208 Reviews)
Cottage
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  • Pool
NEW KITCHEN REMODEL! Amazing View! From US $456
         

10.0 (158 Reviews)
Condo
  • Air Conditioner
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  • Pool
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted From US $689
         

Luxury Places to Stay in Kahoolawe

Over 7632+ Luxury Places to Stay in or Near Kahoolawe
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New
Apartment
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Polo Beach Club POL-109 by KBM From US $9,471
         

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8.0 (1 Review)
Condo
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Wailea Elua Village Resort by KBM From US $9,199
         

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New
Condo
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South Maui's Best Family Reunion Spot From US $7,186
         

9.8 (44 Reviews)
Hotel
  • Air Conditioner
  • TV
  • Balcony/Terrace

Top-Rated Vacation Rentals with a Pool in Kahoolawe

Over 6646+ Top-Rated Vacation Rentals with a Pool in or Near Kahoolawe
Breathtaking ocean views! Steps to the beach! Recently remodeled! From US $430
         

Romantic, Luxury, Sensual Retreat - Couples Only From US $588
         

10.0 (207 Reviews)
Condo
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Pet-Friendly Vacation Rentals in Kahoolawe

Over 50+ Pet-Friendly Vacation Rentals in or Near Kahoolawe
Gated 2-story beach house with big yard From US $1,014
         

10.0 (85 Reviews)
Villa
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  • Pet Friendly
Maui What a Wonderful World Bed & Breakfast From US $270
         

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9.3 (61 Reviews)
Bed & Breakfast
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  • Pet Friendly
The Ocean View Residence From US $676
         

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10.0 (1 Review)
Apartment
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  • Pet Friendly
Maui Sunset Oasis- Top Unit w/AC, watch whales from from Lanai (Dec-Apr) From US $410
         

Bring the Dog to a Kihei Condo with Pool & Tennis From US $653
         

10.0 (2 Reviews)
Condo
  • Air Conditioner
  • Pet Friendly
  • Pool
Condo w/Private Lanai, Ocean View & On-Site Pool! From US $340
         

9.6 (33 Reviews)
Condo
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  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Kahoolawe

Over 284+ Large Vacation Homes & Villas in or Near Kahoolawe
Villa Moana Maui From US $1,892
         

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New
Villa
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BEACHFRONT MAUI KIHEI HOUSE From US $1,442
         

9.8 (173 Reviews)
House
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Spectacular 3rd Row Villa at Ho'olei with Ocean Views From US $1,391
         

10.0 (63 Reviews)
Villa
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5 Star Ocean View, Beach House Chic, Click the Video tour below! From US $485
         

Wheelchair Accessible Vacation Homes in Kahoolawe

Over 2661+ Wheelchair Accessible Vacation Homes in or Near Kahoolawe
Hale Hui Kai #112 From US $420
         

10.0 (1 Review)
House
  • Pool
  • View
  • Wheelchair Accessible
Endless & Elegant Vistas From US $409
         

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10.0 (7 Reviews)
Condo
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Spectacular Wall of Glass! From US $695
         

10.0 (141 Reviews)
Condo
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Direct Oceanfront/Beachfront Luxury! Recently Remodeled From US $737
         

10.0 (113 Reviews)
Condo
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  • Pool

Kahoolawe Vacation Rentals and Airbnb Places to Stay Under $200

Over 184+ Kahoolawe Vacation Rentals and Airbnb Places to Stay Under $200
Maui Vista 1207 From US $197
         

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7.8 (16 Reviews)
Apartment
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  • View
Kamaole Sands One Bedrooms by Coldwell Banker Island Vacations From US $88
         

Deluxe Camper Van with Aloha From US $183
         

10.0 (2 Reviews)
House
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  • Parking
  • Balcony/Terrace
Paradise Jays Maui Island Breeze From US $154
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Security/Safety
Great Rates - Great Location - Clean and Cozy Condo! From US $198
         

9.8 (171 Reviews)
Condo
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Cozy Maui 'Treehouse' with lovely views and amenities From US $194
         

9.8 (98 Reviews)
Cottage
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  • Pool

Instantly Bookable Vacation Homes in Kahoolawe

Over 4981+ Instantly Bookable Vacation Homes in or Near Kahoolawe
Oceanfront, Million-Dollar-View, Newly renovated! B421 From US $725
         

10.0 (178 Reviews)
Condo
  • Air Conditioner
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  • Pool
Amazing view, Close to the beach, Wailea Ekahi Unit 20i From US $567
         

10.0 (137 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Beachfront Condo B303 From US $1,197
         

10.0 (101 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
1BR/1BA BEACHFRONT GREAT LOCATION July 2026-Sept 2026 Discounted! From US $289
         

Maui Family Owned & Managed - Wailea Grand Champions Villa From US $517
         

2BR/1BA BEACHFRONT GREAT LOCATION July 2026-Sept 2026 Discounted! From US $445
         

About Kahoolawe Vacation Rentals

With more than 7641 Kahoolawe vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Travelthehorizon 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 Kahoolawe.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Travelthehorizon Kahoolawe, 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 Kahoolawe. Places to stay near Kahoolawe are 786.3 ft² on average, with prices averaging US $597 a night.

Travelthehorizon makes it easy and safe to find and compare vacation rentals in Kahoolawe 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 Kahoolawe

Type Count
Holiday Apartments 1342
Vacation Homes 749
Resorts 136
Villas 122
Hotels 57
Cottages 15
B&B 8
Cabin Rentals 1

Use these Quick Filters to Find a Vacation Rental in Kahoolawe

Pro Tip: Travelthehorizon makes it easy to compare the best listings on Travelthehorizon homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Travelthehorizon 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 Kahoolawe.

Weather in Kahoolawe

View the weather forecast for Kahoolawe before booking your Kahoolawe 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

Other Places to Stay Near Kahoolawe, HI


Kahoolawe Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Kahoolawe?
How many vacation rentals are available in Kahoolawe?

Currently, the total number of properties listed in 2026 is over 7641 in the Kahoolawe area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Kahoolawe.