Hawaii Beach Comber - Vacation Rentals in Kailua (Maui)

Pole House by Maui Aventure Villa From US $350
         

10.0 (251 Reviews)
House
  • Child Friendly
Bamboo Valley Inn From US $325
         

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9.8 (16 Reviews)
Bed & Breakfast
  • Parking
  • Security/Safety
  • Guest Services
Bamboo Valley Inn From US $314
         

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9.4 (55 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
North shore Maui ocean view B and B room 2 From US $245
         

10.0 (201 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
North Shore Ocean View Cottage From US $631
         

10.0 (151 Reviews)
House
  • Parking
  • TV
  • View
North shore Maui B and B room 1. From US $210
         

10.0 (126 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
Haleakala Cottage - private hot tub, pool access From US $532
         

10.0 (106 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Luxury Places to Stay in Kailua (Maui)

Over 67+ Luxury Places to Stay in or Near Kailua (Maui)
Featured on Staycation TV Stunning Modern Home Surrounded by Nature From US $1,572
         

10.0 (13 Reviews)
House
  • Parking
  • Pool
  • Designated Smoking Area
Tranquil 4-bedroom on Tropical Flower Farm in Haiku, Maui From US $1,390
         

10.0 (1 Review)
House
  • Parking
  • Pool
  • Designated Smoking Area
Waterfall House - Private House Overlooking the Ocean! From US $1,009
         

9.8 (26 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Waterfall House with Ocean Views in Haiku, Maui From US $590
         

8.2 (5 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Cliff House with Ocean Views in Haiku, Maui jungle From US $576
         

9.8 (5 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool

Top-Rated Vacation Rentals with a Pool in Kailua (Maui)

Over 19+ Top-Rated Vacation Rentals with a Pool in or Near Kailua (Maui)
Plumeria Room on a Lush Farm on Maui's North Shore From US $487
         

10.0 (7 Reviews)
Cabin
  • Parking
  • Pool
  • Balcony/Terrace
Jasmine Suite on Lush farm in Haiku, Maui jungle From US $383
         

7.5 (12 Reviews)
Ski Chalet
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Kailua (Maui)

Over 1+ Pet-Friendly Vacation Rentals in or Near Kailua (Maui)
Spacious 3br/1ba home, A/C & WiFi From US $509
         

9.8 (18 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Kailua (Maui)

Over 1+ Large Vacation Homes & Villas in or Near Kailua (Maui)
Maui Eco Retreat From US $385
         

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6.7 (8 Reviews)
Apartment
  • Parking
  • Designated Smoking Area
  • View

Wheelchair Accessible Vacation Homes in Kailua (Maui)

Over 2+ Wheelchair Accessible Vacation Homes in or Near Kailua (Maui)
Welcome to the Dolphin Studio + 1 bathroom with Wifi From US $170
         

4.9 (18 Reviews)
Apartment
  • Wheelchair Accessible
  • Bedding/Linens
  • Internet

Kailua (Maui) Vacation Rentals and Airbnb Places to Stay Under $200

Over 1+ Kailua (Maui) Vacation Rentals and Airbnb Places to Stay Under $200
Tropical Fruit Farm Sanctuary From US $79
         

New
Apartment
  • Security/Safety
  • Bedding/Linens
  • Child Friendly

Instantly Bookable Vacation Homes in Kailua (Maui)

Over 32+ Instantly Bookable Vacation Homes in or Near Kailua (Maui)
Bamboo Bliss: Ocean Views & Waterfalls Await! From US $500
         

10.0 (5 Reviews)
Cottage
  • Parking
  • View
  • Ocean View
Ho’okipa Hideaway - North Shore, Walk to Cafe From US $276
         

10.0 (1 Review)
Apartment
  • Security/Safety
  • Bedding/Linens
  • Wellness Facilities
Evergreen Cottage by Maui Adventure Villa From US $237
         

Gazebo Room Farm Stay in Haiku on Road to Hana From US $285
         

New
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

About Kailua (Maui) Vacation Rentals

With more than 76 Kailua (Maui) vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Hawaiibeachcomber 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 Kailua (Maui).

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Hawaiibeachcomber Kailua (Maui), 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 Kailua (Maui). Places to stay near Kailua (Maui) are 482.81 ft² on average, with prices averaging US $473 a night.

Hawaiibeachcomber makes it easy and safe to find and compare vacation rentals in Kailua (Maui) 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 Kailua (Maui)

Type Count
Vacation Homes 36
Holiday Apartments 15
B&B 6
Cottages 6
Resorts 6
Villas 3
Ski Chalet Rentals 2
Cabin Rentals 1
Others 1

Use these Quick Filters to Find a Vacation Rental in Kailua (Maui)

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

Weather in Kailua (Maui)

View the weather forecast for Kailua (Maui) before booking your Kailua (Maui) 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

Kailua (Maui) Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Kailua (Maui)?
How many vacation rentals are available in Kailua (Maui)?

Currently, the total number of properties listed in 2026 is over 76 in the Kailua (Maui) area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Kailua (Maui).