Hanalei Bay Villas - Vacation Rentals in Kailua (Maui)

Cliff House with Ocean Views in Haiku, Maui jungle in Huelo From US $576
         

9.8 (5 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Waterfall House with Ocean Views in Haiku, Maui in Huelo From US $590
         

8.2 (5 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool

Luxury Places to Stay in Kailua (Maui)

Over 68+ Luxury Places to Stay in or Near Kailua (Maui)
Featured on Staycation TV Stunning Modern Home Surrounded by Nature in Haiku-Pauwela From US $1,461
         

10.0 (13 Reviews)
House
  • Parking
  • Pet Friendly
  • Designated Smoking Area
Waterfall House - Private House Overlooking the Ocean! in Haiku From US $951
         

9.8 (28 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Villa Farm Stay w/Ocean Views on Road to Hana in Haiku From US $767
         

New
Resort
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Priv Hot Tub + Shared Jungle Pool! - Ocean Lookout in Haiku From US $766
         

10.0 (17 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
★Rainbow Lookout - PRIVATE HOT TUB+ACCESS TO POOL in Haiku From US $722
         

10.0 (25 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Bamboo Bliss: Ocean Views & Waterfalls Await! in Maui County From US $626
         

10.0 (5 Reviews)
Cottage
  • Parking
  • View
  • Ocean View

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

Over 18+ Top-Rated Vacation Rentals with a Pool in or Near Kailua (Maui)
Haleakala Cottage - private hot tub, pool access in Haiku From US $532
         

10.0 (106 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Spacious Hawaiian Cottage Suite in the Upcountry of Maui! in makawao From US $396
         

Plumeria Room on a Lush Farm on Maui's North Shore in Haiku From US $501
         

10.0 (7 Reviews)
Cabin
  • Parking
  • Pool
  • Balcony/Terrace
Private Hot Tub + Pool Access + AC - Star Lookout in Haiku From US $595
         

9.8 (17 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Hale Akua Garden Farm & Eco-Retreat in Huelo From US $285
         

9.2 (11 Reviews)
House
  • Parking
  • Pool
  • View

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 in Haiku-Pauwela From US $504
         

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

Large Vacation Homes & Villas in Kailua (Maui)

Over 2+ Large Vacation Homes & Villas in or Near Kailua (Maui)
Tranquil 4-bedroom on Tropical Flower Farm in Haiku, Maui in Haiku From US $1,390
         

10.0 (1 Review)
House
  • Parking
  • Pool
  • Designated Smoking Area
Maui Eco Retreat in Huelo 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 in Haiku-Pauwela 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 in Haiku-Pauwela From US $78
         

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

Instantly Bookable Vacation Homes in Kailua (Maui)

Over 27+ Instantly Bookable Vacation Homes in or Near Kailua (Maui)
Peaceful Haiku Retreat Beach 10 Min & Paia 15 Min in Haiku-Pauwela From US $438
         

9.8 (69 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Peaceful Haiku Retreat Beach 10 Min & Paia 15 Min in Haiku-Pauwela From US $438
         

9.8 (79 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
North shore Maui B and B room 1. in Haiku From US $211
         

10.0 (127 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV

About Kailua (Maui) Vacation Rentals

With more than 3 Kailua (Maui) vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Hanaleibayvillas 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 Hanaleibayvillas 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 1632.53 ft² on average, with prices averaging US $576 a night.

Hanaleibayvillas 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
Villas 3

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

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

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

Currently, the total number of properties listed in 2026 is over 3 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).