Luxury Home Villas - Vacation Rentals in Kailua

Beachfront spectacular Kailua beach From US $2,044
         

10.0 (6 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Newly Upgraded Private Home in Kailua From US $170
         

New
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Villa Frangipani Tropical Beachside Retreat Kailua From US $671
         

Luxury Places to Stay in Kailua

Over 425+ Luxury Places to Stay in or Near Kailua
Luxury beachfront villa on a world class beach in Kailua, HI From US $4,470
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Kailua Luxury Estate: Licensed Rental #1990/NUC-1787 From US $3,717
         

Top-Rated Vacation Rentals with a Pool in Kailua

Over 135+ Top-Rated Vacation Rentals with a Pool in or Near Kailua
Kailua Oceanfront Villa with Heated Pool & Spa From US $710
         

10.0 (112 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Kailua

Over 40+ Pet-Friendly Vacation Rentals in or Near Kailua
Coconut Grove Cottage, Walk to Beach and Downtown From US $275
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Beachfront spectacular Kailua beach From US $1,224
         

9.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxury Coconut Grove, Kailua Vacation Home From US $425
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Coconut Grove Kailua Vacation Home From US $279
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Keolu Hills Haven: Renovated 2/2 & Easy Parking From US $246
         

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

Large Vacation Homes & Villas in Kailua

Over 77+ Large Vacation Homes & Villas in or Near Kailua
Hale Mokulua - Lanikai, Oahu/pools, spa, beach! From US $1,056
         

10.0 (21 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Luxurious five-bedroom modern retreat From US $2,802
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • TV
Hale Oahu Estate Lic. #1990/NUC-1777 BEACHFRONT KAILUA From US $3,102
         

Lanikai Beachfront - AUGUST CANCELLATION - BOOK NOW! From US $1,063
         

Wheelchair Accessible Vacation Homes in Kailua

Over 8+ Wheelchair Accessible Vacation Homes in or Near Kailua
Sunny Kailua Home w/Covered Lanai 1 Mi to Beach! From US $280
         

Available and legal for stays less than 30 days. From US $375
         

10.0 (115 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Beachfront Cottage - Steps to beach, AC From US $1,367
         

Seascape Vista - Pool, AC From US $1,383
         

Kailua Vacation Rentals and Airbnb Places to Stay Under $200

Over 77+ Kailua Vacation Rentals and Airbnb Places to Stay Under $200
Kailani Loft, Kailua Coconut Grove 1-bedroom From US $193
         

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8.4 (57 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • View
Footsteps to Hawaii's Best Beach From US $163
         

10.0 (56 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
Affordable Island Getaway with private yard From US $181
         

Charming 1.5 bedroom cottage, fully furnished in a great location! From US $179
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety

Instantly Bookable Vacation Homes in Kailua

Over 158+ Instantly Bookable Vacation Homes in or Near Kailua
MONTHLY DISCOUNT! 3Bed/2Ba House - 250 Steps to the Beach! From US $516
         

About Kailua Vacation Rentals

With more than 14 Kailua vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Luxuryhomevilla 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.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Luxuryhomevilla Kailua, 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. Places to stay near Kailua are 2191.71 ft² on average, with prices averaging US $2,121 a night.

Luxuryhomevilla makes it easy and safe to find and compare vacation rentals in Kailua 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

Type Count
Villas 14

Use these Quick Filters to Find a Vacation Rental in Kailua

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

Weather in Kailua

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

December - February
High 79°F       Low 64°F
March - May
High 83°F       Low 66°F
June - August
High 84°F       Low 69°F
September - November
High 84°F       Low 66°F

Kailua Vacation Rental Frequently Asked Questions

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

Currently, the total number of properties listed in 2026 is over 14 in the Kailua area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Kailua.