Gulf Blue Vacations - Vacation Rentals in Kailua

Modern Luxury Beach House Kailua From US $275
         

|
9.1 (85 Reviews)
House
  • Parking
  • View
  • Ocean View
Luxurious five-bedroom modern retreat From US $2,802
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • TV
Kailua Oceanfront Villa with Heated Pool & Spa From US $710
         

10.0 (111 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
MONTHLY DISCOUNT! 3Bed/2Ba House - 250 Steps to the Beach! From US $450
         

Luxury Places to Stay in Kailua

Over 450+ Luxury Places to Stay in or Near Kailua
Luxury beachfront villa on a world class beach in Kailua, HI From US $4,254
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Kailua Luxury Estate: Licensed Rental #1990/NUC-1787 From US $4,216
         

Top-Rated Vacation Rentals with a Pool in Kailua

Over 150+ Top-Rated Vacation Rentals with a Pool in or Near Kailua
Amazing Kailua Beach Front Licensed Rental #1990/NUC-1802 From US $2,823
         

10.0 (228 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Kailua

Over 39+ Pet-Friendly Vacation Rentals in or Near Kailua
Charming Hale Mokolea in Lanikai –2BR, 2BA, Full Kitchen From US $255
         

10.0 (5 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • Designated Smoking Area
Beachfront spectacular Kailua beach From US $1,224
         

9.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Coconut Grove Cottage, Walk to Beach and Downtown From US $300
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxury Coconut Grove, Kailua Vacation Home From US $453
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Coconut Grove Kailua Vacation Home From US $307
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Tradewind Bungalow, in Kailua on Oahu From US $186
         

9.8 (145 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
See More Pet-Friendly Vacation Rentals in Kailua on PetFriendly.io

Large Vacation Homes & Villas in Kailua

Over 87+ Large Vacation Homes & Villas in or Near Kailua
Hale Mokulua - Lanikai w/heated pool, spa, steps to Beach! From US $907
         

Zen Home with AC, Pool, Near Kailua Beach From US $1,068
         

9.8 (77 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

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 $270
         

Available and legal for stays less than 30 days. From US $344
         

10.0 (112 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 79+ Kailua Vacation Rentals and Airbnb Places to Stay Under $200
Footsteps to Hawaii's Best Beach From US $141
         

10.0 (55 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
Oahu Camper Adventures From US $125
         

9.1 (65 Reviews)
Boat Rental
  • Parking
  • View
  • Security/Safety
Footsteps to Hawaii's Best Beach From US $134
         

10.0 (45 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
*Affordable Island Getaway with private yard * From US $179
         

Instantly Bookable Vacation Homes in Kailua

Over 165+ Instantly Bookable Vacation Homes in or Near Kailua
Absolutely Oceanfront - 60' Waterfall Lap Pool From US $686
         

9.4 (168 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Kailua Oceanfront-60' Lap Pool - Upscale Quiet Neighborhood - Legal From US $642
         

Pueohala - Kailua Beach Front From US $1,044
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

About Kailua Vacation Rentals

With more than 459 Kailua vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Gulfbluevacations 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 Gulfbluevacations 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 1293.64 ft² on average, with prices averaging $815 a night.

Gulfbluevacations 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
Vacation Homes 298
Holiday Apartments 95
Cottages 39
Villas 15
B&B 5
Others 1
Ski Chalet Rentals 1

Use these Quick Filters to Find a Vacation Rental in Kailua

Pro Tip: Gulfbluevacations makes it easy to compare the best listings on Gulfbluevacations homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Gulfbluevacations 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 459 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.