Surf Break Rentals - Vacation Rentals in Kailua

Oahu Camper Adventures From US $125
         

10.0 (1 Review)
Boat Rental
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Luxurious five-bedroom modern retreat From US $2,802
         

10.0 (1 Review)
House
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Kailua Oceanfront Villa with Heated Pool & Spa From US $710
         

10.0 (111 Reviews)
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MONTHLY DISCOUNT! 3Bed/2Ba House - 250 Steps to the Beach! From US $374
         

Luxury Places to Stay in Kailua

Over 442+ Luxury Places to Stay in or Near Kailua
Kailua Luxury Estate: Licensed Rental #1990/NUC-1787 From US $4,269
         

Luxury beachfront villa on a world class beach in Kailua, HI From US $4,254
         

10.0 (2 Reviews)
House
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Ocean Front Lanikai - Lic. Rental #1990/NUC-1757 From US $3,923
         

10.0 (130 Reviews)
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Top-Rated Vacation Rentals with a Pool in Kailua

Over 149+ Top-Rated Vacation Rentals with a Pool in or Near Kailua
Amazing Kailua Beach Front Licensed Rental #1990/NUC-1802 From US $3,496
         

10.0 (225 Reviews)
House
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Pet-Friendly Vacation Rentals in Kailua

Over 35+ Pet-Friendly Vacation Rentals in or Near Kailua
Beachfront spectacular Kailua beach From US $1,224
         

9.0 (1 Review)
House
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Luxury Coconut Grove, Kailua Vacation Home From US $368
         

10.0 (2 Reviews)
House
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Coconut Grove Kailua Vacation Home From US $283
         

10.0 (2 Reviews)
House
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Coconut Grove Cottage, Walk to Beach and Downtown From US $253
         

10.0 (2 Reviews)
House
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Tradewind Bungalow, in Kailua on Oahu From US $186
         

9.8 (143 Reviews)
House
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See More Pet-Friendly Vacation Rentals in Kailua on PetFriendly.io

Large Vacation Homes & Villas in Kailua

Over 84+ Large Vacation Homes & Villas in or Near Kailua
Lanikai Beach w/heated pool, spa: HOLIDAY SPECIAL - Call now! From US $982
         

Zen Home with AC, Pool, Near Kailua Beach From US $1,132
         

9.8 (75 Reviews)
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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 $263
         

Available and legal for stays less than 30 days. From US $373
         

10.0 (106 Reviews)
Apartment
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Beachfront Cottage - Steps to beach, AC From US $1,367
         

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

Kailua Varoom and Airbnb Places to Stay Under $200

Over 77+ Kailua Varoom and Airbnb Places to Stay Under $200
Footsteps to Hawaii's Best Beach From US $141
         

10.0 (55 Reviews)
Cottage
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Kailani Loft, Kailua Coconut Grove 1-bedroom From US $193
         

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9.0 (50 Reviews)
Apartment
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Footsteps to Hawaii's Best Beach From US $134
         

10.0 (45 Reviews)
Cottage
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*Affordable Island Getaway with private yard * From US $169
         

Instantly Bookable Vacation Homes in Kailua

Over 165+ Instantly Bookable Vacation Homes in or Near Kailua
Charming Lanikai Cottage. Close to beach, A/C, parking. From US $431
         

10.0 (104 Reviews)
Cottage
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Award Winner - Hawaii's Hidden Hideaway - Bed and Breakfast From US $385
         

9.2 (96 Reviews)
Bed & Breakfast
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Absolutely Oceanfront - 60' Waterfall Lap Pool From US $763
         

9.4 (163 Reviews)
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Kailua Oceanfront-60' Lap Pool - Upscale Quiet Neighborhood - Legal From US $780
         

Steps to beach, tropical garden and private pool From US $595
         

9.2 (20 Reviews)
House
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About Kailua Vacation Rentals

With more than 451 Kailua vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Surfbreakrentals 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 Surfbreakrentals 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 1355.55 ft² on average, with prices averaging $824 a night.

Surfbreakrentals 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 293
Holiday Apartments 93
Cottages 38
Villas 16
B&B 5
Ski Chalet Rentals 1

Use these Quick Filters to Find a Vacation Rental in Kailua

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