Explore Kailua Vacation Rentals

Compare Vacation Rentals in Kailua, Hawaii, USA

Beautiful Guest House Kailua Beach
|
9.1 (75 Reviews)
1 Bedroom 2 Guests
Luxurious five-bedroom modern retreat
10.0 (1 Review)
5 Bedrooms 18 Guests
Kailua Oceanfront Villa with Heated Pool & Spa
10.0 (111 Reviews)
3 Bedrooms 6 Guests
Oahu Camper Adventures
FromUS $125 per night
9.1 (65 Reviews)
1 Bedroom 4 Guests
Hawaii's Hidden Hideaway Bed & Breakfast
|
8.4 (67 Reviews)
1 Bedroom 2 Guests
MONTHLY DISCOUNT! 3Bed/2Ba House - 250 Steps to the Beach!
10.0 (72 Reviews)
3 Bedrooms 6 Guests
Beachfront spectacular Kailua beach
FromUS $1,224 per night
9.0 (1 Review)
4 Bedrooms 8 Guests
Kailani Loft, Kailua Coconut Grove 1-bedroom
|
8.6 (52 Reviews)
1 Bedroom 3 Guests
Resort-like Kailua Beach Lanikai Beach LABOR Day & SEPT Special
9.8 (73 Reviews)
3 Bedrooms 6 Guests
Private One Bedroom Side House close to Kailua
3.5 (2 Reviews)
1 Bedroom 2 Guests
Kailua Beachside home
FromUS $1,890 per night
|
New
4 Bedrooms 14 Guests
Lanikai Ohana Hale
FromUS $976 per night
|
New
1 Bedroom 4 Guests
Amazing Kailua Beach Front Licensed Rental #1990/NUC-1802
10.0 (228 Reviews)
5 Bedrooms 14 Guests
Upscale Kailua Getaway Steps to Swim Beach!
|
New
3 Bedrooms 6 Guests
Walker Beach House - Lanikai Ocean Front Lic.#1990/NUC-1757
10.0 (134 Reviews)
5 Bedrooms 14 Guests
A Place of Peace where heaven meets the Ocean
|
New
2 Bedrooms 4 Guests
'Kailua Lani Suite' short walk to Kailua Beach. Air conditioned and private.
10.0 (120 Reviews)
1 Bedroom 2 Guests
Kailua Luxury Estate: Licensed Rental #1990/NUC-1787
9.8 (76 Reviews)
6 Bedrooms 16 Guests
Charming Lanikai Kailua Cottage! Close to Lanikai beach, A/C, parking.
10.0 (107 Reviews)
1 Bedroom 2 Guests
Absolutely Oceanfront - 60' Waterfall Lap Pool
9.4 (167 Reviews)
1 Bedroom 2 Guests
Kailua Oceanfront-60' Lap Pool - Upscale Quiet Neighborhood - Legal
9.4 (163 Reviews)
1 Bedroom 2 Guests
Newly Upgraded Private Home in Kailua
New
1 Bedroom 4 Guests
Hale Mokulua - Lanikai w/heated pool, spa, steps to Beach!
10.0 (21 Reviews)
4 Bedrooms 14 Guests
Kalama Room
FromUS $104 per night
|
New
1 Bedroom 2 Guests
Pueohala - Kailua Beach Front
FromUS $1,034 per night
10.0 (8 Reviews)
4 Bedrooms 8 Guests
Steps to beach, tropical garden and private pool
9.2 (20 Reviews)
3 Bedrooms 6 Guests
PRIVATE BEACHFRONT RENTAL
FromUS $489 per night
10.0 (165 Reviews)
1 Bedroom 2 Guests
Coconut Grove Kailua Vacation Home
10.0 (2 Reviews)
3 Bedrooms 6 Guests
Oahu Ohana Vans LLC
FromUS $300 per night
New
4 Bedrooms 4 Guests
*Affordable Island Getaway with private yard *
10.0 (2 Reviews)
1 Bedroom 2 Guests
Charming 1.5 bedroom cottage, fully furnished in a great location!
10.0 (1 Review)
1 Bedroom 2 Guests
Private Beachfront Rental
FromUS $469 per night
9.8 (259 Reviews)
1 Bedroom 2 Guests
NUC 90/BB-0069, GE-014-134-8864-01, TA-014-134-8864-01
9.8 (161 Reviews)
1 Bedroom 2 Guests
Tradewind Bungalow, in Kailua on Oahu
9.8 (145 Reviews)
2 Bedrooms 6 Guests
Steps to the Beach Guesthouse
FromUS $231 per night
9.8 (89 Reviews)
1 Bedroom 2 Guests
Zen Home with AC, Pool, Near Kailua Beach
9.8 (77 Reviews)
4 Bedrooms 12 Guests
Hale Oahu Estate Lic. #1990/NUC-1777 BEACHFRONT KAILUA
9.8 (50 Reviews)
6 Bedrooms 14 Guests
Beautiful Kailua Hale 1 Bedroom
FromUS $357 per night
9.8 (29 Reviews)
1 Bedroom 4 Guests
Kailua Home Pool & Spa with amazing views
9.8 (29 Reviews)
3 Bedrooms 7 Guests
Lanikai Beachfront - Sunrise over the Mokulua Islands - SPECTACULAR!
9.8 (6 Reviews)
5 Bedrooms 10 Guests

About Kailua Vacation Rentals

There are more than 455 places to stay in Kailua that are available. These options include hotels, resorts, rentals as well as short-term private accommodations (i.e. RVs, Condos, Cabins, Chalets, etc.). The places can provide you with a great option on your next holiday. Compare many places to stay in Kailua.

Are you seeking a last-minute hotel deal, or are you wanting to find the best deals available for hotels, resorts, cottages, condos, private villas, chalets, or a large vacation homes? With Hotala Kailua, you can quickly compare different options to find the hottest deals with a single click. Looking for a resort with an infinity pool, hot tub, is pet-friendly, or features a large master suite bedrooms or has a fireplace? You can find hotels, resorts, or other popular Airbnb-style properties in or near Kailua. Places to stay near Kailua are 1295.79 ft² on average, with prices averaging US $822 a night.

Hotala makes it easy to find and compare hotels, resorts, and holiday rentals in Kailua with prices often listed at a 30-40% off the rack rate. Just enter your destination and secure your reservation today.

Frequently Asked Questions About Kailua?

What are the top vacation rentals in Kailua?

How many Hawaii.Villas vacation rentals are available in Kailua?

At present, HawaiiVillas showcases more than 455 properties available in the Kailua area for 2026, with new listings added regularly. By aggregating listings from multiple sources, HawaiiVillas offers a diverse range of premier properties in Kailua.

Nearby Neighborhood (7)

NeighborhoodProperty Count
Kalama Tract Vacation Rentals in Kailua, Hawaii 125
Lanikai Vacation Rentals in Kailua, Hawaii 79
Coconut Grove Vacation Rentals in Kailua, Hawaii 498
Enchanted Lake Vacation Rentals in Kailua, Hawaii 452
Keolu Hills Vacation Rentals in Kailua, Hawaii 434
Kuulei Tract Vacation Rentals in Kailua, Hawaii 475
Palolo Vacation Rentals in Kailua, Hawaii 159