Kailua Holiday Rentals

Compare Villas, Resorts, & Rentals in Kailua, Hawaii, USA

PRIVATE BEACHFRONT RENTAL
FromZA R8,276 per night
10.0 (166 Reviews)
1 Bedroom 2 Guests
Beautiful Guest House Kailua Beach
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9.1 (75 Reviews)
1 Bedroom 2 Guests
Luxurious five-bedroom modern retreat
10.0 (1 Review)
5 Bedrooms 18 Guests
Oahu Camper Adventures
FromZA R2,117 per night
9.1 (65 Reviews)
1 Bedroom 4 Guests
Hawaii's Hidden Hideaway Bed & Breakfast
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8.4 (67 Reviews)
1 Bedroom 2 Guests
'Kailua Lani Suite' short walk to Kailua Beach. Air conditioned and private.
10.0 (120 Reviews)
1 Bedroom 2 Guests
Beachfront spectacular Kailua beach
FromZA R20,729 per night
9.0 (1 Review)
4 Bedrooms 8 Guests
Available and legal for stays less than 30 days.
10.0 (112 Reviews)
1 Bedroom 2 Guests
Kailani Loft, Kailua Coconut Grove 1-bedroom
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8.6 (52 Reviews)
1 Bedroom 3 Guests
Charming Lanikai Kailua Cottage! Close to Lanikai beach, A/C, parking.
10.0 (107 Reviews)
1 Bedroom 2 Guests
Private One Bedroom Side House close to Kailua
3.5 (2 Reviews)
1 Bedroom 2 Guests
KAILUA-STEPS TO THE BEACH
FromZA R3,243 per night
10.0 (87 Reviews)
2 Bedrooms 5 Guests
Kailua Beachside home
FromZA R32,008 per night
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New
4 Bedrooms 14 Guests
Enchanting Beach Bungalow with Private Garden
10.0 (80 Reviews)
1 Bedroom 2 Guests
Upscale Kailua Getaway Steps to Swim Beach!
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New
3 Bedrooms 6 Guests
BEACHFRONT! Barefoot living on the best spot on Lanikai Beach!
10.0 (77 Reviews)
1 Bedroom 4 Guests
A Place of Peace where heaven meets the Ocean
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New
2 Bedrooms 4 Guests
licensed NUC no 90/TVU-0326 Serenity Beachfront Cottage
10.0 (61 Reviews)
2 Bedrooms 4 Guests
Beautiful Kailua Hale Studio
FromZA R6,453 per night
10.0 (56 Reviews)
1 Bedroom 2 Guests
Footsteps to Hawaii's Best Beach
FromZA R2,382 per night
10.0 (55 Reviews)
1 Bedroom 2 Guests
Footsteps to Hawaii's Best Beach
FromZA R2,262 per night
10.0 (45 Reviews)
1 Bedroom 2 Guests
Kalama Room
FromZA R1,761 per night
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New
1 Bedroom 2 Guests
Lanikai Ohana Hale
FromZA R16,529 per night
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New
1 Bedroom 4 Guests
Secluded Beach Bungalow with Private Garden
10.0 (32 Reviews)
1 Bedroom 2 Guests
Kailua Beach Lofty Bungalow - A premier luxury beachside bungalow
10.0 (29 Reviews)
1 Bedroom 2 Guests
Newly Upgraded Private Home in Kailua
New
1 Bedroom 4 Guests
Quiet, Private, Beachy 2-bedroom, Walk to Kailua Beach, A/C
10.0 (29 Reviews)
2 Bedrooms 4 Guests
The Banyan Beach Bungalow
FromZA R6,228 per night
10.0 (26 Reviews)
1 Bedroom 2 Guests
Lovely Private Kailua Cottage
FromZA R6,811 per night
10.0 (22 Reviews)
1 Bedroom 4 Guests
Entire Fantastic Kailua Cottage. waiting for you!
10.0 (17 Reviews)
1 Bedroom 3 Guests
Beautiful Beachside Bungalow
FromZA R6,214 per night
10.0 (15 Reviews)
1 Bedroom 2 Guests
Kailua Beach/Lanikai LUX apartment w/Ocean Views from Rooftop Sun Deck
10.0 (12 Reviews)
2 Bedrooms 2 Guests
Oahu Ohana Vans LLC
FromZA R5,081 per night
New
4 Bedrooms 4 Guests
Less than a one minute walk to Kailua Beach, Pool, Bikes, BBQ, A/C, and more
9.6 (149 Reviews)
1 Bedroom 3 Guests
Paradise Under the Plumeria Tree
FromZA R4,523 per night
9.6 (49 Reviews)
2 Bedrooms 5 Guests
Kailua Beachside Studio - Monet Room
FromZA R3,621 per night
9.6 (36 Reviews)
1 Bedroom 2 Guests
Lanikai Studio with Stunning Ocean View looking out at the Mokulua Islands
9.6 (35 Reviews)
1 Bedroom 2 Guests
Kailua Palms Guest House with Pool and Views! Parking and wi-fi included
9.6 (13 Reviews)
2 Bedrooms 4 Guests
La Bella's Bed and Breakfast-Nai’a Suite-Walk to beach-In Kailua (O’ahu)
9.6 (10 Reviews)
1 Bedroom 3 Guests
Heavenly Hale Best monthly Vacation rental - walk to beach!
9.6 (4 Reviews)
2 Bedrooms 4 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
Less than 1 min walk to Kailua Beach- NUC#1990/NUC-1760
9.4 (151 Reviews)
2 Bedrooms 5 Guests
Ocean View Guest Cottage - 1990/NUC-1797
9.4 (96 Reviews)
2 Bedrooms 4 Guests
Little Yellow Cottage: Steps to Lanikai Beach
9.4 (57 Reviews)
2 Bedrooms 4 Guests
Award Winner - Hawaii's Hidden Hideaway - Bed and Breakfast
9.2 (102 Reviews)
4 Bedrooms 3 Guests
Relax at Kapakai Cottage – 2-Bedroom Comfort with Full Kitchen & W/D
9.2 (24 Reviews)
2 Bedrooms 4 Guests

About Casai's Private Villas and Holiday Rentals in Kailua

Discover more than 455 vacation rentals available in Kailua. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Kailua.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Kailua, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Kailua. On average, places to stay near Kailua offer 1295.79 ft², with nightly prices averaging ZA R13,912.

With Casai, finding and comparing holiday rentals in Kailua is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

Nearby Neighborhood (7)

NeighborhoodProperty Count
Kalama Tract Vacation Rentals in Kailua, Hawaii 124
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