Kailua Holiday Rentals

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

PRIVATE BEACHFRONT RENTAL
FromUS $469 per night
10.0 (169 Reviews)
1 Bedroom 2 Guests
Sunny Kailua Home w/Covered Lanai 1 Mi to Beach!
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10.0 (1 Review)
3 Bedrooms 7 Guests
Luxurious five-bedroom modern retreat
10.0 (1 Review)
5 Bedrooms 18 Guests
Modern Luxury Beach House Kailua
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9.2 (88 Reviews)
3 Bedrooms 7 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
Beautiful Guest House Kailua Beach
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9.1 (70 Reviews)
1 Bedroom 2 Guests
Available and legal for stays less than 30 days.
10.0 (112 Reviews)
1 Bedroom 2 Guests
Beachfront spectacular Kailua beach
FromUS $1,224 per night
9.0 (1 Review)
4 Bedrooms 8 Guests
Charming Lanikai Kailua Cottage! Close to Lanikai beach, A/C, parking.
10.0 (107 Reviews)
1 Bedroom 2 Guests
Kailani Loft, Kailua Coconut Grove 1-bedroom
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8.6 (52 Reviews)
1 Bedroom 3 Guests
Private One Bedroom Side House close to Kailua
3.5 (2 Reviews)
1 Bedroom 2 Guests
KAILUA-STEPS TO THE BEACH
FromUS $192 per night
10.0 (87 Reviews)
2 Bedrooms 5 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
Beautiful Kailua Hale Studio
FromUS $375 per night
10.0 (56 Reviews)
1 Bedroom 2 Guests
Kalama Room
FromUS $104 per night
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New
1 Bedroom 2 Guests
Footsteps to Hawaii's Best Beach
FromUS $141 per night
10.0 (55 Reviews)
1 Bedroom 2 Guests
Lanikai Ohana Hale
FromUS $976 per night
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New
1 Bedroom 4 Guests
Footsteps to Hawaii's Best Beach
FromUS $134 per night
10.0 (45 Reviews)
1 Bedroom 2 Guests
Newly Upgraded Private Home in Kailua
New
1 Bedroom 4 Guests
Oahu Ohana Vans LLC
FromUS $300 per night
New
4 Bedrooms 4 Guests
Secluded Beach Bungalow with Private Garden
10.0 (32 Reviews)
1 Bedroom 2 Guests
Quiet, Private, Beachy 2-bedroom, Walk to Kailua Beach, A/C
10.0 (29 Reviews)
2 Bedrooms 4 Guests
The Banyan Beach Bungalow
FromUS $367 per night
10.0 (26 Reviews)
1 Bedroom 2 Guests
Lovely Private Kailua Cottage
FromUS $466 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
FromUS $367 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
La Bella’s Bed & Breakfast-Honu (Turtle) Suite-Walk to beach-In Kailua (O’ahu)
10.0 (11 Reviews)
1 Bedroom 4 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 (168 Reviews)
1 Bedroom 2 Guests
Kailua Oceanfront-60' Lap Pool - Upscale Quiet Neighborhood - Legal
9.4 (163 Reviews)
1 Bedroom 2 Guests
Ocean View Guest Cottage - 1990/NUC-1797
9.4 (97 Reviews)
2 Bedrooms 4 Guests
Little Yellow Cottage: Steps to Lanikai Beach
9.4 (57 Reviews)
2 Bedrooms 4 Guests
Less than 1 min walk to Kailua Beach- NUC#1990/NUC-1760
9.2 (155 Reviews)
2 Bedrooms 5 Guests
Award Winner - Hawaii's Hidden Hideaway - Bed and Breakfast
9.2 (104 Reviews)
2 Bedrooms 3 Guests
Light and breezy Kailua apartment
9.0 (2 Reviews)
1 Bedroom 2 Guests
Private Luxury Home, Steps from the Beach w/AC, Ranch Beach House
8.0 (1 Review)
2 Bedrooms 4 Guests

About Casai's Private Villas and Holiday Rentals in Kailua

Discover more than 456 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 1298.04 ft², with nightly prices averaging US $832.

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 112
Lanikai Vacation Rentals in Kailua, Hawaii 61
Coconut Grove Vacation Rentals in Kailua, Hawaii 499
Enchanted Lake Vacation Rentals in Kailua, Hawaii 458
Keolu Hills Vacation Rentals in Kailua, Hawaii 440
Kuulei Tract Vacation Rentals in Kailua, Hawaii 483
Palolo Vacation Rentals in Kailua, Hawaii 167