Kailua, Oahu – Kailua is located on the windward side of Oahu. A relaxing 20-minute drive across the lush Koolau mountain range from Honolulu and Waikiki. On the way over, a short stop at the famous Pali Lookout is definitely worthwhile, where breathtaking views can be seen. Kailua is a town without hotels. This charming community offers, unique shops, boutiques and casual dining.
Conveniently located, Kailua Beach is bordered by reef-protected calm waters and on shore breezes, with endless stretches of white sand and crystal blue waters. For the outdoor enthusiast, there are lots of world-class golf courses just minutes away, along with tennis facilities, botanical gardens and abundant hiking trails for the adventuresome.
From windsurfing, boogie boarding and kayaking, this is a wonderful place for children to build sand castles, swim and enjoy the beach.
![]() |
Kailua
Beach House 7+ Bedroom, 4+ Bath, Beachfront, Pool *12-14 Guests Nightly From: $1,560 - $2,000 Outclean: $700 Deposit: $1,000 Taxes: 14.962% Minimum Stay: 5-10 Nights |
|||
![]() |
Kailua Hideaway 4 Bedroom, 4 Bath, Beachfront, Pool, Jacuzzi, Partial A/C 8 Guests Monthly From: $20,000 - $22,000 Outclean: $600 - $850 Deposit: $2,000 Taxes: 14.962% Minimum Stay: 30 Nights |
|||
![]() |
Kailua
Kai 4 Bedroom, 4+ Bath, Beachfront 8 Guests Nightly From: $920 - $1,475 Outclean: $550 Deposit: $1,000 Taxes: 14.962% Minimum Stay: 7-14 Nights |
|||
![]() |
Kailua Oasis 4 Bedroom, 4 Bath, Pool, Jacuzzi, Central A/C, 100 steps to Kailua Beach 8 Guests Nightly From: $1,350 - $1,600 Outclean: $600 Deposit: $1,000 Taxes: 14.962% Minimum Stay: 7-10 Nights |
|||
![]() |
Kailua
Ocean View Ohana 2 Bedroom, 1 Bath, Ocean view 4 Guests Nightly From: $360 - $410 Outclean: $200 Deposit: $500 Taxes: 14.962% Minimum Stay: 7-14 Nights |
|||
![]() |
Kakela
Kai 4 Bedroom, 3 Bath, Beachfront, Central A/C 10 Guests Nightly From: $1,100 - $1,395 Outclean: $575 Deposit: $1,000 Taxes: 14.962% Minimum Stay: 7-12 Nights |
|||
![]() |
Kaumana 3 Bedroom, 3 Bath, Oceanside, Pool 8-10 Guests Nightly From: $850-$1,500 Outclean: $475 Deposit: $1,000 Taxes: 14.962% Minimum Stay: 5-14 Nights |
|||
![]() |
Mahina Kai |
|||
![]() |
Maluhia |
|||
![]() |
Paddle
House 3 Bedroom, 2 Bath upstairs and 1 Bedroom, 1+ Bath downstairs, Beachfront 8 Guests Monthly From: $22,000 - $30,000 Outclean: $1,000 Deposit: $1,000 Taxes: 14.962% Minimum Stay: 30 Nights |
|||
![]() |
Palione Papalani 6 Bedroom, 5+ Bath, Pool, Jacuzzi, Sauna, Partial A/C, Gated, 100 steps to Kailua Beach 10-12 Guests Nightly From: $1,600 - $5,200 Outclean: $1,500 Deposit: $5,000+cc or Insurance: $89 Taxes: 14.962% Minimum Stay: 5-10 Nights |
|||
![]() |
Place in Paradise 5 Bedroom 5+Bath, Beachfront, Partial A/C, Shared Pool & Tennis Court 14 Guests Nightly From: $1,600 - $5,200 Outclean: $1,200 Deposit: $5,000+cc or Insurance: $89 Taxes: 14.962% Minimum Stay: 5-10 Nights |
|||
![]() |
Plantation
Estate 5 Bedrooms, 5+ Bathroom, Beachfront, Heated Pool, Waterfall / Outdoor Jacuzzi, Central A/C, Fitness Center 10 Guests Nightly From: $4,500 - $6,000 Outclean: $1,000 Deposit: $7,500 Taxes: 14.962% Minimum Stay: 30 Nights |
|||
![]() |
Puukani
Cottage 2 Bedroom, 1 Bath, Partial A/C, Partial Beachfront 4 Guests – Nightly From: $400 - $500 Outclean: $350 Deposit: $500 Taxes: 14.962% Minimum Stay: 5-10 Nights |
|||
![]() |
Puukani Hale 3 Bedroom, 3 Bath, Beachfront, Partial A/C 6-8 Guests – Nightly From: $925 - $1,350 Outclean $795 Deposit $1,500 Taxes: 14.962% Minimum Stay: 10-14 Nights |
|||
![]() |
Tropical Blossom 5 Bedroom, 4 Bath, Outdoor Jacuzzi, 100 yards to the Beach *10-12 Guests Nightly From: $775 - $1,500 Outclean: $550 Deposit: $1,000 Taxes: 14.962% Minimum Stay: 7-10 Nights |
|||
|