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Oahu – The Gathering Place

Vacation Homes Kailua

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.


Bali Hale
4 Bedroom, 3+Bath, Beachfront, Pool, Spa, Waterfall, Sauna, Gym, Tennis Court, Gated, Partial A/C
8 Guests – Nightly From: $3,125 - $7,650   Outclean: $900   Deposit: $10,000
Minimum Stay: 14-30 Nights


Hale Kalaheo
4 Bedrooms, 3 Bath, Beachfront, Gated, Partial A/C
8-12 Guests – Nightly From: $1,100 - $2,500   Outclean: $900   Deposit: $1,500
Minimum Stay: 5-14 Nights

Kailua Beach House
7+ Bedroom, 4+ Bath, Beachfront, Pool
*10-12 Guests – Nightly From: $1,350 - $1,550   Outclean: $750   Deposit: $1,000
Minimum Stay: 7-14 Nights

Kailua Hale
3+ Bedroom, 3 Bath, Beachfront, Pool, Jacuzzi
6-8 Guests – Nightly From: $850 - $975   Outclean: $600   Deposit: 1,000
Minimum Stay: 7-14 Nights

Kailua Kai
4 Bedroom, 4+ Bath, Beachfront
8 Guests – Nightly From: $920 - $1,475   Outclean: $550   Deposit: $1,000
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: $1,250 - $1,600   Outclean: $600   Deposit: $1,000
Minimum Stay: 7-14 Nights

Kailua Ocean View Ohana
2 Bedroom, 1 Bath, Ocean view
4 Guests – Nightly From: $250 - $275   Outclean: $175   Deposit: $500
Minimum Stay: 5-14 Nights

Kailua Surf
5 Bedroom 5+Bath, Beachfront, Partial A/C, Shared Pool & Tennis Court
14 Guests – Nightly From: $1,500 - $3,000   Outclean: $1,200   Deposit: $3,000
Minimum Stay: 5-14 Nights

Kakela Kai
4 Bedroom, 3 Bath, Beachfront, Central A/C
8-9 Guests – Nightly From: $950 - $1,350    Outclean: $475   Deposit: $1,000
Minimum Stay: 10-30 Nights

Mahina Kai
6 Bedroom, 5 Bath, Beachfront, Pool, Sauna, Partial A/C
12 Guests – Nightly From: $2,000 - $2,600    Outclean: $525   Deposit: $2,000
Minimum Stay: 10-30 Nights


Maluhia
4 Bedrooms, 4 Bath, Pool, Jacuzzi, A/C
8-10 Guests – Nightly From: Request   Outclean: $700   Deposit: $7,000
Minimum Stay: 14-30 Nights


Paddle House
3 Bedroom, 2 Bath upstairs and 1 Bedroom, 1+ Bath downstairs, Beachfront
8 Guests – Nightly From: $1,250 - $2,250   Outclean: $600   Deposit: $1,000
Minimum Stay: 10-30 Nights

Plantation Estate
5 Bedrooms, 5+ Bathroom, Beachfront, Heated Pool, Waterfall / Outdoor Jacuzzi, Central A/C, Fitness Center
10 Guests – Nightly: $4,500 - $6,000   Outclean: $1,000   Deposit: $7,500
Minimum Stay: 7-30 Nights

Puukani Cottage
2 Bedroom, 1 Bath, Partial A/C, Partial Beachfront
4 Guests – Nightly From: $395 - $550   Outclean: $350   Deposit: $500
Minimum Stay: 7-14 Nights

Puukani Hale
3 Bedroom, 3 Bath, Beachfront, Partial A/C
6-8 Guests – Nightly From: $850 - $1,350   Outclean $795   Deposit $1,500
Minimum Stay: 7-30 Nights

Seaside Villa
6 Bedroom, 5 Bath, Beachfront
10-12 Guests – Nightly From: $1,050 - $1,750   Outclean: $1,075   Deposit: $2,500
Minimum Stay: 10-30 Nights

Tropical Blossom
5 Bedroom, 4 Bath, Outdoor Jacuzzi, 100 yards to the Beach
10-12 Guests – Nightly Rate: $775 - $1,050   Outclean: $550   Deposit: $1,000
Minimum Stay: 7-30 Nights

Tropical Breeze Estate
6 Bedroom, 6 Bath, Beachfront, Pool, Spa, Air Conditioning
12 Guests – Nightly From: $4,700 - $6,250   Outclean: $1,000   Deposit: $10,000
Minimum Stay: 14-30 Nights


White Sands
4 Bedroom, 3 Bath, Pool, Beachfront, Partial A/C
8 Guests – Nightly From: $1,675 - $2,225   Outclean: $700   Deposit: $3,000
Minimum Stay: 14-30 Nights

Wilikoki Hale
4 Bedroom, 2 Bath, Beachfront, Partial A/C
10 Guests – Monthly From $27,000 - $29,000   Outclean: $450    Deposit: $2,000
Minimum Stay: 30 Nights
* Request property description for further details.

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