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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.


Gigi's Retreat
3 Bedroom, 3 Bath, Beachfront, Pool, Partial A/C
8-10 Guests – Nightly From: $3,400 - $5,000   Outclean: $1,200   Deposit: $5,000 or $89 insurance
Taxes: 14.962% & OTAT 3%
Minimum Stay: 5-7 Nights


Kai Moena

Main House: 3 Bedroom, 3+Bath and Guest House: 4 Bedroom, 3+Bath
Beachfront, Pool, Jacuzzi, Tennis Court, Air Conditioning, Gym, Sauna, Billiard Room, Gated,
Fireplace, Media Room, Security System

12-14 Guests—Nightly From: $8,400 - $16,000+
Outclean: $3,850-$4,300    Deposit: $10,000    Taxes: 14.962% & OTAT 3%
Minimum Stay: 14-30 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% & OTAT 3%
Minimum Stay: 30 Nights

Kailua Kai
4 Bedroom, 4+ Bath, Beachfront, Partial A/C
8-10 Guests—Nightly From: $1,840 - $3,390
Outclean: $1,200    Deposit: $5,000    Taxes: 14.962% & OTAT 3%
Minimum Stay: 7-14 Nights

Kailua Oasis
4 Bedroom, 4 Bath, Pool, Jacuzzi, Central A/C, 100 steps to Kailua Beach
8 Guests—Monthly From: $30,000 - $40,000
Outclean: $750    Deposit: $1,000    Taxes: 14.962% & OTAT 3%
Minimum Stay: 30 Nights

Kakela Kai
4 Bedroom, 3 Bath, Beachfront, Partial A/C
10 Guests—Monthly From: $22,500 - $24,000
Outclean: $695    Deposit: $1,000    Taxes: 14.962% & OTAT 3%
Minimum Stay: 30 Nights

Mahina Kai
6 Bedroom, 5 Bath, Beachfront, Pool, Sauna, Partial A/C
12 Guests—Monthly From: $40,000 - $55,000
Outclean: $850 - $1,200    Deposit: $2,000    Taxes: 14.962% & OTAT 3%
Minimum Stay: 30 Nights


Paddle House
3 Bedroom, 2 Bath upstairs and 1 Bedroom, 1+ Bath downstairs, Beachfront
8 Guests—Nightly From: Request
Outclean: $600    Deposit: $1,000    Taxes: 14.962% & OTAT 3%
Minimum Stay: 30 Nights

Place in Paradise
5 Bedroom 5+Bath, Beachfront, Partial A/C, Shared Pool & Tennis Court
14 Guests—Nightly From: $2,200 - $5,430
Outclean: $1,500    Deposit: $5,000+cc or Insurance: $89    Taxes: 14.962% & OTAT 3%
Minimum Stay: 7-10 Nights

Plantation Estate
5 Bedrooms, 5+ Bathroom, Beachfront, Heated Pool, Waterfall / Outdoor Jacuzzi, Central A/C, Fitness Center
10 Guests—Nightly From: Request
Outclean: $1,000    Deposit: $7,500    Taxes: 14.962% & OTAT 3%
Minimum Stay: 30 Nights

Puukani Cottage
2 Bedroom, 1 Bath, Partial A/C, Partial Beachfront
4 Guests—Nightly From: $400 - $700
Outclean: $350    Deposit: $500    Taxes: 14.962% & OTAT 3%
Minimum Stay: 7-10 Nights

Puukani Hale
3 Bedroom, 3 Bath, Beachfront, Partial A/C
6-8 Guests—Nightly From: $925 - $1,450
Outclean $795    Deposit $1,500    Taxes: 14.962% & OTAT 3%
Minimum Stay: 30 Nights

Tropical Blossom
5 Bedroom, 4 Bath, Outdoor Jacuzzi, 100 yards to the Beach
*10-12 Guests—Nightly From: $775 - $1,500
Outclean: $650    Deposit: $1,000    Taxes: 14.962% & OTAT 3%
Minimum Stay: 30 Nights
* Request property description for further details.

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