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 Kailua Vacation Rentals 
  All Kailua properties
Featured Property
#79 - The Palm Villa
view/book online
1 Bdrm / 1 Bath
Oahu, Hawaii - A beautiful two-level air-conditioned cottage decorated in a contemporary Polynesian motif with a spiral staircase. The lower level has a living room with a queen sofa bed and full kitchen with fine china and cooking utensils. The sparkling, fully tiled swimming pool is surrounded with lush tropical gardens. THIS PROPERTY MAY ALSO BE RENTED AS A 2 Bedroom/2 Bath home which may accomodate 4 occupants for $250.00 per night/$1750 per week and a $150.00 cleaning fee. The upstairs master...[more]

 

Kailua Properties (top)
#81-Dolphin Manor :: Kailua, Oahu view/book online   

Base Rates
3 BDRM, 4 Baths
Nightly: 743.75
Weekly: 5,206.25
Sleeps: 8
Outstanding features, a quiet, secluded setting, and private access to miles of expansive white sands tagged "Best Beach" make this marvelous Kailua Beach House the perfect choice for your Hawaiian holiday sanctuary. This home offers impeccable decor and 3...[more]

#79-The Palm Villa :: Kailua, Oahu view/book online   

Base Rates
1 BDRM, 1 Baths
Nightly: 175.00
Weekly: 1,200.00
Sleeps: 4
A beautiful two-level air-conditioned cottage decorated in a contemporary Polynesian motif with a spiral staircase. The lower level has a living room with a queen sofa bed and full kitchen with fine china and cooking utensils. The sparkling, fully tiled sw...[more]

#80-The Ocean House :: Kailua, Oahu view/book online   

Base Rates
2 BDRM, 2 Baths
Nightly: 281.25
Weekly: 1,968.75
Sleeps: 6
A lovely two bedroom beach house with a ceramic tiled living room, dining room and a fully equipped kitchen including dishwasher, garbage disposal, microwave, and self-cleaning oven. The house is decorated in a Hawaiian plantation motif with a contemporary...[more]

#85-Kailua Hale :: Kailua, Oahu view/book online   

Base Rates
2 BDRM, 2 Baths
Nightly: 230.00
Weekly: 1,400.00
Sleeps: 8
Affordable, casual vacation living awaits you on a quiet lane just footsteps from your place in the sun on the white sands of Kailua Beach. Joe's Kailua Hale has a volley ball court in the back yard with picnic table and gas grill, partial ocean and full m...[more]

#697-Kailua Sunrise Bungalow:: Kailua, Oahu view/book online   

Base Rates
2 BDRM, 1 Baths
Nightly: 125.00
Weekly: 875.00
Sleeps: 5
Aloha! Welcome to Kailua Sunrise Bungalow. Located on a quiet residential street in Kailua on the island on Oahu, you'll find comfort, relaxation here while on vacation. Close to Kailua Beach, it is only a 5 minute walk away. Ethernet cable Internet Conne...[more]

#1036-Maunawili House :: Kailua, Oahu view/book online   

Base Rates
2 BDRM, 1 Baths
Nightly: 150.00
Weekly: 1,050.00
Sleeps: 4
Looking for the ideal Hawaii vacation rental? This Hawaii accommodation located in Kailua on Oahu is perfect for a tropical getaway and Hawaiian holiday. A tropical home away from home decorated with style and comfort. If you appreciate lush and g...[more]

#1141-Kailua Oceanfront Hideaway - Ocean:: Kailua, Oahu view/book online   

Base Rates
2 BDRM, 2 Baths
Nightly: 299.00
Weekly: 2,093.00
Sleeps: 6
This Kailua Oceanfront Duplex Hideaway is about as close as you can stay to the ocean in Kailua. All rooms face out to an incredible ocean view of beautiful Kailua Bay. On wavy days you can feel the light ocean spray as soon as you step outside. Swi...[more]

#1204-Makana's Place:: Kailua, Oahu view/book online   

Base Rates
1 BDRM, 1 Baths
Nightly: 175.00
Weekly: 1,225.00
Sleeps: 7
Makana's Place is a one bedroom, one bath home in quaint Kailua Town. This Central Aircondition Non-Smoking home is very spacious over 1400 square feet living quarters. Equivalent to a Three bedroom home. Beautifully decorated with well quality furniture....[more]

#1345-Kailua Guesthouse Palm Cabana:: Kailua, Oahu view/book online   

Base Rates
0 BDRM, 1 Baths
Nightly: 161.25
Weekly: 998.75
Sleeps: 4
The studio Palm Cabana enjoys lovely Koolau Mountain views. It's your own private world with sweeping vistas from your bed in the morning and evening breezes as you watch the sunset off your lanai. Need to pick plumeria for a lei for a special occasio...[more]

#1346-Kailua Guesthouse Beach Bungalow:: Kailua, Oahu view/book online   

Base Rates
0 BDRM, 1 Baths
Nightly: 148.75
Weekly: 873.75
Sleeps: 4
The studio Beach Bungalow greets the morning sun filtered by neighboring trees and it plants. It's cool and shaded, trade winds blessed, with lovely mountain views. Welcome in. The two "sliding glass" doors open onto a wide lanai for indoor-outdoor livi...[more]

#1418-Ohana Beach House:: Kailua, Oahu view/book online   

Base Rates
5 BDRM, 3 Baths
Nightly: 675.00
Weekly: 4,725.00
Sleeps: 10
Location-- One minute walk or 100 steps from Kailua Beach, on the beautiful island of Oahu. Kailua Beach has continually been rated among the top beaches in the World... Located steps from the most prime area of Kailua Beach sits this well laid out, ...[more]

#89-Hale Nani Villa :: Kailua, Oahu view/book online   

Base Rates
6 BDRM, 4 Baths
Nightly: 1,125.00
Weekly: 7,875.00
Sleeps: 16
Outstanding custom construction, 6 lovely bedrooms, 4 elegant baths, a theater-sized TV screen, quiet, residential setting, optional mini-conference/office area featuring fax, phone, computer and internet access, pool area with Jacuzzi and private access t...[more]

#885-Our Hale:: Kailua, Oahu view/book online   

Base Rates
2 BDRM, 1 Baths
Nightly: 275.00
Weekly: 1,925.00
Sleeps: 6
This spacious private home is 1600 square foot 2 bedroom 1 bath residence on a large 12000 sq.ft. property. It is tastefully decorated with antique furniture throughout. We can accommodate up to 6 guests with a King Bed in the master bedroom and a queen ...[more]

#268-:: Kailua, Oahu view/book online   

Base Rates
2 BDRM, 1 Baths
Nightly: 150.00
Weekly: 1,050.00
Sleeps: 5
Welcome.. Aloha Cottage, a very special accommodation, is located in Kailua near Kailua Beach on the Windward side of Oahu, a scenic 25 minute drive from Honolulu. This charming, spacious two bedroom 1 bath Cottage is only a 2 minute drive or a 10 minute w...[more]

#1445-Tracy's Honu Hale :: Kailua, Oahu view/book online   

Base Rates
7 BDRM, 4 Baths
Nightly: 950.00
Weekly: 6,650.00
Sleeps: 14
Welcome to T’s Honu Hale! "Turtle House." ADDITIONAL RENTAL OPTION!!!! 4 Bedroom 2 Bathroom Rates: 450/night based on 6 people. 5 night minimum 25.00 each additional person up to 8. 300.00 Cleaning Fee. 1000.00 Deposit **Please inquir...[more]

#339-Kailua Suite :: Kailua, Oahu view    call 1-800-754-0905 for availability

Base Rates
1 BDRM, 1 Baths
Nightly: 95.00
Weekly: 665.00
Sleeps: 4
House of waterfalls offers you a truly hawaiian experience with all the amenities of you own private resort. Whether swimming or sunning by the beautiful tropical pool, relaxing in a hammock in the polynesian pavillion while enjoying the tranquility of the...[more]

#776-Ilima Suite:: Kailua, Oahu view    call 1-800-754-0905 for availability

Base Rates
1 BDRM, 1 Baths
Nightly: 105.00
Weekly: 735.00
Sleeps: 4
House of Waterfalls offers you a truly Hawaiian experience with all the amenities of a resort. Whether swimming or sunning by the beautiful tropical pool, relaxing in a hammock in the polynesian pavillion while enjoying the tranquility of the waterfall cas...[more]

#338-Hawaiiana Suite:: Kailua, Oahu view    call 1-800-754-0905 for availability

Base Rates
1 BDRM, 1 Baths
Nightly: 115.00
Weekly: 805.00
Sleeps: 6
House of waterfalls offers you a truly hawaiian experience with all the amenities of you own private resort. Whether swimming or sunning by the beautiful tropical pool, relaxing in a hammock in the polynesian pavillion while enjoying the tranquility of the...[more]

#1339-Wendys Place:: Kailua, Oahu view    call 1-800-754-0905 for availability

Base Rates
1 BDRM, 2 Baths
Nightly: 169.00
Weekly: 1,183.00
Sleeps: 4
Beautiful Hawaiian Living at its best!! Stay in this newly built, modern one bedroom, two bath villa on a private, beach lane just a short 2 minute walk to Kailua Beach. Beautiful Hawaiian tropical décor and open air living room and modern kitchen make t...[more]

#438-Hula Hut:: Kailua, Oahu view    call 1-800-754-0905 for availability

Base Rates
2 BDRM, 2 Baths
Nightly: 0.00
Weekly: 0.00
Sleeps: 4
Newly constructed, 1000 sq.ft. living area and very private, Hula Hut is nestled along beautiful Kailua Beach, with breathtaking panoramic views of the ocean and mountains. Just 300 feet from the white powdery sands and turquoise waters of one of the top t...[more]

#84-Kailua Beach House:: Kailua, Oahu view    call 1-800-754-0905 for availability

Base Rates
4 BDRM, 3 Baths
Nightly: 325.00
Weekly: 2,250.00
Sleeps: 10
Outstanding features, a quiet, secluded setting, and private access to miles of expansive white sands tagged "Best Beach" in 1998 make this marvelous Kailua Beach House the perfect choice for ...[more]

#86-Quiet Kailua Beach House:: Kailua, Oahu view    call 1-800-754-0905 for availability

Base Rates
3 BDRM, 2 Baths
Nightly: 531.25
Weekly: 3,718.75
Sleeps: 6
Where the private back yard green ends, the bright white sands of Kailua Beach begin and go on and on for miles. Clean, casual, quiet, secluded setting, and private access to miles of expansive white sands tagged "Best Beach" in 1998 make this quaint 3 be...[more]

#234-Tropical Hideaway Studio :: Kailua, Oahu view    call 1-800-754-0905 for availability

Base Rates
1 BDRM, 1 Baths
Nightly: 150.00
Weekly: 1,050.00
Sleeps: 3
This modern and spacious artist's studio sparkles with its welcoming call and open, airy, finely furnished décor. Handmade area rugs, original artwork and white tile all add to the bright, yet cool warmth of this tropical hi...[more]

#497-Bamboo Bungalow:: Kailua, Oahu view    call 1-800-754-0905 for availability

Base Rates
1 BDRM, 1 Baths
Nightly: 125.00
Weekly: 875.00
Sleeps: 4
This charming one bedroom, one bath ground floor duplex vacation suite features a full kitchen, fenced-in rear patio with BBQ area, offstreet parking and pleasant, new decor. Two blocks from Kailua's sandy beaches and twenty minutes drive to Waikiki, the G...[more]

#890-Kailua Beach Vacation - Gardinia:: Kailua, Oahu view    call 1-800-754-0905 for availability

Base Rates
1 BDRM, 1 Baths
Nightly: 150.00
Weekly: 1,050.00
Sleeps: 4
Our Gardenia studio has 2 queen size beds, 1 full bath,cable TV,phone, table and chairs,and a kitchenette.It is a very modern, large room with a 10' high ceiling, 3 windows and a patio door leading to a fenced private area with a tiled p...[more]

#891-Kailua Beach Vacation - Hibiscus:: Kailua, Oahu view    call 1-800-754-0905 for availability

Base Rates
bedroom BDRM, 1 Baths
Nightly: 96.00
Weekly: 642.00
Sleeps: 2
Our Hibiscus room has a queen bed with a full bath, ceiling fan and/or air conditioning, 10' high ceiling, walk in closet, and cable TV. This rental can sleep up to 2 people with a queen bed. This unit also has a large walk-in closet. Tastefu...[more]

#892-Kailua Beach Vacation - Jungle Unit:: Kailua, Oahu view    call 1-800-754-0905 for availability

Base Rates
Studio BDRM, 1 Baths
Nightly: 114.00
Weekly: 770.00
Sleeps: 3
Our Jungle unit is a 1 bedroom studio with a king bed and a twin bed,full bathroom. It has a kitchenette including refrigerator, microwave, coffee maker,appliances and dishes. This rental can sleep up to 3 people with its 1 king bed and 1...[more]

#893-Kailua Beach Vacation - Ocean Room:: Kailua, Oahu view    call 1-800-754-0905 for availability

Base Rates
Studio BDRM, 1 Baths
Nightly: 96.00
Weekly: 642.00
Sleeps: 2
Our Ocean room is a bedroom with a full bath that can sleep up to 2 people with two single beds or one king bed. This unit also has 2 large closets, with mirrors and a ceiling fan or air conditioning...[more]

#894-Kailua Beach Vacation - Plumeria:: Kailua, Oahu view    call 1-800-754-0905 for availability

Base Rates
Studio BDRM, 1 Baths
Nightly: 96.00
Weekly: 642.00
Sleeps: 2
Our Plumeria room has a full bed, full bath, 2 large closets,ceiling fan and a nice cool breeze from the ocean with a garden and ocean view. You can sleep up to 2 people in bliss, surrounded by the scent of a Plumeria tree.The room has 2 large closets wi...[more]

#1012-Kailua Kai Guest House:: Kailua, Oahu view    call 1-800-754-0905 for availability

Base Rates
4 BDRM, 5 Baths
Nightly: 550.00
Weekly: 3,850.00
Sleeps: 8
Kailua Kai, Kailua: Newly rebuilt beautiful A-frame beachhouse on large Kailua beachfront property. 4 bedrooms/5 baths, large living/dining room, open kitchen, tv/den area, spiral staircase to upstairs loft bedroom; the most comfortable and relaxing vacati...[more]

#1013-Dolphin House:: Kailua, Oahu view    call 1-800-754-0905 for availability

Base Rates
4 BDRM, 4 Baths
Nightly: 700.00
Weekly: 4,900.00
Sleeps: 8
Hale O Ka Nai'a, Kailua: The Dolphin House. Elegant two-story home just one back from Kailua Beach with 4 bedrooms/4 baths, executive quality furnishings throughout, gourmet kitchen, oceanviews from second story bedrooms, added attraction a third level "cr...[more]

#1142-Exclusive Kailua Beach House:: Kailua, Oahu view    call 1-800-754-0905 for availability

Base Rates
4 BDRM, 2.5 Baths
Nightly: 625.00
Weekly: 4,375.00
Sleeps: 12
This large, Kamaaina, executive home is located in Kailua's most exclusive neighborhood. This nice, quiet, safe, 3500 square foot home is situated just a few steps from your own private gate to the best and most uncrowded part of world-famous Kailua Beach....[more]

#1213-Kailua Beach House II:: Kailua, Oahu view    call 1-800-754-0905 for availability

Base Rates
3 BDRM, 2 Baths
Nightly: 255.36
Weekly: 1,787.50
Sleeps: 8
Kailua Beach House II features, a quiet, secluded setting, and private access to miles of expansive white sands tagged "Best Beach" in 1998 make this marvelous Kailua Beach House II the perfect choice for your Hawaiian holiday sanctuary. This home offers i...[more]

#1239-Bali Mini:: Kailua, Oahu view    call 1-800-754-0905 for availability

Base Rates
2 BDRM, 1 Baths
Nightly: 300.00
Weekly: 2,100.00
Sleeps: 4
Adorable new 2 bedroom, 1 bathroom home in Kailua. Located just steps to the beach. ***RATES ARE ONLY GOOD AT TIME OF BOOKING, AND MAY BE SUBJECT TO CHANGE PRIOR TO NOTICE.... PLEASE CALL US AT 1-800-754-0905 FOR CURRENT RATES ON THIS PROPERTY....[more]

#1277-Kailua Bay Estate:: Kailua, Oahu view    call 1-800-754-0905 for availability

Base Rates
6 BDRM, 4 Baths
Nightly: 1,531.25
Weekly: 10,718.75
Sleeps: 12
Gracious living and tropical paradise are yours to enjoy in this magnificent plantation-style Hawaiian vacation home. Designed for the discriminating traveler, the home welcomes you with professionally appointed amenities and exquisite details. Beautiful h...[more]

#1281-Villa Luana:: Kailua, Oahu view    call 1-800-754-0905 for availability

Base Rates
4 BDRM, 4.5 Baths
Nightly: 1,900.00
Weekly: 13,300.00
Sleeps: 12
4 bedrooms, 4.5 bathrooms in the main home with a separate apartment that has its own entrance and 2 bedrooms, 1 bathroom. Kailua beachfront home with pool and spa. ***RATES ARE ONLY GOOD AT TIME OF BOOKING, AND MAY BE SUBJECT TO CHANGE PRIOR TO NO...[more]

#1284-Bali Resort:: Kailua, Oahu view    call 1-800-754-0905 for availability

Base Rates
3 BDRM, 3.5 Baths
Nightly: 2,142.86
Weekly: 15,000.00
Sleeps: 8
This new Kailua beachfront estate is located the north end of the #1 rated beach in America. Features include gourmet kitchen, den/bedroom, game room, original artwork, worldclass furnishings, 3.5 bathrooms guest house on a newly built estate on Kailua bea...[more]

#1287-Oahulani:: Kailua, Oahu view    call 1-800-754-0905 for availability

Base Rates
9 BDRM, 9.5 Baths
Nightly: 6,250.00
Weekly: 43,750.00
Sleeps: 18
Large 9 bedroom, 9.5 bathroom house on Kailua beach with A/C throughout and modern kitchen. Large custom pool, Two wading pools, Large poolside entertaining area with hot tub and barbeque. Large master suit, Guest rooms with private lanais, televisions and...[more]

#1294-Place in Paradise:: Kailua, Oahu view    call 1-800-754-0905 for availability

Base Rates
4 BDRM, 4.5 Baths
Nightly: 1,000.00
Weekly: 7,000.00
Sleeps: 10
4 bedroom, 4.5 bath beachfront home with partial a/c. Located in Hale Kai Surf and Racquet club offering shared pool and tennis courts. Type/View: Beachfront Pool: NO Jacuzzi: no Appx SQ Ft Home: 4500 ***RATES ARE ONLY GOOD AT TIME OF BOOKING...[more]

#1300-Kakela Kai:: Kailua, Oahu view    call 1-800-754-0905 for availability

Base Rates
4 BDRM, 3 Baths
Nightly: 850.00
Weekly: 5,950.00
Sleeps: 8
4 bedrooms, 3 bathrooms Kailua beachfront home in a security gated neighborhood. Island style furnishings and a fenced in yard. Sleeps 8. ***RATES ARE ONLY GOOD AT TIME OF BOOKING, AND MAY BE SUBJECT TO CHANGE PRIOR TO NOTICE.... PLEASE CALL ...[more]

#1301-Pikake Hale :: Kailua, Oahu view    call 1-800-754-0905 for availability

Base Rates
5 BDRM, 4 Baths
Nightly: 900.00
Weekly: 6,300.00
Sleeps: 12
5 bedrooms, 4 bathrooms. Located just one home back from Kailua beach. Tasteful Hawaiiana furnishings in a relaxing, peaceful setting with lots of indoor and outdoor living space. Beautiful landscaping with the scent of night blooming jasmine (pikake). ...[more]

#1304-Kailua Kai:: Kailua, Oahu view    call 1-800-754-0905 for availability

Base Rates
4 BDRM, 5 Baths
Nightly: 1,187.50
Weekly: 8,312.50
Sleeps: 8
Newly remodeled beachfront home with all modern amenities; cool, white tile throughout, granite counters in kitchen and granite touches in bathrooms. Large open beachfront living/dining room flows into the gourmet kitchen and adjacent TV sitting area, spir...[more]

#1384- Wailana Kai :: Kailua, Oahu view    call 1-800-754-0905 for availability

Base Rates
5 BDRM, 4 Baths
Nightly: 1,485.00
Weekly: 10,395.00
Sleeps: 12
5 bedroom, 4 bathroom beachfront estate is located on Kailua beach and features a pool in the courtyard, gourmet kitchen, 20' ceilings in the living room, and 30,000sqft of land. One of only ten beachfront residences in exclusive Kainalu Park....[more]

Can't Find What You're Looking For? call 1-800-754-0905 for availability

Looking for something you didn't see here? Call us! Our reservations agents have access to hundreds of vacation rental properties - far too many to display on this site. We can email you pictures and links to many more properties in this area - just give us a call at 1-800-754-0905/808-695-9536!



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