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Vacation Rentals in Kailua, HI

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From
$330
Per Night
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1 / 19
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3 Bedrooms, 1 Bathroom, Sleeps 7
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$1,000
Per Night
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1 / 24
6 Bedrooms, 4 Bathrooms, Sleeps 15
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$5,600
Per Week
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1 / 18
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8 Bedrooms, 4 Bathrooms, Sleeps 18
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$165
Per Night
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1 / 11
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Studio, 1 Bathroom, Sleeps 3
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  • # Of Bathrooms
  • Guest Count
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  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Our newly renovated studio is the perfect get-away located in the heart of Kailua. Light-filled and breezy this is the perfect space for one or a couple, just minutes away from the beach by foot or bike. Kailua Seahorse Studio is PERFECT. It's even more beautiful in person than in the pictures.... View all property information
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From
$995
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1 / 38
4 Bedrooms, 4 Bathrooms, Sleeps 9
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Amenities & Details
  • Parking
  • Patio
  • Garage
  • Grill
  • Refrigerator
  • TV
  • Hot Tub
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Kapoho Hale, situated on Kapoho Cape in the Kaimalino neighborhood of Kailua, Oahu was newly constructed in 2007 and remains in immaculate condition. This amazing home has views of the entire east side of the island- from Makapuu Lighthouse to Kaaawa! Check out our YouTube video at:... View all property information
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From
$1,800
Per Month
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1 / 10
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Studio, 1 Bathroom, Sleeps 2
Booking
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Amenities & Details
  • Parking
  • Wi-Fi
  • Ceiling Fans
  • TV
  • Patio
  • Washer
  • Grill
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Enjoy peace and quiet in this quaint, private cottage with queen-size bed and kitchenette, lovely tropical yard with covered lanai, beach shower, and 1-1/2 blocks to famous Kailua beach. Walking/biking distance to boutiques and restaurants in Kailua town. There is a washer/dryer on premises and... View all property information
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From
$165
Per Night
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1 / 30
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Studio, 1 Bathroom, Sleeps 2
Bookings
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Amenities & Details
  • Parking
  • Grill
  • TV
  • Stereo System
  • Dryer
  • Stove
  • Refrigerator
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Footsteps to Hawaii's best beach and a short walk to town, shopping, restaurants, farmers markets and community center for tennis, pool and gym. Ideally located for many ocean sports, hiking and cycling to just about anywhere in this pedestrian and bike friendly beach town. The cottage is fully... View all property information
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From
$175
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1 / 18
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Studio, 1 Bathroom, Sleeps 4
Bookings
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Amenities & Details
  • Safe
  • Parking
  • Microwave
  • Stove
  • Patio
  • Washer
  • TV
  • Ceiling Fans
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Footsteps to Hawaii's best beach. Newly constructed and fully furnished with all the amenity. It is a short walking distance to Kailua and Lanikai beaches, hiking, shopping, restaurants and fun. View all property information
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From
$425
Per Night
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1 / 18
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3 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
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Amenities & Details
  • TV
  • DVD Player
  • Safe
  • Washer
  • Refrigerator
  • Grill
  • Microwave
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
This three bedroom Lanikai home, plus attached, but private entrance to a completely self contained studio with kitchenette and fully enclose courtyard, is just one short block to Lanikai Beach. Bring the family, and let the grandparents, friends be with you but also have the privacy they need! We... View all property information
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From
$650
Per Night
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1 / 19
5 Bedrooms, 4 Bathrooms, Sleeps 12
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Amenities & Details
  • DVD Player
  • Washer
  • Grill
  • Patio
  • TV
  • Fireplace
  • Microwave
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • ?
About this property
Aloha from the island of Oahu, and welcome to paradise! Ko'olau Vista Villa is a large, private, two-story family home with, four-bedrooms plus bonus room ( 5th bedroom), four-bath property located in beautiful Kailua, Hawaii. Known for its small town charm and friendliness, Kailua also offers... View all property information
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From
$175
Per Night
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1 / 19
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Studio, 1 Bathroom, Sleeps 4
Booking
Details Reviews (36) Make Inquiry
Amenities & Details
  • Deck
  • DVD Player
  • Washer
  • Mountain Views
  • Air Conditioning
  • Wi-Fi
  • Refrigerator
  • Stereo System
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Kailua Bay & Mountain Views! Only 100 yards to Kailua Beach Park! This property is located in Kailua, on Windward Oahu. Relax and unwind in this spacious 3rd floor 1000 sq ft studio. Enjoy your morning coffee on the lanai while listening to the breeze, ocean and rambunctious birds. Watch the... View all property information
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From
$425
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1 / 42
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4 Bedrooms, 2 Bathrooms, Sleeps 10
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Amenities & Details
  • TV
  • Stove
  • DVD Player
  • Parking
  • Washer
  • Grill
  • Patio
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Hawaiian Style Home, Pool, Tropical Setting, 4 Bdrm, 2 Bath, Short Walk To The Beach, Sparkeling Pool, Lush Tropical Yard Hale Pulelehua “The Butterfly House' has a spacious open feeling inside and out. The large windows front and back allow the trade winds to carry the sweet scent of Hawaiian... View all property information
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From
$200
Per Night
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1 / 16
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Studio, 1 Bathroom, Sleeps 3
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Amenities & Details
  • Dryer
  • Refrigerator
  • DVD Player
  • Microwave
  • Stereo System
  • TV
  • Safe
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Enjoy the secluded breath taking beach from our fully furnished one-bedroom hideaway for groups from 1-3. Relaxed, casual beach home living, just steps away to Lanikai’s heavenly reef-protected waters and natural stretch of white sand beach, with an amazing sunrise and moonrise of one of the... View all property information
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From
$425
Per Night
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1 / 27
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4 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Refrigerator
  • Grill
  • Dryer
  • Ceiling Fans
  • Microwave
  • Patio
  • Washer
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
E Komo Mai! (welcome) Your memorable stay starts as you drive down your private lane into the serenity of a tropical outdoor paradise, providing you with the ultimate island vacation location. Staying true to its Hawaiian charm the 3 bedroom 2 bathroom main home and 1 bed 1 bath separate cottage... View all property information
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From
$1,250
Per Night
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1 / 24
4 Bedrooms, 4 Bathrooms, Sleeps 8
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Amenities & Details
  • Boat Available
  • Grill
  • Wi-Fi
  • Parking
  • # Of Bathrooms
  • Number Of Bedrooms
  • Guest Count
  • Linens Provided
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Description Our BEACHFRONT home is designed to provide you with a perfect vacation retreat. The house is as close to the beach as you legally can build. The beach of Kailua is renown for its fine white sand, blue green waters and safety. This is not a crowded beach, but has a pleasant neighborhood... View all property information
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From
$695
Per Night
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1 / 6
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4 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Dishwasher
  • Parking
  • DVD Player
  • TV
  • Refrigerator
  • Microwave
  • Grill
  • Stove
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • ?
  • x
About this property
Built in the early 20's, this family beach home offers the perfect setting for a memorable vacation getaway. Situated on the water at Lanikai Beach, Longs at Lanikai is ideal for those in favor of a secluded retreat. This four-bedroom abode is full of classic island architecture and furnishings.... View all property information
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From
$180
Per Night
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1 / 14
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1 Bedroom, 1 Bathroom, Sleeps 2
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Amenities & Details
  • TV
  • Parking
  • Ceiling Fans
  • Refrigerator
  • Grill
  • Microwave
  • Wi-Fi
  • Porch
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Spacious private studio, just 100 yards to lovely Lanikai Beach. Newly renovated interior with Balinese teak and bamboo furnishings, secluded tropical garden with outdoor dining area. The studio is furnished with wood flooring, two comfortable arm chairs, teak furnishings and is adorned with works... View all property information
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From
$850
Per Night
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1 / 17
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3 Bedrooms, 2 Bathrooms, Sleeps 7
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Amenities & Details
  • # Of Bathrooms
  • Guest Count
  • Number Of Bedrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
The epitome of island living is experienced in Kailua, Oahu. This home is located at the top of a private road, with direct private access to world renowned Kailua Beach. Enjoy the outdoors and relax in your spacious backyard and private swimming pool. Kailua town is just a short bike ride away,... View all property information
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From
$1,500
Per Night
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1 / 21
4 Bedrooms, 11 Bathrooms, Sleeps 6
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Amenities & Details
  • Number Of Bedrooms
  • # Of Bathrooms
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Presented by Elite Pacific Properties Oahu's top volume luxury brokerage firm. This home is professional managed by a licensed property manager, BBB A+ rated. Maluhia - House of Peace! Newly available!! View all property information
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From
$450
Per Night
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1 / 15
5 Bedrooms, 3 Bathrooms, Sleeps 13
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Amenities & Details
  • Garage
  • DVD Player
  • Washer
  • Microwave
  • Dishwasher
  • Grill
  • Dryer
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
A very nice updated 5 bedroom home that is located on a side street with no traffic. The beach entrance is a private street entrance 2 blocks away so you can walk to the beach but not have a large crowd of people on the beach. It is a very safe all white sand beach that is great for family's and... View all property information
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From
$775
Per Night
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1 / 19
4 Bedrooms, 11 Bathrooms, Sleeps 6
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Amenities & Details
  • Number Of Bedrooms
  • Guest Count
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Presented by Elite Pacific Properties Oahu's top volume luxury brokerage firm. This home is professional managed by a licensed property manager, BBB A+ rated. Ke'aloha meaning love is all around is your home away from home less than a minute walk to the world famous Kailua beach via the... View all property information
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From
$995
Per Night
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1 / 25
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6 Bedrooms, 4 Bathrooms, Sleeps 20
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Amenities & Details
  • Guest Count
  • Number Of Bedrooms
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
About this property
Welcome to Paradise in beautiful Kailua, Hawaii! Our beach villa is about 6000 sqft, is the perfect retreat for everyone. From fresh flowers and sand chairs, kayak, to a blender for tropical drinks, come and have an unforgettable vacation. Take long walks in the morning and enjoy the... View all property information
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From
$250
Per Night
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1 / 10
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1 Bedroom, 1 Bathroom, Sleeps 3
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Amenities & Details
  • TV
  • Grill
  • VCR
  • Dryer
  • Patio
  • Refrigerator
  • Parking
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Enjoy a restful respite in this private cozy cottage. We are in Lanikai, across the street from the ocean and the beautiful Mokulua islands. The cottage is a separate building located on the back corner of a 10,000 sq. ft. lot. It is a comfortable roomy self-contained one-bedroom cottage... View all property information
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From
$147
Per Night
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1 / 17
Studio, 1 Bathroom, Sleeps 3
Details Reviews (21) Make Inquiry
Amenities & Details
  • Terrace
  • Air Conditioning
  • Ceiling Fans
  • TV
  • Wi-Fi
  • Internet Access
  • Refrigerator
  • Balcony
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Blossoms and palms welcome you as you enter the property. You are surrounded shading trees and tropical flora. Just steps away is beautiful Lanikai Beach approximately 30 yards, just across the street. Lanikai is a quaint beachside community in Oahu. Our studios are spacious with private entries... View all property information
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From
$1,200
Per Night
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1 / 24
5 Bedrooms, 6 Bathrooms, Sleeps 14
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Amenities & Details
  • Ceiling Fans
  • Refrigerator
  • Microwave
  • Grill
  • Dishwasher
  • Satellite TV
  • Air Conditioning
  • Stove
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Casual accommodations located on Kailua Beach, voted 'Best Beach in the United States' by a variety of publications. Five bedrooms and five and half baths make this an ideal home to enjoy on your next Oahu visit. Large outdoor deck spaces provide the perfect place to relax in the sun or enjoy a... View all property information
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From
$1,325
Per Night
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1 / 29
6 Bedrooms, 4 Bathrooms, Sleeps 14
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Amenities & Details
  • Stove
  • Grill
  • Ceiling Fans
  • Patio
  • Microwave
  • Garage
  • Dishwasher
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Kailua Beach House is a casual, two-story 6 bedroom, 4.5 bath beachfront home with 5,000 square feet of living space. The 1/2 acre privacy-fenced property features a large, free-form swimming pool which has a poolside cabana with a shower and a built-in BBQ. The property decor features light... View all property information
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From
$220
Per Night
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1 / 18
1 Bedroom, 1 Bathroom, Sleeps 3
Details Reviews (4) Make Inquiry
Amenities & Details
  • Patio
  • Ceiling Fans
  • Stove
  • Grill
  • Parking
  • Stereo System
  • Microwave
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
This is the best oceanfront vacation rental in Kailua. Period... Kailua oceanfront deluxe vacation rentals - located in a oceanfront home in Kailua on the ocean. The units provides mountain and ocean views. It has separate entrances, bathrooms, and kitchen facilities. It has 16-foot vaulted... View all property information
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From
$95
Per Night
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1 / 11
1 Bedroom, 1 Bathroom, Sleeps 2
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Amenities & Details
  • TV
  • Ceiling Fans
  • Microwave
  • Air Conditioning
  • Hairdryer
  • Outdoor Dining Area
  • Patio
  • Internet Access
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • ?
About this property
Studio with private bath, private entrance and kitchenette, close to Kailua Beach Park and Kailua town, very reasonable accommodation. The 240 sq foot Studio features a queenbed, loveseat, table and chairs, ceiling fan, TV, AC and telephone. High speed internet access. The kitchenette counter is... View all property information
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From
$1,050
Per Night
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1 / 31
6 Bedrooms, 5 Bathrooms, Sleeps 12
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Amenities & Details
  • Guest Count
  • # Of Bathrooms
  • Grill
  • Parking
  • TV
  • Waterfront
  • Linens Provided
  • Number Of Bedrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Seaside is a classic beachfront estate reminiscent of 'Old Hawaii'. Coconut trees abound throughout the spacious lush green lawns. WIth large open spaces, both inside and out, this home is perfect for big families or family reunions. Seaside sits on Kailua Beach, one of the most beautiful beaches... View all property information
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From
$575
Per Night
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1 / 13
4 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Washer
  • Stereo System
  • Refrigerator
  • Grill
  • Stove
  • Microwave
  • Dryer
  • Garage
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Just one house off the beach this 4 bedroom 3 three bedroom home is perfect for the family holiday. It was completely renovated in December 2014. New walls, new floors (travertine stone and hardwood, carpet in the bedrooms new bathrooms. New cabinets, new granite counter tops. New appliances well... View all property information
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From
$1,950
Per Night
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1 / 22
4 Bedrooms, 5 Bathrooms, Sleeps 7
Details Reviews (1) Make Inquiry
Amenities & Details
  • Ceiling Fans
  • Internet Access
  • # Of Bathrooms
  • Guest Count
  • Number Of Bedrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Kanani O'Ke Kai is a stunningly elegant, yet subtle, oceanfront home only footsteps away from white, sandy Kailua Beach. Step onto your lanai and be rewarded with gorgeous views of the Koolau mountain range and Kailua Bay. From the lawn, watch brillant sunrises melt into morning skies and see the... View all property information
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From
$775
Per Night
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1 / 16
4 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Stove
  • Garage
  • Parking
  • Microwave
  • Patio
  • Dryer
  • Refrigerator
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Kakela Kai is a well-maintained, nicely furnished four bedroom, three bath contemporary home with den and approx. 2,200 sq. ft. located in a security-gated neighborhood near the center of Kailua Beach. High ceilings and sliding glass doors in the main living areas provide a feeling of spaciousness... View all property information
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From
$650
Per Night
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1 / 19
6 Bedrooms, 3 Bathrooms, Sleeps 12
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Amenities & Details
  • DVD Player
  • TV
  • Number Of Bedrooms
  • Guest Count
  • Internet Access
  • Grill
  • # Of Bathrooms
  • Satellite TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This home & location is a beach lovers paradise. Ideally set within a few steps to Kalama Beach park & world famous Kailua Beach. Fantastic family home with back yard that doesn’t end. Newly refinished pool & deck with an extra 6th bedroom (cabana) for more privacy. Gorgeous solarium for breakfast... View all property information
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From
$750
Per Night
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1 / 19
3 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Number Of Bedrooms
  • Grill
  • # Of Bathrooms
  • Guest Count
  • Internet Access
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Enjoy sunrises from the deck overlooking the beach, and sunsets from your own private perch in the sand. This beautifully decorated 3 bedroom beachfront home pampers you with a large, well-appointed kitchen, upstairs master suite with soaking tub and killer views. A large living room and dining... View all property information
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From
$1,200
Per Night
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1 / 24
5 Bedrooms, 4 Bathrooms, Sleeps 14
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Amenities & Details
  • Microwave
  • Patio
  • Refrigerator
  • Parking
  • Washer
  • Grill
  • Dryer
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Welcome to the world of John Walker. A Scotsman who made his way to Hawaii as a young man in the 1870's to become a contractor of choice to Queen Liliuokalani, and erect such notable buildings as the Bishop Museum and Honolulu Hale (City Hall). Mr. Walker's inviting presence is felt in the... View all property information
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From
$2,190
Per Night
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1 / 17
3 Bedrooms, 3 Bathrooms, Sleeps 7
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Amenities & Details
  • DVD Player
  • Dryer
  • Dishwasher
  • Stereo System
  • Safe
  • Washer
  • Parking
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Ensconce yourself in unpretentious luxury. Soft sands, the warm embrace of the Pacific, cooling tradewinds, ocean vistas that never end... Welcome to Hale Hikina. Set on the shore of Lanikai, Hale Hikina offers the perfect backdrop for a dream Hawaiian vacation with the indoors flowing seamlessly... View all property information
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From
$3,125
Per Night
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1 / 25
6 Bedrooms, 6 Bathrooms, Sleeps 12
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Amenities & Details
  • Safe
  • Ceiling Fans
  • TV
  • Stereo System
  • Hot Tub
  • DVD Player
  • Washer
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Luxury, custom home with all the amenities, right on the sands of world renowned Kailua Beach. Enjoy a front row seat for spectacular sunrises, sandcastles, kite surfing and more as you unwind and kick back in this special property. Feel the tropical breezes as you relax in the gorgeous great room;... View all property information
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From
$1,350
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6 Bedrooms, 5 Bathrooms, Sleeps 12
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Amenities & Details
  • Washer
  • Patio
  • Stereo System
  • DVD Player
  • Dishwasher
  • Fax
  • Sauna
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
***As of August, 2014, the Kailua Beachfront Retreat will require at least 10 night stays year round.*** With over 3,000 square feet of living space, this 6 bedroom, 5 bath, Kailua Luxury Beachfront Retreat is the perfect place for friends and family to gather and enjoy an amazing experience... View all property information
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From
$4,500
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1 / 26
5 Bedrooms, 6 Bathrooms, Sleeps 10
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Amenities & Details
  • Washer
  • TV
  • Stereo System
  • Ceiling Fans
  • Satellite TV
  • Dishwasher
  • Grill
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
The Kailua Plantation Estate is a rare jewel that comes fully appointed with Plantation style finishes and furnishings from around the world. Step from a secure entry and motor court into beachfront luxury that whispers old Hawaii, yet offers all of the latest amenities and technologies of a modern... View all property information
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From
$185
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1 / 41
1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Dryer
  • DVD Player
  • Microwave
  • Parking
  • Patio
  • TV
  • Grill
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Our ohana (family) welcomes you to 'Kauhale' our beautiful Hawaiian home. We offer a large cool and breezy 1000 sq ft, 1 bedroom, 1 bath, private, 2nd floor apartment, includes all utilities, located in a great family neighborhood, vaulted open beam ceilings with 5 ceiling fans, full kitchen,... View all property information
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From
$1,350
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1 / 30
5 Bedrooms, 6 Bathrooms, Sleeps 14
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Amenities & Details
  • Stereo System
  • Terrace
  • Ceiling Fans
  • Satellite TV
  • Dryer
  • Air Conditioning
  • Grill
  • Internet Access
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Family style accommodations located on Kailua Beach, voted 'Best Beach in the United States' by a variety of publications. Five bedrooms and five and half baths make this an ideal home to enjoy with extended family and friends. Large outdoor deck spaces provide ideal places to relax in the sun or... View all property information
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From
$3,200
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1 / 20
4 Bedrooms, 6 Bathrooms, Sleeps 2
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  • DVD Player
  • Guest Count
  • Air Conditioning
  • Number Of Bedrooms
  • Internet Access
  • TV
  • # Of Bathrooms
  • Water Views
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Located on the most pristine beach in all of Oahu and just 20 minutes from the airport/Waikiki, this spectacular custom estate is a stunning beachfront architectural masterpiece. As you approach the home, you are greeted by a contemporary gated entry made of beautiful African Sapele wood. Behind... View all property information
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From
$1,200
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1 / 28
5 Bedrooms, 5 Bathrooms, Sleeps 14
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Amenities & Details
  • Ceiling Fans
  • Satellite TV
  • Dryer
  • Microwave
  • Safe
  • DVD Player
  • Grill
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Family style accommodations located on Kailua Beach, voted 'Best Beach in the United States' by a variety of publications. Five bedrooms and five and half baths make this an ideal home to enjoy with extended family and friends. Large outdoor deck spaces provide ideal places to relax in the sun or... View all property information
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From
$6,000
Per Night
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1 / 24
7 Bedrooms, 8 Bathrooms, Sleeps 14
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Amenities & Details
  • Fireplace
  • Grill
  • Terrace
  • DVD Player
  • Internet Access
  • Hot Tub
  • Air Conditioning
  • Number Of Bedrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Royal Kailua Estate is the crown jewel of Kailua beachfront property. The gated entrance surrounded in lush tropical foliage is a modest inclination of what lies behind. A long pathway of oversized stones met with manicured grass provides the driveway that meanders past the luscious green lawn,... View all property information
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From
$500
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1 / 15
4 Bedrooms, 3 Bathrooms, Sleeps 10
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Amenities & Details
  • Stove
  • Parking
  • Microwave
  • Patio
  • Washer
  • Stereo System
  • Grill
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Come experience the beauty of Kailua. Stay in our charming 'Hale Nalu Palekaiko ' Surf Paradise Home. See why people call Kailua 'Papalani' Heaven on earth! Relax in our charming and comfortable 3 bedroom, 2 bathroom hale. We also have a ohana/cottage that can be rented with the main hale. The... View all property information
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From
$180
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1 / 31
1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • DVD Player
  • Patio
  • Refrigerator
  • Ceiling Fans
  • Microwave
  • Deck
  • Dryer
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Ocean Air gives you the best of both Kailua town is only minutes away and Lanikai Beach and Kailua Beach park are within walking distance of this location Lanika beach and Kailua Beach have been ranked the best in the world many times .This apartment is totally separate and has a full kitchen and... View all property information
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From
$145
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1 / 20
5 Bedrooms, 5 Bathrooms, Sleeps 10
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Amenities & Details
  • Number Of Bedrooms
  • # Of Bathrooms
  • Internet Access
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
From 1 to 5 bedrooms, private, air conditioned vacation rental units on world class Kailua Beach. Just 20 minutes away from Honolulu airport and Waikiki hotels. These surrounded by tropical gardens luxurious villas offer 2 studios, 3 bedrooms condo or a 5 bedrooms house. If you are planning... View all property information
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From
$399
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1 / 25
4 Bedrooms, 2 Bathrooms, Sleeps 12
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Amenities & Details
  • Wi-Fi
  • Air Conditioning
  • # Of Bathrooms
  • Number Of Bedrooms
  • Grill
  • Hot Tub
  • Linens Provided
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Description This European tropical retreat home is located in one of the most convenient areas of Kailua, easy access to Waikiki, Honolulu, the airport and both Waimanalo and Kailua beaches. Executive house is fully furnished and has everything you will need. Beautiful mountain views as soon as you... View all property information
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$535
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1 / 18
5 Bedrooms, 3 Bathrooms, Sleeps 13
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Amenities & Details
  • Shared Outdoor Pool...
  • Parking
  • Linens Provided
  • Number Of Bedrooms
  • Grill
  • Wi-Fi
  • Guest Count
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Description A very nice updated 5-bedroom home located on small cul de sac street with no traffic. You can walk to Kailua Beach accessible just 2 blocks away. The beach entrance is a private street entrance so you can walk to the beach and not have a large crowd on the beach. The white sands of... View all property information
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From
$1,000
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1 / 16
6 Bedrooms, 5 Bathrooms, Sleeps 12
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Amenities & Details
  • Patio
  • Fireplace
  • Dishwasher
  • Washer
  • Stove
  • Refrigerator
  • DVD Player
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
With over 3,000 square feet of living space, this 6 bedroom, 5 bath, Kailua Luxury Beachfront Retreat is the perfect place for friends and family to gather and enjoy an amazing experience together without the hassle of renting out numerous hotel rooms. Located at the end of a private street of... View all property information
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Kailua Vacation Rentals

Kailua's pristine beaches and strong trade winds make it an excellent destination for swimming, sailing, kite-flying, or just relaxing and enjoying the view. If you are planning a trip to Kailua for your next vacation, why not try renting your very own vacation home instead of staying at a hotel? There are cozy rental condos perfect for a romantic beach getaway, luxurious beachfront houses spacious enough for the whole family, and everything in between. With the amazing assortment of vacation rentals in Kailua, there is sure to be a perfect rental for any budget or need. Vacation rentals provide a truly one-of-a-kind experience when traveling to Kailua, with all the privacy and space of your own home away from home.

A Kailua Vacation

Kailua Beach Park is one of the major destinations in the area, and has the unique distinction of being two separate and very different beaches divided by a small area. Both Kailua and Lanikai beaches attract swimmers, surfers, and boaters alike due to their soft white sand, beautiful waters, and postcard views of the two islands in the distance. After you hit the beach, how about a shopping trip to Kailua Farmer's Market for some fresh food, or Mu'umu'u Heaven for some unique island wear? Barbie lovers rejoice; Kailua is home to the Hawaii Loves Barbie Dolls Museum, a private collection that is free to check out if you make an appointment in advance. No matter how you decide to spend your time in Kailua, at the end of the day staying at your very own vacation rental will make your trip even more special.

Family-Friendly Kailua

From flying kites at the beach to enjoying the Barbie Dolls museum, there is plenty to do in Kailua that children will love. With vacation rentals, it is easy to bring along the entire family without worrying about renting extra hotel rooms. Your rental condo, villa, or beachfront home will have enough space for everyone. For large groups, it is the more comfortable and economical choice, and children will feel more secure knowing they are staying in a place that feels like home.