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Kailua Hawaii Vacation Rentals - Villa
1 / 33

Kailua Villa
5 BR / 5 BA / Sleeps 12 5 12 Min stay varies
Villa / 5 Bedrooms / Sleeps 12
5 bedrooms 5 bathrooms Sleeps 12
High Speed Internet • Microwave • Washer/Dryer
Beautiful 1- 5 bedrooms private vacation rental units on #1 rated Kailua/Lanikai beach. Just 18 minutes away from Honolulu airport and Waikiki hotels. These surrounded by tropical gardens luxurious villas offer 2 studi...
(23) Excellent (23 reviews)
Kailua Hawaii Vacation Rentals - Home
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Kailua Home
1 BR / 1 BA / Sleeps 5 1 5 3 night min stay
Home / 1 Bedroom / Sleeps 5
1 bedrooms 1 bathroom Sleeps 5
High Speed Internet • Microwave • TV (Cable/Satellite)
Charming Cottage in beautiful Lanikai. Short walk to the beach. Enjoy comforts of home with efficiency kitchen and own washer and dryer. One split AC unit. Large lanai to extend the living space and room to BBQ and dine....
Kailua Hawaii Vacation Rentals - Home
1 / 40

Kailua Home
6 BR / 5 BA / Sleeps 12 6 12 30 night min stay
Home / 6 Bedrooms / Sleeps 12
6 bedrooms 5 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
Step back in time and experience a peaceful, private Hawaiian lifestyle at this one of a kind beach house located on a million dollar beach front lot. This home has over 3, 100 spacious square feet of living space. The...
(7) Excellent (7 reviews)
Kailua Hawaii Vacation Rentals - Home
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Kailua Home
2 BR / 2 BA / Sleeps 6 2 6 Min stay varies
Home / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Microwave • Washer/Dryer
Blossoms, palms, and tikis await you as you enter the one- fourth acre, tropical paradise tucked away beach side on a private lane. This newly renovated, two bedroom, two bath vacation rental is a split level un...
(2) Excellent (2 reviews)
Kailua Hawaii Vacation Rentals - Home
1 / 21

Kailua Home
4 BR / 3 BA / Sleeps 11 4 11 Min stay varies
Home / 4 Bedrooms / Sleeps 11
4 bedrooms 3 bathrooms Sleeps 11
High Speed Internet • Microwave • TV (Antenna)
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, which means “ love, ” ...
Kailua Hawaii Vacation Rentals - Bed & Breakfast
1 / 19

Kailua Bed & Breakfast
2 BR / 2 BA / Sleeps 8 2 8 Min stay varies
Bed & Breakfast / 2 Bedrooms / Sleeps 8
2 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Microwave • Washer/Dryer
The lovely Kailua Beachside House is a 2 bedroom 2 bath house that is great for families and couples alike. It's location can't be beat only 2 houses from the world famous white sands of Kailua Beach. This house is p...
Kailua Hawaii Vacation Rentals - Home
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Kailua Home
1 BR / 1 BA / Sleeps 3 1 3 3 night min stay
Home / 1 Bedroom / Sleeps 3
1 bedrooms 1 bathroom Sleeps 3
High Speed Internet • Microwave • Washer/Dryer
Kailua oceanfront deluxe vacation rentals - two units located in oceanfront home in Kailua on the ocean. One unit faces the mountains and the outer faces the ocean. Both have separate entrances, bathrooms, and kitchen...
(1) Excellent (1 review)
Kailua Hawaii Vacation Rentals - Home
1 / 37

Kailua Home
6 BR / 4.5 BA / Sleeps 18 6 18 Min stay varies
Home / 6 Bedrooms / Sleeps 18
6 bedrooms 4.5 bathrooms Sleeps 18
High Speed Internet • Dishwasher • Microwave
Privacy and comfort are provided in this luxury Hawaiian/Asian furnished home. This 4000 sq ft. gated property with an 8 ft wall surrounding the perimeter is on a double lot in the heart of Kailua, less than one mile fr...
(1) Excellent (1 review)
Kailua Hawaii Vacation Rentals - Home
1 / 21

Kailua Home
5 BR / 3 BA / Sleeps 10 5 10 Min stay varies
Home / 5 Bedrooms / Sleeps 10
5 bedrooms 3 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
Description Breath- taking views... luxurious details... this is Shangri- La by the sea. Leave your worries behind as you step into this magical home. Nourish your soul as the waves break just outside your door. Re...
(1) Excellent (1 review)
Kailua Hawaii Vacation Rentals - Home
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Kailua Home
3 BR / 2.5 BA / Sleeps 8 3 8 5 night min stay
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 2.5 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
5 Minute Walk To Beach Ocean View Beachside Home Wrap- around Lanai Spacious 2, 200 SF 3BR, 2. 5BA Home Pool Full Service Gourmet Kitchen BBQ Huge Master Indoor Laundry TV & WIFI Parking 2 Mile Walking Loop Golf Hiking...
(8) Excellent (8 reviews)
Kailua Hawaii Vacation Rentals - Home
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Kailua Home
2 BR / 2 BA / Sleeps 6 2 6 30 night min stay
Home / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Come and relax on the Nation's #1 beach, Lanikai! ! It is the ultimate beach house with a yard just off the beach with seating and a BBQ for guests use. Beautiful and tranquil turquois blue waters to view and sw...
(1) Excellent (1 review)
Kailua Hawaii Vacation Rentals - Home
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Kailua Home
3 BR / 3 BA / Sleeps 6 3 6 6 night min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 3 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Kaimalino Kai is a two story, 3 bedroom, 3 bathroom oceanfront gem perched elegantly against the backdrop of Kailua Bay. Hear the sound of the waves crashing against the rocky shoreline while magical ocean views comple...
Kailua Hawaii Vacation Rentals - Home
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Kailua Home
4 BR / 3 BA / Sleeps 9 4 9 7 night min stay
Home / 4 Bedrooms / Sleeps 9
4 bedrooms 3 bathrooms Sleeps 9
High Speed Internet • Dishwasher • Microwave
This executive beachfront home is right on Kailua Beach. Decorated with island- style rattan furnishings, ceiling fans throughout, cool white tile, and wood flooring. Central air conditioning, wonderful ocean views a...
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Kailua Home
5 BR / 5.5 BA / Sleeps 10 5 10 Min stay varies
Home / 5 Bedrooms / Sleeps 10
5 bedrooms 5.5 bathrooms Sleeps 10
High Speed Internet • Microwave • Washer/Dryer
The Paradise Point 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...
Kailua Hawaii Vacation Rentals - Home
1 / 15

Kailua Home
5 BR / 3 BA / Sleeps 13 5 13 Min stay varies
Home / 5 Bedrooms / Sleeps 13
5 bedrooms 3 bathrooms Sleeps 13
High Speed Internet • Dishwasher • Microwave
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 ...
(1) Excellent (1 review)
Kailua Hawaii Vacation Rentals - Cottage
1 / 8

Kailua Cottage
1 BR / 1 BA / Sleeps 2 1 2 30 night min stay
Cottage / 1 Bedroom / Sleeps 2
1 bedrooms 1 bathroom Sleeps 2
High Speed Internet • Microwave • Washer/Dryer
AWAKE IN PARADISE in your own private and spacious 1, 000 sq. ft. monthly rental. Queen bed, bathroom, full kitchen Private lanai with dining and swimming pool. Wireless internet, Cable TV, A/C, Washer/Dryer and...
(5) Very Good (5 reviews)
Kailua Hawaii Vacation Rentals - Home
1 / 15

Kailua Home
4 BR / 3 BA / Sleeps 10 4 10 4 night min stay
Home / 4 Bedrooms / Sleeps 10
4 bedrooms 3 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
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 bathro...
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Kailua Home
5 BR / 3 BA / Sleeps 12 5 12 Min stay varies
Home / 5 Bedrooms / Sleeps 12
5 bedrooms 3 bathrooms Sleeps 12
High Speed Internet • Washer/Dryer • Air Conditioning
This Hawaiian style home is a perfect peaceful getaway for you and your extended family. It's just steps from one of the most beautiful tourist- free beaches on the island of Oahu. Listen to the waves crashing as you rel...
Kailua Hawaii Vacation Rentals - Home
1 / 17

Kailua Home
3 BR / 2 BA / Sleeps 6 3 6 Min stay varies
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Microwave • Washer/Dryer
Description The Jungle Waterfall Retreat is tucked into the rainforest of Kailua. Get the quiet relaxation of living surrounded by mountains while only being a 5- minute drive to the beach. It's just 20 minutes to the ...
Kailua Hawaii Vacation Rentals - Home
1 / 44

Kailua Home
7 BR / 8 BA / Sleeps 15 7 15 Min stay varies
Home / 7 Bedrooms / Sleeps 15
7 bedrooms 8 bathrooms Sleeps 15
High Speed Internet • Dishwasher • Microwave
The Essence of Kailua Beach LivingCastle Point Estateis an estate built to embody the essence of luxury Kailua Beach living. Bringing in the elements of the ocean, bold colors bounce off soft hues and simplicity offers ...
Kailua Hawaii Vacation Rentals - Home
1 / 23

Kailua Home
5 BR / 5 BA / Sleeps 10 5 10 7 night min stay
Home / 5 Bedrooms / Sleeps 10
5 bedrooms 5 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
This gated, landmark property was designed with natural spaces and architecture that reflect the social and welcoming Polynesian lifestyle - a home that' s not only beautiful, but also strikes the perfect balance...
Kailua Hawaii Vacation Rentals - Home
1 / 26

Kailua Home
5 BR / 4 BA / Sleeps 10 5 10 14 night min stay
Home / 5 Bedrooms / Sleeps 10
5 bedrooms 4 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
Over the canal, past the boat ramp and round the bend is where you’ ll find the Ocean’ s Edge in Lanikai. Just a walk on the beach, afternoon swim or bike ride away! This 5 bedroom, 3. 5 bath oceanfront...
Kailua Hawaii Vacation Rentals - Home
1 / 33

Kailua Home
5 BR / 4 BA / Sleeps 12 5 12 14 night min stay
Home / 5 Bedrooms / Sleeps 12
5 bedrooms 4 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
Experience true island living in this stunning beachfront villa on the white sandy shores of Lanikai. This home has so much history as one of the original mansions built on Lanikai Beach in the 1940' s, and has bee...
Kailua Hawaii Vacation Rentals - Villa
1 / 26

Kailua Villa
5 BR / 5 BA / Sleeps 10 5 10 Min stay varies
Villa / 5 Bedrooms / Sleeps 10
5 bedrooms 5 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
Those who are familiar with Hawaiian history know that pineapples played a crucial role in the island's development. The sweet fruit were grown out of large plantation estates, which serve as the inspiration for Plantat...
Kailua Hawaii Vacation Rentals - Home
1 / 44

Kailua Home
8 BR / 9 BA / Sleeps 16 8 16 Min stay varies
Home / 8 Bedrooms / Sleeps 16
8 bedrooms 9 bathrooms Sleeps 16
High Speed Internet • Dishwasher • Microwave
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 manicu...
Kailua Hawaii Vacation Rentals - Villa
1 / 37

Kailua Villa
8 BR / 10 BA / Sleeps 16 8 16 7 night min stay
Villa / 8 Bedrooms / Sleeps 16
8 bedrooms 10 bathrooms Sleeps 16
High Speed Internet • Dishwasher • Microwave
Grand Kailua Beachside 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 w...
Kailua Hawaii Vacation Rentals - Villa
1 / 24

Kailua Villa
8 BR / 8 BA / Sleeps 16 8 16 7 night min stay
Villa / 8 Bedrooms / Sleeps 16
8 bedrooms 8 bathrooms Sleeps 16
High Speed Internet • Air Conditioning • DVD Player
Royal Kailua Estate is a veritable Polynesian palace of unrivaled opulence located in Kailua, on Oahu's northern coast in the great state of Hawaii. The estate spans an astonishing 11, 000 square feet atop a moderate i...
Kailua Hawaii Vacation Rentals - Villa
1 / 38

Kailua Villa
7 BR / 7 BA / Sleeps 14 7 14 Min stay varies
Villa / 7 Bedrooms / Sleeps 14
7 bedrooms 7 bathrooms Sleeps 14
High Speed Internet • Dishwasher • TV (Antenna)
Built by famous stylist Paul Mitchell in the late 1980s. This gated, beachfront, landmark property was designed with natural spaces and architecture that reflect the social and welcoming Polynesian lifestyle - a home ...
Kailua Hawaii Vacation Rentals - Home
1 / 28

Kailua Home
6 BR / 6 BA / Sleeps 14 6 14 Min stay varies
Home / 6 Bedrooms / Sleeps 14
6 bedrooms 6 bathrooms Sleeps 14
High Speed Internet • Air Conditioning • DVD Player
With access to the world- famous Kailua Beach and its turquoise waters being just four houses away and shops, restaurants and grocery nearby, the location of Helen's Beach House could not be more ideal. The exterior ma...
Kailua Hawaii Vacation Rentals - Home
1 / 31

Kailua Home
6 BR / 3 BA / Sleeps 14 6 14 Min stay varies
Home / 6 Bedrooms / Sleeps 14
6 bedrooms 3 bathrooms Sleeps 14
High Speed Internet • Dishwasher • Microwave
MINIMUMREQUIREMENTSAPPLY. INQUIREFOR DETAILS. One- of- a- kind beachside home on an exclusive street in Kailua. Perfect for a large family with kids or two families to share. Single level architect- designed home was com...
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About Kailua

Kailua is one of the most picturesque places to visit in Hawaii. From white sand beaches to green forest canopies, Kailua offers the perfect setting for an island vacation. Book your choice of seaside Kailua vacation rentals, and enjoy an island adventure on Oahu.

Climate

When you visit Kailua, you'll enjoy a tropical climate with consistently warm temperatures every month of the year. In January, July, and every month in between, temperatures top out in the mid-80s during the day and drop to the low 70s or high 60s overnight. December and January tend to be the rainiest months, and June and July are typically the driest. Other than occasional rain, the other element that sometimes keeps the sun out is vog, a sort of volcano fog that results from Kilauea volcano activity.

Transit

Located on the island of Oahu, Kailua is a short drive from the Honolulu International Airport. To get around the town without a car, hop on the island's TheBus system, which has four routes through town. To reach the island's top parks, reserves, and attractions from most Kailua vacation homes, consider renting a car to travel at your own pace.

Things to do

No trip to Kailua is complete without a visit to the beach. Kailua Beach has won numerous awards, thanks to its three miles of soft white sand, crystal clear turquoise water, and crescent shape. The water temperature is about 75 degrees year-round, which makes it a great spot for swimming. The combination of strong winds and protective bay make it a top pick for surfers and other water sports enthusiasts. Nearby, Lanikai Beach is another popular place to catch some rays and gaze out at the distant Mokulua Islands.

Explore the Kailua area's natural beauty with a visit to the Kawai Nui Marsh, the most extensive wetland in Hawaii. This 800-acre marsh is home to more than 60 species of native fish and birds, making it a great place for wildlife spotting. Get some height with a hike along the Olomana Trail. This scenic trail features three peaks of varying difficulty, and each boasts spectacular views.

Kaloko-Honokohau National Park is also on the to-do list for many families that visit Kailua. Hike this park to see its landscape of lava formations. Here visitors will also see fish ponds, birds, turtles and native plant life while some may even spy a Hawaiian monk seal relaxing in the sun. 

Families who want to observe the ocean life would be wise to reserve a tour with Sea Quest snorkel tours. On these excursions, visitors are able to snorkel in an area of calm water. Sea Quest welcomes people with snorkeling experience as well as those who have never gone before, and also offers tours by boat to marvel at Hawaii’s sea caves and lava tubes. 

Dining

Give your day a sunny start with breakfast at Cinnamon's Restaurant, one of the city's most highly-rated spots for over 30 years. If you're in a savory mood, you can't beat the Hawaiian omelet, pork eggs benedict, or skillet with home fries. Diners with a sweet tooth should pay close attention to the restaurant's lengthy specialty pancake menu, which features delicacies like guava chiffon pancakes, red velvet pancakes, or cinnamon rolls.

For lunch or dinner, Uahi Island Grill serves up Hawaiian specialties with an Asian twist. Start with the Furikake calamari with Sriracha glaze, and try the Korean steak salad with kimchi vinaigrette or the poke bowl with fresh ahi tuna dressed with shoyu and sesame oil.

With miles of sandy beaches and natural beauty as far as the eye can see, it's no wonder Kailua is a top vacation spot on Oahu. Take your pick from dozens of Kailua vacation homes right on the beach, and settle into island life in Hawaii.