Make a holiday rental beach house or self-catering holiday home in Kailua, Hawaii your home away from home

The small beach town of Kailua is located on the beautiful windward side of Hawaii’s Oahu Island. The Koolau Mountains create a stunning backdrop to the town, which stretches along some of the most beautiful beaches in Hawaii. From white sandy beaches and tall volcanic peaks to lush tropical forests, Kailua holidays are the perfect solution for visitors looking for luxury, tranquility and good surfing.

Things to do on holiday in Kailua, Hawaii, USA

The beautiful sandy Kailua beach has consistently been voted one of the best beaches in the world and it’s easy to understand why. The soft white sandy beach is perfect for a walk in the morning, and the clear blue waters are ideal for surfing. Located on the windward side of Oahu, Kailua beach has perfect windsurfing conditions. Other water sports in the area include snorkeling, scuba diving, sailing, jet skiing and parasailing. If you’re feeling adventurous you can rent a kayak and explore the 3 deserted islands located just off the Kailua coast.

The Koolau Mountains that surround Kailua are perfect for hiking. The lush tropical vegetation that covers the mountainside is punctuated by dozens of picturesque waterfalls.

There are 6 world-class golf courses within 10 miles of Kailua villas. After a day on the golf course visitors can enjoy typical Hawaiian cuisine at a Kailua restaurant. A cross between east and west, Hawaiian cuisine includes dishes such as poi, Kalua pig and laulau, and of course, fresh fish.

Places to visit on holiday in Kailua, Hawaii, USA

No visit to Oahu would be complete without a trip to the world’s most famous surfing beach – the Pipeline on the North Shore, which hosts some of the biggest surfing competitions in the world. Even if you don’t plan to surf, just watching the spectacular 30ft waves make it worth the trip.

The bustling cities of Waikiki and Honolulu are both within an hour’s driving distance of beach cottages in Kailua. Both cities are excellent spots for shopping and have vibrant nightlife to suit a variety of tastes.

Another must-see on Oahu is the historic town of Pearl Harbor. Here visitors can see the USS Arizona Memorial that marks the resting place of sailors who lost their lives in the 1941 attack on Pearl Harbor.

Weather in Kailua, Hawaii, USA

The island of Oahu is blessed with warm, sunny weather throughout the year. Temperatures in the middle of winter can reach as high as 27°C. Kailua is located on the windward side of the island, which frequently has afternoon showers.

Flights to Kailua, Hawaii, USA

Reaching Kailua accommodation has never been easier. Honolulu International Airport (HNL) is 14 miles away from beach houses in Kailua. There are no direct flights from the UK to Hawaii, however British Airways offers flights from London to Honolulu via Los Angeles. It is recommended that visitors to Oahu rent a car and drive to their Kailua accommodation.

Self-catering holiday homes in Kailua

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Tropical private home, opens on lush garden

— Property 118607
Kailua house rental - Kitchen, Dining area
3 Bedrooms, Sleeps 8,
House, 2 Bathrooms, near the sea, garden
Rates - per property (GBP)
£1,082 - £1,631/week
£3,171 - £3,598/month
Calendar Updated 15 Nov 2009

Property Review

We recently returned from a wonderful stay at Mala Pua Hale in Kailua, HI. The property is exactly as represented in the photos and description and we would stay there again. The property...
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Ke Ohana Hale

— Property 217470
Kailua house rental - Living area (1)
3 Bedrooms, Sleeps 8,
House, 2 Bathrooms, near the sea, garden
Rates - per property (GBP)
£1,082 - £1,631/week
£3,171 - £3,598/month
Calendar Updated 9 Nov 2009

Property Review

This home worked out great for us -- a family with 5 kids. Kailua is a great town . . . we wouldn't go anywhere else on Oahu. From this home you can walk to the grocery store and Pizza...
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'Koi Palms Luxury Cottage' Short Walk to Kailua Beach

— Property 241024
Kailua property rental - Charming and Tropical
1 Bedroom, Sleeps 2,
1 Bathroom, near the sea, garden
Rates - per property (GBP)
£91/night
£576/week
£2,195/month
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Cottage with 1 bedroom, private bathroom, a couple minutes to the beach

— Property 515304
Kailua apartment rental
Studio, Sleeps 4,
Apartment, 1 Bathroom, near the sea, town, garden
Rates - per property (GBP)
£58/night
£405/week
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Affordable, Private and Convenient - Golf Course View, Pool

— Property 169982
Kailua property rental - Peaceful and Private
4 Bedrooms, Sleeps 8,
2 Bathrooms, near the sea, private pool
Calendar Updated 5 Oct 2009

Property Review

Our family of 8 stayed for a week. The house was very nice and we felt like we were at home. It was quiet and relaxing and close to beaches. The pool was a plus. We would stay there again if we...
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Stay ON the Beach, as Close as you can Get, LOADED with Extras

— Property 191624
Kailua house rental - Exterior of House from Beach
4 Bedrooms, Sleeps 8,
House, 3 Bathrooms, 1 Separate Toilet, beach, waterfront, internet access
Rates - per property (GBP)
£3,628/week
Calendar Updated 2 Sep 2009

Property Review

Wow. What a wonderful home and amazing place. The home has all the amenieties you could ever want, and the beach toys kept us entertained without fail. The views from the home are...
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Kailua house rental - Comfortable & Casual. Read, Relax, Converse
3 Bedrooms, Sleeps 8,
House, 2 Bathrooms, beach, village, pool
Rates - per property (GBP)
£243 - £341/night
£2,435/week
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Lovely 1 bedroom tropical cottage, 1 block to Kailua Beach

— Property 75682
Kailua cottage rental
1 Bedroom, Sleeps 4,
Cottage, 1 Bathroom, beach, garden
Calendar Updated 20 May 2009

Property Review

I had initially reserved the cottage for May but due to change in work situation was required to delay stay until October 2009. The Ad needs to reflect that the air conditioning is confined...
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Kailua Beach House

— Property 88603
Kailua house rental - Our home sits right on famous Kailua beach
6 Bedrooms, Sleeps 12,
House, 5 Bathrooms, beach, near the sea, pool
Rates - per property (GBP)
£18,293/night
£18,293/week
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1 Bedroom1 Bathroom Studio (Sleeps 3 beach, near the sea, garden, internet access, satellite or cable, TV, DVD, starting at £82/night £491/week £2,104/month
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1 Bedroom/1 Bathroom Apartment (Sleeps 4
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Hale Hali'a Aloha in Kailua

— Property 228621
1 Bedroom/1 Bathroom Apartment (Sleeps 3 near the sea, waterfront, garden, air-conditioning, internet access, satellite or cable, TV, DVD, starting at £91/night £640/week
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Kailua Hawaiiana Home Right on the Beach

— Property 266942
4 Bedrooms/4 Bathrooms House (Sleeps 10 beach, waterfront, internet access, satellite or cable, TV, DVD
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Available Dec.15th-22nd! Special rate for these dates: Short walk to beach

— Property 255274
1 Bedroom Studio (Sleeps 3 beach, communal pool, garden, internet access, satellite or cable, TV, DVD, parking, starting at £470/week £1,829/month
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Beachside Paradise

— Property 154516
2 Bedrooms/2 Bathrooms House (Sleeps 6 beach, garden, air-conditioning, internet access, satellite or cable, TV, DVD, parking
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Resort-Like, Spa, Pool, Pool Cabana, 2 Min. Walk to Beach, Kailua-Lanikai

— Property 266779
3 Bedrooms/3 Bathrooms House (Sleeps 7 beach, mountain, private pool, garden, air-conditioning, internet access, TV, DVD, barbecue, starting at £241/night £1,686/week £5,488/month
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Hilltop Hale

— Property 264283
2 Bedrooms/1 Bathroom House (Sleeps 4 near the sea, internet access, satellite or cable, TV, DVD, starting at £168/night
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Wailea Lani - Most Luxurious Lanikai Living

— Property 7016964h
4 Bedrooms/4 Bathrooms House (Sleeps 9 adventure, air-conditioning, beach, beach towels, clothes dryer, cycling, wooden decking, DVD, starting at £1,006/night
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Olu'olu House

— Property 7017017h
4 Bedrooms/4 Bathrooms House (Sleeps 8 books - fiction/non-fiction, books - kids, bottled water, computer macintosh, luxury, music library, piano, veranda, starting at £732/night
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Ho'o Nanea 210

— Property 264266
4 Bedrooms/3 Bathrooms House (Sleeps 8 near the sea, satellite or cable, TV, starting at £183/night
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Cottage at Lanikai

— Property 7017029h
2 Bedrooms/1 Bathroom Cottage (Sleeps 4 adventure, alarm clock, beach, beach towels, clothes dryer, cycling, wooden decking, dish washer, starting at £241/night
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Hale Aloha

— Property 7017031h
3 Bedrooms/2 Bathrooms House (Sleeps 6 beach, beach towels, books - kids, mobile phone, clothes dryer, cycling, dish washer, diving, starting at £244/night
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8 BD/ 5 BA 2 Blocks to the Beach

— Property 162641
8 Bedrooms/5 Bathrooms Estate (Sleeps 22 beach, mountain, private pool, jacuzzi, air-conditioning, internet access, satellite or cable, TV, DVD
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Memorable Kailuana Beachfront Estate

— Property 227708
4 Bedrooms/2 Bathrooms, 1 Separate Toilet Estate (Sleeps 12 beach, waterfront, air-conditioning, internet access, satellite or cable, TV, DVD, parking, barbecue, starting at £335/night
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Tropical Paradise -Affordable

— Property 214589
2 Bedrooms/1 Bathroom House (Sleeps 5 beach, garden, internet access, satellite or cable, TV, DVD, barbecue, starting at £1,067/week
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Island Hale - Charming and Quiet--Summer Special Pricing!!!

— Property 193209
1 Bedroom1 Bathroom Studio (Sleeps 2 beach, near the sea, garden, internet access, satellite or cable, TV, DVD, barbecue, starting at £55/night £366/week
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Stunning Kailua Oceanfront House with Beach Walk Right Outside

— Property 221336
3 Bedrooms/3 Bathrooms House (Sleeps 6 resort, waterfront, private pool, garden, balcony, air-conditioning, internet access, satellite or cable, TV, starting at £457/night
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Studio1 Bathroom Studio (Sleeps 2 beach, near the sea, garden, internet access, satellite or cable, TV, DVD, starting at £37/night £247/week £1,098/month
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1 Bedroom/1 Bathroom House (Sleeps 5 beach, near the sea, air-conditioning, internet access, satellite or cable, TV, DVD, parking
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Hawaiian Style Studio Cabana - Steps to Beach!

— Property 140016
Studio/1 Bathroom Cottage (Sleeps 2 beach, near the sea, garden, internet access, satellite or cable, TV, DVD, parking