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Kailua Holiday Rentals

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84 rentals in Kailua.
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4 Bedroom/ 2 Bath Unit -5 Min Walk to Kailua Beach, holiday rental in Kailua

4 Bedroom/ 2 Bath Unit -5 Min Walk to Kailua Beach

4 bedrooms
2 bathrooms
Sleeps 8
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Tropical Kailua Studio on the Water w/Private Pool, holiday rental in Kailua

Tropical Kailua Studio on the Water w/Private Pool

0 bedrooms
1 bathroom
Sleeps 2
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Sheffield Suite Walk to Kailua Beach or Town, holiday rental in Kailua

Sheffield Suite Walk to Kailua Beach or Town

1 bedroom
1 bathroom
Sleeps 3
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SUITE ALOHA – Romantic Island Retreat 2 Blocks from Kailua Beach Park & Downtown, holiday rental in Kailua

SUITE ALOHA – Romantic Island Retreat 2 Blocks from Kailua Beach Park & Downtown

1 bedroom
1 bathroom
Sleeps 2
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Pristine X lg 1 bdrm 1 bath aprt w/Sweeping Views of Kailua, holiday rental in Kailua

Pristine X lg 1 bdrm 1 bath aprt w/Sweeping Views of Kailua

1 bedroom
1 bathroom
Sleeps 4
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The Perfect Kailua Retreat!, holiday rental in Kailua

The Perfect Kailua Retreat!

0 bedrooms
1 bathroom
Sleeps 2
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Pikake Hale - Large, beautiful 5 Bedroom home steps from the beach, holiday rental in Kailua

Pikake Hale - Large, beautiful 5 Bedroom home steps from the beach

5 bedrooms
5 bathrooms
Sleeps 13
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Steps to Kailua Beach - Heated Pool - Air Conditioned - Ask Owner/Rates, holiday rental in Kailua

Steps to Kailua Beach - Heated Pool - Air Conditioned - Ask Owner/Rates

4 bedrooms
4 bathrooms
Sleeps 8
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Barefoot living on Lanikai Beach -- BEACHFRONT!, holiday rental in Kailua

Barefoot living on Lanikai Beach -- BEACHFRONT!

1 bedroom
1 bathroom
Sleeps 4
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KAILUA-STEPS TO THE BEACH, holiday rental in Kailua

KAILUA-STEPS TO THE BEACH

2 bedrooms
1 bathroom
Sleeps 5
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Close to the Beautiful Kailua Beach-A/C-Full Kitchen-WiFi-Covered Patio-Laundry, holiday rental in Kailua

Close to the Beautiful Kailua Beach-A/C-Full Kitchen-WiFi-Covered Patio-Laundry

1 bedroom
1 bathroom
Sleeps 4
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Kailua Beach Vacation Cottage, holiday rental in Kailua

Kailua Beach Vacation Cottage

1 bedroom
2 bathrooms
Sleeps 6
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1 house from the beach - solar heated pool - AC - Contact Owner for Rates, holiday rental in Kailua

1 house from the beach - solar heated pool - AC - Contact Owner for Rates

4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Lanikai Hillside Cozy Cottage with Spectacular Ocean View with Mokulua Islands., holiday rental in Kailua

Lanikai Hillside Cozy Cottage with Spectacular Ocean View with Mokulua Islands.

2 bedrooms
1 bathroom
Sleeps 4
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Bring your aloha shirt and visit Kailua  TAX I.D.W********-01 NUC 90/BB-0069, holiday rental in Kailua

Bring your aloha shirt and visit Kailua TAX I.D.W********-01 NUC 90/BB-0069

0 bedrooms
1 bathroom
Sleeps 2
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Private Beachside Kailua Home - Remodeled w/AC - 3 min walk to beach!, holiday rental in Kailua

Private Beachside Kailua Home - Remodeled w/AC - 3 min walk to beach!

4 bedrooms
3 bathrooms
Sleeps 8
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5 Minute Walk to Kailua Beach, holiday rental in Kailua

5 Minute Walk to Kailua Beach

0 bedrooms
1 bathroom
Sleeps 2
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Minutes to Largest,Bluest Swimming Pool on the Planet, Amazing Hiking, holiday rental in Kailua

Minutes to Largest,Bluest Swimming Pool on the Planet, Amazing Hiking

1 bedroom
1 bathroom
Sleeps 4
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CHRISTMAS DATES AVAILABLE!! Prime Location Across from Kailua Beach Park w/AC, holiday rental in Kailua

CHRISTMAS DATES AVAILABLE!! Prime Location Across from Kailua Beach Park w/AC

2 bedrooms
2 bathrooms
Sleeps 5
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Kahela - Paradise for Rent, holiday rental in Kailua

Kahela - Paradise for Rent

4 bedrooms
4 bathrooms
Sleeps 8
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Luxury Home in Gated Community Steps from Kailua Beach, holiday rental in Kailua

Luxury Home in Gated Community Steps from Kailua Beach

4 bedrooms
4 bathrooms
Sleeps 10
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Beachside Kailua,  Immaculate & Private 1 BR,  stones throw to Kailua Beach!, holiday rental in Kailua

Beachside Kailua, Immaculate & Private 1 BR, stones throw to Kailua Beach!

1 bedroom
1 bathroom
Sleeps 4
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Nancy's Kailua Cottage Mauka, holiday rental in Kailua

Nancy's Kailua Cottage Mauka

0 bedrooms
1 bathroom
Sleeps 4
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Beautiful Kailua Home, looking for a family to share it's Aloha, holiday rental in Kailua

Beautiful Kailua Home, looking for a family to share it's Aloha

4 bedrooms
3 bathrooms
Sleeps 10
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Steps to the Beach Guesthouse, holiday rental in Kailua

Steps to the Beach Guesthouse

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Kailua Beach Park Cottage - 1BR, holiday rental in Kailua

Kailua Beach Park Cottage - 1BR

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Kailua Beach Park Cottage - 2BR, holiday rental in Kailua

Kailua Beach Park Cottage - 2BR

2 bedrooms
1 bathroom
Sleeps 5
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Very Close To Kailua Town And Beach! Last minute discounted rates!, holiday rental in Kailua

Very Close To Kailua Town And Beach! Last minute discounted rates!

2 bedrooms
1 bathroom
Sleeps 5
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Walk to Beach,  Bright, Spacious studio. Upstairs w/ mountain view, holiday rental in Kailua

Walk to Beach, Bright, Spacious studio. Upstairs w/ mountain view

0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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3 Bedroom Kailua Fire Captain's Home, Simple & Clean with Max Speed WiFi, holiday rental in Kailua

3 Bedroom Kailua Fire Captain's Home, Simple & Clean with Max Speed WiFi

3 bedrooms
2 bathrooms
Sleeps 6
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'Tropical Garden Paradise' Steps to Beach & Very Affordable, holiday rental in Kailua

'Tropical Garden Paradise' Steps to Beach & Very Affordable

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Wow!   Home just steps from the Beach with Pool, holiday rental in Kailua

Wow! Home just steps from the Beach with Pool

5 bedrooms
4 bathrooms
Sleeps 10
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Prime Location! Sleeps 8 next to BEST beaches in Kailua & Lani Kai, holiday rental in Kailua

Prime Location! Sleeps 8 next to BEST beaches in Kailua & Lani Kai

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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New 3 Bdrm, Large Lanai, Quiet area, Ocean Breezes, Short Walk to the Beach, holiday rental in Kailua

New 3 Bdrm, Large Lanai, Quiet area, Ocean Breezes, Short Walk to the Beach

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Nancy's Kailua Cottage Makai, holiday rental in Kailua

Nancy's Kailua Cottage Makai

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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$4500/30-day off-season rate in Lanikai (30-day minimum stay), holiday rental in Kailua

$4500/30-day off-season rate in Lanikai (30-day minimum stay)

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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A New Beautiful Kailua Home, near the beach and Kailua town, holiday rental in Kailua

A New Beautiful Kailua Home, near the beach and Kailua town

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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New Beautiful Kailua Home, near the beach and 6 minutes walk to Kailua town, holiday rental in Kailua

New Beautiful Kailua Home, near the beach and 6 minutes walk to Kailua town

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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25% OFF 11/15/20 - 12/3/20 7 DAY STAY/ OR BOOK 7 DAYS - GET 8 DAYS! -, holiday rental in Kailua

25% OFF 11/15/20 - 12/3/20 7 DAY STAY/ OR BOOK 7 DAYS - GET 8 DAYS! -

8 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Cozy Cottage 5 Minute Walk to Kailua Beach, holiday rental in Kailua

Cozy Cottage 5 Minute Walk to Kailua Beach

1 bedroom
1 bathroom
Sleeps 4
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Secluded Beach Bungalow with Private Garden, holiday rental in Kailua

Secluded Beach Bungalow with Private Garden

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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For a New Beautiful Kailua Home, Near the Beach, holiday rental in Kailua

For a New Beautiful Kailua Home, Near the Beach

2 bedrooms
1 bathroom
Sleeps 5
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Plantation Charm in Kailua, holiday rental in Kailua

Plantation Charm in Kailua

4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Nice 2bd/1bath. 3blk. Walk to beach. Private entry& bathroom, holiday rental in Kailua

Nice 2bd/1bath. 3blk. Walk to beach. Private entry& bathroom

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Kailua, Cozy, 2 bedroom, duplex home, carport, yard, BBQ, holiday rental in Kailua

Kailua, Cozy, 2 bedroom, duplex home, carport, yard, BBQ

2 bedrooms
1 bathroom
Sleeps 4
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New Beautiful Kailua House, near the beach and Kailua town, holiday rental in Kailua

New Beautiful Kailua House, near the beach and Kailua town

3 bedrooms
1 bathroom
Sleeps 5
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Sheffield Studio  Walk to Kailua Beach or Town, holiday rental in Kailua

Sheffield Studio Walk to Kailua Beach or Town

0 bedrooms
1 bathroom
Sleeps 2
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Kailua, Cozy, Spacious Duplex Home, carport, yard, BBQ, holiday rental in Kailua

Kailua, Cozy, Spacious Duplex Home, carport, yard, BBQ

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Private 2 Bedroom Across The Street From Kailua Beach!!, holiday rental in Kailua

Private 2 Bedroom Across The Street From Kailua Beach!!

2 bedrooms
1 bathroom
Sleeps 6
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Large Spacious Studio - 5 Min Walk to Kailua Beach, holiday rental in Kailua

Large Spacious Studio - 5 Min Walk to Kailua Beach

1 bedroom
1 bathroom
Sleeps 4
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Frequently Asked Questions about Kailua





Kailua holiday rentals
Kailua is a town on the Windward Coast of Oahu in Hawaii. The coast in general is renowned as an area of outstanding natural beauty, and Kailua is a great place to see some spectacular sunrises. With some great beaches and a laidback lifestyle, Kailua is the ideal destination for a relaxed family holiday. And with a huge amount of self-catered accommodation available in the town, you can find a home from home in this idyllic island setting. A trip to Hawaii might not sound like a money saving holiday, but there are rental homes available to suit every budget, and free up cash to enjoy the rest of your family holiday.
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Kailua holiday rentals
Kailua is a town on the Windward Coast of Oahu in Hawaii. The coast in general is renowned as an area of outstanding natural beauty, and Kailua is a great place to see some spectacular sunrises. With some great beaches and a laidback lifestyle, Kailua is the ideal destination for a relaxed family holiday. And with a huge amount of self-catered accommodation available in the town, you can find a home from home in this idyllic island setting. A trip to Hawaii might not sound like a money saving holiday, but there are rental homes available to suit every budget, and free up cash to enjoy the rest of your family holiday.
What to do in Kailua
Kailua Beach Park will be the first stop for many tourists, and this amazing ocean beach is bound to take up a few days of your visit. Work on your tan, and admire the sea turtles which can be seen in the area. Also, watersports enthusiasts will love the opportunities provided by Kailua Beach, including kayaking, windsurfing, kiteboarding and scuba diving. All necessary equipment can be hired nearby for some unforgettable holiday experiences. Quite apart from exploring the rest of the Windward Coast and Oahu in general, you will also have to take a boat out to the Mokulua Islands, two small islands just off Oahu's coast which provide great surfing opportunities and slightly less crowded white sandy beaches.
Renting an apartment in Kailua
With a huge variety of family friendly rental homes available in and around Kailua, it is easy to find deals on luxurious apartment rentals. With rental costs starting from just £390 for apartments large enough to accommodate a family of four or more, it can work out much less expensive than booking hotel rooms for the entire family. Many of the apartments come with spectacular ocean views, as well as access to private pools, tennis courts and other facilities, so it will certainly not feel like a low cost option! The extra privacy and space that comes with a rented holiday property also means that they're great for kids - the youngest members of your family can run around and let off steam without you having to worry about them disturbing the neighbours!