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Waimanalo Holiday Rentals

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50 rentals in Waimanalo.
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Luxury Estate~Spectacular Location~Heated Pool~Private Beach Access!, holiday rental in Waimanalo

Luxury Estate~Spectacular Location~Heated Pool~Private Beach Access!

9 bedrooms
8 bathrooms
Sleeps 20
Match: Sleeps
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Island Beach Cottage with a deck !! Gated, Air Conditioning,steps to beach, holiday rental in Waimanalo

Island Beach Cottage with a deck !! Gated, Air Conditioning,steps to beach

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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LUXURY BEACH ESTATE/BEACH FRONT/GATED AND PRIVATE// JUST LISTED !, holiday rental in Waimanalo

LUXURY BEACH ESTATE/BEACH FRONT/GATED AND PRIVATE// JUST LISTED !

3 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful Island Beach Home, Steps To Beach. Make memories!, holiday rental in Waimanalo

Beautiful Island Beach Home, Steps To Beach. Make memories!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Secluded garden cottage a half block from Waimanalo Beach, holiday rental in Waimanalo

Secluded garden cottage a half block from Waimanalo Beach

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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LARGE COUNTRY HOME ON THE BEACH /5 Master Suites/Central Air conditioning /, holiday rental in Waimanalo

LARGE COUNTRY HOME ON THE BEACH /5 Master Suites/Central Air conditioning /

5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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All the TOYS: Kayaks, surf&boogie boards, snorkeling, chairs, cooler & more., holiday rental in Waimanalo

All the TOYS: Kayaks, surf&boogie boards, snorkeling, chairs, cooler & more.

2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Beachfront Waimanalo Home w/ Pergola & Ocean Views, holiday rental in Waimanalo

Beachfront Waimanalo Home w/ Pergola & Ocean Views

3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Steps to Kailua Beach - Heated Pool - Air Conditioned - Ask Owner/Rates, holiday rental in Waimanalo

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

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

Barefoot living on Lanikai Beach -- BEACHFRONT!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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1 house from the beach - solar heated pool - AC - Contact Owner for Rates, holiday rental in Waimanalo

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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Kailua Beach Vacation Cottage, holiday rental in Waimanalo

Kailua Beach Vacation Cottage

1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
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Lanikai Hillside Cozy Cottage with Spectacular Ocean View with Mokulua Islands., holiday rental in Waimanalo

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

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Minutes to Largest,Bluest Swimming Pool on the Planet, Amazing Hiking, holiday rental in Waimanalo

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

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

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

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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New Lanikai Oceanfront Listing, Just Steps Away From Secluded White Sand Beach!, holiday rental in Waimanalo

New Lanikai Oceanfront Listing, Just Steps Away From Secluded White Sand Beach!

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Luxury Home in Gated Community Steps from Kailua Beach, holiday rental in Waimanalo

Luxury Home in Gated Community Steps from Kailua Beach

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful Kailua Home, looking for a family to share it's Aloha, holiday rental in Waimanalo

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

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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SUITE ALOHA – Romantic Island Retreat 2 Blocks from Kailua Beach Park & Downtown, holiday rental in Waimanalo

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

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

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 Waimanalo

Kailua Beach Park Cottage - 2BR

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

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 Waimanalo

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

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Prime Location! Sleeps 8 next to BEST beaches in Kailua & Lani Kai, holiday rental in Waimanalo

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

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

Tropical Kailua Studio on the Water w/Private Pool

0 bedrooms
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 Waimanalo

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

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

Nancy's Kailua Cottage Mauka

0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Nancy's Kailua Cottage Makai, holiday rental in Waimanalo

Nancy's Kailua Cottage Makai

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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4 Bedroom/ 2 Bath Unit -5 Min Walk to Kailua Beach, holiday rental in Waimanalo

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

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

Cozy Cottage 5 Minute Walk to Kailua Beach

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

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

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Seabreeze Vacation Home - Quiet/Pool/Free Wi-Fi/Parking, holiday rental in Waimanalo

Seabreeze Vacation Home - Quiet/Pool/Free Wi-Fi/Parking

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Orchid House | Your Hawaiian home awaits your arrival for the Holidays!, holiday rental in Waimanalo

Orchid House | Your Hawaiian home awaits your arrival for the Holidays!

3 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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Large Spacious Studio - 5 Min Walk to Kailua Beach, holiday rental in Waimanalo

Large Spacious Studio - 5 Min Walk to Kailua Beach

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Relaxing Private Room- 5 Min Walk to Kailua Beach, holiday rental in Waimanalo

Relaxing Private Room- 5 Min Walk to Kailua Beach

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Kailua, Entire 3 Bedroom Home, carport, yard, BBQ, holiday rental in Waimanalo

Kailua, Entire 3 Bedroom Home, carport, yard, BBQ

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Steps to Lanikai Beach~3 living spaces w/pool  *August cancellation rate*!, holiday rental in Waimanalo

Steps to Lanikai Beach~3 living spaces w/pool *August cancellation rate*!

5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Mokulua Aina~Lanikai  Steps to Lanikai Beach.  SPECIAL FALL RATES!, holiday rental in Waimanalo

Mokulua Aina~Lanikai Steps to Lanikai Beach. SPECIAL FALL RATES!

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Beachtown Getaway, holiday rental in Waimanalo

Cozy Beachtown Getaway

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Perfect Beachtown Retreat, holiday rental in Waimanalo

Perfect Beachtown Retreat

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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* LAST MINUTE OPENING * D+D's Cottage - Best Location in Kailua, holiday rental in Waimanalo

* LAST MINUTE OPENING * D+D's Cottage - Best Location in Kailua

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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LAST MINUTE OPENING * D&D's B&B *sweet island style Studio, holiday rental in Waimanalo

LAST MINUTE OPENING * D&D's B&B *sweet island style Studio

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Island style Homebase * 2 bedroom & 1 bath - Central Air, holiday rental in Waimanalo

Island style Homebase * 2 bedroom & 1 bath - Central Air

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Lovely Pool Studio with private entrance & bath, holiday rental in Waimanalo

Lovely Pool Studio with private entrance & bath

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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* LAST MINUTE OPENING * Tropical Garden Cottage, holiday rental in Waimanalo

* LAST MINUTE OPENING * Tropical Garden Cottage

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Sunny Apartment in excellent location - short walk to Kailua beach & town, holiday rental in Waimanalo

Sunny Apartment in excellent location - short walk to Kailua beach & town

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Immaculate, private, fully furnished studio in Beautiful Lanikai, holiday rental in Waimanalo

Immaculate, private, fully furnished studio in Beautiful Lanikai

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Lanikai Beach Front - Sunrise over the 'Mokes', holiday rental in Waimanalo

Lanikai Beach Front - Sunrise over the 'Mokes'

4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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***PARADISE FOUND: The Orchid Room at Seal Cove*** PRIVATE BATHROOM (not shared), holiday rental in Waimanalo

***PARADISE FOUND: The Orchid Room at Seal Cove*** PRIVATE BATHROOM (not shared)

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Large Lanikai Ocean Front w/Pool, holiday rental in Waimanalo

Large Lanikai Ocean Front w/Pool

6 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps
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