Diamond Head Vacation Rentals

Diamond Head vacation rentals place you near Oahu's iconic crater, offering scenic hikes, panoramic views, and quick access to Waikiki Beach. Enjoy a tranquil neighborhood setting with upscale homes, ocean-view condos, and easy access to dining, shopping, and Honolulu's top attractions.

Diamond Head is one of Oahu's most recognizable landmarks, a volcanic crater that offers panoramic views of Honolulu and the Pacific Ocean. Staying in a vacation rental near Diamond Head means you're just steps away from the trailhead of one of Hawaii's most scenic hikes. The walk to the summit is a favorite among visitors, rewarding hikers with sweeping vistas and a deeper appreciation for the island's natural beauty.

In addition to outdoor adventure, this area places you just minutes from the heart of Waikiki. Enjoy world-class shopping, acclaimed restaurants, and the famous Waikiki Beach - all while returning to a quieter, more residential setting near Diamond Head. This location offers the perfect balance of convenience and tranquility for travelers seeking to experience both nature and urban attractions.

Vacation rentals in the Diamond Head area combine comfort, style, and an unmatched location. Whether you're seeking a refined residence with ocean views or a peaceful home near the beach, you'll find exceptional options that cater to a high standard of travel. Let Diamond Head be your base for a sophisticated and scenic stay on Oahu.

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$Kahala Seaside: Beautiful Nautical-Themed Home w\/AC, Yard, Private Pool & Spa!$

Kahala Seaside: Beautiful Nautical-Themed Home w/AC, Yard, Private Pool & Spa!

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.

Welcome to Kahala Seaside, a spacious two-story garden view home featuring four bedrooms, three-and-a-half bathrooms, and lush garden views.
Registration Number: 350040510000, TA-188-470-4768-01, GE-188-470-4768-01

4 bedroom
3 bathroom
Sleeps 7

from $741

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Honolulu Condo for Rent Steps to Kahala Beach

Honolulu Condo for Rent Steps to Kahala Beach

Ask owner about available dates/rates. The perfect studio for a couple on their Hawaiian get-away who want to live like locals during their stay. Please inquire about your specific dates and we can try to accommodate your stay. This beautiful and spacious studio with 1 bathroom is kept immaculately with a shaded, private patio area with grass and lush landscaping for relaxing in a quiet neighborhood.
Registration Number: TA-094-014-7712-01, GE-151-279-8208-01, 1350300320000

1 bedroom
1 bathroom
Sleeps 2

from $284

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Magnificent views, spacious and breezy, affordable 3-bedroom home in Paradise

Magnificent views, spacious and breezy, affordable 3-bedroom home in Paradise

Enjoy magnificent unobstructed views of the ocean, Diamondhead and Waikiki from this historic vacation home while living in a spacious, updated house with loads of amenities. Plan your day, drinking a mellow cup of Kona coffee on the lanai, deciding whether to go to Hanauma Bay, the North Shore, Pearl Harbor or a beach on the Windward Side of the island.
Registration Number: GE-107-728-0768-01, TA-107-728-0768-01, 330310160000

3 bedroom
1 bathroom
Sleeps 6

from $305

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Charming Historical Home - Crutchfield Estate

Charming Historical Home - Crutchfield Estate

This spectacular French Tudor exudes a casual elegance and the comfort of the islands. Inside you will find gleaming wood floors, an elegant fireplace, crown molding and spacious bright rooms. The kitchen is fully equipped with a new refrigerator and dishwasher.
Registration Number: TA-112-501-9648-01, GE-112-501-9648-01

4 bedroom
2 bathroom
Sleeps 8

from $1,602

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$Close to Kahala Beach\/Air Conditioning\/Heated Pool\/Clean\/Quiet Neighborhood$

Close to Kahala Beach/Air Conditioning/Heated Pool/Clean/Quiet Neighborhood

Ask owner about available dates/rates. Elegantly remodeled in 2018, this one level, very clean, 4 bedroom & 3 bath home, has 2 master suites, a gourmet kitchen, air conditioning in every bedroom & high end finishes throughout this private oasis.
Registration Number: GE-094-014-7712-01, TA-094-014-7712-01, 1350300320000

4 bedroom
3 bathroom
Sleeps 8

from $2,241

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Comfort and Elegance with stunning views of Diamond Head

Comfort and Elegance with stunning views of Diamond Head

5 bath home on Maunalani Hts. Tastefully furnished with high quality bedroom, living room and dining room furniture. s in living room, kitchen and bedroom. Fully functional kitchen with new dishes, silverware, glassware, pots and pans. Large decks with views of the ocean, Diamond Head and Waikiki.
Registration Number: TA-187-879-4240-02, 330180700000, GE-186-879-4240-01

0 bedroom
0 bathroom
Sleeps 6

from $267

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Kahala Oceanside – Coastal Sanctuary with Panoramic Views

Kahala Oceanside – Coastal Sanctuary with Panoramic Views

Kahala Oceanside is a private paradise retreat that comfortably sleeps 14. This luxurious ocean front hideaway on the South Shore of Oahu, known for its spectacular sunsets, is just minutes away from fine eateries, world-famous hikes, and the endless attractions of downtown Honolulu and Waikiki.
Registration Number: 1350030350000, GE-053-250-7136-01, TA-053-250-7136-01

6 bedroom
6 bathroom
Sleeps 15

from $4,190

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Island Adventure: Minivan Rental, Contact Us

Island Adventure: Minivan Rental, Contact Us

UNPARALLELED VIEWS!
Endless hypnotizing panoramic views await you from this well maintained 3 bedroom, 3 bathroom cottage style house nestled in the highly coveted hills adjacent to Waikiki Beach.
Our home offers over 2,000 sq ft of entertaining space, all situated at a perfect location for your group to tour everywhere on the island of Oahu.
Registration Number: GE-123-456-7890-01, TA-123-456-7890-01, 1234567890000

3 bedroom
3 bathroom
Sleeps 8

from $383

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Fabulous, Renovated Large 3BR Condo on Kahala Beach

Fabulous, Renovated Large 3BR Condo on Kahala Beach

Welcome to our newly renovated slice of paradise at Kahala Beach! Nestled in one of the most sought-after neighborhoods in Honolulu, this spacious 3-bedroom, 2-bathroom property promises a luxurious escape for your Hawaiian getaway.

Step inside and be greeted by a contemporary interior adorned with modern furnishings and thoughtful touches throughout.
Registration Number: TA-052-736-1536-01, GE-052-736-1536-01, 1350230020025

3 bedroom
2 bathroom
Sleeps 6

from $381

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Gorgeous Estate on the Slopes of Diamond Head, 5 minute walk to great beach

Gorgeous Estate on the Slopes of Diamond Head, 5 minute walk to great beach

5M home on 15,000 sq ft lot in one of the most desired locations on Oahu's south shore. Nestled on the slopes of Diamond Head just outside of Waikiki, this exquisite estate is a 5-MINUTE WALK TO A SECLUDED WHITE SAND BEACH with excellent surfing.
Registration Number: 350020180000, GE-047-203-9424-01, TA-047-203-9424-01

4 bedroom
4 bathroom
Sleeps 9

from $718

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$Kahala Breeze: Modern Tropical Home w\/Pool, Private Yard, & A\/C. Kahala Breeze$

Kahala Breeze: Modern Tropical Home w/Pool, Private Yard, & A/C. Kahala Breeze

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.

An abundance of windows in the living area allows for maximum light and fresh air, while the neutrally-hued color palette provides an upscale yet casual vibe.
Registration Number: 350030310000, TA-065-534-9760-01, GE-065-534-9760-01

4 bedroom
4 bathroom
Sleeps 8

from $897

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$Ho'okipa Villa: Historic Home+Guest Cottage in Kahala near the Beach w\/Pool & AC$

Ho'okipa Villa: Historic Home+Guest Cottage in Kahala near the Beach w/Pool & AC

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.

Kahala Luxury Living

Welcome to Ho'okipa Villa!
Registration Number: TA-088-184-4224-01, 350100100000, GE-088-184-4224-01

5 bedroom
4 bathroom
Sleeps 14

from $955

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Cottage with Private Salt Water Pool

30 night minimum
This beautiful recently updated cottage is nestled in the quiet, safe, and upscale neighborhood of Kahala. Excellent location! Just minutes to Waikiki, nearby parks and the pretty white-sand beaches of the East Honolulu coast.
Registration Number: TA-108-852-8384-01, GE-108-852-8384-01, 13526023

1 bedroom
1 bathroom
Sleeps 5

from $218

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$Kahala Cottage by Gather: Cottage w\/ Private Pool, A\/C, Walk to Beach and Shops$

Kahala Cottage by Gather: Cottage w/ Private Pool, A/C, Walk to Beach and Shops

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.

Welcome to Kahala Cottage by Gather, your home-away-from-home in the heart of Oahu’s exclusive Kahala neighborhood.
Registration Number: TA-038-170-4192-01, GE-038-170-4192-01, 350150260000

2 bedroom
2 bathroom
Sleeps 6

from $386

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$Spacious Home In Kahala That's Centrally Located w\/AC, Pool, Lanai 5BR\/4Bath$

Spacious Home In Kahala That's Centrally Located w/AC, Pool, Lanai 5BR/4Bath

Upscale neighborhood of Kahala that is walking distance to Kahala Mall. It's about a One mile drive to the nearest beach, Kahala Hotel, Waialae Country club. 6-minute drive to the world famous Waikiki Beach, Diamond Head hiking, Rainbow's plate lunch, Leonard’s malasadas, Uncle Clay's shave ice.
Registration Number: 230360390448, TA-008-444-7232-01, GE-008-444-7232-01

5 bedroom
4 bathroom
Sleeps 10

from $556

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Kahala Beachfront Estate – Private Resort-Style Living

Kahala Beachfront Estate – Private Resort-Style Living

For discounted rates on Main house only, please inquire. 7 Night Minimum over any major holiday except Christmas. 10- 12 Night Minimum over the Christmas/New Years Holiday Season at $8,400 per night.

Spacious beachfront estate is situated on lush tropical grounds, nestled in between palm trees.
Registration Number: GE-005-323-3664-01, TA-005-323-3664-01, 90/TVU-0376, 350060160000

7 bedroom
7 bathroom
Sleeps 14

from $6,745

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$Hale Mahie by Gather: Spanish Colonial Historic Home w\/ Ocean Views & AC$

Hale Mahie by Gather: Spanish Colonial Historic Home w/ Ocean Views & AC

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.

A 10-minute walk from Waikiki, discover your own private paradise nestled at the base of Diamond Head in Honolulu’s renowned Gold Coast.
Registration Number: TA-044-602-3680-01, 310330200000, GE-044-602-3680-01

4 bedroom
3 bathroom
Sleeps 8

from $790

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BIG ALOHA & AWESOME VIEW AT THIS HAWAIIAN HOME!

BIG ALOHA & AWESOME VIEW AT THIS HAWAIIAN HOME!

~Breezy Spacious and Welcoming Vacation Home~
This Hawaiian home sits up on the mountain with unbelievable, panoramic views of the Pacific Ocean, Diamond Head, Waikiki, and downtown. Watch sunsets, fireworks, whales, and rainbows from the lanai.
Registration Number: GE-122-615-2448-01, TA-122-615-2448-01, 330310320000

3 bedroom
2 bathroom
Sleeps 7

from $258

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$A Quiet Honolulu LUX STUDIO near Diamond Head & Waikiki w\/ private yard space$

A Quiet Honolulu LUX STUDIO near Diamond Head & Waikiki w/ private yard space

Welcome to the Bird of Paradise, similar to a boutique hotel experience in the Diamond Head/Kahala neighborhood. This Honolulu vacation rental is a short drive from Waikiki, International Marketplace, Ala Moana Shopping Center, Waikiki ZOO, and many attractions nearby.
Registration Number: TA-188-577-3824-01, GE-188-577-3824-01, 350140350000

1 bedroom
1 bathroom
Sleeps 2

from $167

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$Kahala Valley 2Bed Cottage, Sleeps 6, Quiet backyard w\/ peekaboo views$

Kahala Valley 2Bed Cottage, Sleeps 6, Quiet backyard w/ peekaboo views

This 2 bedroom sleeps up to 6 in the valley above Diamond Head known as Kahala. Its the perfect balance of close to Waikiki and the highway but away from the hustle and bustle of things. Less than a $15 Uber/Lyft ride to Waikiki if you want to have a few Mai Tais with dinner or a night on the town.
Registration Number: TA-157-641-9328-01, GE-157-641-9328-01, 1350550410000

3 bedroom
1 bathroom
Sleeps 6

from $289

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Magnificent Waikiki Mountain Views! Free Parking, Wi-Fi, Pool & More!

Magnificent Waikiki Mountain Views! Free Parking, Wi-Fi, Pool & More!

Waikiki Sunset #2503 – 229 Paoakalani Ave.

Enjoy the lush greenery of the Ko'olau Mountains and exquisite Hawaiian trade winds from your private lanai! This cozy rental features central A/C, a full kitchen, and free Wi-Fi—perfect for couples and small families!

Registration Number: 260280110249, GE-159-961-1904-01, TA-159-961-1904-01

1 bedroom
1 bathroom
Sleeps 4

from $269

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Spacious Family Home With Gorgeous Sunset Views of Diamond Head

Spacious Family Home With Gorgeous Sunset Views of Diamond Head

This property located in a quit serene setting with lots of home privacy. Also this home can offer family members seperated space with upstairs & downstairs living room areas. Just have fun and enjoy the Aloha of this great properties Hawaiian charms.

Registration Number: TA-105-889-1776-01, GE-105-889-1776-01

4 bedroom
2 bathroom
Sleeps 7

from $517

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Right on the beach near Diamond Head and 4 miles from Waikiki!

Right on the beach near Diamond Head and 4 miles from Waikiki!

On the beach, in a coveted luxury resort location are the Kahala Beach condos, adjacent to the Kahala Hotel, the only 5-star Hawaiian destination. Secure, with 24/7 guards, keyed building access, and a private underground parking garage. Sited on an idyllic cove beach, surrounded by a grassy park-like setting with swaying palms, the surf is gentle, protected by a reef.
Registration Number: GE-165-278-3616-01, TA-165-278-3616-01, 1350230020146

1 bedroom
1 bathroom
Sleeps 4

from $219

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Breezy Ocean View Waikiki Condo with Free Parking!

Breezy Ocean View Waikiki Condo with Free Parking!

The pool and all associated amenities will be closed starting April 7, 2025, for an estimated duration of 10 to 14 months to accommodate the Recreation Deck renovation project.

Waikiki Banyan Ocean View Corner Condo comes with a fully equipped kitchen, which includes a refrigerator, stove-range, dishwasher, microwave, coffee maker, and all the kitchen supplies you need to have an at home cooking experience while on vacation.
Registration Number: 260250050092, TA-121-578-0864-01, GE-121-578-0864-01

1 bedroom
1 bathroom
Sleeps 4

from $309

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Kahala Beach #446 Vacation Rental

This highly desirable top-floor unit overlooks the lovely koi pond and provides the best views of the sky and stars. The lanai is oriented to the afternoon sun and sunset. Importantly, its top floor position makes it one of the most quiet apartments at Kahala Beach.
Registration Number: GE-003-036-7744-01, TA-003-036-7744-01, 1350230020145

2 bedroom
2 bathroom
Sleeps 4

from $326

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The Kahala Mansion – Opulent Oceanview Estate in Honolulu’s Elite Neighborhood

The Kahala Mansion – Opulent Oceanview Estate in Honolulu’s Elite Neighborhood

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.

Luxury, Privacy, and Grand-Scale Elegance at Honolulu’s Most Exclusive Estate
Discover The Kahala Mansion, a luxury estate on prestigious Kahala Avenue steps away from the beach.
Registration Number: GE-132-155-2896-01, TA-132-155-2896-01, 350040280000

5 bedroom
5 bathroom
Sleeps 12

from $7,107

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$Kahala Zen by Gather: Spacious 5BR Modern Oasis w\/ Studio & Lush Garden$

Kahala Zen by Gather: Spacious 5BR Modern Oasis w/ Studio & Lush Garden

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.

Welcome to Kahala Zen

Nestled in the prestigious Kahala neighborhood of Honolulu, Hawaii, Kahala Zen is a historic 5-bedroom, 4-bathroom retreat blending timeless charm with modern amenities.
Registration Number: 350040310000, GE-183-524-3008-01, TA-183-524-3008-01

5 bedroom
4 bathroom
Sleeps 10

from $852

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$Kahala Beachside Villa: Lux Condo w\/ Pool, Balcony Views & Beach Access$

Kahala Beachside Villa: Lux Condo w/ Pool, Balcony Views & Beach Access

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.

Escape to paradise at Kahala Beachfront Villa by Gather, a luxurious two-bedroom, two-bathroom condo perfect for up to six guests.
Registration Number: 1350230020117, GE-004-895-1296-02, TA-004-895-1296-01

2 bedroom
2 bathroom
Sleeps 6

from $362

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Kahala Beachside Estate – Premier Luxury Living on Oahu’s Gold Coast

Kahala Beachside Estate – Premier Luxury Living on Oahu’s Gold Coast

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.

Boasting an extraordinary beachfront location, this private Kahala vacation rental estate provides all the modern luxury features your large group requires, with the charm of old Hawaii.
Registration Number: TA-104-487-9872-01, 350060190000, GE-104-487-9872-01

7 bedroom
8 bathroom
Sleeps 14

from $6,147

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$Pili Pono by Gather: Elegant Honolulu Retreat w\/ Pool & Private Oasis$

Pili Pono by Gather: Elegant Honolulu Retreat w/ Pool & Private Oasis

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.
5-bathroom estate in Honolulu’s prestigious Black Point neighborhood.
Registration Number: 350020170000, TA-167-134-8224-02, GE-167-134-8224-01

5 bedroom
6 bathroom
Sleeps 12

from $2,043

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$Diamond Head Grandeur by Gather: Luxury Villa w\/ Ocean View & Private Pool$

Diamond Head Grandeur by Gather: Luxury Villa w/ Ocean View & Private Pool

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.
5-bathroom villa here at Diamond Head Grandeur in the centralized neighborhood of Kahala on Oahu.
Registration Number: 310400040001, TA-076-121-8560-01, GE-076-121-8560-01

5 bedroom
5 bathroom
Sleeps 10

from $2,258

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One of a Kind Luxury

FEATURED IN ARCHITECTURAL DIGEST MAGAZINE!

Are you ready to graduate from the Presidential Suite? Are you looking for the most relaxing vacation accommodation?

*Specials not available during Peak Season*

This OCEANFRONT CROWN JEWEL – A MODERN DIAMOND HEAD HOME – offers a penthouse atmosphere for entertaining or quiet days watching ocean waves.
Registration Number: GE-092-683-8784-01, TA-180-161-9456-01, 31040027

4 bedroom
4 bathroom
Sleeps 8

from $4,758

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Pet Friendly Guesthouse + Parking

LOCATION
This is location is absolutely amazing! It's very walkable and safe in the morning, and evening. Walk to Waikiki Beach/Waikiki International Marketplace, Diamond Head Hiking trail, Safeway grocery store, restaurants, Starbucks, Jamba Juice, Honolulu Zoo, Aquarium, close to Kapiolani Community College, and UH college campus, and more within minutes.

Registration Number: no, TA-124-162-4576-01, GE-124-162-4576-01, 31012073

1 bedroom
1 bathroom
Sleeps 2

from $125

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$Luxury Kahala Oasis by Gather: Spacious 6BR Retreat w\/ Pool, Spa & Near Beach$

Luxury Kahala Oasis by Gather: Spacious 6BR Retreat w/ Pool, Spa & Near Beach

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.

Welcome to Kahala Oasis by Gather, an expansive 6-bedroom, six-and-a-half-bathroom luxury retreat nestled along the prestigious Kahala Avenue in Honolulu, Hawaii.
Registration Number: 1350070050000, TA-153-997-3120-01, GE-153-997-3120-01

6 bedroom
6 bathroom
Sleeps 12

from $1,129

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Kahala Lani: Balinese-inspired Home immersed in nature, Private Pool

Kahala Lani: Balinese-inspired Home immersed in nature, Private Pool

This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.

Ideal for multi-generational families and golf enthusiasts, this exquisite five bedroom, four bath home blends both island-style and Balinese touches to create the ultimate vacation home.
Registration Number: TA-048-116-5312-01, GE-048-116-5312-01, 350080310000

5 bedroom
4 bathroom
Sleeps 14

from $1,938

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