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.

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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...

🛏 4 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 7
📍 Honolulu, Hawaii

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...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Honolulu, Hawaii

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...

🛏 3 Bedrooms
🛁 1 Bathroom
👤 Sleeps 6
📍 Honolulu, Hawaii

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. Morning...

🛏 4 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 8
📍 Honolulu, Hawaii

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. Please inquire about...

🛏 4 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Honolulu, Hawaii

Comfort and Elegance with stunning views of Diamond Head

Newly renovated 3 bedroom, 2.5 bath home on Maunalani Hts. Tastefully furnished with high quality bedroom, living room and dining room furniture. HD Smart T.V.s in living room, kitchen and bedroom. Fully functional kitchen with new dishes, silverware, glassware, pots...

🛏 0 Bedrooms
🛁 0 Bathrooms
👤 Sleeps 6
📍 Honolulu, Hawaii

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...

🛏 6 Bedrooms
🛁 6 Bathrooms
👤 Sleeps 15
📍 Honolulu, Hawaii

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...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Honolulu, Hawaii

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...

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Honolulu, Hawaii

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

Treat yourself to ultimate island luxury in this architecturally designed $5.5M 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...

🛏 4 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 9
📍 Honolulu, Hawaii

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.Experience the laidback luxury and authentic...

🛏 4 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 8
📍 Honolulu, Hawaii

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...

🛏 5 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 14
📍 Honolulu, Hawaii

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. Also, in very short...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 5
📍 Honolulu, Hawaii

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...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Honolulu, Hawaii

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...

🛏 5 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 10
📍 Honolulu, Hawaii

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,...

🛏 7 Bedrooms
🛁 7 Bathrooms
👤 Sleeps 14
📍 Honolulu, Hawaii

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...

🛏 4 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 8
📍 Honolulu, Hawaii

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. Situated only 2 miles...

🛏 3 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 7
📍 Honolulu, Hawaii

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....

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Honolulu, Hawaii

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...

🛏 3 Bedrooms
🛁 1 Bathroom
👤 Sleeps 6
📍 Honolulu, Hawaii

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!The...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Honolulu, Hawaii

Spacious Family Home With Gorgeous Sunset Views of Diamond Head

This is a truly a local style experience property and the area of Kahala is full of the best of the best of locations on the Island of Oahu with everything close by: City Life , Awesome Beaches , Great Dinning , Tropical Hiking Trails & Views Galore , Look at the Famous...

🛏 4 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 7
📍 Honolulu, Hawaii

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,...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Honolulu, Hawaii

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...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Honolulu, Hawaii

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....

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Honolulu, Hawaii

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...

🛏 5 Bedrooms
🛁 5 Bathrooms
👤 Sleeps 12
📍 Honolulu, Hawaii

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 ZenNestled in the...

🛏 5 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 10
📍 Honolulu, Hawaii

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...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Honolulu, Hawaii

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,...

🛏 7 Bedrooms
🛁 8 Bathrooms
👤 Sleeps 14
📍 Honolulu, Hawaii

Pili Pono: Elegant Honolulu Retreat with 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.Welcome to Pili Pono by GatherExperience the...

🛏 5 Bedrooms
🛁 6 Bathrooms
👤 Sleeps 12
📍 Honolulu, Hawaii

Diamond Head Grandeur: Kahala Luxury Villa with Ocean View

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.Find peace and tranquility in your very own...

🛏 5 Bedrooms
🛁 5 Bathrooms
👤 Sleeps 10
📍 Honolulu, Hawaii

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 –...

🛏 4 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 8
📍 Honolulu, Hawaii

Pet Friendly Guesthouse + Parking

LOCATIONThis 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,...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Honolulu, Hawaii

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...

🛏 6 Bedrooms
🛁 6 Bathrooms
👤 Sleeps 12
📍 Honolulu, Hawaii

Kahala Lani: Balinese-Inspired Home with 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...

🛏 5 Bedrooms
🛁 4 Bathrooms
👤 Sleeps 14
📍 Honolulu, Hawaii

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