Diamond Head vacation rentals

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Top-rated vacation rentals in Diamond Head

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Apartment in Honolulu

4.81 out of 5 average rating, 310 reviews

RARE HAWAIIAN DIAMOND

This rare space with fabulous views of Waikiki and world famous Diamond Head (unobstructed by other buildings), is located in a safe & newly renovated building very, very, very close to the beach! Many friendly & helpful owners live here. Located in the BEST part of Waikiki Beach. Many returning guests that have become friends. With its perfectly placed lanai (balcony) the view hypnotizes you as you watch the sunset, the ocean & the smiles. A truly colorful experience! You will return! Aloha

Feb 28 – Mar 7

G$36,015 GYD per night

Guest favorite

Guest suite in Honolulu

4.8 out of 5 average rating, 198 reviews

DIAMOND ON DIAMOND HEAD

Located on the slope of Diamond Head, our apartment is at a walking distance of Waikiki beach, restaurants, nightlife, public transport. You’ll love my place because of the coziness, the location. I put a special attention on having the mattress spray monthly for bugs and also the apartment for insects. It is very important for me to offer a super clean, cozy, comfy and secure apartment. You will be able also to have our personal massage therapist for $80/H or $110/1.5 Hours to your apartment

Dec 15 – 22

G$30,255 GYD per night

Guest favorite

Condo in Honolulu

4.89 out of 5 average rating, 246 reviews

Newly Renovated Cozy Home

Experience the charm of our newly renovated studio, legally permitted for your peace of mind. Revel in the modern ambiance featuring wood-like floors, luxurious marble countertops, and a stylishly tiled bathroom. Immaculately maintained for your comfort, the studio boasts SUPER CLEAN interiors and offers FANTASTIC CANAL VIEWS. Conveniently located within walking distance to the famous beaches, shopping malls, delectable dining options, and all your essentials. Your dream getaway begins here!

Jan 13 – 20

G$25,019 GYD per night

Guest favorite

Condo in Honolulu

4.95 out of 5 average rating, 141 reviews

Full Remodeled/ Panoramic Ocean View/ Full Kitchen

Your dream Vacation to Waikiki, Hawaii is about to begin! Wake up to breathtaking sweeping corner view, including ocean, canal, city, sunrise and partial Diamond Head from our 26th floor, Beautifully full remodeled studio with everything BRAND NEW! Then, after a day of adventuring in the world-famous island O'ahu, come back to a comfortable NEW KING BED, brand new FULL KITCHEN with range oven to relax and unwind. This is your vacation to enjoy, and we can't wait to host you.

Oct 14 – 21

G$34,089 GYD per night

Guest favorite

Condo in Honolulu

4.94 out of 5 average rating, 192 reviews

STUNNING PENTHOUSE - 100FT TO BEACH - LEGAL!!

Location, Location, Location! Beautiful NEW Penthouse condo just steps (1/2 block) to Waikiki Beach. Newly Renovated Condo is on the top floor of the Waikiki Grand Hotel! Enjoy sunrise and sunset from the large sundeck just out your sliding doors. PARKING INCLUDED, but a car is not needed being you're literally steps from Waikiki Beach, shopping, & entertainment. Great for families, business, or solo! LEGAL VACATION RENTAL! ALL taxes/fees & parking included in FINAL PRICE.

Mar 26 – Apr 2

G$95,783 GYD per night

Guest favorite

Condo in Honolulu

4.87 out of 5 average rating, 164 reviews

Small studio in the heart of Waikiki next to beach

Small studio with full bathroom w/ tub and a small kitchen with stove&oven, microwave, toaster oven and all kitchen utensils. Large Lanai with ocean view. One short block away from the beach in the heart of Waikiki. The unit on the six floor .This studio is designed for one occupant or a couple on a full size bed. The unit has fully equip kitchen, bath tub, cable TV, free WiFi. Great beach and sunset view from the lanai. Parking available $35 per day, reservation in advance.

Feb 3 – 10

G$24,245 GYD per night

Guest favorite

Apartment in Honolulu

4.98 out of 5 average rating, 120 reviews

Eight Thousand Waves

This modern studio was personally renovated with the help of my closest friends and family, and our “ideal day in Honolulu” in mind. We prioritized quality, function and comfort. - Unbeatable location! Steps to Waikiki, Ala Moana Beach, and Ala Moana Mall - Newly renovated and designed - High speed internet + WIFI (for those living that remote life!) - Parking available ($28/night - this is cheap for Waikiki) - Laundry room right next to the unit (accessible via app)

Nov 4 – 11

G$34,946 GYD per night

Guest favorite

Condo in Honolulu

4.91 out of 5 average rating, 280 reviews

Ocean ∘ City ∘ Mountain views in the ❤️ of Waikiki

ALOHA! Welcome to our studio on the 26th floor of the Pacific Monarch, centrally located in the ♥ of Waikiki. You will only be a 3 minute walk from the world famous Waikiki beach and the main streets of downtown where you will find countless shopping plazas, cafes, restaurants, and food trucks that will satisfy every palate. Book with confidence! This is a LEGAL Oahu vacation rental operating in a Resort Zoned District and is not affected by the passage of Bill 89.

Mar 13 – 20

G$36,727 GYD per night

Superhost

Hotel room in Honolulu

4.81 out of 5 average rating, 858 reviews

Cute Private Studio in Waikiki

Fully renovated to modern-retro style, with breathtaking views of ocean, Diamondhead and mountains. Desirable location -in Waikiki - minutes walking distance to Convention Center, beach, shopping, dining, entertainment... Sleeps two in full size bed. With kitchenette, suitable for long- and short-stays. Condohotel with 24/7 security, pool, jacuzzi, BBQ, laundry, shops, bar, ATM.... Parking and fitness is available, but must be paid separately. TA-029-819-2896-01

Mar 17 – 24

G$31,202 GYD per night

Guest favorite

Condo in Honolulu

4.93 out of 5 average rating, 130 reviews

ENCHANTED BAMBOO FOREST

As the sun dances through the cool breeze and lush green trees, the bamboo motif surrounds you with Aloha! Just a minute walk to the beach! Look to your right of the beach, and you will experience the lively exciting activities, exotic foods, merry song, hula shows and shopping! Look to your left of the beach and you will find the Honolulu Zoo, Aquarium, tennis courts, parks and how about an adventurous Diamond Head hike!

Apr 13 – 20

G$36,015 GYD per night

Guest favorite

Apartment in Honolulu

4.87 out of 5 average rating, 332 reviews

Ocean View Studio in Waikiki

Ocean view studio with awesome balcony just minutes walk to the famous Waikiki Beach. Renovated bathroom with Toto Washlet system. Queen size hybrid bed with coffee maker, refrigerator and microwave. Brand new split AC. Interior of unit is small but there's a private balcony with awesome ocean views. It's hard to get a nice ocean view in Waikiki for this price! Location is in central Waikiki, only a minutes walk to the beach.

Feb 2 – 9

G$34,685 GYD per night

Superhost

Condo in Honolulu

4.81 out of 5 average rating, 145 reviews

LEGAL VACATION RENTAL!! CLEAN WAIKIKI GRAND STUDIO

Waikiki Grand Hotel only a half block from the beach & boogie boarding at the Wall. Perfect for one or two people. It's cozy and comfortable. Full sized fridge and two burner built in cooktop. NO SMOKING in the building or on the lanai. Pool for guests. Roof top deck with fabulous views. Paid parking available. Managed by Tiare Dutcher (RS-22030), Principal Broker of DW Realty (RB-22573.

Nov 22 – 29

G$29,457 GYD per night