Vacation Rentals in Diamond Head, HI: Compare 10+ Sites & Save

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  5.  Honolulu
  6.  Diamond Head

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2013 Best Vacation Rentals in Diamond Head (Starting from $89)

Monsarrat Apt. C
Monsarrat Apt. C
Apartment
Honolulu, HI, USA
1.0k from Diamond Head center

Apartments, Accommodations, Lodgings, Places to stay

2 Bedrooms4 Guests
New to Booking
$89
Average price / night
Check Availability
Barefoot Luxury Steps to Beach Diamond Head Kahala Waikiki. SPRING BREAK!
Barefoot Luxury Steps to Beach Diamond Head Kahala Waikiki. SPRING BREAK!
House
Honolulu, HI, 96816, United States
0.7k from Diamond Head center

AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Hot Tub, Internet

4 Bedrooms12 Guests
9.0

Fabulous

12 reviews

$1390
Average price / night
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Honolulu Vacation Rental Walk to Beaches
Honolulu Vacation Rental Walk to Beaches
Apartment
Honolulu, HI, USA
1.2k from Diamond Head center

Apartments, Accommodations, Pools, Parking, Lodgings, Vacation rentals, Places to stay, Beach rentals

1 Bedroom4 Guests
New to Booking
$142
Average price / night
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Private 3BR Home Near Diamond Head
Private 3BR Home Near Diamond Head
House
Honolulu, HI, 96816, United States
0.8k from Diamond Head center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Kitchen, Microwave, No Smoking, Outdoor Space

3 Bedrooms6 Guests
New to Booking
$1451
Average price / night
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Garden Cottage Unit B
Garden Cottage Unit B
House
Honolulu, HI, USA
1.3k from Diamond Head center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Beach rentals

2 Bedrooms4 Guests
New to Booking
$124
Average price / night
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Five-Bedroom Estate Near Diamond Head
Five-Bedroom Estate Near Diamond Head
House
Honolulu, HI, 96816, United States
0.8k from Diamond Head center

AC, Balcony, Barbecue, Dryer, Free Parking, Hot Tub, Kitchen, Microwave, No Smoking

5 Bedrooms10 Guests
New to Booking
$1765
Average price / night
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Garden Cottage Unit A
Garden Cottage Unit A
House
Honolulu, HI, USA
1.3k from Diamond Head center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Beach rentals

2 Bedrooms4 Guests
New to Booking
$122
Average price / night
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Diamond Head/Waikiki Surf Shack 2-Bedroom Private Ohana Unit
Diamond Head/Waikiki Surf Shack 2-Bedroom Private Ohana Unit
Apartment
Honolulu, HI, 96815, United States
0.9k from Diamond Head center

AC, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

2 Bedrooms4 Guests
New to Booking
$173
Average price / night
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Garden Cottage A & B
Garden Cottage A & B
House
Honolulu, HI, USA
1.3k from Diamond Head center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Beach rentals

4 Bedrooms8 Guests
New to Booking
$245
Average price / night
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Diamond Head Luxury Beachfront Estate
Diamond Head Luxury Beachfront Estate
Villa
Honolulu, HI, 96816, United States
1.0k from Diamond Head center

AC, Arcade, Balcony, Barbecue, Dryer, Free Parking, Hot Tub, Kitchen, Microwave

5 Bedrooms10 Guests
New to Booking
$6056
Average price / night
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Kove Villa
Kove Villa
House
Honolulu, HI, USA
1.5k from Diamond Head center

Hot Tub, Balcony/Terrace, Child Friendly, Air Conditioner, Parking

4 Bedrooms10 Guests
New to Booking
$909
Average price / night
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Diamond Head Luxe Private Estate with Pool | Sleeps 11
Diamond Head Luxe Private Estate with Pool | Sleeps 11
House
Honolulu, HI, 96816, United States
1.0k from Diamond Head center

AC, Balcony, Barbecue, Dryer, Free Parking, Kitchen, Microwave, No Smoking, Outdoor Space

6 Bedrooms11 Guests
New to Booking
$919
Average price / night
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Sanctuary by the Sea/Studio Apt.
Sanctuary by the Sea/Studio Apt.
Apartment
Honolulu, HI, USA
1.6k from Diamond Head center

Apartments, Cheap, Accommodations, Lodgings, Beach, Places to stay, Self-catering

1 Bedroom4 Guests
8.4

Very Good

5 reviews

$267
Average price / night
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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
Villa
Honolulu, HI, 96816, United States
1.0k from Diamond Head center

AC, Balcony, Barbecue, Dryer, Free Parking, Hot Tub, Kitchen, Laundry, Microwave

5 Bedrooms10 Guests
New to Booking
$2359
Average price / night
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Diamond Head Beach, Queen Studio, Balc, Ocean View
Diamond Head Beach, Queen Studio, Balc, Ocean View
Apartment
Honolulu, HI, USA
1.6k from Diamond Head center

Apartments, Accommodations, Parking, Lodgings, Places to stay, Family

1 Bedroom2 Guests
10.0

Exceptional

1 reviews

$186
Average price / night
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Near Beach, Great Views, Pool, Splitpac AC, Parking, Fast Wifi.. Garden setting.
Near Beach, Great Views, Pool, Splitpac AC, Parking, Fast Wifi.. Garden setting.
Apartment
Honolulu, HI, 96815, United States
1.1k from Diamond Head center

AC, Barbecue, Dryer, Elevator, Free Parking, Internet, Kitchen, Laundry, Living Area

1 Bedroom2 Guests
10.0

Exceptional

33 reviews

$140
Average price / night
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@ Marbella Lane - Breezy Studio@Diamond Head Beach Hotel
@ Marbella Lane - Breezy Studio@Diamond Head Beach Hotel
Apartment
Honolulu, HI, USA
1.6k from Diamond Head center

Apartments, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay, Self-catering, Beach rentals

1 Bedroom4 Guests
7.0

Good

3 reviews

$120
Average price / night
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3 Month Min; NO instant bookings: 3-bdrm Floor thru; Chill; Magical Apt/Location
3 Month Min; NO instant bookings: 3-bdrm Floor thru; Chill; Magical Apt/Location
Apartment
Honolulu, HI, 96815, United States
1.2k from Diamond Head center

AC, Dryer, Free Parking, Internet, Laundry, Microwave, No Smoking, TV, Washer

3 Bedrooms6 Guests
New to Booking
$1391
Average price / night
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Kalakaua Adventures
Kalakaua Adventures
House
Honolulu, HI, USA
1.6k from Diamond Head center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach, Places to stay, Beach rentals

3 Bedrooms8 Guests
New to Booking
$751
Average price / night
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Call Diamond Head Hidden Paradise booking req.
Call Diamond Head Hidden Paradise booking req.
House
Honolulu, HI, 96815, United States
1.2k from Diamond Head center

AC, Balcony, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
9.8

Exceptional

139 reviews

$593
Average price / night
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Diamond Head Beach Hotel
Diamond Head Beach Hotel
Apartment
Diamond Head, Honolulu, Hawaii, USA
1.6k from Diamond Head center

Apartments, Accommodations, Parking, Serviced apartments, Lodgings, Vacation rentals, Beach, Places to stay, Self-catering

10 Bedrooms26 Guests
7.4

Good

191 reviews

$140
Average price / night
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One of a Kind Luxury
One of a Kind Luxury
House
Honolulu, HI, 96816, United States
1.2k from Diamond Head center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

4 Bedrooms8 Guests
New to Booking
$5381
Average price / night
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@ Marbella Lane -Coastal retreat near Diamond Head
@ Marbella Lane -Coastal retreat near Diamond Head
Apartment
Honolulu, HI, USA
1.6k from Diamond Head center

Apartments, Cheap, Accommodations, Parking, Serviced apartments, Lodgings, Beach, Places to stay, Family

1 Bedroom4 Guests
10.0

Exceptional

2 reviews

$343
Average price / night
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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
House
Honolulu, HI, 96816, United States
1.3k from Diamond Head center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Free Parking, Hot Tub, Kitchen

5 Bedrooms12 Guests
10.0

Exceptional

2 reviews

$1051
Average price / night
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Newly-upgraded home with Diamond Head views - walk to Waikiki Beach
Newly-upgraded home with Diamond Head views - walk to Waikiki Beach
Cottage
Honolulu, HI, 96815, United States
1.3k from Diamond Head center

AC, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

2 Bedrooms4 Guests
9.2

Superb

20 reviews

$214
Average price / night
Check Availability
Charming cottage close to everything - walk to beach, zoo, & park
Charming cottage close to everything - walk to beach, zoo, & park
Cottage
Honolulu, HI, 96815, United States
1.3k from Diamond Head center

AC, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space

2 Bedrooms4 Guests
9.0

Fabulous

12 reviews

$214
Average price / night
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Two Hawaiian cottages with Diamond Head views - walk to Waikiki
Two Hawaiian cottages with Diamond Head views - walk to Waikiki
Cottage
Honolulu, HI, 96815, United States
1.3k from Diamond Head center

AC, Dryer, Free Parking, Kitchen, Laundry, Living Area, Microwave, No Smoking, Outdoor Space

4 Bedrooms8 Guests
9.0

Fabulous

9 reviews

$427
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Diamond Head.

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Diamond Head Vacation Rentals on the Map

Frequently Asked Questions

You can explore 2013 verified vacation rentals in Diamond Head. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Diamond Head vary depending on the season, property size, and location. Rates typically start from around $89 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Diamond Head include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Diamond Head welcome pets. Currently, 2 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Diamond Head often include amenities such as View, Laundry, and Sports/Activities. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.