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

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  6.  Diamond Head

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1056 Best Family 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
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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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1-Br Oceanview Diamond-Head Condo...\nSteps to Beaches.  Oahu, near Waikiki.
1-Br Oceanview Diamond-Head Condo...\nSteps to Beaches. Oahu, near Waikiki.
Condo
Honolulu, HI, 96815, United States
1.2k from Diamond Head center

AC, Balcony, Crib, Elevator, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

1 Bedroom4 Guests
10.0

Exceptional

1 reviews

$519
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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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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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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Quiet Beachfront Home at the Base Of Diamond Head
Quiet Beachfront Home at the Base Of Diamond Head
House
Honolulu, HI, 96815, United States
1.4k from Diamond Head center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
10.0

Exceptional

29 reviews

$1740
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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Paradise Rental w/ Pool & Spa - 30 day min
Paradise Rental w/ Pool & Spa - 30 day min
House
Honolulu, HI, 96816, United States
1.4k from Diamond Head center

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

5 Bedrooms10 Guests
10.0

Exceptional

20 reviews

$848
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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Oceanfront on the Gold Coast, Diamond Head, Hawaii.\nWhere Ocean Dreams Come True
Oceanfront on the Gold Coast, Diamond Head, Hawaii.\nWhere Ocean Dreams Come True
Villa
Honolulu, HI, 96815, United States
1.5k from Diamond Head center

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

3 Bedrooms6 Guests
New to Booking
$1303
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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True Top Floor Penthouse Residence with 360 Degree Views & A/C
True Top Floor Penthouse Residence with 360 Degree Views & A/C
Apartment
Honolulu, HI, 96815, United States
1.6k from Diamond Head center

AC, Balcony, Barbecue, Elevator, Free Parking, Internet, Kitchen, Living Area, Microwave

3 Bedrooms6 Guests
9.4

Superb

25 reviews

$1127
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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Gold Coast Ocean View One Bedroom w/ Full Kitchen & WiFi
Gold Coast Ocean View One Bedroom w/ Full Kitchen & WiFi
Condo
Honolulu, HI, 96815, United States
1.6k from Diamond Head center

AC, Barbecue, Elevator, Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking

1 Bedroom2 Guests
8.8

Fabulous

31 reviews

$266
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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⛰Diamond Head Beach Hotel 1005 GOLD COAST 2Full Beds Amazing Ocean Views w/Lanai
⛰Diamond Head Beach Hotel 1005 GOLD COAST 2Full Beds Amazing Ocean Views w/Lanai
Condo
Honolulu, HI, 96815, United States
1.6k from Diamond Head center

AC, Balcony, Dryer, Elevator, Free Parking, Internet, Kitchen, Laundry, Microwave

1 Bedroom4 Guests
8.6

Fabulous

27 reviews

$206
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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〽High Floor〰Ocean-View〰Queen-Bed〰Studio w/Kitchenette, Very Quiet Building
〽High Floor〰Ocean-View〰Queen-Bed〰Studio w/Kitchenette, Very Quiet Building
Apartment
Honolulu, HI, 96815, United States
1.6k from Diamond Head center

AC, Dryer, Elevator, Extra Bed, Free Parking, Internet, Kitchen, Laundry, Microwave

1 Bedroom3 Guests
8.8

Fabulous

24 reviews

$254
Average price / night
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Spacious 2 Bedroom Oceanfront Condo with Full Kitchen & 'Wrap around' Lanai
Spacious 2 Bedroom Oceanfront Condo with Full Kitchen & 'Wrap around' Lanai
Apartment
Honolulu, HI, 96815, United States
1.6k from Diamond Head center

AC, Balcony, Barbecue, Dryer, Elevator, Free Parking, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
8.8

Fabulous

16 reviews

$571
Average price / night
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Pet Friendly Guesthouse With Private Yard + Free Prkg
Pet Friendly Guesthouse With Private Yard + Free Prkg
Apartment
Honolulu, HI, 96816, United States
1.6k from Diamond Head center

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

1 Bedroom2 Guests
10.0

Exceptional

1 reviews

$179
Average price / night
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A Family Favorite on Hawaii's Gold Coast 11th Floor Oceanfront Condo
A Family Favorite on Hawaii's Gold Coast 11th Floor Oceanfront Condo
House
Honolulu, HI, 96815, United States
1.6k from Diamond Head center

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

2 Bedrooms6 Guests
9.6

Exceptional

50 reviews

$652
Average price / night
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Stunning! Diamond Head Oceanfront Lanai Condo - Sleeps 5
Stunning! Diamond Head Oceanfront Lanai Condo - Sleeps 5
Apartment
Honolulu, HI, 96815, United States
1.6k from Diamond Head center

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

1 Bedroom5 Guests
9.0

Fabulous

12 reviews

$581
Average price / night
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Top Remodel of a gorgeous Diamond Head Oceanfront Lanai Condo - Sleeps 4
Top Remodel of a gorgeous Diamond Head Oceanfront Lanai Condo - Sleeps 4
Condo
Honolulu, HI, 96815, United States
1.6k from Diamond Head center

AC, Balcony, Dryer, Elevator, Extra Bed, Free Parking, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

22 reviews

$577
Average price / night
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A Gem of a Studio at The Diamond Head Beach Hotel
A Gem of a Studio at The Diamond Head Beach Hotel
Apartment
Honolulu, HI, 96815, United States
1.6k from Diamond Head center

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

1 Bedroom4 Guests
9.4

Superb

21 reviews

$241
Average price / night
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Remodeled in 2022, Diamond Head 2 Bedroom Oceanfront condo
Remodeled in 2022, Diamond Head 2 Bedroom Oceanfront condo
Apartment
Honolulu, HI, 96815, United States
1.6k from Diamond Head center

AC, Balcony, Elevator, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms4 Guests
9.2

Superb

15 reviews

$567
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 Family Vacation Rentals in Diamond Head.

Where to stay in Diamond Head? Best neighborhoods & areas

Diamond Head Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 1056 verified family-friendly vacation rentals in Diamond Head. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Diamond Head vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $89 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Diamond Head offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Diamond Head are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Diamond Head often include amenities such as Child Friendly, View, and Guest Services. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.