
Holiday rentals near Waikiki Historic Trail
We found 5,850 holiday rentals — enter your dates for availability
If you are looking to stay near Waikiki Historic Trail, take a look at private holiday rentals to choose your home away from home. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll find the amenities that you need and want, which might include parking and a washer and dryer. No matter what you're looking for, you're sure to find a property to rent to meet everyone's needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - Waikiki Historic Trail
Showing deals for:21 Nov - 28 Nov
Image gallery for Luxury Beachfront Condo w/ AC

9.49.4 out of 10 rating
Exceptional
(40 reviews)
Luxury Beachfront Condo w/ AC
Punaluu, HI
7% off
Price is AU$5,632
AU$5,632
AU$805 nightly
Includes taxes & fees
Image gallery for 15th Floor Panoramic Ocean View Penthouse. BEST VIEW in Ko Olina!

1010 out of 10 rating
Exceptional
(84 reviews)
15th Floor Panoramic Ocean View Penthouse. BEST VIEW in Ko Olina!
Kapolei, HI
8% off
Price is AU$16,124
AU$16,124
AU$2,303 nightly
Includes taxes & fees
Image gallery for Largest Private Patio on the Ocean and Air-Conditioning

9.09.0 out of 10 rating
Wonderful
(58 reviews)
Largest Private Patio on the Ocean and Air-Conditioning
Punaluu, HI
7% off
Price is AU$3,580
AU$3,580
AU$511 nightly
Includes taxes & fees
Image gallery for Remodeled oasis in the heart of Waikiki! Min. from beach, shops, & restaurants!

9.69.6 out of 10 rating
Exceptional
(30 reviews)
Remodeled oasis in the heart of Waikiki! Min. from beach, shops, & restaurants!
Honolulu, HI
7% off
Price is AU$2,743
AU$2,743
AU$392 nightly
Includes taxes & fees
Image gallery for Marriott's Ko Olina. Amazing Two Bedroom villa in a Beachfront Resort.

1010 out of 10 rating
Exceptional
(9 reviews)
Marriott's Ko Olina. Amazing Two Bedroom villa in a Beachfront Resort.
Kapolei, HI
9% off
Price is AU$9,494
AU$9,494
AU$1,356 nightly
Includes taxes & fees
Image gallery for Beachfront Condo w/ Amazing View

8.88.8 out of 10 rating
Excellent
(20 reviews)
Beachfront Condo w/ Amazing View
Punaluu, HI
7% off
Price is AU$4,121
AU$4,121
AU$589 nightly
Includes taxes & fees
Image gallery for the Birdcage - Waikiki Hideaway, Steps to the Beach

9.49.4 out of 10 rating
Exceptional
(117 reviews)
the Birdcage - Waikiki Hideaway, Steps to the Beach
Honolulu, HI
7% off
Price is AU$2,266
AU$2,266
AU$324 nightly
Includes taxes & fees
Image gallery for Condo on beach with AC

9.29.2 out of 10 rating
Wonderful
(7 reviews)
Condo on beach with AC
Punaluu, HI
7% off
Price is AU$5,502
AU$5,502
AU$786 nightly
Includes taxes & fees
Image gallery for Luxury resort accommodations. Ocean view. You'll never wanna leave.

1010 out of 10 rating
Exceptional
(168 reviews)
Luxury resort accommodations. Ocean view. You'll never wanna leave.
Kapolei, HI
8% off
Price is AU$9,616
AU$9,616
AU$1,374 nightly
Includes taxes & fees
Image gallery for Oceanfront, Yacht Harbor, Luxury, Friday Fireworks front row seat, FAB!

9.49.4 out of 10 rating
Exceptional
(185 reviews)
Oceanfront, Yacht Harbor, Luxury, Friday Fireworks front row seat, FAB!
Honolulu, HI
7% off
Price is AU$3,283
AU$3,283
AU$469 nightly
Includes taxes & fees
Image gallery for @ Marbella Lane - Breezy Studio@Diamond Head Beach Hotel

9.49.4 out of 10 rating
Exceptional
(40 reviews)
@ Marbella Lane - Breezy Studio@Diamond Head Beach Hotel
Honolulu, HI
15% off
Price is AU$2,145
AU$2,145
AU$306 nightly
Includes taxes & fees
Image gallery for @ Marbella Lane - Executive Suite | Steps to Beach

9.29.2 out of 10 rating
Wonderful
(28 reviews)
@ Marbella Lane - Executive Suite | Steps to Beach
Honolulu, HI
15% off
Price is AU$2,725
AU$2,725
AU$389 nightly
Includes taxes & fees
Image gallery for The Best View in Waikiki, only steps away from the best beach in the world

9.89.8 out of 10 rating
Exceptional
(136 reviews)
The Best View in Waikiki, only steps away from the best beach in the world
Honolulu, HI
7% off
Price is AU$2,306
AU$2,306
AU$329 nightly
Includes taxes & fees
Image gallery for Next to Ocean, 120/nt. monthly rate May 1 - Oct 31, fully renovated condo

9.49.4 out of 10 rating
Exceptional
(136 reviews)
Next to Ocean, 120/nt. monthly rate May 1 - Oct 31, fully renovated condo
Honolulu, HI
8% off
Price is AU$2,731
AU$2,731
AU$390 nightly
Includes taxes & fees
Image gallery for Magnificent Ocean View Penthouse, FREE PARKING- Pool renovation until 2026

9.89.8 out of 10 rating
Exceptional
(230 reviews)
Magnificent Ocean View Penthouse, FREE PARKING- Pool renovation until 2026
Honolulu, HI
7% off
Price is AU$3,361
AU$3,361
AU$480 nightly
Includes taxes & fees
Image gallery for Oceanfront Waikiki/Ilikai Condo with stunning ocean views and free parking

9.69.6 out of 10 rating
Exceptional
(266 reviews)
Oceanfront Waikiki/Ilikai Condo with stunning ocean views and free parking
Honolulu, HI
7% off
Price is AU$4,165
AU$4,165
AU$595 nightly
Includes taxes & fees
Image gallery for 23rd Floor Studio with Free Parking

9.49.4 out of 10 rating
Exceptional
(13 reviews)
23rd Floor Studio with Free Parking
Honolulu, HI
7% off
Price is AU$2,193
AU$2,193
AU$313 nightly
Includes taxes & fees
Image gallery for Gorgeous High Floor Ocean View 1bdrm at Waikiki Banyan 3802-T2

9.29.2 out of 10 rating
Wonderful
(24 reviews)
Gorgeous High Floor Ocean View 1bdrm at Waikiki Banyan 3802-T2
Honolulu, HI
7% off
Price is AU$3,197
AU$3,197
AU$457 nightly
Includes taxes & fees
Image gallery for Fantastic Views, Prime Location, No resort fees, Wifi included

9.49.4 out of 10 rating
Exceptional
(85 reviews)
Fantastic Views, Prime Location, No resort fees, Wifi included
Honolulu, HI
7% off
Price is AU$2,532
AU$2,532
AU$362 nightly
Includes taxes & fees
Image gallery for Entire 2 Bedroom Condo, King Bed, FREE Parking, Sleeps 6, Walk to Waikiki Beach

8.68.6 out of 10 rating
Excellent
(40 reviews)
Entire 2 Bedroom Condo, King Bed, FREE Parking, Sleeps 6, Walk to Waikiki Beach
Honolulu, HI
7% off
Price is AU$4,348
AU$4,348
AU$621 nightly
Includes taxes & fees
Image gallery for 2 min walk to the beach Ocean &mountain view. Central AC, Parking is available .

9.69.6 out of 10 rating
Exceptional
(36 reviews)
2 min walk to the beach Ocean &mountain view. Central AC, Parking is available .
Honolulu, HI
7% off
Price is AU$3,001
AU$3,001
AU$429 nightly
Includes taxes & fees
Image gallery for Waikiki Condo - Ocean View - Minutes from the Beach!

9.49.4 out of 10 rating
Exceptional
(199 reviews)
Waikiki Condo - Ocean View - Minutes from the Beach!
Honolulu, HI
7% off
Price is AU$2,891
AU$2,891
AU$413 nightly
Includes taxes & fees
Image gallery for 1 BR Top floor stunning views from 2 Lanais. Jeep & Parking Available thru Turo

1010 out of 10 rating
Exceptional
(46 reviews)
1 BR Top floor stunning views from 2 Lanais. Jeep & Parking Available thru Turo
Honolulu, HI
7% off
Price is AU$2,904
AU$2,904
AU$415 nightly
Includes taxes & fees
Image gallery for Oceanview Central AC. 2min walk to Waikiki beach , on site parking is available

9.49.4 out of 10 rating
Exceptional
(38 reviews)
Oceanview Central AC. 2min walk to Waikiki beach , on site parking is available
Honolulu, HI
11% off
Price is AU$2,472
AU$2,472
AU$353 nightly
Includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Waikiki Historic Trail
Aston at the Waikiki Banyan
Sleeps 4 · 1 bedroom
7.27.2 out of 10
Goodgood
2,618 reviews(2,618 reviews)
Resort Style with Hula Show, Fireworks and even Tiki Torches!
Sleeps 4 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
99 reviews(99 reviews)
Breathtaking Ocean Views Beach Cottage
Sleeps 4 · 2 bedrooms · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
145 reviews(145 reviews)
🌺🌺 Last-minute Special!! 399 USD night Aug 20- Sept 2, 2025!BEACHFRONT RESORT 🏖️🏖️
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
147 reviews(147 reviews)
Top rated rentals - Waikiki Historic Trail
Paradise
1010 out of 10
Exceptionalexceptional
130 reviews(130 reviews)
Awesome location and holiday
Lucy S.
Stayed July 2024
Perfect
1010 out of 10
Exceptionalexceptional
138 reviews(138 reviews)
This was the perfect property and place for us to begin our Hawaiian stay. We moved away from Kailua six years ago and it was our first visit back. The view of Kailua beach and the ocean from the room's window is gorgeous. Waking to the sound of the waves crashing is wonderful. The unit was immaculate. The bed was very comfy, and the shower was also very good. Communication with the owner, Shari, is excellent. We highly recommend this beautiful little slice of heaven on earth. Aloha.
Jim and Sharon B.
Stayed Apr 2024
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value