Oahu Holiday Rentals

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Holiday Rentals in Oahu

Pool
Updated and Contemporary. Close to Kailua Beach w/heated pool and spa!
10.0 out of 10, Exceptional, (3)
"My husband and I enjoyed six wonderful weeks in this house. From the moment we drove down that palm tree-lined road and stepped into the walled off courtyard, we knew we had picked the right place for our get-away. The house was tastefully and comfortably appointed. The kitchen, laundry room and bathrooms were all fully outfitted. We slept so well in the luxurious bedrooms, lulled by trade winds at night and waking to birds chirping in the morning. The outdoor lanai and backyard furniture made...
Updated and Contemporary. Close to Kailua Beach w/heated pool and spa!
Beach
Oceanside Estate - Spacious home with Pool & AC
10.0 out of 10, Exceptional, (1)
"We all enjoyed the property. It was a ways away from most activities but was quiet and we fit perfectly. The family all travel extensively and use B and B's and other means.. We did enjoy our stay and would recommend it."
Oceanside Estate - Spacious home with Pool & AC
Property grounds
East Oahu Manor - Incredible Ocean Views from most rooms! AC
10.0 out of 10, Exceptional, (5)
"Wonderful property, very clean, spacious with great views. Location was perfect - close enough for a quick drive to Waikiki yet far enough away to enjoy peace and quiet. Hosts - Taylor was amazing - responsive and always available. Would highly recommend this property."
East Oahu Manor - Incredible Ocean Views from most rooms! AC
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Beach
Modern Turtle Bay Ilima West Kuilima Estates #18 near Golf Course
10.0 out of 10, Exceptional, (4)
"This property is top notch. Nicely furnished, clean and a fabulous location. I highly recommend it for a carefree and comfortable stay. The ladies who manage the property are professional and easily contacted. The communication before our stay was the best I’ve ever experienced."
Modern Turtle Bay Ilima West Kuilima Estates #18 near Golf Course
Outdoor pool
Espacio The Jewel Of Waikiki
5.0 star property
9.8 out of 10, Exceptional, (14)
"Beautiful property and condo like accommodations with the floor all to ourselves. Highest level concierge services I have experienced with transportation services to and from airport included in stay. Will definitely be back! "
The price is NZ$3,853
includes taxes & fees
4 Jun - 5 Jun
Espacio The Jewel Of Waikiki
View from property
Aloha Suite Near the Sea I, 3 min Walk to Beach! Great Location!
9.8 out of 10, Exceptional, (137)
"Nice clean room, water off one day but not host problem. Nice safe entry with security present. Secure elevator and room. Room very clean and everything we needed to make our stay wonderful."
The price is NZ$473
includes taxes & fees
21 May - 22 May
Aloha Suite Near the Sea I, 3 min Walk to Beach! Great Location!
Comfort Suite, 2 Bedrooms | Terrace/patio
Hawaiian Princess at Makaha Beach
3.5 star property
9.6 out of 10, Exceptional, (4)
"Great hidden gem… nice people who made us feel like “locals”! Would recommend highly."
Hawaiian Princess at Makaha Beach
Property grounds
COZY STUDIO WITH WAIKIKI, OCEAN AND DIAMOND HEAD VIEW. FREE WI-FI.
9.6 out of 10, Exceptional, (108)
"Mike’s place was perfect! Clean, comfortable, and well appointed. He had starters for coffee, hair dryer, a beach chair and cooler and even an umbrella. Location is great - quick walk to beach, restaurants, shopping. Pool and surrounding deck was clean and very nice. Great host- I hope to stay again during my next visit to Honolulu. Mahalo Mike."
COZY STUDIO WITH WAIKIKI, OCEAN AND DIAMOND HEAD VIEW. FREE WI-FI.
Beach/ocean view
Cozy Beach front condo in Makaha
9.6 out of 10, Exceptional, (135)
"We stayed at this property in a different unit 5 years ago. We love the water facing patio/deck and simi private beach. Very quiet. They provide everything you could need for beach and water fun. We did bring our own binoculars and were glad we did. Would have liked shampoo, conditioner, body wash in the shower."
Cozy Beach front condo in Makaha
View from property
Aston Waikiki Beach Tower
4.0 star property
9.2 out of 10, Wonderful, (1636)
"The front desk is so great!!!!"
The price is NZ$1,184
includes taxes & fees
21 May - 22 May
Aston Waikiki Beach Tower
On the beach, sun-loungers, beach umbrellas, beach towels
Ocean Villas at Turtle Bay
4.5 star property
9.2 out of 10, Wonderful, (80)
"We had a fantastic time- thank you!!"
The price is NZ$1,564
includes taxes & fees
31 May - 1 Jun
Ocean Villas at Turtle Bay
Studio | Pool
Kuhio Village 904a Condo by RedAwning
3.0 star property
9.0 out of 10, Wonderful, (2)
Kuhio Village 904a Condo by RedAwning
Beach nearby
Royal Kuhio
3.5 star property
8.6 out of 10, Excellent, (330)
"I liked pretty much the whole experience of staying at this property."
The price is NZ$443
includes taxes & fees
19 May - 20 May
Royal Kuhio
Exterior
Hilton Grand Vacations Club at Hilton Hawaiian Village
4.0 star property
8.6 out of 10, Excellent, (691)
"We had an amazing time. We will book again in the future"
The price is NZ$730
includes taxes & fees
16 Jun - 17 Jun
Hilton Grand Vacations Club at Hilton Hawaiian Village
Pool
Clean studio in the heart of Waikiki!!
8.6 out of 10, Excellent, (22)
"Great spot for the price, perfect walking distance to pretty much everything. A ton of food trucks right across the street and just around the corner from some really cheap (for hawaii) bars. Will definitely be staying here again."
Clean studio in the heart of Waikiki!!
Exterior
King Bed Suite at The Waikiki Grand - Just steps away from Waikiki Beach
8.6 out of 10, Excellent, (18)
"This room was nice, and located near the beach, zoo, park, and aquarium. I had a blast and was away from the room most of the time. I slept great and the sun deck is great during sunrise. Thank You!"
King Bed Suite at The Waikiki Grand - Just steps away from Waikiki Beach
Exterior
Castle Waikīkī Shores
3.0 star property
8.2 out of 10, Very good, (1104)
"I loved the location, the property was very nice. However, the person who checked us in gave us all the information but, seemed very bored."
Castle Waikīkī Shores
Beach nearby, white sand, sun-loungers, beach umbrellas
Tropical Studios at Marine Surf Waikiki
3.0 star property
8.2 out of 10, Very good, (291)
"Good location "
The price is NZ$428
includes taxes & fees
18 May - 19 May
Tropical Studios at Marine Surf Waikiki
Pool
Two Studios at the Turtle Bay Resort! ❤️ Price listed is for BOTH Studios ❤️
8.2 out of 10, Very good, (146)
"Our group was divided in two different condos so we never needed to cook in the unit as we were together more in the larger one for gathering. We only used it for sleeping and showers. The absolute best perk of the unit is the hook-up to surf lessons on the North Shore from the owners. Best day of the trip for the teenagers in the group. Thank you so much for that amazing activity. Five star service! My only suggestion is to be more clear that it really isn't two units (there are two sleeping...
The price is NZ$530
includes taxes & fees
19 May - 20 May
Two Studios at the Turtle Bay Resort! ❤️ Price listed is for BOTH Studios ❤️
Corner Unit Studio@Waikiki Hotel Building 1 day min
8.2 out of 10, Very good, (63)
"Perfect location! The wind is a little loud in early February but otherwise was perfectly well appointed and comfortable for my husband and I asked our co-sleeping toddler!"
The price is NZ$378
includes taxes & fees
10 Jun - 11 Jun
Corner Unit Studio@Waikiki Hotel Building 1 day min
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Oahu you may be interested in

On the beach, beach towels
Hyatt Regency Waikiki Beach Resort & Spa
4.0 star property
8.6 out of 10, Excellent, (3261)
"Very good experience "
The price is NZ$578
includes taxes & fees
16 Jun - 17 Jun
Hyatt Regency Waikiki Beach Resort & Spa
View from room
Hilton Hawaiian Village Waikiki Beach Resort
4.0 star property
8.2 out of 10, Very good, (6480)
"Very convention dining and shopping options without leaving the property. "
The price is NZ$603
includes taxes & fees
19 May - 20 May
Hilton Hawaiian Village Waikiki Beach Resort
Fireplace
'Alohilani Resort Waikiki Beach
5.0 star property
8.2 out of 10, Very good, (2099)
"The front entrance and the coffee shop inside on the first floor."
The price is NZ$772
includes taxes & fees
19 May - 20 May
'Alohilani Resort Waikiki Beach
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Oahu holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Oahu. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Oahu. Seeing all the best attractions is bound to make you fall in love with Oahu. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Oahu short-term rentals, that won’t be hard to do.

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