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Looking for the best Hawaii vacation rentals? Whether you’re dreaming of city lights and surf in Waikiki or a laid-back beach town on Maui’s south shore, the right place to stay makes all the difference.
With so many listings online, it can be hard to know which ones you can trust. That’s where Midway Vacations comes in. We’re a locally owned, fully licensed property management company with offices in Waikiki and Kihei, and every condo we manage is cleaned and cared for by our own in-house team.
Here’s a look at some of our favorite buildings for Hawaii vacation rentals on Oahu and Maui.
Why Book Hawaii Vacation Rentals With Midway?
- Local teams on both islands: Our offices at the Waikiki Banyan, the Ilikai Hotel, and in Kihei mean help is never far away.
- In-house housekeeping: Every condo is cleaned by our own team, not an outside contractor.
- Transparent pricing: See the full price breakdown, including fees and taxes, before you book.
- Book direct: Reserve on our website and get local support from the people who know the property best.
Best Waikiki Vacation Rentals on Oahu
Waikiki is Hawaii’s most famous beach neighborhood, with surf lessons, shopping, dining, and nightlife all within walking distance. These buildings put you right in the middle of it.
Waikiki Banyan
Located at 201 ‘Ōhua Avenue, the Waikiki Banyan is a two-tower high-rise just a short walk from Waikiki Beach and Kapiolani Park. It’s home to one of the largest selections of professionally managed vacation condos in the area, and our main Waikiki office is right in the building.
The building’s recreation deck is a favorite with families, and many units have lanais with ocean or Diamond Head views. It’s a great home base for exploring the south shore of Oahu.
Waikiki Sunset
At 229 Paoakalani Avenue, Waikiki Sunset offers one- and two-bedroom condos about a five-minute walk from Waikiki Beach. Many units have views toward Diamond Head or the ocean, and the location is perfect for walking to dinner, shopping, and the beach.
Ilikai Hotel
At the gateway to Waikiki, the Ilikai Hotel is one of Oahu’s most iconic high-rises, famously featured in the opening credits of the original Hawaii Five-0. It sits next to the Ala Wai Harbor and is a short walk to Ala Moana Center and the beach.
Scandia Towers
Just half a block from Waikiki Beach, Scandia Towers offers a quieter, boutique alternative to the big resort towers. Its two-bedroom condos are a great fit for families and small groups.
See every Waikiki building we manage on our Oahu vacation rentals page.
Best Kihei Vacation Rentals on Maui
Kihei, on Maui’s sunny south shore, is known for its long stretch of beaches, easygoing pace, and great snorkeling. It’s a perfect base for families and anyone looking to slow down.
Kihei Ali’i Kai
Kihei Ali’i Kai is a relaxed condo complex near the Kamaole beach parks and a short walk from Charley Young Beach. With a pool, hot tub, and BBQ area, it’s an easy place to unwind after a day in the sun.
Kamaole Sands
Kamaole Sands sits right across the street from Kamaole Beach Park III, with soft sand, clear water, and great sunsets. The landscaped grounds include a pool, a children’s wading pool, hot tubs, tennis courts, and BBQ areas, making it a favorite for families.
Kihei Akahi
Located at 2531 South Kihei Road, directly across from Kamaole Beach Park II, Kihei Akahi is a landscaped complex in the heart of South Kihei with two outdoor pools and gas BBQ areas.
Maui Banyan
Maui Banyan is a popular South Kihei condo complex close to the Kamaole beach parks, local restaurants, and shops.
See every Maui building we manage on our Maui vacation rentals page.
FAQs
What types of vacation rentals does Midway offer?
We manage condos in Waikiki on Oahu and in Kihei on Maui, from studios to multi-bedroom units, many with ocean or mountain views.
How do I make a reservation?
You can book directly on our website or call our team for help choosing the right condo.
Are your vacation rentals pet-friendly?
Most of our vacation rentals are not pet-friendly. Check each property listing for its pet policy, or read our guide to pet-friendly Waikiki vacation rentals.
Should I stay in Waikiki or Kihei?
Waikiki is best if you want city energy, dining, and nightlife near the beach. Kihei is best for a slower pace and easy beach days. Our Waikiki vs Kihei guide can help you decide.
Book Your Hawaii Vacation Rentals Today
A trip to Hawaii is something special, and you deserve a place to stay that makes it even better. Whether you choose Waikiki or Kihei, our local team is here to help you find the right condo and make your stay easy from check-in to checkout.
Aloha, and we can’t wait to welcome you!
