Maui
1,244 homesWhere most of our Hawaii book sits. Kaanapali, Wailea, Kihei and Kapalua between them hold more homes than the other three islands put together, which makes Maui the island with the widest choice of both condos and private houses.
Hawaii vacation rentals,
island by island
Four islands, and they ask for very different trips. Luxury private estates with pools, staff and ocean views; beachfront homes and villas with private pools; beachfront condos with shared pools and views. All of them locally owned and professionally managed.
1,833Homes listed
20Destinations
4Islands
Where to stay
All 20 destinations →
Hawaii's most-booked destinations
The places our guests return to most, ranked by how many homes we currently represent there.
Kaanapali - Maui Vacation Rentals433 homes
Wailea - Maui Vacation Rentals253 homes
Koloa/Poipu - Kauai Vacation Rentals172 homes
Kohala Coast - Big Island Vacation Rentals169 homes
Kihei - Maui Vacation Rentals163 homes
Kapalua - Maui Vacation Rentals139 homes
Lahaina - Maui Vacation Rentals127 homes
Kahana - Maui Vacation Rentals111 homes
Every corner of Hawaii
Which island is right for your trip?
Hawaii is not one destination. Rainfall, beaches, driving distances and pace change sharply from island to island, and picking the right one matters more than picking the right house.
Kauai
244 homesThe oldest and greenest of the main islands. Poipu on the sunny south shore carries most of our Kauai homes; Princeville and Hanalei sit up on the north shore under the Na Pali cliffs, where it rains more and the pace drops further.
Hawaii - Big Island
239 homesLarger than every other Hawaiian island combined, with an active volcano at one end and a dry resort coastline at the other. Almost all of the homes we represent here are on the Kohala Coast or around Kailua-Kona.
Oahu
106 homesThe island most visitors fly into, and the one where a city break and a beach week are the same trip. Honolulu, Diamond Head and Kahala sit minutes from Waikiki; Kailua, Lanikai and the North Shore trade that for quieter water.
Handpicked in Hawaii
Search all homes →
Hawaii homes worth the flight
A rotating selection of top-tier Hawaii properties, each one professionally managed and photographed.
Platinum 
Koloa/Poipu - Kauai
Kauai South Shore Vacation Villa Overlooking Golf Course
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Plan the trip
Getting your Hawaii trip right
How the four islands split
Maui carries most of what we represent in Hawaii - Kaanapali, Wailea, Kihei and Kapalua alone hold more homes than Kauai, the Big Island and Oahu combined - so it gives you the widest choice of both houses and condos. The other three are smaller books and quieter islands.
Estate, villa or condo?
Our Hawaii homes run from luxury private estates with pools, staff and ocean views, through beachfront homes and villas with private pools, to beachfront condos with shared pools and views. A condo usually buys you the beachfront position for less; an estate buys you privacy, space and, in some cases, staff.
What the tier badges mean
Platinum, Gold, Silver and Value rank a property on its interior furnishings only, not on price or location. A Platinum or Gold home can cost less than a Silver one with a better view, and we move a ranking up or down as a home is upgraded or left to age.
Why we book by phone
We do not encourage online bookings. Your agent should be someone who knows the island, and every home here is run by a local management company responsible for cleaning, maintenance, and guest support. A call is also the fastest way to find out what is genuinely open on your dates.
Guest stories
What travellers say about Hawaii
Unedited notes sent to the Emerald Kite team after their stay.
“Madeline, I was going to leave a Google review but couldn’t figure out quite how to do it, so I thought I would send this email instead to be used as a testimonial: We recently used Emerald Kite to rent a vacation home for a week on the island of Kauai....”
HKHanalei - KauaiOctober 2025“We stayed at a two bedroom condo at Royal Kahana. The property was beautiful we were not disappointed. Very clean, everything we needed for our stay. Partial Ocean View. Access to pool and exercise room. Parking. Walk to the beach, small shops, restaurants...”
KMKahana - MauiNovember 2024“We had an amazing stay at the property. The host was extremely responsive. The pictures looked just like what we experienced in real life! Having the private, beautiful pool was fantastic. We would absolutely stay here again. Thank you for everything! Jen...”
KMKahana - MauiJuly 2024
Good to know
Hawaii vacation rental questions
The things travellers ask us most before they book.
Which Hawaiian island should we choose?
It depends on what you want from the week. Maui is where most of the homes we represent are, concentrated in Kaanapali, Wailea, Kihei and Kapalua, so it offers the widest choice. Kauai is the greenest and quietest, with most of its homes on the sunny south shore at Poipu. The Big Island is the largest and driest on its Kohala Coast resort side. Oahu is the island where a city break and a beach week can be the same trip.
Are Emerald Kite Hawaii rentals professionally managed?
Yes. Every home on this page is privately owned but represented by an established local property-management company that handles cleaning, maintenance and guest support during your stay. Before a property joins our portfolio it is vetted on location, quality of the accommodation, access to amenities and the reputation and responsiveness of the management company, and it is removed if it stops meeting that standard.
Can I bring a dog to a Hawaii rental?
Some homes accept pets and some do not, and it varies by property rather than by island. Use the pet-friendly filter above to see the homes that currently allow them, then confirm the type and size limits with your agent at the start of the selection process rather than after booking.
What do Platinum, Gold and Silver mean on a listing?
They are our own rankings, and they describe the interior furnishings only - not the price, the view or the location. A newly fitted kitchen can earn a home a Platinum ranking even though a Silver-ranked property nearby is more expensive because it has a better position. We revise rankings over time, up when a home is upgraded and down when it has not been refreshed in a while.
How is my payment protected?
Payment schedules, cancellation terms, and protections vary by property manager. Your Villa Specialist will identify the contracting property manager and provide the applicable rental agreement and payment terms for review before you book.
What does a Hawaii vacation rental cost?
It depends on the island, the season and how close to the water you are. Where an owner has published a starting rate you will see it on the listing; where they have not, rates are quoted on request, because they change constantly with season and length of stay and we would rather price your exact dates than show you a number that has moved.
Not sure which island fits your group?
Tell us who is travelling and when, and a destination specialist will narrow four islands of homes down to the handful that actually suit you.