Eating in Wailea - Maui
Wailea dining has to be considered among the best in all Hawaii. Fine
Hawaii · Maui
Wailea - Maui
Wailea - Maui
vacation rentals
Explore privately owned Wailea - Maui vacation rentals, professionally managed with a destination specialist available to help you compare the options.
253 homes listed
73 beachfront
Up to 4 bedrooms
Sleeps up to 10
253Homes listed
73Beachfront
22Houses & villas
228Condos
About Wailea - Maui vacation rentals
Choosing a vacation rental in Wailea - Maui
Emerald Kite currently represents 253 professionally managed Wailea - Maui vacation rentals. The collection includes houses, villas and condos, including layouts with up to 4 bedrooms, homes sleeping up to 10 guests and 73 beachfront options. Each property is privately owned and represented by an established property-management company responsible for guest support during the stay.
Beachfront
Villas & houses
Condos
Pet-friendly
253homes listed here
Your destination specialist
Call our local agents
An Emerald Kite specialist for Wailea - Maui, 7 days a week, 9 a.m. to 10 p.m. EST.
Find the right fit
Explore Wailea - Maui vacation rentals by size & style
Start with the space your group needs, then use the available property and experience links to narrow the collection. Each direct link opens matching Wailea - Maui vacation rentals, with the closest bedroom and guest-capacity matches shown first.
Wailea - Maui rentals by bedroom count
Property types and featured collections
Handpicked in Wailea - Maui
Search all 253 homes →
Featured Wailea - Maui vacation rentals
Compare a rotating selection of professionally managed houses, villas and condos in Wailea - Maui. Each card shows bedrooms, bathrooms, sleeping capacity and a starting rate where one has been supplied.
Around Wailea - Maui
Ways to spend the week
Shopping in Wailea - Maui
We invite you to spend a glorious day visiting “The Shops at Wailea”, an
Good to know
Planning your trip to Wailea - Maui
House or condo?
Of the homes represented here, 22 are houses and 228 are condos. A private house may offer more outdoor space and separation between generations; a condo may offer a convenient position or shared amenities.
Why book with us
Booking Wailea - Maui with Emerald Kite
Every home on this page is privately owned and represented by an established property-management company, with a destination specialist available to help you compare the options.
- Privately owned homes, each represented by an established management company
- Vetted on location, quality, amenities and the manager’s responsiveness — and removed if that slips
- A destination specialist helps compare the homes that fit your trip
- Payment, cancellation and check-in terms supplied before you book
- Villa Specialists available by phone
- A complimentary concierge service for dining, activities and directions
Guest stories
What guests wrote after staying in Wailea - Maui
Unedited notes sent to the Emerald Kite team after their stay.
“Thank you so much for your help! We are still here at the Kealani – what a lifesaver!!!! -Rhiannon”
Wailea - MauiSeptember 2014
Good to know
Wailea - Maui vacation rental FAQs
Answers to common questions about choosing and booking a professionally managed stay in Wailea - Maui.
Are these Wailea - Maui homes professionally managed?
Yes. Every home is privately owned but represented by an established property-management company responsible for cleaning, maintenance and guest support during your stay. Before a property joins the portfolio it is assessed on location, the 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 we bring a dog?
It varies by property rather than by destination. Ask your agent to identify homes that currently accept pets, then confirm the type, number and size limits before booking. Property rules, including smoking policies, are supplied for the individual home.
How is my payment protected?
Payment schedules, cancellation terms and any protections vary by property manager and destination. Your agent will identify the contracting property manager and provide the applicable rental agreement and payment terms for review before you book.
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 Platinum or Gold home can cost less than a Silver one in a better position. Rankings move up when a home is upgraded and down when it has not been refreshed in a while.
How much does a rental cost, and when do we check in?
Where a manager has supplied a starting rate you will see it on the listing; where they have not, rates are quoted on request because they change with season and length of stay. Check-in and checkout times vary by property and manager, and your agent will confirm both for the home you choose.
Need help choosing?
Tell us who is travelling and when, and a destination specialist will shortlist the homes that suit you.