HiCheeLogoColorful
  • Currency (USD)
  • $ USD
  • Watchlists
  • Contact Support
  • Log In

Wailea-Makena, HI, USA Vacation Rentals | 

Price Comparison Results
Listings
Listings
Open on
Open search on
United States Hawaii Kihei vacation rental compare prices direct by owner 2638541
Verified Host
4.9 (34)
SOM 109 Remodeled Condo Across Ocean w Pool AC
Up to 4 guests
Verified Host
Airbnb
Vrbo
United States Hawaii Kihei vacation rental compare prices direct by owner 44134
Verified Host
4.9 (131)
GC 124 3BD Wailea Condo wAC Pool Hot Tub
Up to 8 guests
Verified Host
Vrbo
Airbnb
United States Hawaii Kihei vacation rental compare prices direct by owner 10090532
Verified Host
4.8 (13)
KAS 10203 Summer Retreat Remodel 1BD Across Beach
Up to 4 guests
Verified Host
Airbnb
Vrbo
United States Hawaii Kihei vacation rental compare prices direct by owner 10090537
Verified Host
4.8 (32)
KM 608 OceanFront 1BD w Heated Pools and AC
Up to 4 guests
Verified Host
Airbnb
Vrbo
United States Hawaii Wailuku vacation rental compare prices direct by owner 58318
Verified Host
4.8 (115)
IS 210 OceanFront Condo Expansive Ocean Views Pool
Up to 4 guests
Verified Host
Vrbo
Airbnb
HiChee Chrome Extension

Use our Chrome Extension. It's Free!

Get instant price-comparison savings while browsing Airbnb, Booking.com, and Vrbo!

Install HiChee Chrome Extension
Find out more
United States Hawaii Kihei vacation rental compare prices direct by owner 44097
Verified Host
4.8 (29)
Considered the Best Location Oceanfront on Maui
Up to 3 guests
Verified Host
Airbnb
Vrbo
United States Hawaii Kihei vacation rental compare prices direct by owner 2613573
Verified Host
4.8 (26)
WEK 40E Dream Getaway w AC Pools Beaches Golf
Up to 4 guests
Verified Host
Vrbo
Airbnb

Curious howHiCheeLogoColorfulgets its data?

ShakaCode Data logoShakaCodedata

ShakaCode scrapes. So you don't have to.

Delegate your web scraping needs to us. Get the data you need.
Focus on your primary goals.

HiCheeLogoColorfulHiChee is built and owned byShakaCode logoShakaCode

Learn more
United States Hawaii Kihei vacation rental compare prices direct by owner 58684
Verified Host
4.8 (54)
ISF 306 1BD w Ocean Views AC Pool Near Beach
Up to 4 guests
Verified Host
Airbnb
Vrbo
United States Hawaii Kihei vacation rental compare prices direct by owner 4447792
Verified Host
4.8 (44)
GC 163 2BD Wailea Condo w AC Pool Close to Beach
Up to 7 guests
Verified Host
Vrbo
Airbnb

Smarter Planning with Watchlists

Create your Watchlists boards and see price comparisons for multiple listings at once. You'll also get notified about price and availability changes and can share it with others.

Check out Watchlists
HiChee Watchlists
United States Hawaii Kihei vacation rental compare prices direct by owner 2665380
Verified Host
4.8 (47)
AKH C302 Spacious 2BD Condo w Ocean Breeze AC Pool
Up to 6 guests
Verified Host
Vrbo
Airbnb
United States Hawaii Kihei vacation rental compare prices direct by owner 95816
Verified Host
4.8 (116)
Oceanfront 3rd Floor Unit at Maalaea Kai Complex
Up to 4 guests
Verified Host
Vrbo
Airbnb
United States Hawaii Wailuku vacation rental compare prices direct by owner 65592
Verified Host
4.8 (99)
LOA 105 2BD OceanFront Getaway w AC Pool
Up to 6 guests
Verified Host
Vrbo
Airbnb
United States Hawaii Kihei vacation rental compare prices direct by owner 176018
Verified Host
4.8 (8)
MB P301 Remodeled 2BD Condo Across Beach Pool AC
Up to 6 guests
Verified Host
Airbnb
Vrbo
United States Hawaii Kihei vacation rental compare prices direct by owner 97097
Verified Host
4.7 (47)
WEK 34A Spacious Wailea Condo w AC Pool Near Beach
Up to 4 guests
Verified Host
Vrbo
Airbnb
United States Hawaii Wailea vacation rental compare prices direct by owner 97146
Verified Host
4.7 (56)
Huge Ocean Views
Up to 6 guests
Verified Host
Vrbo
Airbnb
United States Hawaii Kihei vacation rental compare prices direct by owner 10090545
Verified Host
4.7 (42)
NKH 605 Remodeled BeachFront w Pool AC Sandy Beach
Up to 4 guests
Verified Host
Vrbo
Airbnb
United States Hawaii Kihei vacation rental compare prices direct by owner 6660846
Verified Host
4.7 (52)
WEK 32B Remodeled Wailea Getaway w AC Pool
Up to 2 guests
Verified Host
Vrbo
Airbnb
United States Hawaii Kihei vacation rental compare prices direct by owner 5682823
Verified Host
4.7 (63)
Maui Banyan H506 - Walk to Beaches
Up to 4 guests
Verified Host
Vrbo
Airbnb
United States Hawaii Kihei vacation rental compare prices direct by owner 2626769
Verified Host
4.7 (47)
PAW 2108 Remodeled Wailea Condo w AC Infinity Pool
Up to 4 guests
Verified Host
Vrbo
Airbnb
United States Hawaii Kihei vacation rental compare prices direct by owner 56020
Verified Host
4.7 (76)
KKP 208 Renovated Condo w AC Near Beach Shops
Up to 4 guests
Verified Host
Vrbo
Airbnb
United States Hawaii Kihei vacation rental compare prices direct by owner 54969
Verified Host
4.7 (90)
KAK A207 Renovated Kihei Condo Near Beach AC Pool
Up to 4 guests
Verified Host
Vrbo
Airbnb
United States Hawaii Kihei vacation rental compare prices direct by owner 2849651
Verified Host
4.7 (34)
WEK 17D Wailea Retreat w Ocean View Pool AC
Up to 4 guests
Verified Host
Vrbo
Airbnb
United States Hawaii Kihei vacation rental compare prices direct by owner 16845
Verified Host
4.6 (103)
Fun in the Sun at Maui Sunset-Ocean View 1BR/2BA
Up to 5 guests
Verified Host
Vrbo
Airbnb
United States Hawaii Kihei vacation rental compare prices direct by owner 55924
Verified Host
4.6 (112)
PacSB102 Family Getaway 3BD Across Beach
Up to 6 guests
Verified Host
Vrbo
Airbnb
United States Hawaii Kihei vacation rental compare prices direct by owner 10090544
Verified Host
4.6 (45)
MKO E202 Remodeled 2BD Retreat wAC Pool Near Beach
Up to 6 guests
Verified Host
Vrbo
Airbnb
Angle left icon12345Double arrow right iconAngle left icon
  1. United States
  2. Hawaii
  3. Maui
  4. South Maui
  5. Wailea-Makena Vacation Rental Price Comparison

Wailea Makena Vacation Rentals

Welcome to the tropical wonderland known as Wailea-Makena, on the island of Maui in Hawaii. While in the area be sure to visit Makena State Park. This park contains on of the biggest and most beautiful beaches on the Maui shoreline. Spend a day or more on the beach tanning, swimming, and surfing. This area is also home to various companies offering horseback riding excursions. Saddle up and head down a few of the tropical hiking trails and marvel and the breathtaking tropical scenery. Fun Fact you can cover roughly double the distance on the hiking trails if you traverse them by horseback instead of on foot. While riding through trails on horseback is a blast there are some trails, specifically the ones on and around mountain ranges or volcanoes that you will need to traverse by foot. When you are ready to hop back into the ocean consider hiring a company to take you out for a day of snorkeling or scuba diving. It is a privilege to get to snorkel above or dive next to the majestic marine life native to the area. If luck is on your side, you may even come across a school of dolphins while snorkeling! If you a need a break from all the adventurous activities head just up the road to Wailea Golf Club and play a round of eighteen. This beautiful golf course has breathtaking tropical forestry and ocean views and is one of the most scenic golf courses in Hawaii! With all the fun and exciting opportunities for adventure in the area, guests are sure to have a memorable trip while vacationing in Wailea-Makena.

Compare Airbnb, VRBO and direct by owner prices and get the best deal

Search for your Wailea Makena vacation rental in HiChee and compare prices between Airbnb, VRBO and direct by owner for the same rental. See our live price comparison and take a look at how much you can save by getting the best deal.

Wailea Makena vacation rental direct by owner

We not only offer a wide selection of Airbnb and VRBO vacation rentals on Wailea Makena but also the possibility of direct communication with the owner.

Activities in Wailea Makena

  • Visit Makena State Park
  • Tan, swim, and surf on the beaches
  • Traverse hiking trails by horseback
  • Traverse mountain and volcano trails by foot
  • Scuba dive or snorkel
  • Play a round of eighteen holes at a local golf course

With all the great activities offered in the area guest are sure to work up an appetite. Looking for a sophisticated take on traditional Hawaiian cuisine with breathtaking scenery? Look no further than Gannon’s. This restaurant is known for the innovative take on Hawaiian cuisine and top-notch service. For the carnivores in your group make sure to stop by Duo Steak and Seafood. This fine dining restaurant serves hand cut prime steaks as well as fresh from the ocean seafood. Looking to mix up the style of cuisine your eating while on vacation? Stop into Ferraro’s Bar E Ristorante for mouth watering delicious Italian cuisine. Bistro Molokini is also located in the area and serves California style food. Get fresh fruits and veggies paired with lean seafood for a healthy and delicious lunch or dinner in this fine establishment. After a fun but exhausting day of adventuring around Maui there is only one way to cap off your evening, and that is with a visit to The Pint and Cork. Stop in for an adult beverage of your choosing and relax in this cozy bar and restaurant. The Pint and Cork serves predominately bar food, but is known for there diverse selection of wine and craft beers.

Restaurants in Wailea Makena

  • Gannon’s
  • Duo Steak and Seafood
  • Ferraro’s Bar E Ristorante
  • Bistro Molokini
  • The Pint and Cork.
  • Many More

With the variety of exhilarating and relaxing activities offered in the area as well as the diverse culinary scene, the only thing left to explore to make your vacation complete is the shopping. Be sure to visit The Shops at Wailea for a variety of retail locations conveniently all grouped together. Wailea-Makena is also in proximity to Rainbow Mall. Rainbow Mall is packed to the brim with retail outlets and even has a few restaurants on site. If you are looking for top quality leather goods look no further than the world-renowned Louis Vuitton Maui Wailea location. From purses to wallets this famous high-fashion designer brand is sure to excite fashion enthusiasts from around the world. This area a boutique retail outlet from the high-fashion designer Prada. If you are looking for souvenirs to commemorate your trip or to bring home to friends and family that couldn’t make the trip be sure to visit Sand People. With the perfect mixture of high-fashion boutiques, malls, and souvenir/gift shops, Wailea-Makena is a premium location for shopping on the island of Maui!

Shopping in Wailea Makena

  • The Shops at Wailea
  • Luis Vuitton
  • Prada
  • Rainbow Mall
  • Sand People
  • Many More

HiChee.com is the best and most efficient place for finding, planning, and booking your Hawaiian vacation. From the beautiful scenery and beaches located all over the islands to the unique small-town surf vibes and truly unparalleled shopping, guests of all ages are sure to have an unforgettable time. HiChee.com aims to take the hassle and stress out of booking your vacation rental property, so all you must do is decide if you would rather hit the beach or head into town first. Book now, the experience of a lifetime awaits!

More price comparison of vacation rental locations

  1. Haiku-Pauwela
  2. Haliimaile
  3. Hana
  4. Kaanapali
  5. Kahului
  6. Kapalua
  7. Ke'Anae
  8. Kihei
  9. Kipahulu
  10. Kula
  11. Lahaina
  12. Launiupoko
  13. Maalaea
  14. Mahinahina
  15. Makawao
  16. Nahiku
  17. Napili-Honokowai
  18. Olinda
  19. Paia
  20. Pukalani
  21. Spreckelsville
  22. Waihee-Waiehu
  23. Waihee-Waikapu
  24. Waikapu
  25. Wailuku

Compare Airbnb vs. Booking.com vs. Vrbo prices for vacation rentals in Wailea-Makena, HI, USA

© 2025 HiChee.com. All Rights Reserved.

Check it before you book it! ™

  • Facebook
  • TikTok
Privacy PolicyTerms of Service
  • Company

  • About
  • Blog
  • Careers
  • Newsroom
  • Partners
  • Our Fans
  • Pricing
  • Privacy policy
  • Vacation Rental Data
  • Web Scraping Services
  • Hosting

  • Boost Direct Bookings
  • Verify Your Listing
  • Host Features Waitlist
  • Blog for Hosts
  • OwnerRez Integration
  • For Travelers

  • Contact Host
  • HiChee Watchlists
  • Sample Watchlists
  • Chrome Extension
    Try thisTry it!
  • Help

  • FAQ
  • Share Feedback
  • Contact Host
  • Follow Us

  • TikTokFacebook
© HiChee.com. All rights reserved.
•
Terms of service
•
Sitemap
$ USD
This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.
Check it before you book it! ™