HiCheeLogoColorful
Search
  • Log In
  • Currency (USD)
  • $ USD
  • Watchlists
  • IncognitoAngle Down
    • ClockHistory
    • SignLog In
Best price vacation rentals in Wailea-Makena, HI, USA • 150 Listings

Open this search on

Wailea-Makena, HI, USA Vacation Rentals | 

Price Comparison Results
Default SortingSettings
Open this search on
No photo yet
Book Direct
5.0 (2)
Kihei Akahi D304
Up to 4 guests
Verified Host$177
Airbnb$240
Vrbo$194
Average Nightly Rate
No photo yet
Book Direct
4.9 (80)
Kihei Akahi D-211: Ocean View, Opposite Kamaole Beach, Perfect for Couples
Up to 2 guests
EstimatedVerified Host$194
Vrbo$203
Airbnb$194
Average Nightly Rate
No photo yet
Book Direct
4.8 (128)
Spacious 3 BR, Walk to Best Beaches & Shops in South Kihei! Sleeps 8
Up to 8 guests
EstimatedVerified Host$299
Vrbo$320
Airbnb$450
Average Nightly Rate
No photo yet
Book Direct
4.9 (115)
1BR/2BA Maui Kamaole/Wailea Border. K Cluster @ Tropical Pool!
Up to 4 guests
EstimatedVerified Host$150
Vrbo$239
Average Nightly Rate
No photo yet
Book Direct
4.9 (56)
5 Star Reviews! Ocean Views! 🏝 Steps to Golf. ⛳️ All you could ask for!
Up to 4 guests
EstimatedVerified Host$265
Vrbo$291
Average Nightly Rate
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
No photo yet
Book Direct
0.0 (0)
"Dancing Turtle, Mother-in-Law-Apt" in North -Kihei
Up to 2 guests
EstimatedVerified Host$135
Average Nightly Rate
No photo yet
Book Direct
0.0 (0)
$149/Night Fantastic location, Steps to Beach, newly renovated
Up to 4 guests
EstimatedVerified Host$249
Average Nightly Rate

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
No photo yet
Book Direct
0.0 (0)
Escape2Maui:Maui Banyan
Up to 4 guests
EstimatedVerified Host$170
Average Nightly Rate
No photo yet
Book Direct
5.0 (69)
KM | 312 - Brand New Luxury Remodel - OceanView
Up to 6 guests
EstimatedVerified Host$379
Vrbo$379
Airbnb$423
Average Nightly Rate

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
No photo yet
Book Direct
5.0 (84)
New Listing! Oceanfront with Spectacular Views
Up to 2 guests
EstimatedVerified Host$329
Vrbo$329
Airbnb$381
Average Nightly Rate
No photo yet
Book Direct
5.0 (17)
WEK 34A Oasis Near Keawakapu Beach! Getaway From It All!
Up to 4 guests
EstimatedVerified Host$400
Vrbo$400
Airbnb$400
Average Nightly Rate
No photo yet
Book Direct
5.0 (39)
Modern Luxury Remodel - Ocean View - MK J114
Up to 4 guests
EstimatedVerified Host$349
Vrbo$395
Airbnb$349
Average Nightly Rate
No photo yet
Book Direct
5.0 (60)
NEW! Menehune Shores 407 | Stunning Ocean Views!
Up to 6 guests
EstimatedVerified Host$395
Vrbo$395
Airbnb$523
Average Nightly Rate
No photo yet
Book Direct
5.0 (11)
SOM 109 NEW UNIT! Beach Days, Surf & Sunsets! Ocean Views from Kihei Maui
Up to 4 guests
EstimatedVerified Host$198
Vrbo$198
Airbnb$198
Average Nightly Rate
No photo yet
Book Direct
5.0 (3)
AKH C302 NEW UNIT! Experience South Maui Breezes from Your Private Lanai
Up to 6 guests
EstimatedVerified Host$221
Vrbo$221
Airbnb$221
Average Nightly Rate
No photo yet
Book Direct
5.0 (2)
Hawaii Life Rentals Presents Tropical Oasis - 2 bed/2bath
Up to 6 guests
EstimatedVerified Host$250
Vrbo$250
Airbnb$265
Average Nightly Rate
No photo yet
Book Direct
5.0 (19)
MV 1116 Beautiful Unit, Steps to the Beach and Snorkeling!
Up to 4 guests
EstimatedVerified Host$149
Vrbo$149
Airbnb$149
Average Nightly Rate
No photo yet
Book Direct
5.0 (8)
GC 163 NEW UNIT! Luxurious Wailea Just Moments from the Beach and Shops!
Up to 7 guests
EstimatedVerified Host$375
Vrbo$375
Airbnb$375
Average Nightly Rate
No photo yet
Book Direct
5.0 (12)
GC 179 NEW UNIT! 3b / 2B Resort Condo - A Perfect Family Getaway
Up to 8 guests
EstimatedVerified Host$572
Vrbo$572
Airbnb$572
Average Nightly Rate
No photo yet
Book Direct
5.0 (15)
Grand Champions 105 I Spacious Wailea 3bd on Golf Course
Up to 6 guests
EstimatedVerified Host$549
Vrbo$549
Airbnb$706
Average Nightly Rate
No photo yet
Book Direct
5.0 (17)
Maui Kamaole I-201: 2 BR, 2 BA Condominium in Kihei, Sleeps 4
Up to 4 guests
EstimatedVerified Host$468
Vrbo$479
Airbnb$468
Average Nightly Rate
No photo yet
Book Direct
5.0 (37)
Bright 2bd Kihei Gardens Near Beach
Up to 6 guests
EstimatedVerified Host$339
Vrbo$358
Airbnb$339
Average Nightly Rate
No photo yet
Book Direct
5.0 (125)
Beachfront - Top Floor Sunset Views - Newly Appointed - As Seen on HGTV
Up to 4 guests
EstimatedVerified Host$379
Vrbo$379
Airbnb$408
Average Nightly Rate
No photo yet
Book Direct
4.9 (36)
KKN 373 Remodeled Private Sanctuary Across the Beach with AC
Up to 4 guests
EstimatedVerified Host$153
Vrbo$153
Airbnb$153
Average Nightly Rate
No photo yet
Book Direct
4.9 (32)
KKP 208 Ocean View Two-Bedroom One Block From The Beach! New Listing!
Up to 4 guests
EstimatedVerified Host$238
Vrbo$238
Airbnb$238
Average Nightly Rate
  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
  • Web Scraping Services
  • Hosting

  • Boost Direct Bookings
  • Verify Your Listing
  • Host Features Waitlist
  • Blog for Hosts
  • 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! ™