Wailea-Makena Rentals
From $536 per night (USD)VRBO
Indoor-Outdoor Tropical Living - Wailea Ekahi 47B
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to your tropical retreat at Wailea Ekahi Village 47B—an ideal vacation escape for families or a group of frien ...
From $536 per night (USD)VRBO
From $524 per night (USD)Expedia
Recently Renovated - Walk to the Beach
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Wailea Ekahi Village 23C. This residence was fully renovated in the fall of 2024 and features beautiful furni ...
From $524 per night (USD)Expedia
From $454 per night (USD)VRBO
Wailea Ekahi Village 10F | Tropical Garden Views, Resort Pools & Beach Access
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekahi Village 10F Nestled inside 34 acres of lush botanical gardens, ...
From $454 per night (USD)VRBO
From $440 per night (USD)Expedia
Walk to Favorite Beach - Wailea Ekahi 50C
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Experience the ultimate in island luxury with a stay at Wailea Ekahi 50C, a beautiful one-bedroom, one-bathroom vacation ...
From $440 per night (USD)Expedia
From $647 per night (USD)VRBO
Walk to Waves & Snorkeling - Great for Families
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Wailea Ekahi Village tropical vacation condos are situated above Maui's beautiful Keawakapu Beach and close to all the t ...
From $647 per night (USD)VRBO
From $446 per night (USD)Expedia
Stylish Beach Studio - Professional Managed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Wailea Ekahi 4D is a charming studio vacation rental perfect for the couple or solo traveler. This second-floor unit off ...
From $446 per night (USD)Expedia
From $1151 per night (USD)VRBO
Polo Beach Club 801 | 8th Floor Ocean Views, Beachfront Pool & Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
CORAL TREE RESIDENCE MAUI COLLECTION presents... Polo Beach Club 801 Experience an elevated Hawaiian getaway at this t ...
From $1151 per night (USD)VRBO
From $454 per night (USD)Expedia
Wailea Ekahi Village 39A | Garden Views, Private Lanai Grill & Beach Access
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekahi Village 39A Some settings at Wailea Ekahi face the ocean. 39A ...
From $454 per night (USD)Expedia
From $873 per night (USD)VRBO
5th Floor Elevated Ocean Views | Polo Beach Club 508
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Polo Beach Club 508 is a stunning oceanfront vacation rental located in the heart of the luxurious Wailea area of Maui. ...
From $873 per night (USD)VRBO
From $536 per night (USD)Expedia
Wailea Ekolu Village 1404 | Ocean Views, Golf Clubs & Walkable to Wailea
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekolu Village 1404 Perched above Wailea on the second floor, this 1, ...
From $536 per night (USD)Expedia
From $484 per night (USD)VRBO
Spacious Wailea Condo - Professionally Managed - Ekolu 1607
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Wailea Ekolu 1607 is a stunning one-bedroom, two-bathroom vacation rental that offers an exceptional escape in beautiful ...
From $484 per night (USD)VRBO
From $451 per night (USD)Expedia
Wailea Ekahi Village 9A – 4 Resort Pools, Pickleball, at Keawakapu Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekahi Village 9A This spacious 945 sq.ft. ground-floor condo offers l ...
From $451 per night (USD)Expedia
From $585 per night (USD)VRBO
Wailea Ekolu Village 1107 | Ocean Views, Walkable Wailea Base & Golf Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekolu Village 1107 Perched above Wailea, 1107 is the most walkable c ...
From $585 per night (USD)VRBO
From $483 per night (USD)Expedia
Wailea Ekolu Village 1203 | Golf Walk-Out, Renovated, Pools & Walkable
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekolu Village 1203 Step off the private lanai at 1203 and you're on ...
From $483 per night (USD)Expedia
From $476 per night (USD)VRBO
Wailea Ekahi Village 7B | Spacious Garden Retreat, 1-min Walk to Pool & Beach
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekahi Village 7B A spacious 1,160 sq.ft. 1-bedroom ground-floor condo ...
From $476 per night (USD)VRBO
From $624 per night (USD)Expedia
Wailea Ekahi Village 54D | Sweeping Ocean Views, Updated Kitchen & Resort Pools
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekahi Village 54D Picture your evening: golden Maui sunsets lighting ...
From $624 per night (USD)Expedia
From $528 per night (USD)VRBO
Steps to Keawakapu Beach — Renovated Wailea Condo w/ Pool
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Steps from Keawakapu Beach in the heart of Wailea, this fully renovated 1-bedroom, 2-bath condo sleeps up to 4 and puts ...
From $528 per night (USD)VRBO
From $454 per night (USD)Expedia
Wailea Ekahi Village 44B – Remodeled Garden-View Studio by the Pool and Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekahi Village 44B A recently remodeled 600 sq.ft. ground-floor studio ...
From $454 per night (USD)Expedia
From $466 per night (USD)VRBO
Wailea Ekahi Village 54B – 4 Resort Pools & Pickleball on Keawakapu Beach
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekahi Village 54B A recently remodeled 1,180 sq.ft. ground-floor cond ...
From $466 per night (USD)VRBO
From $440 per night (USD)Expedia
Spacious Condo on Favorite Local Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Wailea Ekahi 3E is a charming one-bedroom vacation rental located in the picturesque Wailea Ekahi Village. Situated on t ...
From $440 per night (USD)Expedia
From $466 per night (USD)VRBO
Walk to Locals Favorite Beach - Wailea Ekahi 40F
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover the charm of Maui from the comfort of Wailea Ekahi 40F, a beautifully appointed one-bedroom, one-bathroom condo ...
From $466 per night (USD)VRBO
From $879 per night (USD)Expedia
Beachfront & Modern | Makena Surf A102
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The recently renovated Makena Surf A102 is a prime oceanfront vacation home spanning 1,510 square feet. This ground-floo ...
From $879 per night (USD)Expedia
From $519 per night (USD)VRBO
Wailea Ekolu Village 912 – Ocean-View Couple’s Retreat, Walk to Wailea Village
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekolu Village 912 An exquisite 1,000 sq.ft. 1-bedroom condo offering ...
From $519 per night (USD)VRBO
From $454 per night (USD)Expedia
Ekahi 4C - 4 Pools | Beach Access | Professional Managed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Wailea Ekahi 3C is a captivating vacation rental that offers a truly idyllic island getaway in the heart of Maui's pictu ...
From $454 per night (USD)Expedia
From $488 per night (USD)VRBO
Wailea Ekolu Village 1703 – Ocean-View Walkout by the Golf, Walk to Wailea Villa
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekolu Village 1703 An elegant 1,069 sq.ft. 1-bedroom condo offering a ...
From $488 per night (USD)VRBO
From $480 per night (USD)Expedia
Wailea Ekahi Village 3B | Garden-View Studio Near Pool & Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekahi Village 3B A cozy 600 sq.ft. ground-floor studio, offering step ...
From $480 per night (USD)Expedia
From $587 per night (USD)VRBO
Fairway + Pacific Ocean Views | Wailea Ekolu 910
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Discover the perfect Hawaiian retreat at Wailea Ekolu Village with this stunning two-bedroom, two-bathroom ocean view re ...
From $587 per night (USD)VRBO
From $939 per night (USD)Expedia
Beachfront Condo with Postcard Views - Makena Surf F306
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Experience effortless mingling and entertaining in Makena Surf F306, where the open living area seamlessly connects to a ...
From $939 per night (USD)Expedia
From $947 per night (USD)VRBO
Ground Floor Bliss By The Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Makena Surf G105 is a prime oceanfront vacation condo that spans 1,510 sq. ft. and is situated on the ground floor. This ...
From $947 per night (USD)VRBO
From $854 per night (USD)Expedia
Oceanfront Makena Surf G202 - Professionally Managed
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Makena Surf G202 is a charming oceanfront vacation residence located on the serene south side of this luxurious resort. ...
From $854 per night (USD)Expedia
From $883 per night (USD)VRBO
Beachfront Condo – Location, Location, Location
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Makena Surf F305, your ideal vacation rental for a dream-filled island getaway! This stunning oceanfront resi ...
From $883 per night (USD)VRBO
From $798 per night (USD)Expedia
Polo Beach Club 409 | Ocean View Lanai, Beachfront Pool & Direct Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CORALTREE RESIDENCE COLLECTION presents... Polo Beach Club 409 Experience the laid-back Hawaiian getaway at this spaci ...
From $798 per night (USD)Expedia
From $999 per night (USD)VRBO
Recently Renovated - Iconic Ocean Views | Polo Beach 609
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Polo Beach Club 609 is a newly remodeled and well-appointed retreat, perfect for small families and groups seeking comfo ...
From $999 per night (USD)VRBO
From $588 per night (USD)Expedia
Wailea Ekolu Village 1205 | Ocean & Fairway Views, Walkable Wailea Base
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekolu Village 1205 Perched above Wailea, 1205 is situated in the mos ...
From $588 per night (USD)Expedia
From $455 per night (USD)VRBO
Beachfront condo w/ ocean views and 4 resort pools
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Experience this elegant one-bedroom, two-bathroom retreat set within the highly sought-after Wailea Ekahi Village in Wai ...
From $455 per night (USD)VRBO
From $515 per night (USD)Expedia
Wailea Grand Champions 177 | Golf Course Views, Tennis & Walk to Wailea Shops
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
CORALTREE RESIDENCE COLLECTION presents... Wailea Grand Champions 177 Wailea Grand Champions is an 11-acre country club ...
From $515 per night (USD)Expedia
From $516 per night (USD)VRBO
Watch the Golfers Play Through
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Wailea Grand Champions 97 is a premier vacation rental located in the serene tourist retreat of Wailea. This exquisite p ...
From $516 per night (USD)VRBO
From $698 per night (USD)Expedia
3BD Golf Haven - Great for Families
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Wailea Grand Champions 84 is a beautifully appointed vacation rental located in the prestigious Wailea area of Maui. Thi ...
From $698 per night (USD)Expedia
From $763 per night (USD)VRBO
Recent Renovation - Close to Golf & Dining
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Do your Maui vacation right! Wailea Grand Champions 95 is surrounded by tropical landscaping and rolling green fairways, ...
From $763 per night (USD)VRBO
From $915 per night (USD)Expedia
Wailea Perfection - Professionally Managed
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your dream vacation in Wailea, Maui! This beautiful two-bedroom residence combines comfort, style, and conven ...
From $915 per night (USD)Expedia
From $542 per night (USD)VRBO
Wailea Grand Champions 43 | Golf, Tennis, Resort Pools & 5-Min Walk to Wailea
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CORALTREE RESIDENCE COLLECTION presents... Wailea Grand Champions 43 Wailea Grand Champions is an 11-acre country club- ...
From $542 per night (USD)VRBO
From $581 per night (USD)Expedia
Golf + Partial Ocean Views - Grand Champions 71
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Wailea Grand Champions 71 is a beautifully updated ground-floor vacation rental that offers both fairway and ocean views ...
From $581 per night (USD)Expedia
From $515 per night (USD)VRBO
Golf + Partial Ocean Views - Grand Champions 73
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Wailea Grand Champions Villa 73 is a recently renovated vacation rental that offers a perfect blend of luxury, comfort, ...
From $515 per night (USD)VRBO
From $549 per night (USD)Expedia
Golf Retreat Great for Families
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Wailea Grand Champions 75 is an exceptional vacation rental situated in the picturesque Wailea region of Maui. This luxu ...
From $549 per night (USD)Expedia
From $586 per night (USD)VRBO
Wailea Grand Champions 183 | Ground Floor, Resort Pools & Walk to Wailea
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CORALTREE RESIDENCE COLLECTION presents... Wailea Grand Champions 183 Wailea Grand Champions is an 11-acre country club ...
From $586 per night (USD)VRBO
From $578 per night (USD)Expedia
Platinum Rated & Golf Course Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled in the heart of Wailea, this charming Grand Champions residence offers a tranquil retreat that feels like your o ...
From $578 per night (USD)Expedia
From $573 per night (USD)VRBO
Golfer's Dream | Condo on Wailea Course
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Wailea Grand Champions 31 is a recently updated vacation rental that offers a perfect blend of comfort, style, and conve ...
From $573 per night (USD)VRBO
From $1139 per night (USD)Expedia
Wailea Elua Village 1504 | Panoramic Ocean Views, Remodeled, 2 Min to Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
CORALTREE RESIDENCE COLLECTION presents... Wailea Elua Village 1504 Elua Village sits right on Ulua Beach and connects ...
From $1139 per night (USD)Expedia
From $3105 per night (USD)VRBO
Recently Renovated & Professionally Managed Ocean View Villa
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Villa G302, your luxurious Hawaiian escape where relaxation meets elegance. This stunning ocean view villa fe ...
From $3105 per night (USD)VRBO
From $729 per night (USD)Expedia
Wailea Elua Village 1501 | XL Lanai, 2 Min to Ulua Beach, 2 Pools & Pickleball
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CORALTREE RESIDENCE COLLECTION presents... Wailea Elua Village 1501 Elua Village sits right on Ulua Beach and connects ...
From $729 per night (USD)Expedia
From $2801 per night (USD)VRBO
Voted Top 10 Resort in Hawaii - Wailea Beach Villas F201
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Villa F201, an expansive vacation retreat that embodies upscale relaxation. Spanning a generous 3,676 square ...
From $2801 per night (USD)VRBO
From $930 per night (USD)Expedia
Wailea Elua Village 1502 | Ocean View, 2 Min to Ulua Beach, Pools & Pickleball
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CORALTREE RESIDENCE COLLECTION presents... Wailea Elua Village 1502 Elua Village sits right on Ulua Beach and connects ...
From $930 per night (USD)Expedia
From $1799 per night (USD)VRBO
Wailea Elua Village 1303 - 2 Bedroom Oceanfront Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
When vacationing in Wailea Elua 1303, you’ll feel pampered by the extra touches that await you in this suite featuring ...
From $1799 per night (USD)VRBO
From $2316 per night (USD)Expedia
Conde Nast Award Winning Property - Wailea Beach Villas E202
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Warm breezes and lush tropical gardens greet guests of Wailea Beach Villas E202 as the spacious and comfortably appointe ...
From $2316 per night (USD)Expedia
From $332 per night (USD)VRBO
Direct Ocean Views, Private Lanai
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Maui Parkshore 310 – Your Oceanfront Paradise! Experience the best of Maui living at Maui Parkshore 310, a be ...
From $332 per night (USD)VRBO
From $981 per night (USD)Expedia
Beautifully Upgraded Oceanview Condo Steps to the Beach at Makena Surf #F-109
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Makena Surf F109 Welcome to Makena Surf F-109, a luxurious ground-floor condo in the exclusive Makena Surf. With its pri ...
From $981 per night (USD)Expedia
From $981 per night (USD)VRBO
Breathtaking Views -Remodeled Ocean Front Condo - Makena Surf Resort F-111
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Makena Surf #F-111 – Oceanfront Comfort with Ground-Floor Convenience Enjoy luxurious oceanfront living at Makena Surf ...
From $981 per night (USD)VRBO
From $483 per night (USD)Expedia
Tropical Garden & Pool Views - Professionally Managed
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
"Welcome to your serene oasis at Wailea Ekahi Village 42D, a meticulously designed 1-bedroom garden view condo that prom ...
From $483 per night (USD)Expedia
From $1107 per night (USD)VRBO
Makena Surf F207 Beachfront Resort
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to the Makena Surf F207, where luxury meets the ocean's edge. This beautifully renovated 2-bedroom, 2-bathroom o ...
From $1107 per night (USD)VRBO
From $415 per night (USD)Expedia
Charming Beachside Garden Vistas
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: **Bright, modern, and spacious—**this completely remodeled one-bedroom, two-bath condo has been carefully desi ...
From $415 per night (USD)Expedia
From $350 per night (USD)VRBO
Rock 'n' Aloha Oceanview Paradise Waits - 2 bd/2br
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Rock 'n' Aloha is a spacious and beautifully appointed 2-bedroom apartment on the second and third floors of the charmin ...
From $350 per night (USD)VRBO
From $332 per night (USD)Expedia
Tropical Garden Retreat right by the Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Maui Kamaole C-109, a tranquil ground-floor condo perfectly situated in the heart of South Maui and the in th ...
From $332 per night (USD)Expedia
From $1505 per night (USD)VRBO
Wailea Elua Village 1603
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to the serene and luxurious Wailea Elua Village 1603, a stunning 2-bedroom ocean front condo nestled in the hear ...
From $1505 per night (USD)VRBO
From $3465 per night (USD)VRBO
NEW AND MODERN PANORAMIC OCEANVIEW 4 BEDROOM VILLA WITH HEATED PLUNGE POOL AND LUX INTERIOR
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Our collection of Maui vacation residences are HOTEL-Zoned or have LEGAL short-term rental permits. Reserve with Private ...
From $3465 per night (USD)VRBO
From $322 per night (USD)VRBO
Maui Bliss Garden Lanai, Dual AC, Beach, Pool, Gym
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Paradise awaits at Maui Bliss, a beautiful 1-bedroom, 2-bathroom retreat. This first-floor unit offers an open-plan livi ...
From $322 per night (USD)VRBO
From $519 per night (USD)Expedia
Wailea Grand Champions. Walk to shops, dining & golf. Nice Ocean View. From 225
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
*Include specific travel dates on the calendar to automatically show available discounts* We offer discounts for early ...
From $519 per night (USD)Expedia
From $346 per night (USD)VRBO
Recently updated oceanview retreat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Maui Parkshore 306 — Your Maui Beach Retreat Awaits! Say aloha to your island getaway at Maui Parkshore 306, ...
From $346 per night (USD)VRBO
From $931 per night (USD)Expedia
Ground Floor with Instant Beach Access - Polo Beach 102
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to the serene Polo Beach Club 102, your perfect ocean retreat in Wailea. This stunning 2-bedroom, 2-bathroom con ...
From $931 per night (USD)Expedia
From $915 per night (USD)VRBO
Makena Surf B201 | 2nd Floor Oceanfront, On the Beach & Turtle Reef
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CORALTREE RESIDENCE COLLECTION presents... Makena Surf B201! Experience an intimate Hawaiian retreat at this carefully ...
From $915 per night (USD)VRBO
From $995 per night (USD)Expedia
601 - 2 Bedroom end-unit with Breathtaking Ocean Views!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This sixth floor oceanfront condo at the Kihei Surfside Resort is located at the ocean end of the building. This end uni ...
From $995 per night (USD)Expedia
From $1005 per night (USD)VRBO
Makena Surf B305 Beachfront Resort
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Makena Surf B305, an extraordinary oceanfront retreat offering some of the most breathtaking views on all of ...
From $1005 per night (USD)VRBO
From $1006 per night (USD)Expedia
Wailea Elua | Steps to Ulua Beach, Ocean Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: New to our portfolio — not new to hospitality. We're the same 5-star team behind other top-rated Wailea Elua v ...
From $1006 per night (USD)Expedia
From $1536 per night (USD)VRBO
Luxury Oceanfront 3-Bedroom Escape at Makena Surf Resort - Makena Surf #E-304
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Luxury Oceanfront Escape at Makena Surf Resort – Makena Surf #E-304 Welcome to Makena Surf #E-304, a rare three-bedroom ...
From $1536 per night (USD)VRBO
From $591 per night (USD)Expedia
Spectacular Ocean View Condo with Remodeled Interior - Mana Kai Maui #804C
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Mana Kai Maui Resort #804C – Penthouse-Level Oceanfront Luxury with Split-Duct AC and Panoramic Views Welcome to Mana K ...
From $591 per night (USD)Expedia
From $413 per night (USD)VRBO
Wailea Ekahi 52D - Wailea 1BR Condo, Garden Lanai, AC, Island Luxury Beach Condo
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
* * * * The Wailea Ekahi main pool area will be closed for renovations from August 10, 2026 to October 15, 2026. The 3 ...
From $413 per night (USD)VRBO
From $1140 per night (USD)Expedia
Wailea Elua Unit 806
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
An incredible 1,250 sq ft three bedroom / two bath condo in Wailea's Luxury Resort. It includes access to Wailea Elua Vi ...
From $1140 per night (USD)Expedia
From $1006 per night (USD)VRBO
Wailea Elua 1507 in the Wailea Resort
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beautiful finishes and amenities define this restful space. Access to pickleball courts, workout center, two pools and j ...
From $1006 per night (USD)VRBO
From $2061 per night (USD)Expedia
Wailea Elua #1903: 1 BR, 1.5 BA Condominium in Kihei, Sleeps 2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Unparalleled oceanfront views and serene location with a privacy garden and spacious outdoor area for relaxing and havin ...
From $2061 per night (USD)Expedia
From $3612 per night (USD)VRBO
Beachfront / Oceanfront Private Home Sleeps 8
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
ONLY DIRECTLY MANAGED listing site. This home defines the best of Maui with direct access to a sandy, swimming beach on ...
From $3612 per night (USD)VRBO
From $747 per night (USD)Expedia
Rare Dual-Suite Wailea Ekahi Condo, Sleeps 6
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Experience a rare and uniquely spacious retreat in the heart of Wailea Ekahi Village, one of South Maui’s most sought-af ...
From $747 per night (USD)Expedia
From $566 per night (USD)VRBO
Remodeled 2BD Wailea Condo w/ Lanai, Pools, AC & Near Beach & Golf - Grand Champions 62
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Escape to Wailea Maui at this 2 Bedroom, 2 Bathroom Condo, Steps from the Pool, Minutes to the Beach - Grand Champions 6 ...
From $566 per night (USD)VRBO
From $745 per night (USD)Expedia
Serene Maui Retreat Walk to Beach & Shops
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Prime Location Walk to beach dining shops Tranquil Balcony Enjoy morning coffee w lush views Luxury Beds ...
From $745 per night (USD)Expedia
From $1088 per night (USD)VRBO
Wailea Luxury Retreat Walk to Beach & Shops
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Prime Location Walk to beaches top dining King Suite Sofa Bed Comfort space for all Private Lanai Re ...
From $1088 per night (USD)VRBO
From $1277 per night (USD)Expedia
Beachfront Bliss | Walk to Sand, Pool, Restaurants
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Prime Location Walk to Kamaole Beach dining Serene Lanai Views Relax in a peaceful oasis Luxury King Bed ...
From $1277 per night (USD)Expedia
From $873 per night (USD)VRBO
Luxury Maui Condo | Ocean Views + Resort Perks
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Summary: Prime Location Steps to White Sand Beaches Ocean Mountain Views from Private Lanai Resort Perks Pool Hot ...
From $873 per night (USD)VRBO
From $683 per night (USD)Expedia
Mana Kai 304 - Renovated Oceanfront 2BR/2BA Condo, Split AC, Beach Access, Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Mana Kai 304, your private slice of oceanfront paradise on Maui. This fully renovated two-bedroom, two-bathro ...
From $683 per night (USD)Expedia
From $728 per night (USD)VRBO
SUMMER SALE! Hillside Condo w/ AC & Ocean Views Near Beaches-Wailea Ekolu 1605
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLASH SUMMER SALE! We're offering exclusive discounts on all summer stays booked this week—don't miss out on these updat ...
From $728 per night (USD)VRBO
From $467 per night (USD)Expedia
Spacious Ground Floor Maui Retreat, Grand Champion
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: 🌴 Prime Location – 5-min stroll to Charley Young Beach 🏊 Resort-Style Living – Pool, hot tub, BBQ & tennis co ...
From $467 per night (USD)Expedia
From $813 per night (USD)VRBO
Incredibly roomy, adjacent to the best beaches/Wailea
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 3
Extremely roomy, high-end 1-bedroom 2-bathroom, deluxe 1039 square feet condo at the gateway to Wailea. Remodled and fea ...
From $813 per night (USD)VRBO
From $814 per night (USD)Expedia
Maui Kamaole H-208 – Oceanview Poolside Condo Close to Beaches and Dining
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Maui Kamaole #H-208 – Partial Ocean View Comfort in South Kihei Experience the beauty of Maui from Maui Kamaole #H-208, ...
From $814 per night (USD)Expedia
From $554 per night (USD)VRBO
Ground-Floor Gem in Wailea Ekahi Village
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Discover true island elegance in this beautifully updated ground-floor residence at Wailea Ekahi Village, one of Maui’s ...
From $554 per night (USD)VRBO
From $383 per night (USD)Expedia
Sunset View Penthouse! Large 2bed/2bath Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Haleakala Shores: a vibrant island community with diverse amenities and a welcoming neighborhood atmosphere ...
From $383 per night (USD)Expedia
From $1039 per night (USD)VRBO
Maui Luxury with Island Serenity - Wailea Beach Villas Penthouse K107
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Wailea Beach Villas Penthouse K107 - A luxurious and spacious 2-bedroom, 2-bath with a den that functions as ...
From $1039 per night (USD)VRBO
From $3150 per night (USD)Expedia
Wailea Beach | Oceanfront 3 BR, Sleeps 6 | Car Incl. w/ 6+ Nights | WBV-PH505 by KBM
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and Decembe ...
From $3150 per night (USD)Expedia
From $803 per night (USD)VRBO
SUMMER SALE! Experience luxury in a spacious 2BR Stunning Ocean views- WE 1106
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLASH SUMMER SALE! We're offering exclusive discounts on all summer stays booked this week—don't miss out on these updat ...
From $803 per night (USD)VRBO
From $942 per night (USD)Expedia
$125/nt SUMMER/FALLStunning Maui Kamaole! Grd Flr,AC!PARADISE! NEW LISTING!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
A perfect Maui getaway! We love to invite guests to stay at our well-appointed 1 bedroom, 2 bathroom, fully air-conditi ...
From $942 per night (USD)Expedia
From $1860 per night (USD)VRBO
3BD Wailea Villa w/ Luxury Interiors, Ocean Views & Pool - Hoolei Residences 23-3
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Breathtaking Full Ocean View Wailea Luxury Vacation Rental Residence Perfect for Family and Group Travel - Ho'olei Resid ...
From $1860 per night (USD)VRBO
From $1860 per night (USD)Expedia
SUMMER SALE! Luxurious 3BR Villa Sleeps 8 - Hoolei Residences 93-3
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
FLASH SUMMER SALE!!! We're offering exclusive discounts on all summer stays booked this week—don't miss out on these upd ...
From $1860 per night (USD)Expedia
From $1161 per night (USD)VRBO
Wailea Beach penthouse w/ ocean view and pool access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Wailea Beach Villas has been ranked #4 in Hawaii by Condé Nast Readers. This recognition places WBV among the very best ...
From $1161 per night (USD)VRBO
From $462 per night (USD)Expedia
NICELY UPDATED-OCEAN VIEWS-PRIME LOCATION-LARGE LANAI-AC-WELL EQUIPPED
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Feel right at home in this nicely updated, well equipped 2 bedroom, 2 bathroom (1188 sq ft.) condo at Kamaole Sands with ...
From $462 per night (USD)Expedia