Spend the Holidays in Paradise
Escape to Wailea and Makena this holiday season, where warm island breezes, sparkling beaches, and the festive aloha spirit turn your winter getaway into a tropical celebration.
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22 properties available
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Experience effortless mingling and entertaining in Makena Surf F306, where the open living area seamlessly connects to a spacious lanai. Enjoy the refreshing ocean breezes beneath the cathedral ceilings while taking in the stunning ocean views. This residence boasts natural wood accents and original artwork, all set within a contemporary beachside
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Festive Availability
Festive Availability
This residence is still available over the high-demand travel dates between Christmas and New Years.
Makena Surf (23)
Makena Surf F306 Beachfront Resort
2 Bedroom Oceanfront Condo - Platinum
5
(13)
2
bedrooms
2
baths
6
guests
Wailea, HI
Oceanfront View
Complex Pool
Private Outdoor space
Welcome to your serene oasis at Wailea Ekahi Village 35D, a stunning 1-bedroom, 1-bathroom ocean view condo nestled in the heart of Wailea. This meticulously designed retreat offers a luxurious escape for up to four guests, combining modern elegance with the natural beauty of Hawaii.Step inside to discover a spacious, open-concept living area where
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Festive Availability
Festive Availability
This residence is still available over the high-demand travel dates between Christmas and New Years.
Wailea Ekahi Village (45)
Wailea Ekahi Village 35D
1 Bedroom Ocean View Condo – Platinum
5
(9)
1
bedrooms
1
baths
4
guests
Wailea, HI
Ocean View
Complex Pool
Private Outdoor space
Wailea Elua 2004 is a luxurious vacation rental located along the shores of Maui's southern coastline. This one-bedroom, one-bathroom condominium offers an ideal retreat for couples or small families, featuring a spacious layout that maximizes comfort and ocean views from almost every room. The vacation residence is designed for both relaxation a
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Festive Availability
Festive Availability
This residence is still available over the high-demand travel dates between Christmas and New Years.
Wailea Elua Village (42)
Wailea Elua Village 2004
1 Bedroom Ocean View Condo – Gold
5
(10)
1
bedrooms
2
baths
4
guests
Wailea, HI
Ocean View
Complex Pool
Private Outdoor space
CORALTREE RESIDENCE COLLECTION presents... Wailea Elua Village 104Elua Village sits steps from Ulua Beach and connects directly to the 3.2-mile Wailea Beach Walk — the most beach-accessible address in the area. This 1,025-square-foot, 1-bedroom, 2-bathroom condo features a private balcony with ocean views, two resort pools, a shared hot tub, and 24
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Festive Availability
Festive Availability
This residence is still available over the high-demand travel dates between Christmas and New Years.
Wailea Elua Village (42)
Wailea Elua Village 104
1 Bedroom Ocean View Condo – Gold
5
(3)
1
bedrooms
2
baths
4
guests
Wailea, HI
Ocean View
Complex Pool
Private Outdoor space
CORALTREE RESIDENCE COLLECTION presents... Wailea Grand Champions 183Wailea Grand Champions is an 11-acre country club-style resort set along the Wailea Blue Golf Course and Wailea Tennis Club. Unit 183 is a ground-floor 2-bedroom, 2-bathroom retreat that comfortably sleeps 6, fully equipped for the perfect workation. Enjoy a shaded private lanai p
Festive Availability
Festive Availability
This residence is still available over the high-demand travel dates between Christmas and New Years.
Wailea Grand Champions 183
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2 Bedroom Garden View Condo - Gold
5
(10)
2
bedrooms
2
baths
6
guests
Wailea, HI
Complex Pool
Private Outdoor space
Resort Golf
Wailea Ekolu 1607 is a stunning one-bedroom, two-bathroom vacation rental that offers an exceptional escape in beautiful Wailea. This beautifully appointed condo features calming views of the lush landscapes of the Wailea Blue Golf Course, providing a serene backdrop for your Hawaiian getaway. Upon entering, guests are welcomed by a spacious open-c
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Festive Availability
Festive Availability
This residence is still available over the high-demand travel dates between Christmas and New Years.
Wailea Ekolu Village (10)
Wailea Ekolu Village 1607
1 Bedroom Garden View Condo – Gold
5
(11)
1
bedrooms
2
baths
4
guests
Wailea, HI
Garden View
Steps to Shopping
Complex Pool
CORALTREE RESIDENCE COLLECTION presents... Wailea Grand Champions 177Wailea Grand Champions is an 11-acre country club-style resort set along the Wailea Blue Golf Course and Wailea Tennis Club. Unit 177 is a peaceful 1-bedroom, 2-bathroom retreat set directly on the golf course with immediate access to the tennis courts. Enjoy a private lanai with
Festive Availability
Festive Availability
This residence is still available over the high-demand travel dates between Christmas and New Years.
Wailea Grand Champions 177
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1 Bedroom Golf Course View Condo - Gold
5
(5)
1
bedrooms
2
baths
4
guests
Wailea, HI
Golf View
Complex Pool
Private Outdoor space
CORALTREE RESIDENCE COLLECTION presents... Wailea Grand Champions 73Wailea Grand Champions sits along the Wailea Blue Golf Course, next door to the Wailea Tennis Club and a 5-min walk from Wailea's shops and dining. This recently renovated 1,069 sq.ft. ground-floor 1-bedroom has 2 full bathrooms and a lanai on the 2nd fairway, with views to the oce
Festive Availability
Festive Availability
This residence is still available over the high-demand travel dates between Christmas and New Years.
Wailea Grand Champions 73
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1 Bedroom Partial Ocean View Condo - Gold
5
(6)
1
bedrooms
2
baths
4
guests
Wailea, HI
Golf View
Complex Pool
Private Outdoor space
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekolu Village 1203Step off the private lanai at 1203 and you're on the Wailea Blue Golf Course — literally. The fairways roll out in front of you, with the Pacific glinting beyond. A fully renovated 1-bedroom condo, one of the most praised in the complex. Wailea Village is steps away for morning cof
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Festive Availability
Festive Availability
This residence is still available over the high-demand travel dates between Christmas and New Years.
Wailea Ekolu Village (10)
Wailea Ekolu Village 1203
1 Bedroom Ocean View Condo – Gold
5
(9)
1
bedrooms
2
baths
4
guests
Wailea, HI
Ocean View
Steps to Shopping
Complex Pool
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekahi Village 54DPicture your evening: golden Maui sunsets lighting up the Pacific from the private lanai. A 1-bedroom, 2-bathroom condo with an updated kitchen and an unobstructed west-facing view that turns evenings into events. Keawakapu Beach is a short walk through the gardens, where sea turtle
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Festive Availability
Festive Availability
This residence is still available over the high-demand travel dates between Christmas and New Years.
Wailea Ekahi Village (45)
Wailea Ekahi Village 54D
1 Bedroom Ocean View Condo – Gold
4.9
(28)
1
bedrooms
2
baths
4
guests
Wailea, HI
Ocean View
Complex Pool
Private Outdoor space
CORALTREE RESIDENCE COLLECTION presents... Wailea Ekahi Village 44BA recently remodeled 600 sq.ft. ground-floor studio, offering step-free access and a lovely garden lanai with private gas BBQ. Located just steps from 1 of 4 resort pools, pickleball courts and a pleasant walk down a grassy hill to the beachfront pavilion and Keawakapu Beach. Perfec
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Festive Availability
Festive Availability
This residence is still available over the high-demand travel dates between Christmas and New Years.
Wailea Ekahi Village (45)
Wailea Ekahi Village 44B
Studio Garden View Condo – Gold
4.8
(7)
1
baths
2
guests
Wailea, HI
Garden View
Complex Pool
Private Outdoor space
Welcome to your serene oasis at Wailea Ekahi Village 47D, a stunning 1-bedroom, 1-bathroom ocean view condo nestled in the heart of Wailea. This meticulously designed retreat offers a perfect blend of comfort and luxury, ideal for your Hawaiian getaway. Step inside to discover a spacious, open-concept living area that seamlessly flows into a privat
View Details
Festive Availability
Festive Availability
This residence is still available over the high-demand travel dates between Christmas and New Years.
Wailea Ekahi Village (45)
Wailea Ekahi Village 47D
1 Bedroom Ocean View Condo – Gold
5
(3)
1
bedrooms
2
baths
4
guests
Wailea, HI
Ocean View
Complex Pool
Private Outdoor space
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