We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation rentals in Wailea, HI

Payment Protection
Use a credit card to book with our Peace of Mind Protection.Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
More filters
Find more rentals you can book on TripAdvisor!   We're showing you properties you can book on TripAdvisor first.
All 221 Rentals in Wailea
loading...
Sort by
From
$262
Per Night
1 / 13
Payment Protection
1 Bedroom, 2 Bathrooms, Sleeps 2
Details Reviews (1) Make Enquiry
From
$221
Per Night
1 / 23
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (1) Make Enquiry
From
$809
Per Night
1 / 44
Payment Protection
3 Bedrooms, 4 Bathrooms, Sleeps 10
Details Reviews (27) Make Enquiry
From
$232
Per Night
1 / 21
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (5) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Enjoy sitting on your lanai enjoying spectacular ocean views in a peaceful, private 1 bedroom, 1 bath, 500 sq. ft. completely furnished cottage with full kitchen This cottage has it all. Spectacular furnishings and ocean views! Completely remodeled 1 bedroom cottage in Maui Meadows (Maui Meadows... View all property information
Make Enquiry
5 of 5 stars Reviewed 28 November 2014
This is an amazing place to stay. 15 minutes from almost a dozen beaches and less than 5 minutes from the closest one, with a great view above the fray of the resort area. Very...
5 of 5 stars Reviewed 11 September 2014
Many people visit Maui every year with the idea of having grand island adventures. It's the perfect place for all kinds of outdoor fun. Whether you are in the mood for scuba...
See all reviews
From
$430
Per Night
1 / 19
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Beautifully furnished two bedroom Condo overlooking the Golf Course. The kitchen has been recently renovated. This unit offers many upgrades throughout and has many new furnishings. The bedrooms have all new furniture and the master bedroom features a beautiful wooden canopy bed. The accommodations... View all property information
Make Enquiry
From
$6,603
Per Week
1 / 27
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Reviews (7) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Hot Tub
  • Internet Access
  • Pool
  • Satellite TV
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Special Fall 2014 Rates - Please inquire ! Enjoy more than 2700 feet of comfortable yet lavish, uniquely and professionally decorated living space. The great room is aptly named. Vaulted ceiling, HD TV, DVD, IPod dock, wireless internet, and formal dining area are a few of the many features. The... View all property information
Make Enquiry
3 of 5 stars Reviewed 29 October 2014
We stayed here with a total of 3 couples. The condo is spacious (even for 6), well furnished and well appointed with kitchen and dining requirements. Two bedrooms had king sized...
See all reviews
From
$221
Per Night
1 / 11
Payment Protection
2 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Our spacious Wailea Ekolu Condominium is fully appointed and includes phone, radio, CD/DVD player, cable TV, and WiFi Internet connection. Three flat screen TVs have been installed. Personal touches for your enjoyment and convenience. This unit is a 2,000-square-foot townhouse, occupying both the... View all property information
Make Enquiry
From
$1,456
Per Night
1 / 23
Payment Protection
4 Bedrooms, 3 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Housekeeping...
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
About this property
** $$$ DISCOUNTS for SPRING 2015! Rate is based on number of guests and nights. Please inquire now! Great for family vacation/reunions and adult getaways! Welcome to Nani Pulelehua ('Beautiful Butterfly'), a luxurious panoramic ocean view estate. 1.5 miles from beaches, dining and shopping. A... View all property information
Make Enquiry
Enquire for rates
1 / 15
1 Bedroom, 2 Bathrooms, Sleeps 4
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Hot Tub
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Special 2014 Rates - Please Ask. The living area has air conditioning, 2 ceiling fans, separate dining area, 40" LCD TV with surround sound, DVD, CD player, high speed and wireless internet. The furnishing are tasteful, tropical and comfortable. The kitchen is upgraded with granite counters and... View all property information
Make Enquiry
From
$162
Per Night
1 / 25
Payment Protection
1 Bedroom, 2 Bathrooms, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Beautiful 1 BR/2 bath 908 square foot interior + 200 square foot lanai overlooking thed7th fairway of the Blue Golf Course in exclusive Wailea Maui. Maui's best beaches, top notch dining, golf and tennis are 5-10 minutes walking distance. Enjoy sunsets and ocean views from lanai! Our completely... View all property information
Make Enquiry
Get the List
From
$233
Per Night
1 / 17
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 2
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Enjoy sitting on your lanai enjoying spectacular ocean views in a peaceful, private 1 bedroom, 1 bath, 500 sq. ft. completely furnished cottage with full kitchen This cottage has it all. Spectacular furnishings and ocean views! Completely remodeled 1 bedroom cottage in Maui Meadows (Maui Meadows... View all property information
Make Enquiry
From
$344
Per Night
1 / 7
Payment Protection
1 Bedroom, 2 Bathrooms, Sleeps 3
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Over 1100 square feet of an exquisite & total remodel of our one bedroom, two bath condo in Wailea, Maui, HI provides a fabulous vacation spot as well as our Maui winter home. First floor, designer furnished with central AC, select comfort sleep number king bed, walk in showers, sophisticated AV... View all property information
Make Enquiry
From
$338
Per Night
1 / 17
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Live luxuriously while on vacation! Beautiful Hawaiian art, travertine floors, granite countertops, tall bath vanities, and elegant new furniture make this condo a place of comfort and serenity. The two bedrooms are private, each with an en suite bathroom. The master bedroom offers a California... View all property information
Make Enquiry
From
$232
Per Night
1 / 25
1 Bedroom, 2 Bathrooms, Sleeps 4
Details Reviews (13) Make Enquiry
Amenities & Details
  • Grill
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
The fabulous Keawakapu Beach is just a short 10 minute stroll from the Palms at Wailea. This beach is world famous for its great snorkeling and long white sandy shoreline. The Palms at Wailea is a gorgeous property; lush with tropical landscaping. There is a large pool and hot tub that is perfect... View all property information
Make Enquiry
From
$600
Per Night
1 / 19
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
  • Waterfront
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Please ask for our Fall 2014 rates! Wailea Ekahi 27B offers Ocean views from the upstairs master bedroom Living area and Lanai. The master bedroom has a king bed, ocean view and en-suite bath. The guest bedroom has a new Queen bed and beautiful garden view. Both bedrooms have air conditioning and... View all property information
Make Enquiry
From
$1,267
Per Night
1 / 37
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (5) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Gym
  • Internet Access
  • Mountain Views
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
GRAND WAILEA RENTAL PROGRAM BENEFITS FOR OUR GUESTS: * Complimentary on-demand transportation to and from The Grand Wailea Resort * Enjoy the use of all the pools, water slides, spa and restaurants at The Grand Wailea Resort * Exclusive charging privileges at The Grand Wailea Resort *... View all property information
Make Enquiry
5 of 5 stars Reviewed 11 August 2014
I must say that this was one of the best vacation rentals I've stayed at. The house, staff and property was simply amazing. Everyone there was extremely courteous, friendly and...
See all reviews
From
$232
Per Night
1 / 21
2 Bedrooms, 3 Bathrooms, Sleeps 6
Details Reviews (1) Make Enquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Gym
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Wailea Ekolu is one of most sought after properties in Wailea.. Wailea Ekolu has several lovely pool areas as well as a large pavilion area for larger groups. There are also additional barbecue and picnic areas on the grounds with panoramic views of the ocean and the sunsets. The beautiful Mokapu... View all property information
Make Enquiry
From
$274
Per Night
1 / 19
2 Bedrooms, 4 Bathrooms, Sleeps 6
Details Reviews (21) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Hot Tub
  • Internet Access
  • Ocean Views
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Come enjoy our newly remodeled, 'PEACEFUL MAUI CONDO,' unit 164 Our Family-Friendly 2 Bedroom, 2 Bath Ocean & Fairway View condo awaits you. Perfect for families, or two couples! Fully Air-Conditioned Top Floor unit features Vaulted Ceilings 2 Master Suites with en-suite bathroom King size beds... View all property information
Make Enquiry
4 of 5 stars Reviewed 15 May 2014
This was our first stop on our trip to the Hawaiian Islands and we wish we could have stayed longer. The condo was spacious and well appointed with almost everything you would...
5 of 5 stars Reviewed 25 September 2013
I stayed at the Grand Champions Villa for five nights and let me tell you WOW!!! It was so comfortable and amazing. You wake up in the morning and you have this fantastic view of...
See all reviews
From
$472
Per Night
1 / 16
1 Bedroom, 2 Bathrooms, Sleeps 4
Details Reviews (16) Make Enquiry
Amenities & Details
  • Grill
  • Hot Tub
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
About this condo: Wailea Elua Village #1601 is an inviting ground floor one bedroom, two bath oceanfront condo plus sofa sleeper with a large wrap-around lanai: the perfect location for watching stunning Maui sunsets and enjoying the lush tropical landscaping. Imagine stepping off of your lanai and... View all property information
Make Enquiry
4 of 5 stars Reviewed 12 July 2014
We have spent the last 16 years at many of the Elua condos managed by a different company. Ali'i proved to be the most accommodating and attentive. Their website is also...
See all reviews
From
$844
Per Night
1 / 34
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Gym
  • Hot Tub
  • Internet Access
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
WAILEA BEACH VILLA PENTHOUSE #306 (LUXURY 2 BR + DEN + 2 BA) PANORAMIC OCEAN VIEWS!!! LUXURY AND EXCLUSIVE 2 BR + DEN. NOW OFFERED AT AN AMAZING RATE!!! LOOK NO FURTHER! THIS IS THE NEWEST EXCLUSIVE, LUXURY WAILEA BEACHFRONT CONDO OFFERED AT AN AMAZING RATE!!! OVER 1900 SQ. FT + LANAI + BBQ... View all property information
Make Enquiry
From
$215
Per Night
1 / 20
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (4) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Our professionally decorated spacious 2 bedroom 2 bathroom air conditioned condo has been tastefully furnished in modern decor with tropical accents. This spacious 1148 square foot condo has a great layout for privacy. The large bedrooms are on opposite sides of the condo with their own private... View all property information
Make Enquiry
From
$512
Per Night
1 / 16
2 Bedrooms, 2 Bathrooms, Sleeps 5
Details Reviews (16) Make Enquiry
Amenities & Details
  • Grill
  • Hot Tub
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Notes from the Owner: Wailea Elua Village #801 is located in the center of the Elua Village just across from the small pool and Jacuzzi area and just steps to the paddle court. Enjoy ocean views as well as secluded garden views from this quiet ground floor, two bedroom, two bath unit. The lanai... View all property information
Make Enquiry
5 of 5 stars Reviewed 29 August 2014
This was a fantastic stay. The accommodation was booked through mauivacationadvisors.com. The agency represents many properties. They were a huge help, offering suggestions...
See all reviews
From
$279
Per Night
1 / 21
Payment Protection
1 Bedroom, 2 Bathrooms, Sleeps 4
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
About this property
We recently remodeled our condo with all new upgraded tumbled travertine flooring and tropical faux painting through out. Why stay in a resort hotel like the Four Season or the Grand Wailea when you can save 2/3rds of the cost and not have to purchase every meal in a resort hotel. You'll have a... View all property information
Make Enquiry
From
$460
Per Night
1 / 29
2 Bedrooms, 2 Bathrooms, Sleeps 5
Details Reviews (3) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Note: *** Our calendar is always up to date. Low Season Rate (Apr 16 - Dec 15) $395.00 per night High Season Rate (Dec 16 - Apr 15) $450.00 per night Are you looking for a quiet peaceful alternative vacation experience away from the hotel zone but minutes away from South Maui's best beaches,... View all property information
Make Enquiry
5 of 5 stars Reviewed 27 July 2014
We were traveling with our three kids and we really liked the house. Very comfortable with enough space for every one. By looking at the pictures we knew what to expect and were...
5 of 5 stars Reviewed 8 July 2014
The wife and I and are 3 children (9, 9 and 3) stayed here for 8 nights! Looked at many homes in Maui and man did I nail it with this one! Perfect location, perfect owners...
See all reviews
From
$1,456
Per Night
1 / 18
Payment Protection
4 Bedrooms, 3 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Trip Advisor Guests Describe L409 as 'Perfect & Well Worth the Money'. Visit our website for additional pictures to see why this villa is the most popular unit there based on travelers reviews. Luxurious 3000' Panoramic Oceanview Villa Available at Owner Direct Low Prices. This breath taking... View all property information
Make Enquiry
From
$215
Per Night
1 / 28
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (6) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Hot Tub
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Our professionally decorated spacious 2 bedroom 2 bathroom air conditioned condo has been tastefully furnished in modern decor with tropical accents. Our condo has a terrific layout with the bedrooms being on opposite sides of the condo. Each has its own private washroom, flat screen TV and... View all property information
Make Enquiry
5 of 5 stars Reviewed 18 September 2013
Once again, I loved everything about this condo. Beautiful first class furnishings, close to wonderful beaches in Wailea & Makena, & great shopping. The extra touches like the...
5 of 5 stars Reviewed 20 November 2012
The condo was beautifully furnished. We appreciated all the extras that made this stay so relaxing like the Tommy Bahama beach chairs, boogie boards, beach towels, & beach...
See all reviews
From
$309
Per Night
1 / 26
1 Bedroom, 2 Bathrooms, Sleeps 4
Details Reviews (4) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Beautifully remodeled 1 bedroom 1.5 bath Ekahi Townhouse Condo. Enjoy outdoor living on our large ground floor lanai with peaceful ocean views just 20 seconds from a quiet pool or take breakfast or year round sunset breaks on the upstairs lanai with sweeping ocean views. Completely remodeled in... View all property information
Make Enquiry
From
$477
Per Night
1 / 21
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (25) Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Mountain Views
  • Safe
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Beautifully remodeled and updated, our 1500 sf 2-Bedroom luxury condo in Wailea Resort's popular ocean front Wailea Ekahi Village is a few steps from gorgeous Keawakapu Beach. Fall asleep listening to the sounds of the surf . We are about a 5 iron (level 1-2 min walk) from the beach and Ekahi’s... View all property information
Make Enquiry
5 of 5 stars Reviewed 16 November 2014
Very nicely maintained and equipped, right down to the candles. No complaints - only compliments. The TV went out in one of the bedrooms and it was replaced the next day with a...
4 of 5 stars Reviewed 19 August 2014
Highly recommend this condo unit. would have given it an "excellent" if it had a good ocean view-- which it once did, until some new construction between it and the ocean...
See all reviews
From
$303
Per Night
1 / 16
1 Bedroom, 1 Bathroom, Sleeps 2
Details Reviews (5) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
  • Waterfront
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Fall 2014 Specials - please inquire! Wailea Ekahi 3C is a charming one bedroom, one bath, first floor garden view condo. It is a great choice for singles or couples wanting a reasonably priced condo close to the beach. The private garden setting is great for relaxing and enjoying the soft sands of... View all property information
Make Enquiry
5 of 5 stars Reviewed 4 November 2011
We love staying at Ekahi Village condos. We have stayed here multiple times, this last time in 3C. What we love most is that there are no surprises, everything is exactly as...
See all reviews
From
$5,240
Per Night
1 / 21
4 Bedrooms, 5 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Grill
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Slip into your own personal haven on the south coast of Maui. Home to the most discerning guests, Andaz Maui at Wailea's oceanfront, residential-style beach villas offer a secluded hideaway, just steps from the sands of Mokapu Beach. With the ocean as your backdrop, entertain on your own outdoor... View all property information
Make Enquiry
From
$512
Per Night
1 / 23
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (10) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Hot Tub
  • Internet Access
  • Pool
  • Satellite TV
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Beautiful three bedrooms, two bath condominium on the golf course with wrap around deck and ocean/golf views. Totally renovated in the fall of 2010 with granite throughout, stainless steel appliances, new carpet, paint and furniture. The living area is a large open floor plan with ceiling fans and... View all property information
Make Enquiry
5 of 5 stars Reviewed 9 October 2014
My friends an i find the Grand Champions condos to be quiet an peaceful. It's close to three great golf courses and several good restaurants. We live in Honolulu, where we have...
See all reviews
From
$530
Per Night
1 / 16
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Special Fall 2014 Rates ! Please inquire. Beautifully decorated three bedroom two bath condominium on the golf course with wrap around deck and ocean/golf views. Totally renovated the summer of 2011 with granite throughout, stainless appliances, new carpet, paint and furniture. The living area is... View all property information
Make Enquiry
From
$373
Per Night
1 / 19
1 Bedroom, 2 Bathrooms, Sleeps 2
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Please ask for our Fall 2014 Special Rates!! This beautiful condo has been upgraded throughout. It has a king bed, air conditioning in the living room, bedroom and ceiling fans throughout. The extended lanai runs the full length of the condo. Conveniently located, this condo is just a short walk... View all property information
Make Enquiry
5 of 5 stars Reviewed 16 July 2014
Very well appointed unit and beautifully maintained grounds. Went over for my niece's wedding. We had a pre-wedding function with 15 people and everything had we needed...
See all reviews
From
$233
Per Night
1 / 14
Payment Protection
1 Bedroom, 2 Bathrooms, Sleeps 4
Details Reviews (10) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Renovated 1 bedroom / 2 bathroom upstairs end unit with high-end furnishings and decorations. View is towards the island of Lanai, the West Maui coastline, and Ma'alaea Bay. Oversized master bedroom has a King size bed with study and sitting area. Large living/dining room area that harbors a... View all property information
Make Enquiry
4 of 5 stars Reviewed 9 November 2014
We had a great week at Wailea Ekahi, enjoying both the unit we rented and the location of the Ekahi resort. Would highly recommend for a couple or a family with young children...
4 of 5 stars Reviewed 17 August 2014
Skip and Mickey were fantastic from the beginning. They have taken special care to stock the condo with everything you might need for a relaxing, fun trip to the beach. From...
See all reviews
From
$1,857
Per Night
1 / 12
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Spend your vacation at Ho'olei luxury villas at Grand Wailea on Maui! Located just minutes from the world-class Grand Wailea Resort Hotel & Spa on Maui's southern shore, each two-story villa offers a luxurious home in paradise. Every villa has three bedrooms and 3.5 baths with finely appointed... View all property information
Make Enquiry
From
$232
Per Night
1 / 19
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (16) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Mountain Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Relax in the luxury and convenience of being in a world class resort, but enjoy the privacy and beauty of our fabulous 2 bd/2ba ground floor 'home away from home' that fronts the 7th Fairway of the famed Wailea Blue Course. Our spacious 1100 sq ft. unit has a tropical decor with world-class art... View all property information
Make Enquiry
5 of 5 stars Reviewed 7 November 2011
The condo and resort exceeded our expectations with the rental agent for the owners going above and beyond. Grand Champions is so convenient to the beautiful Shops of Wailea, the...
See all reviews
From
$7,418
Per Week
1 / 19
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (6) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Hot Tub
  • Internet Access
  • Pool
  • Satellite TV
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Fall 2014 - Super Special Rates for Ocean's Invitation! Please Inquire by E-Mail or Phone. Enjoy more than 2700 feet of comfortable yet lavish, uniquely and professionally decorated living space. The great room is aptly named with vaulted ceiling, HD TV, DVD, wireless internet and formal dining... View all property information
Make Enquiry
5 of 5 stars Reviewed 23 July 2014
Our vacation rental was clean, spacious, quiet and most importantly, had great views. If you are looking for a great family rental on your vacation, I highly recommend Ho'Olei!
See all reviews
From
$297
Per Night
1 / 16
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Two-bedroom, two bath Ekolu condo with breathtaking ocean view! 180 degrees spanning from West Maui, to Lanai, across Maalaea Bay, above the Wailea Resorts, past Molokini, and even beyond the island of Kahoolawe. Some condos provide fantastic sunsets part of the year, this one guarantees you'll... View all property information
Make Enquiry
5 of 5 stars Reviewed 11 November 2011
We booked this condo for 8 days. It was everything that had been described to us and more. The view was fantastic. Everything we needed was there, all we had to bring was our food...
See all reviews
From
$367
Per Night
1 / 18
Studio, 1 Bathroom, Sleeps 2
Details Reviews (6) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Pool
  • Satellite TV
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Wailea Ekahi 16B is located on the First floor with Ocean and Green Belt views. This Totally Remodeled Studio Condo is Beautifully furnished with Custom Bamboo Cabinets and Beautiful Tile throughout. New Queen Bed, Full First Class Kitchen, A/C, Ceiling fan, new Flat screen TV and Private lanai.... View all property information
Make Enquiry
4 of 5 stars Reviewed 27 November 2014
Great location ..... condo well set-up ....would reccommend having "basics" in kitchen eg. salt &pepper, oil, flour,sugar,tea or coffee,foil .... we have stayed in other condos...
See all reviews
From
$291
Per Night
1 / 7
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Wailea Ekolu provides a beautiful, relaxing environment and is located on the Wailea Blue golf course in Maui. This low-rise complex has beautiful grounds and unit 906 has a 180 degree view of the ocean!! The amenities include 2 solar heated pools, party pavilion, BBQ areas, Wailea Tennis Club... View all property information
Make Enquiry
From
$477
Per Night
1 / 19
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (14) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
DIRECT PANORAMIC OCEAN VIEWS. IF OTHERS DON'T SHOW IT, CHANCES ARE THEY DON'T HAVE IT. THE PHOTO TO THE LEFT TAKEN IN THE DINING ROOM. Stunning Ocean Views from recently renovated, lower village condominium. Two Master Suites, one with a King bed, the other with a King and twin brd, also a Queen... View all property information
Make Enquiry
5 of 5 stars Reviewed 30 September 2014
This is a well maintained, spacious two bedroom unit that was ideal for our family of four, with two girls aged 10 and 13. There was a short walk to the beach and pool, and the...
5 of 5 stars Reviewed 26 June 2014
Our party of two adult couples stayed for a week at 2A at the beginning of May, and thoroughly enjoyed this lovely and immaculately-maintained condo. The location allows easy...
See all reviews
From
$134
Per Night
1 / 24
1 Bedroom, 1 Bathroom, Sleeps 2
Details Reviews (9) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
FREE HIGH SPEED WIRELESS INTERNET AND UNLIMITED PHONE CALLS TO US MAINLAND AND CANADA!! NEWLY RENOVATED BATHROOM Enjoy sunny South Maui in one of our lovely and affordable Wailea studio units at the award-winning Wailea Grand Champions Villas. Both studios have been upgraded. Unit #22A has dark... View all property information
Make Enquiry
5 of 5 stars Reviewed 13 June 2013
My boyfriend and I stayed at Wailea Grand Champions for a couple of nights and we loved it. The property is beautifully maintained and it is located very close to several great...
See all reviews
From
$1,500
Per Night
1 / 45
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Gym
  • Hot Tub
  • Satellite TV
  • Sauna
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Modern Maui, our ocean view villa located in the heart of beautiful Wailea, combines all the best elements of a premium vacation home: Location, space, amenities and Grand Wailea Resort access. EXCLUSIVE GRAND WAILEA RESORT BENEFITS FOR OUR GUESTS: * On-demand, free transportation to and from... View all property information
Make Enquiry
From
$1,159
Per Night
1 / 32
Payment Protection
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (5) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Gym
  • Hot Tub
  • Internet Access
  • Mountain Views
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
'Wailea Beach Villas is the #1 Specialty Lodging in Wailea' - Trip Advisor 'Wailea Beach Villas is one of the top 100 hotels in the USA' - Conde Nast Readers Choice Award The Wailea Orchid is an amazing 3 bedroom / 3 full baths penthouse villa located in the prestigious Wailea Beach Villas.... View all property information
Make Enquiry
From
$576
Per Night
1 / 34
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Gym
  • Hot Tub
  • Internet Access
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Come stay with us here in sunny south Maui at our beautiful, lovingly remodeled ocean view home with private pool. There are amazing ocean views from almost all rooms in the house and the wrap around covered deck is perfect for indoor/outdoor style island living. Several beautiful white sand... View all property information
Make Enquiry
From
$185
Per Night
1 / 31
1 Bedroom, 2 Bathrooms, Sleeps 4
Details Reviews (6) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Mountain Views
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Aloha, E Komo Mai..... Welcome to Hale Makamae-Maui, a recently renovated luxury first floor condo in Wailea's premier Grand Champions Villas. Our home is unit #103 on the east side of the complex. Spend your vacation enjoying this 1 bedroom, 2 bath unit that provides ample space to spread out,... View all property information
Make Enquiry
4 of 5 stars Reviewed 23 April 2014
I must say this was the best condo we have rented in Maui, for being very generous with stocking you up with supplies. Soaps and paper towels in kitchen, in bathrooms-shampoo and...
5 of 5 stars Reviewed 10 September 2013
I can't say enough great things about this condo. It is centrally located in Wailea (we mostly walked everywhere). Beyond what you'd expect from a Hawaii rental (i.e. wi-fi and...
See all reviews
From
$431
Per Night
1 / 16
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (1) Make Enquiry
Amenities & Details
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Wailea Ekahi - Nicely appointed 2 bedroom, 2 bath condo with garden and partial oceanview in the Upper Village over looking the top pool. Kitchen along with Masterbath was just freshly renovated. There is a King, 2 twin beds and a queen sofa sleeper and 3 separate lanais with a gas bbq on the... View all property information
Make Enquiry
From
$154
Per Night
1 / 7
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 2
Details Reviews (9) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
JANUARY AVAILABILITY: Arrive Jan. 5th, depart Jan 9th AND arrive Jan. 26th, depart Jan. 29th - Call for pricing. (888) 320-0898. MARCH AVAILABILITY: Arrive Mar. 5th departh Mar. 7th AND arrive Mar. 14th, depart Marach 16th - Call for pricing (888) 320-0898 APRIL AVAILABILITY: Arrive Apr.... View all property information
Make Enquiry
5 of 5 stars Reviewed 25 January 2014
My partner and I came to Maui to run the Maui Oceanfront Marathon. We had booked a room at the Marriott for which the marathon had a room block. However, because we wanted to...
5 of 5 stars Reviewed 3 February 2013
Three of us (wife, toddler girl and myself) rented this place in early January. The condo is just the right size for us. We love the location. It's in an upscale area of Maui...
See all reviews
From
$378
Per Night
1 / 16
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Hot Tub
  • Internet Access
  • Pool
  • Satellite TV
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Special Fall 2014 Rates! Please inquire. Grand Champions 163 is a delightful ground floor two bedroom tiled throughout with the exception of the bedrooms. Beautiful, New Kitchen and Vanity Cabinets with Granite Counter tops in 2011. The living room has a cozy sectional sofa, flat screen TV, DVD,... View all property information
Make Enquiry
From
$1,042
Per Night
1 / 28
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Gym
  • Hot Tub
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Features of our 2500 sq oceanview condo include: Two full master suites Second bedroom can have two twins or king sized bed A den that closes off completely to sleep up two additional guests (either twin or king sized bed) Private Elevator Waterworks Bathrooms with large soaking tub Studio... View all property information
Make Enquiry
Go to map view
Book Online(11)
Use filters to find the best results!

Suitability

  • Wheelchair access (16)
  • Elder access (59)
  • Suitable for children (13)
  • Pet friendly (0)
  • Smoking allowed (0)

Amenities

  • Grill (176)
  • Internet (176)
  • Air Conditioning (142)
  • Other outdoor space (139)
  • All pools (132)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List
Wailea Vacation Rentals

Wailea is a great destination if you are looking to relax, unwind, and soak up some sun. With its amazing beaches and luxurious spas, it is a pampering and refreshing vacation that you will never want to return from. Why go back to a simple hotel room when your accommodations can make you continue feeling like royalty even after the activities of the day are done? With a wide variety of vacation rentals, from cozy condos to large beachside villas, you can experience Wailea like one of the locals in your very own rental home no matter what your budget or space needs are.

A Wailea Vacation

No matter how you like to relax, there is sure to be a great place to do it in Wailea. From an indulgent day at the Spa Grande to tee time at Wailea Old Blue Course, it is full of ways to treat yourself and have a great time. If you're feeling adventurous, Hawaiian Sailing Canoe Adventures allows small groups to enjoy sailing in an outrigger canoe, or if you just want to relax on the beach, Keawakapu is a perfect choice for everything from sunning to snorkeling. Whatever the day's adventures bring, choosing a vacation rental to stay in means you can go back to the privacy and comfort of your very own rental home away from home for a truly authentic experience.

Family-Friendly Wailea

From exploring the beaches to catching a dinner show at Honua'ula Luau, there are a variety of great experiences for children when vacationing to Wailea. With vacation rentals, you can rent a property to accommodate nearly any size family, and it is a fantastic excuse to bring everyone along. Without having to pay for extra hotel rooms, it can also be a great money saver when traveling with a large group. Enjoying a Wailea vacation with the entire family at your very own rental home will be sure to create wonderful memories for years to come.