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
All 226 Rentals in Wailea
loading...
Sort by
From
$369
Per Night
1 / 19
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (1) Make Inquiry
From
$190
Per Night
1 / 11
Payment Protection
2 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
Details Make Inquiry
From
$295
Per Night
1 / 7
Payment Protection
1 Bedroom, 2 Bathrooms, Sleeps 3
Details Make Inquiry
From
$290
Per Night
1 / 17
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
Details Make Inquiry
Amenities & Details
  • Hot Tub
  • TV
  • Washer
  • Dryer
  • Microwave
  • Stereo System
  • DVD Player
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • 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 Inquiry
From
$190
Per Night
1 / 23
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 2
Details Reviews (1) Make Inquiry
Amenities & Details
  • Dryer
  • Microwave
  • Grill
  • Washer
  • Dishwasher
  • Hot Tub
  • DVD Player
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
We are pleased to offer our new 1 bedroom,1 bath upper level condo for rental. It has been redecorated throughout, is newly furnished and equipped to high standards, is very comfortable and located in well maintained lush Ekahi Village. The condo is close to the best of everything we enjoy, 3+... View all property information
Make Inquiry
5 of 5 stars Reviewed September 15, 2014
I thoroughly enjoyed my time at the condo, a few little issues which were actually my fault but these were seen to immediately. All the facilities that you would want, Weather...
See all reviews
From
$290
Per Night
1 / 16
1 Bedroom, 1 Bathroom, Sleeps 2
Details Reviews (3) Make Inquiry
Amenities & Details
  • Waterfront
  • Air Conditioning
  • Pool
  • Ceiling Fans
  • DVD Player
  • Internet Access
  • Grill
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Please ask about our Fall 2014 Discounted Rates!! Wailea Ekahi Village 4E second floor condominium is adjacent to a landscaped ravine and has beautiful tropical garden views. This location provides a quiet location, away from any road noise and a couple minutes' walk to the main swimming pool,... View all property information
Make Inquiry
From
$695
Per Night
1 / 44
Payment Protection
3 Bedrooms, 4 Bathrooms, Sleeps 10
Details Reviews (27) Make Inquiry
Amenities & Details
  • TV
  • Gym
  • Hot Tub
  • Dishwasher
  • Refrigerator
  • Safe
  • Parking
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Our luxury ocean view town home is located in the gated community of Ho'olei, across the street from the Grand Wailea Resort. Our 3 bedroom/3bath home comfortably accommodates up to 10 guests. Our home features a finely appointed interior, private elevator, and attached garage. Built in 2007,... View all property information
Make Inquiry
5 of 5 stars Reviewed April 12, 2014
Our first trip to Maui, Hawaii for our Daughters wedding. We were a family of 8 (including grandparents).Plenty of room,Condo is immaculate, amazing, beautiful, photo's were...
5 of 5 stars Reviewed December 30, 2013
Upon our arrival, we immediately knew we hit the jackpot! The spacious condo was beautiful and full of every necessity needed for our vacation. The views from the lanai were...
See all reviews
From
$199
Per Night
1 / 21
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 2
Details Reviews (5) Make Inquiry
Amenities & Details
  • TV
  • DVD Player
  • Washer
  • Dryer
  • Grill
  • Patio
  • Refrigerator
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • 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 Inquiry
5 of 5 stars Reviewed November 28, 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 September 11, 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
$260
Per Night
1 / 16
1 Bedroom, 1 Bathroom, Sleeps 2
Details Reviews (5) Make Inquiry
Amenities & Details
  • Internet Access
  • Pool
  • Refrigerator
  • VCR
  • Air Conditioning
  • Wi-Fi
  • Microwave
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
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 Inquiry
5 of 5 stars Reviewed November 4, 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
$200
Per Night
1 / 17
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 2
Details Make Inquiry
Amenities & Details
  • # Of Bathrooms
  • Guest Count
  • Number Of Bedrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • 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 Inquiry
Get the List
From
$225
Per Night
1 / 13
Payment Protection
1 Bedroom, 2 Bathrooms, Sleeps 2
Details Reviews (1) Make Inquiry
Amenities & Details
  • Parking
  • Dishwasher
  • Stove
  • Hot Tub
  • Grill
  • Microwave
  • Washer
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Looking for a completely remodeled, gorgeous condo? Experience one of Wailea's finest........... EVERYTHING in this beautifully appointed unit is BRAND NEW and is professionally decorated. The ground floor condo features high end finishes and furnishings which include: beautiful custom walnut... View all property information
Make Inquiry
5 of 5 stars Reviewed May 14, 2014
We travelled to Maui in March, stayed for two weeks in a lovely condo at Grand Champions, Wailea. We went with 10 other friends, who also rented condos there. The manager...
See all reviews
From
$1,250
Per Night
1 / 23
Payment Protection
4 Bedrooms, 3 Bathrooms, Sleeps 10
Details Make Inquiry
Amenities & Details
  • DVD Player
  • Grill
  • Washer
  • Refrigerator
  • Stove
  • Dishwasher
  • Hot Tub
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
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 Inquiry
From
$139
Per Night
1 / 25
Payment Protection
1 Bedroom, 2 Bathrooms, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Stove
  • Grill
  • DVD Player
  • Patio
  • Microwave
  • Dryer
  • TV
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • 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 Inquiry
From
$210
Per Night
1 / 24
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (5) Make Inquiry
Amenities & Details
  • DVD Player
  • Refrigerator
  • Internet Access
  • Satellite TV
  • Telephone
  • Stereo System
  • Microwave
  • Ceiling Fans
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
This 2-bedroom condo is comfortably appointed, and located in a great spot on property. The spacious living room opens to the Lanai, where there is ample space for stretching out and relaxing in the sun, barbecuing on your own private grill, or admiring the tropical grounds of The Palms at Wailea.... View all property information
Make Inquiry
4 of 5 stars Reviewed August 2, 2014
We loved the location of the property. Maui Car and Condo was great to work with. They are very reliable, retuned my email every quickly and made the process to check in very...
4 of 5 stars Reviewed July 25, 2014
This was our first trip with our grandaughters. The location is ideal for the snorkling beaches with lifegaurds. The location is also close to all types of dining and fine...
See all reviews
From
$195
Per Night
1 / 13
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (7) Make Inquiry
Amenities & Details
  • TV
  • Ceiling Fans
  • VCR
  • Internet Access
  • Air Conditioning
  • Dishwasher
  • Stereo System
  • Pool
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This is a great property with a real tropical "Tommy Bahama" feel...Upscale furnishings and attention to detail complete this two bedroom two bath apartment. It is a first floor location with a spacious covered lanai-perfect for reading the latest novel or enjoying a nap . Each room has a ceiling... View all property information
Make Inquiry
From
$225
Per Night
1 / 24
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (6) Make Inquiry
Amenities & Details
  • DVD Player
  • Refrigerator
  • Telephone
  • Stereo System
  • Ceiling Fans
  • Satellite TV
  • Microwave
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Welcome to your home away from home! This beautifully remodeled 2-bedroom condo is a guest favorite. You'll enjoy the open layout, as well as the many upgrades that this condo has to offer. Entering the condo, you'll find yourself in the spacious and bright living room, which has been newly tiled... View all property information
Make Inquiry
4 of 5 stars Reviewed October 26, 2014
We cannot seem to branch out from the Palms at Wailea having stayed here a dozen or more times in the last decade. We have used many units for many purposes bring anywhere from 2...
2 of 5 stars Reviewed April 19, 2013
We stayed here April 11 - 20, 2013. This is actually a relatively nice unit. Great patio deck with pass through window from kitchen. Nice decorations and televisions. I like...
See all reviews
From
$695
Per Night
1 / 30
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (18) Make Inquiry
Amenities & Details
  • Hot Tub
  • TV
  • Parking
  • Refrigerator
  • Microwave
  • Dishwasher
  • Grill
  • Garage
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Unbelievable 2 bedroom plus den / 2 bath penthouse villa located in the prestigous Wailea Beach Villas. Second floor location with 2000 interior square feet and 375 square foot covered lanai. Formal entry hall with artwork. Spacious living room with Tommy Bahama furniture. Dining room with table... View all property information
Make Inquiry
From
$995
Per Night
1 / 32
Payment Protection
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (5) Make Inquiry
Amenities & Details
  • Parking
  • TV
  • DVD Player
  • Microwave
  • Hot Tub
  • Safe
  • Dishwasher
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
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 Inquiry
From
$170
Per Night
1 / 23
Payment Protection
1 Bedroom, 2 Bathrooms, Sleeps 4
Details Reviews (9) Make Inquiry
Amenities & Details
  • Microwave
  • Refrigerator
  • Washer
  • Dishwasher
  • Dryer
  • Stove
  • VCR
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Wailea Ekahi is a wonderful beachfront complex. It boasts 4 pools, a great beach side pavilion . It is part of the Wailea Golf association, so you can enjoy a discount at all the famous Wailea golf courses, or join the Wailea tennis club nearby. 43 B is a single-level, ground floor condominium... View all property information
Make Inquiry
1 of 5 stars Reviewed September 27, 2014
I booked this condo in July as 3 of us are attending a conference. I was notified that my final payment was due, which I paid promptly. On Mon. I received a notification that my...
5 of 5 stars Reviewed April 3, 2014
We ran across this particular condo because we needed to fill in 3 additional days on our recent stay in Maui. The only regret is we didn't know about it earlier. The condo itself...
See all reviews
From
$1,595
Per Night
1 / 71
Payment Protection
4 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (9) Make Inquiry
Amenities & Details
  • Grill
  • Wi-Fi
  • Refrigerator
  • Pool
  • Fax
  • Dishwasher
  • Air Conditioning
  • Stereo System
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
In all of Hawai'i, Mer Et Soleil Villa K408, is one of the most spectacular private residences available for visitor accommodations. This elegantly contemporary residence boasts over 3,300 square feet of indoor and outdoor prime "Tower Building" living space. With 4 bedrooms, a wine fridge, a baby... View all property information
Make Inquiry
From
$900
Per Night
1 / 20
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (1) Make Inquiry
Amenities & Details
  • Grill
  • Washer
  • Microwave
  • Safe
  • Dishwasher
  • Hot Tub
  • DVD Player
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
If you prefer spaciousness and the utmost in comfort for your family, then instead of getting two or three hotel rooms, this property offers an ideal alternative. Every superlative applies to this property but let's just say it's the ultimate residence resort in all of Hawaii. Wailea Beach Villas... View all property information
Make Inquiry
5 of 5 stars Reviewed August 18, 2014
From the moment we arrived with the greeter to the accommodations, the grounds and the concierge Tracy, it was perfect. Great condo, stocked better than our home, beautiful...
See all reviews
From
$700
Per Night
1 / 14
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (1) Make Inquiry
Amenities & Details
  • Pool
  • Refrigerator
  • Hot Tub
  • Dishwasher
  • Parking
  • DVD Player
  • Microwave
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
There's no doubt this is the best beachfront choice on Maui if you have 6-8 persons, This long-time favorite condo resort on Maui, Makena Surf, is now better than ever with recently renovated units and wonderful "semi-private" kid-friendly beaches. Please be sure to tell us how many are in your... View all property information
Make Inquiry
From
$132
Per Night
1 / 7
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 2
Details Reviews (9) Make Inquiry
Amenities & Details
  • DVD Player
  • Dishwasher
  • Washer
  • Parking
  • Refrigerator
  • Patio
  • Stove
  • Hot Tub
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • 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 Inquiry
5 of 5 stars Reviewed January 25, 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 February 3, 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
$755
Per Night
1 / 15
3 Bedrooms, 4 Bathrooms, Sleeps 8
Details Reviews (1) Make Inquiry
Amenities & Details
  • Washer
  • Hot Tub
  • DVD Player
  • Dishwasher
  • Microwave
  • Pool
  • Safe
  • Garage
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
HO'OLEI VILLAS: 3-bedroom 3.5-bath luxury vacation villas Gated residential condo resort w/ maximum privacy and security in the Wailea area, Wailea Beach walking distance away Fully equipped gourmet kitchens Spacious living area with sliding doors that lead out to a large lanai Large deck area... View all property information
Make Inquiry
From
$1,250
Per Night
1 / 83
Payment Protection
3 Bedrooms, 4 Bathrooms, Sleeps 6
Details Reviews (1) Make Inquiry
Amenities & Details
  • Pool
  • Patio
  • Refrigerator
  • Microwave
  • Dishwasher
  • Fax
  • Hot Tub
  • Stove
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Reserve this villa C201 Castaway Cove and receive all of the following newly expanded and enhanced benefits (and more) now!Our posted “Affordable Luxury” rates apply for all reservations. Reserve at anytime, subject to availability. If we have availability, you get our posted already-affordable... View all property information
Make Inquiry
5 of 5 stars Reviewed August 14, 2014
We rented Castaway Cove, Unit C201 at the Wailea Beach Villas on Maui in July 2014. This unit is managed by Tropical Villas Vacations. Our first visit to Maui and "wow" what a...
See all reviews
From
$750
Per Night
1 / 17
3 Bedrooms, 4 Bathrooms, Sleeps 8
Details Reviews (1) Make Inquiry
Amenities & Details
  • Microwave
  • Hot Tub
  • Grill
  • Safe
  • Patio
  • Garage
  • Parking
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
PLEASE NOTE: OUR CALENDAR APPEARS OPEN BECAUSE WE OWN 5 HOMES AT THE HO'OLEI RESORT. IN MOST CASES, I DO HAVE A HOME AVAILABLE! Come enjoy our Luxury Residence in what we call our Executive Model! This home is the Hibiscus Model, which is the largest home at Ho'olei (3,301 sq. ft. and a 686 sq.... View all property information
Make Inquiry
5 of 5 stars Reviewed August 12, 2013
We stayed in unit 24-1. The accommodations were first class. There aren't enough words to describe the luxury. We took our adult kids and their children. There was lots of...
See all reviews
From
$450
Per Night
1 / 16
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (5) Make Inquiry
Amenities & Details
  • DVD Player
  • Washer
  • Microwave
  • Dishwasher
  • Pool
  • Hot Tub
  • Grill
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
This long-time oceanfront favorite condo rental on Maui, Makena Surf, is now better than ever with recently renovated units and wonderful "semi-private" kid-friendly beaches. Featuring beachfront, oceanfront and oceanview condo accommodations. 2-8 person occupancy. Please be sure to tell us how... View all property information
Make Inquiry
5 of 5 stars Reviewed November 13, 2014
From the moment we walked in the door, we were in love with our condo. The furnishings were perfect, the view was spectacular, the beach was fabulous, and the management was very...
5 of 5 stars Reviewed August 2, 2012
The place, location, beach was perfect for my family. We had three little kids and it was ideal. I will be back.
See all reviews
From
$895
Per Night
1 / 42
Payment Protection
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (81) Make Inquiry
Amenities & Details
  • Grill
  • TV
  • Microwave
  • DVD Player
  • Gym
  • Garage
  • Dishwasher
  • Hot Tub
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Luxury awaits in this exquisite three bedroom, three full baths, 2500 square feet Penthouse Villa J205 with gorgeous ocean view. The Aloha Kai Suite is elegant and refined to the last detail--sophisticated furnishings and spectacular art. Formal entry hall. Spacious living room. Formal dining with... View all property information
Make Inquiry
5 of 5 stars Reviewed December 5, 2014
the first words out of my moms' mouth when we got inside the condo was that she had never seen a place like this in her 65 years!!! There was 3 generations of family on this...
5 of 5 stars Reviewed August 24, 2014
We were so thrilled with our stay at unit J205 Wailai Villas. From the moment we arrived and were met with a lovely welcome basket, we felt right at home. It was a perfect amount...
See all reviews
From
$250
Per Night
1 / 8
Payment Protection
1 Bedroom, 2 Bathrooms, Sleeps 5
Details Reviews (17) Make Inquiry
Amenities & Details
  • Dishwasher
  • DVD Player
  • Parking
  • Dryer
  • Refrigerator
  • VCR
  • Patio
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Located on world famous Keawakapu Beach in Wailea, Ekahi Village is one of the most sought after locations. Our totally renovated condo offers complete privacy, but is only steps to the beach. Unwind after a day at the beach or pool by watching our 46" Sony Bravia flat screen with surround sound... View all property information
Make Inquiry
4 of 5 stars Reviewed February 27, 2013
My husband and I stayed in this unit for 3 weeks another couple joined us for 2 weeks. The owner was easy to work with and provided all the needed information to make our stay...
See all reviews
From
$795
Per Night
1 / 14
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Reviews (29) Make Inquiry
Amenities & Details
  • Microwave
  • Dishwasher
  • Ceiling Fans
  • Stereo System
  • Grill
  • Hot Tub
  • Air Conditioning
  • Pool
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
The “crown jewel” of Wailea- A gated beachfront location, an oceanfront adult pool with a Jacuzzi, a children’s pool with a Jacuzzi in a garden setting- all with attendants offering towel, umbrella and chaise lounge service. There is a top notch work out facility and business center.... View all property information
Make Inquiry
5 of 5 stars Reviewed October 3, 2014
Another wonderful holiday at I203 in beautiful Wailea. The house is so conventiently located for pool/beach access as well as to restaurants and main roads. Looking forward to...
5 of 5 stars Reviewed September 20, 2014
Excellent hotel alternative for Adults who like to swim, sun, exercise and shop in a low key, well managed waterfront location @ Wailea. Five story "Penthouse units" near Shops at...
See all reviews
From
$4,500
Per Night
1 / 21
4 Bedrooms, 5 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • Grill
  • Internet Access
  • DVD Player
  • Hairdryer
  • TV
  • Safe
  • Stereo System
  • Satellite TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • 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 Inquiry
From
$800
Per Night
1 / 16
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Microwave
  • Hot Tub
  • Parking
  • Patio
  • Pool
  • Grill
  • Refrigerator
  • Safe
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Choose from our selection of PREMIER beachfront units. This is our preferred property choice for those looking to be within walking distance of the other hotels, restaurants, and shops in Wailea for under $1000/night. Please be sure to tell us how many are in your party, how many adults and how... View all property information
Make Inquiry
From
$210
Per Night
1 / 24
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Ceiling Fans
  • Stereo System
  • Toaster
  • Internet Access
  • Fitness Room
  • DVD Player
  • Microwave
  • VCR
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Grand Champions 123 is located in a quiet setting in Wailea. Large green belts, manicured grounds and wide golf course fairways abound. To the east, views of Mt. Haleakala, the world’s largest dormant volcano. To the west, the sparkling blue Pacific Ocean. A quieter, more peaceful resort, this... View all property information
Make Inquiry
From
$750
Per Night
1 / 25
3 Bedrooms, 4 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • Dishwasher
  • Parking
  • Hot Tub
  • Safe
  • Refrigerator
  • Garage
  • Patio
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
This spacious, professionally decorated town home has all the comforts you expect from a five star experience. The world renowned Grand Wailea resort located across the street, offers a world class spa, shopping and beach. Whether you group has many children, adults or seniors, this home is... View all property information
Make Inquiry
From
$250
Per Night
1 / 16
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (13) Make Inquiry
Amenities & Details
  • Heated Pool
  • Grill
  • DVD Player
  • Hot Tub
  • Wi-Fi
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Wailea Grand Champions Golf Villas is a modern property located between the Wailea Blue Golf Course and the Wailea Tennis Club. This quiet low density development consists of twenty mostly two-story buildings set amongst lush tropical landscaping and is a convenient short walk to the renowned... View all property information
Make Inquiry
5 of 5 stars Reviewed November 5, 2012
Since I was the vacation planner for 6 other people beside's myself, I was also charged with finding a suitable place for us to hang our hats at the end of each day. By a stroke...
See all reviews
From
$1,795
Per Night
1 / 31
3 Bedrooms, 4 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • DVD Player
  • Microwave
  • Satellite TV
  • Internet Access
  • TV
  • Ceiling Fans
  • Dryer
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Ocean Bliss is a stunning beachfront estate that provides the best of all worlds...Privacy and ocean access as the house borders South Maui's Polo Beach with it's golden sands and shallow swimming area on one side of the villa and a dramatic lava rock beach on the other side. The vistas of the sea... View all property information
Make Inquiry
From
$500
Per Night
1 / 19
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Microwave
  • Parking
  • Patio
  • Grill
  • Hot Tub
  • Washer
  • Refrigerator
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Choose from our selection of PREMIER oceanview units. This is our preferred property choice for those looking to be within walking distance to the beach and the other hotels, restaurants, and shops in Wailea for under $500/night. Please be sure to tell us how many are in your party, how many... View all property information
Make Inquiry
From
$250
Per Night
1 / 24
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Refrigerator
  • DVD Player
  • Dishwasher
  • Air Conditioning
  • Fitness Room
  • Microwave
  • Ceiling Fans
  • Toaster
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Look no further! This open and spacious premium condo at The Palms at Wailea will be ideal for your island getaway! Major renovations throughout, a partial ocean view, and central A/C* are just some of the features of this gorgeous 2-Bedroom condo. Pride in ownership is apparent when entering this... View all property information
Make Inquiry
From
$159
Per Night
1 / 31
1 Bedroom, 2 Bathrooms, Sleeps 4
Details Reviews (6) Make Inquiry
Amenities & Details
  • Microwave
  • Dryer
  • Washer
  • Safe
  • Stove
  • Dishwasher
  • Refrigerator
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • 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 Inquiry
4 of 5 stars Reviewed April 23, 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 September 10, 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
$440
Per Night
1 / 16
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (6) Make Inquiry
Amenities & Details
  • Hot Tub
  • Grill
  • Wi-Fi
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Wailea Elua Village is an exclusive beachfront property located in the heart of the resort community of Wailea. This relaxing low-density property consists of two-story buildings terraced over twenty-four acres of immaculate tropical landscaping. Beautiful Ulua Beach fronting the property is a... View all property information
Make Inquiry
From
$725
Per Night
1 / 24
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (21) Make Inquiry
Amenities & Details
  • Guest Count
  • Number Of Bedrooms
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Located 'down in front' on the water at Wailea Elua Village, this Second Floor AIR CONDITIONED Condominium recently received a TOTAL Custom-Designed Interior Renovation. Everything is new - flooring, furniture, artwork, lighting, and fixtures - including a fully upgraded kitchen with granite... View all property information
Make Inquiry
5 of 5 stars Reviewed September 24, 2013
This is the condo to rent! I spent a long time looking at condos on various websites and I feel so fortunate to have found this condo! The owners are easy to work with and...
5 of 5 stars Reviewed August 4, 2011
This was a very beautiful, upscale condo with a wonderful, well-stocked kitchen; there was a grill so we had 3 meals in and enjoyed dining on the lanai -- gorgeous view. It was...
See all reviews
From
$119
Per Night
1 / 7
1 Bedroom, 2 Bathrooms, Sleeps 4
Details Reviews (3) Make Inquiry
Amenities & Details
  • DVD Player
  • Grill
  • Stove
  • Dishwasher
  • Refrigerator
  • Stereo System
  • Washer
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Location: Ekahi Village, Wailea, South Maui, Maui, Hawaii, USA (Maiu Airport & Town of Kahalui 12 mi. Kihei Town 6 mi.) Accommodations: Condo, 1 Bedroom + Convertible bed(s), 2 Baths (Sleeps 2-4) Keywords: Condominium This Wialea Ekahi unit is a one bedroom, two bath unit (with a queen... View all property information
Make Inquiry
5 of 5 stars Reviewed November 4, 2014
We would like any potential renter to read this review and say to themselves, "Ah, finally I've found the place I've been looking for!" We know what it's like to pick a place...
5 of 5 stars Reviewed July 30, 2014
Our family of four stayed at this condo for five days in July. It was a comfortable and pleasant home away from home. Pros: great price for Wailea area, very responsive owner...
See all reviews
From
$400
Per Night
1 / 19
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (37) Make Inquiry
Amenities & Details
  • Microwave
  • Refrigerator
  • Dryer
  • Washer
  • Grill
  • Dishwasher
  • DVD Player
  • Stove
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Wow ! What a GREAT view! We've heard this comment many times from vacation rental guests and friends visiting our Maui Wailea, Ekahi Village condo (28D). Sweeping ocean views greet you as you enter, and are visible from nearly every room. The walk to the beach is less than four minutes.When you... View all property information
Make Inquiry
5 of 5 stars Reviewed December 12, 2014
Ekahi village is our favorite place to stay in Wailea with condos just steps to one of the best beaches in Maui, numerous pools, great grounds and a low-key family atmosphere...
5 of 5 stars Reviewed September 21, 2014
I have been to Ekahi for 5 years, staying in other condos. None compare with this one. Stunning views of the vegetation, ocean, and small pool. The condo is very cozy and has...
See all reviews
From
$395
Per Night
1 / 29
2 Bedrooms, 2 Bathrooms, Sleeps 5
Details Reviews (3) Make Inquiry
Amenities & Details
  • DVD Player
  • Stove
  • Grill
  • Washer
  • TV
  • Ceiling Fans
  • Microwave
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
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 Inquiry
5 of 5 stars Reviewed July 27, 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 July 8, 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
$174
Per Night
1 / 32
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (30) Make Inquiry
Amenities & Details
  • Hot Tub
  • Pool
  • Ceiling Fans
  • DVD Player
  • Dishwasher
  • TV
  • Refrigerator
  • Deck
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
The nearby Ulua and Mokapu Beaches are a quick drive down the hill from the The Grand Champions Villas in Wailea. The complex is surrounded by lovely tropical gardens. It is located in the exclusive Wailea Resort. The complex offers two swimming pools, sundecks, spa tubs, restrooms, showers and... View all property information
Make Inquiry
5 of 5 stars Reviewed October 6, 2014
We stayed in unit 48 for 9 nights in mid-September. We were extremely pleased with our stay, and I'm hoping that this post is helpful for others. This unit was in much better...
3 of 5 stars Reviewed April 2, 2012
We've stayed in units in the Grand Champions complex before. Not on the beach, but an easy 3 minute walk to the Shops at Wailea....and easy beach access from the adjoining...
See all reviews
From
$200
Per Night
1 / 14
Payment Protection
1 Bedroom, 2 Bathrooms, Sleeps 4
Details Reviews (10) Make Inquiry
Amenities & Details
  • Refrigerator
  • Microwave
  • Grill
  • Parking
  • DVD Player
  • Washer
  • Dryer
  • Stereo System
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • 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 Inquiry
4 of 5 stars Reviewed November 9, 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 August 17, 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
$115
Per Night
1 / 24
1 Bedroom, 1 Bathroom, Sleeps 2
Details Reviews (9) Make Inquiry
Amenities & Details
  • Grill
  • TV
  • Washer
  • Microwave
  • Dryer
  • DVD Player
  • Parking
  • Hot Tub
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • 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 Inquiry
5 of 5 stars Reviewed June 13, 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
$275
Per Night
1 / 22
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Reviews (2) Make Inquiry
Amenities & Details
  • Parking
  • Refrigerator
  • Microwave
  • Hot Tub
  • Washer
  • TV
  • Dryer
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
This ground floor corner villa at Grand Champions Resort features three bedrooms, two baths, a fully equipped gourmet kitchen, and two lanais. Surrounded by the manicured fairways of Wailea's famed Blue Golf Course and the spectacular grounds of the Wailea Tennis Club, this quiet, well-managed... View all property information
Make Inquiry
4 of 5 stars Reviewed December 21, 2013
We were a group of 6 adults and one toddler and we felt totally at home here and would definitely recommend this condo our friends. Set in an amazing area with world class...
See all reviews
From
$265
Per Night
1 / 16
1 Bedroom, 1 Bathroom, Sleeps 4
Details Reviews (25) Make Inquiry
Amenities & Details
  • Washer
  • DVD Player
  • TV
  • Parking
  • Refrigerator
  • Grill
  • Microwave
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
20B is a delightful, spacious condo in the Lower Village of Ekahi, at the bottom of the hill and closest to the beach. In fact it's only a two minute walk to world renowned Keawakapu Beach! And because the walk path is nearly level, you avoid hiking up the hill after being at the beach all day --... View all property information
Make Inquiry
5 of 5 stars Reviewed October 1, 2014
The condo was beautiful and had all the amenities we could ask for. The grounds were well maintained and had several pools to choose from. The beach was close and excellent. I...
5 of 5 stars Reviewed September 29, 2014
It was wonderful.... Great location and VERY clean. We loved it and will return to this same condo. thanks, Greg
See all reviews
From
$1,295
Per Night
1 / 83
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Dishwasher
  • Grill
  • Air Conditioning
  • Parking
  • Hot Tub
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Reserve this villa K507 Wailea Seashore Suite, a premiere ultra-deluxe and all-new top-floor panoramic full ocean view villa and receive all of the following newly expanded and enhanced benefits (and more) now!Our posted “Affordable Luxury” rates apply for all reservations. Reserve at anytime,... View all property information
Make Inquiry
Go to map view
Book Online(15)
Use filters to find the best results!

Suitability

  • Wheelchair access (16)
  • Elder access (60)
  • Suitable for children (21)
  • Pet friendly (0)
  • Smoking allowed (0)

Amenities

  • Grill (183)
  • Internet (181)
  • Air Conditioning (149)
  • Other outdoor space (141)
  • All pools (137)
  • 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

More Romance destinations:

More Beach destinations:

More Family destinations:

Filter search results by:
Book Online(15)

Suitability

  • Wheelchair access (16)
  • Elder access (60)
  • Suitable for children (21)
  • Pet friendly (0)
  • Smoking allowed (0)

Amenities

  • Grill (183)
  • Internet (181)
  • Air Conditioning (149)
  • Other outdoor space (141)
  • All pools (137)
  • View all amenities
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.