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Condos and Vacation Rentals in Wailea, HI

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    Travelers to Wailea are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 25
    5 of 5 bubbles (18) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    5 of 5 bubbles (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    5 of 5 bubbles (3) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 74
    4.5 of 5 bubbles (3) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    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
    Location Information
    Wailea, Maui 96753
    4 of 5 bubbles Reviewed January 22, 2017
    This condo was great for location and proximity to good walking in Wailea. The pool and beach area was amazing. The Barbecue facilities were at the opposite side of the complex...
    5 of 5 bubbles Reviewed October 25, 2016
    This place is truly a paradise of sorts. Close to the beach and the condo itself is very clean, well kept and has everything you need to enjoy your stay. The Condo is stocked...
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    1 / 35
    5 of 5 bubbles (3) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Waterfront
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    • Wi-Fi
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    • Mountain Views
    • Ocean Views
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    We recently remodeled our condo with all new upgraded tumbled travertine-style flooring, new window shades and new furniture. Why stay in a resort hotel like the Four Season or the Grand Wailea when you can save 2/3 of the cost and not have to purchase every meal in a resort hotel? You'll have a... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed December 11, 2016
    The owner, Cara, was great to deal with by email, everything that was represented of the property was true. It was a lovely home away from home, very comfortable and great...
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    1 / 14
    5 of 5 bubbles (8) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    SUMMER SPECIAL: Stay 2 weeks in June/July for only $175/night. Simply request the special rate when you inquire. If you love to swim in the ocean, if you have kids who like to play in the sand and go wading, if you want to stroll on a beach holding hands as the sun sets, then our well-equipped,... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed November 10, 2016
    There were 7 adults why stayed in this place. It was dated, but clean and lovely! Would stay again!!
    4 of 5 bubbles Reviewed October 30, 2016
    A lovely comfortable condo with plenty of space for two couples, equal standard rooms and bathrooms for each. A couple of minutes walk to an uncrowded extremely clean beach, and...
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    1 / 15
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed March 29, 2015
    We were very pleased with our stay. Condo fully stocked. Beautiful views. Convenient location. Comfortable and roomy. Would stay here again.
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    1 / 28
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Bring the most special person in your life to our beautiful condo. Our condo has one of the best ocean views in ekolu. Experience the pleasure of tropical living in a quiet and relaxing environment. Enjoy a tranquil retreat overlooking the ocean with breathtaking views of Molokini. Completely... View all property information
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    Wailea, Maui 96753
    1 / 23
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Aloha Maui vacation planners, Welcome to beautiful Wailea, a Master Planned Community which ensures good community planning and utilizes design guidelines to help preserve Maui's sophisticated island environment. Grand Champions Villas is located in the heart of Wailea and nestled between The... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed October 6, 2016
    This was a wonderful vacation for myself, husband and daughter. We were delighted with our stay and all the tips left by Paul and Jessica. So close to beaches and excellent food...
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    1 / 21
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Ocean Views
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    • Hot Tub
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    QUIET PRIVACY IN PARADISE This is a luxurious one-bedroom two-bath ground floor villa tucked away in a private and quiet corner in one of the nicest locations in the property. Often the only sound you will hear is the waves crashing on the nearby beaches. The Palms at Wailea is one of the upscale... View all property information
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    Wailea, Maui 96753
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    1 / 24
    5 of 5 bubbles (24) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 3 | Quick View
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    • Washer
    • Mountain Views
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • x
    About this property
    Enjoy sitting on your lanai enjoying spectacular ocean views in a peaceful, private 1 bedroom, 1 and 1/2 baths, 550 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... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed 3 days ago
    We arrived at Maui Hale Olina (Maui House Of Joy) as Dennis and Cynthia, the wonderful hosts have named the cottage, on February 8th, 2017 and what a beautiful surprise that day...
    5 of 5 bubbles Reviewed 5 weeks ago
    Such a beautiful cottage!! Pictures do not do it justice. Dennis was amazing and very helpful upon arrival, even brought us fresh fruit from his trees. Very clean well cared for...
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    1 / 14
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Satellite TV
    • DVD Player
    • Shared Outdoor Pool...
    • Ocean Views
    • Grill
    • Wi-Fi
    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Our beautiful ocean view unit is situated in upper Wailea Ekahi Village. It is a 952 square foot unit on the second floor with one bedroom and two full bathrooms. It comfortably sleeps 4 guests. Two in the bedroom and two on the memory foam sofa sleeper. It is conveniently located near one of the... View all property information
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    Wailea, Maui 96753
    1 / 24
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Hot Tub
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    • Sauna
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    TAKE ADVANTAGE OF THE BEST DEAL IN HOOLEI. SPECIAL CANCELLATION RATE IS FOR MINIMUM 7 NIGHT BOOKING DURING 5/7-17/2016. Check availability and BOOK before its gone! Newly built state-of-the-art luxury townhome. Beautiful three bedroom, three and one-half baths, 3363 square foot villa with large... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed November 29, 2016
    Well stocked kitchen, very nice bathrooms, ample sized bedrooms except the smaller one downstairs. Good location.
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    1 / 8
    4.5 of 5 bubbles (19) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 5 | Quick View
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    • DVD Player
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • 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
    Location Information
    Wailea, Maui 96753
    4 of 5 bubbles Reviewed September 12, 2016
    A wonderful, spacious one bedroom condo. No view of water, just lush greenery since its a ground floor unit. Very close to pool and beach access. Wailea shopping just a short...
    4 of 5 bubbles 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...
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    1 / 25
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Shared Outdoor Pool...
    • Mountain Views
    • Ocean Views
    • Air Conditioning
    • Housekeeping...
    • Satellite TV
    • DVD Player
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Beautifully furnished and well appointed, with gorgeous views and 3 large Lanais. This is a very comfortable "home away from home" with many special amenities, full kitchen and BBQ. Newly remodeled and next to the Quiet Upper Pool, it is private, quiet and very spacious 1550 sq ft. Surrounded by... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed July 24, 2016
    This is the perfect place to stay while exploring Maui. The Condo is in a superb landscaped setting and is fully equiped with everything that you are likely to need. If you read...
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    1 / 82
    5 of 5 bubbles (1) Excellent
    Studio, 3 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    About this property
    <b>Sandy Surf K508 is located on Maui island, voted #1 best island in the WORLD by TripAdvisor’s 2016 Travelers’ Choice Awards! Maui island was also voted #1 best island in the U.S. by Conde Nast Traveler’s Readers’ Choice Awards published on October 18, 2016.</b> The Wailea Beach Villas is ranked... View all property information
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    Wailea, Maui 96753
    1 / 24
    5 of 5 bubbles (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
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    • Waterfront
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    • x
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    • ?
    About this property
    Newly remodeled, Two bedroom / Two bathroom, second floor condominium right on the Beach! It is perfect for two couples or a family of four. You are literally steps from the beach! This condominium is at the front of the building closest to the ocean making for spectacular views! Upgraded... View all property information
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    Wailea, Maui 96753
    1 / 13
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Mountain Views
    • Housekeeping...
    • DVD Player
    • Ocean Views
    • Air Conditioning
    • Hot Tub
    • Wi-Fi
    • Children's Pool
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    OUR UNIT WAS COMPLETELY UPGRADED, NEW STAINLESS APPLIANCES, AC's, TILE, PAINT, MOLDINGS, FURNITURE, T.V.'S, DISHES, TOWELS, ART AND MUCH MORE! NEW WHIRLPOOL DUET WASHER AND DRYER. FULLY FURNISHED WITH ALL COOKING, TOWELS, BEACH EQUIPMENT, UMBRELLA'S AND TOYS FOR YOUR STAY IN PARADISE. RIGHT ON... View all property information
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    Wailea, Maui 96753
    1 / 18
    4.5 of 5 bubbles (3) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Internet Access
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    • Air Conditioning
    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
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    • ?
    About this property
    Special Rates Available for the Spring of 2017 - Promo Code: SPRINGSAVER! This ground floor, Wailea Ekahi condominium has a garden and partial ocean view. There is a King bed in the master bedroom and Queen pull out sofa sleeper in the living room. Air conditioning in both the bedroom and living... View all property information
    Location Information
    Wailea, Maui 96753
    4 of 5 bubbles Reviewed May 7, 2014
    This was our first trip to Maui so we weren't quite sure what to expect. All I can say is that we loved it! The condo worked out brilliantly with lots of space; very well equipped...
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    1 / 29
    4.5 of 5 bubbles (3) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Grill
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    • Satellite TV
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    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Ask us about our other Ekahi Village condos for rent Aloha ! Condo # 50-C - Luxury at an affordable price - perfect for a getaway or honeymoon. (4maximum) Low Season rate (Apr 16 - Dec 15) $175.00 per night High Season rate (Dec 16 - Apr 15) $275.00 per night This is a romantic 1bed/1bath,... View all property information
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    Wailea, Maui 96753 9533
    3 of 5 bubbles Reviewed February 2, 2012
    This one-bedroom condo (with hide-a-bed couch in living room) was obviously recently updated - the kitchen, bathroom and bedroom all had nice, tasteful, simple furniture...
    5 of 5 bubbles Reviewed May 4, 2011
    I don't know about you, but if I wanted to stay in a resort with a million it other people and had a 3 mile treck to the beach or pool....I could stay anywhere! Valley Isle #302...
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    1 / 16
    5 of 5 bubbles (16) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • DVD Player
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    • Pet-friendly
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    • x
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    • x
    About this property
    A note from the owner: Welcome to Wailea Elua Village #307, our newly remodeled ground floor condo and our piece of paradise. With outstanding views, beach access through beautifully sculpted gardens, and Hawaiian-home class, it has everything you need for your Maui vacation. We've stocked our... View all property information
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    Wailea, Maui 96753
    1 / 19
    5 of 5 bubbles (4) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Waterfront
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    • x
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    About this property
    Come enjoy condominium living at its finest at Wailea Ekahi #17D. Located in the heart of Wailea, Maui - is a One bedroom, Two bathroom deluxe condominium on the 2nd floor with panoramic ocean views. Enjoy fabulous ocean and outer island views from the living room, dining room, kitchen and main... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed October 25, 2014
    Stayed at Wailea Ekahi 17D.Everything about this condo was PERFECT. It was well kept; pristine....the view was breathtaking. This whole community was WONDERFUL. Pool area and...
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    1 / 21
    5 of 5 bubbles (26) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Shared Outdoor Pool...
    • Mountain Views
    • DVD Player
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Nestled in a quiet lower village setting right on the green belt, our Maui home has recently undergone a complete professional remodel. The ceiling has a real Hawaiian feel with beams and matting, we've opened the kitchen to the living room and created two master suites with private bathrooms. The... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed October 7, 2016
    This condo is beautiful, fully equipped and in a great location. Has a great layout with the bedrooms on opposite sides of the condo. Traveled with another couple so the layout...
    5 of 5 bubbles Reviewed August 1, 2016
    Probably one of the nicest vacation rentals we have experienced. Every amenity is provided from the kitchen appliances to the comfy beds and linens. A spectacular ocean view...
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    1 / 20
    5 of 5 bubbles (2) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Internet Access
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    • Grill
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • ?
    About this property
    Special Spring 2017 Deals - Book Early!! This beautifully updated condominium offers ocean views and greenbelt views. It has a King bed in the bedroom, Queen pull out sofa sleeper in the living room, air conditioning in the living room and bedroom, ceiling fans throughout and an extended lanai that... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed September 12, 2015
    My wife and I were married in Maui and have had family members who lived on Maui for many years, so we have stayed in condos,and hotels all over the island and I can honestly say...
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    1 / 19
    4.5 of 5 bubbles (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    • ?
    About this property
    Spring Saver Rates 2017! Book Early ! Grand Champions 163 is a delightful ground floor two bedroom tiled throughout with the exception of the bedrooms. Beautiful, Kitchen and Vanity Cabinets with Granite Counter tops. The Living room has a cozy sectional sofa, flat screen TV, DVD, wireless... View all property information
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    Wailea, Maui 96753
    1 / 16
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    • x
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    • 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
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    Wailea, Maui 96753
    1 / 22
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    About this property
    Spring Saver Rates 2017! Grand Champions 8 is a top floor tropical delight with lush foliage surrounding the lanai for privacy. There is a spacious airy feeling with vaulted ceilings and ceiling fans in the living area. It is comfortably furnished, has A/C if needed, large flat screen TV, DVD... View all property information
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    Wailea, Maui 96753
    1 / 22
    5 of 5 bubbles (4) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Mountain Views
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    • Pet-friendly
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    • x
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    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
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed September 6, 2016
    Travelled with my wife and two teenage sons. Condo was very roomy and was located on the fairway #2 of the Blue course. Was a quiet unit with very nice views towards the ocean...
    5 of 5 bubbles Reviewed April 20, 2015
    The condo was spacious, clean and homely. They had everything we needed and the complex was well maintained. very close to Wailea town centre and 15 min walk to resort area. BBQ...
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    1 / 20
    4.5 of 5 bubbles (2) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    • Waterfront
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    • Satellite TV
    • Balcony
    • Wi-Fi
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • ?
    About this property
    Spring 2017 Discounted Rates ! Promo code: SPRINGSAVER! This condominium home has been beautifully upgraded throughout and boasts a wonderful kitchen, dining room and living room. Summer 2014 new carpet was added throughout and new living room furniture greets you as you walk in the front door. The... View all property information
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    Wailea, Maui 96753
    1 / 19
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    About this property
    Spring Saver Rates 2017 - Book Early! Use Promo Code: SPRINGSAVER!! Wailea Ekolu 1606 is a top floor two bedroom two bath condo with a wonderful ocean view. Beautiful wood flooring throughout, vaulted ceilings, spectacular kitchen and classy island decor. The living area is Air Conditioned, has a... View all property information
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    Wailea, Maui 96753
    1 / 21
    5 of 5 bubbles (3) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    • Air Conditioning
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    • x
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    About this property
    Beautiful ocean views, swimming and snorkeling from the property, and a fully refurbished condominium awaits you at our Elua Village 2011. This one bedroom two bath is tiled throughout, has central air conditioning along with ceiling fans. The living area offers flat screen TV, high speed wireless... View all property information
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    Wailea, Maui 96753
    1 / 74
    Studio, 3 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    About this property
    <b>Orient Pacific Suite J505 is located on Maui island, voted #1 best island in the WORLD by TripAdvisor’s 2016 Travelers’ Choice Awards! Maui island was also voted #1 best island in the U.S. by Conde Nast Traveler’s Readers’ Choice Awards published on October 18, 2016.</b> The Wailea Beach Villas... View all property information
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    Wailea, Maui 96753
    1 / 17
    5 of 5 bubbles (13) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Shared Outdoor Pool...
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    • Pet-friendly
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    • x
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    • ?
    About this property
    Special Spring Saver Rates 2017 - Book Early ! Grand Champions #35 is an inviting third floor, two bedroom, two bath, Ocean View condo. The living room has sofa and love seat, A/C, Large Flat Screen TV, and Blu-Ray player. The newly updated kitchen has granite counters, new tile floor and full size... View all property information
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    Wailea, Maui 96753
    1 / 34
    5 of 5 bubbles (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Children's Pool
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    • Ocean Views
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Wailea Ekahi 20F is a 2 bedroom unit featuring panoramic ocean views, a great, quiet location with a short, 2 minute walk to Keawakapu Beach. As new owners, we welcome you to enjoy our condo and all that it has to offer! Wailea Ekahi Village is a premier ocean front condominium community located... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed August 17, 2016
    Me and my family had a wonderful visit at Ekahi 20F! The view was beautiful and th beach was so close! The condo was amazing and we had so much fun hanging out and using all of...
    5 of 5 bubbles Reviewed August 17, 2016
    This condo worked out great for our family of four. I do a lot of research when booking a rental, and I know what I want. So, the best outcome is when the place turns out to be...
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    1 / 78
    4.5 of 5 bubbles (3) Very good
    Studio, 4 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    About this property
    <b>Golden Mandarin Pool Villa D102 is located on Maui island, voted #1 best island in the WORLD by TripAdvisor’s 2016 Travelers’ Choice Awards! Maui island was also voted #1 best island in the U.S. by Conde Nast Traveler’s Readers’ Choice Awards published on October 18, 2016.</b> The Wailea Beach... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed January 30, 2015
    We have been coming to Wailea for the past 15 years and the Golden Mandarin was by far the best place we have ever stayed. The Villa was exquisite and was stocked with every...
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    1 / 18
    5 of 5 bubbles (30) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Satellite TV
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    • Grill
    • Patio
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    • Waterfront
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Ekahi 1BD/2BA 20B is a beautiful, 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 2 minute walk to world renowned Keawakapu Beach! And because the walk path is nearly level, you avoid hiking up the hill with all your beach gear... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed July 24, 2016
    Great. Would return. Close to beach. Comfortable beds. Beautiful community. Nice pools. Shopped at costico close by. Great value. Great patio.
    5 of 5 bubbles Reviewed March 15, 2016
    This rental is fantastic, my wife and my 2 year old went in February. Not only was the rental a great space, with nice appliances (and the sharpest chef knife I've ever had in a...
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    1 / 24
    5 of 5 bubbles (14) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 5 | Quick View
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    • Ocean Views
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    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Maui Rendezvous, Wailea Ekahi 33A, is a luxury (beautiful, romantic, and family friendly) 1,100 square-foot 1 bedroom 2 bath condo that sleeps 5. It is in a magnificent, lush tropical paradise resort on spectacular Keawakapu beach. Views are of a tropical garden with partial ocean and mountain... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed September 13, 2014
    We loved the condo and the owners are great. We also loved it as a base camp for exploring the island. Very convenient to other resorts and highways. They provide everything you...
    5 of 5 bubbles Reviewed September 10, 2013
    Our family of 3 stayed at Maui Rendezvous for 4 nights in August. We had a great time! The condo was clean and spacious. It was well equipped and everything was in good...
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    1 / 16
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    A Note from the Owner: We enjoy spending time out on the lanai, which has a large grassy area behind it that is great for our grandchildren to play ball on. Ulua beach is just a short walk and it's great for paddle boarding, boogie boarding and snorkeling. The Shops at Wailea are also just a short... View all property information
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    Wailea, Maui 96753
    1 / 20
    5 of 5 bubbles (37) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Our Prime Oceanfront 2 bedroom, 2 bathroom Makena Surf F304 condo in the Wailea area provides Unsurpassed Ocean Views from Molikini to West Maui Mountains. A major designer coordinated remodel and upgrade has been completed resulting in a home away from home with only highest quality finishes.... View all property information
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    Wailea, Maui 96753
    4 of 5 bubbles Reviewed February 27, 2016
    Welcome basket with tasty local treats greeted us! Makena Surf is a super location on Maui - front row seats to see whales in February (bring binoculars), steps from the beach...
    5 of 5 bubbles Reviewed February 25, 2015
    I was told about this condo in Australia and could not believe what I was told...then I arrived there and it was beyond what I could have imagined! The condo is fitted out...
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    1 / 17
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
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    • Terrace
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    • Pet-friendly
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    • x
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    • x
    About this property
    Our beautiful two bedroom (with queen beds), two bath condo is in a 150-unit complex, unit #704. Our second (top) floor location allows for privacy and the ability to leave the doors wide open to welcome the tropical breezes. A short walk to fabulous Wailea beaches and an even shorter walk to the... View all property information
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    Wailea, Maui 96753
    1 / 19
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    • Satellite TV
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    • Shared Outdoor Pool...
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    • Pet-friendly
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    • x
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    About this property
    Spring Saver Rates 2017 - Book Early! Promo Code: SPRINGSAVER!! This modern condo is located on the Second floor with Ocean and Greenbelt views. It is furnished with a King bed, fully stocked kitchen, air conditioning and ceiling fans throughout. The extended lanai runs the full length of the condo... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed July 16, 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...
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    1 / 16
    5 of 5 bubbles (10) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • DVD Player
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    • Pet-friendly
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    • x
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    • x
    About this property
    About this condo: Wailea Elua Village #2306 is a two bedroom, two bath second floor unit with beautiful ocean and mountain views that has been completely remodeled and upgraded with marble floors and granite counter tops, all new appliances, all new furniture, all new fixtures, top of the line Sony... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed January 30, 2015
    The condo was extremely comfortable and very well equipped. The views of the ocean and the grounds were fantastic and the sounds of the waves crashing and the birds singing were...
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    1 / 18
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • x
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    About this property
    Spring 2017 Deals Available! Book Early! Promo Code: SPRINGSAVER! Wailea Ekahi #41B is a lovely ground floor condominium furnished with a King bed in the master bedroom as well as air conditioning in both the living room and bedroom. There are ceiling fans throughout, Flat screen TV in living room... View all property information
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    Wailea, Maui 96753
    1 / 16
    4.5 of 5 bubbles (2) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
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    • x
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    • 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
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    Wailea, Maui 96753
    4 of 5 bubbles Reviewed May 21, 2016
    Large roomy one bedroom, two bath, large lani, all the comforts of home and daily maid service. Less than 100 yards from the beach and pool. Gated resort, quite, well manicured...
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    1 / 23
    4.5 of 5 bubbles (13) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed 6 days ago
    This the second time we have rented this unit in the last 2 years. We have been very satisfied with our experience. Well maintained and good prices. Easy walk or drive to beach...
    5 of 5 bubbles Reviewed July 13, 2015
    I stayed for ten days with my two children 19 & 14. The condo is lovely, contains everything you need to make you feel that you are at home. Upon walking into the condo, you...
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    1 / 88
    5 of 5 bubbles (6) Excellent
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    • ?
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    About this property
    <b>Sandcastles Suite L509 is located on Maui island, voted #1 best island in the WORLD by TripAdvisor’s 2016 Travelers’ Choice Awards! Maui island was also voted #1 best island in the U.S. by Conde Nast Traveler’s Readers’ Choice Awards published on October 18, 2016.</b> The Wailea Beach Villas is... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed June 12, 2016
    We booked through Tropical Villas Vacations. Yvonne was so great fielding all of our questions beforehand and providing us with an amazing about of information on the property...
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    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • ?
    About this property
    Spring Saver Rates 2017 - Book Early! Promo Code: SPRINGSAVER! Enjoy views of Kahoolawe, Molokini and Lana’i all from this condo’s wonderful location. Vaulted ceilings, fresh paint, and brand new furnishings throughout entire condo. Comfortable living room furniture for conversing, watching a... View all property information
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    Wailea, Maui 96753
    1 / 16
    4.5 of 5 bubbles (21) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • DVD Player
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    • x
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    • x
    About this property
    About this condo: Wailea Elua Village #1402 is a 2nd story, one bedroom, one bath oceanfront condo complete with a fully remodeled kitchen, new carpet and a sofa sleeper. Enjoy the complimentary wireless internet service on your lanai as you enjoy the beautiful view of the sun-kissed Ulua Beach.... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed June 19, 2014
    My wife & I stayed at Elua #1402 from 5/31-6/7/14. This was our second stay in 1402 and we will undoubtedly be back. The unit is very well located within the complex as it has...
    5 of 5 bubbles Reviewed June 10, 2012
    My wife and I stayed at Wailea Elua 1402 from 5/27/12 to 6/4/12. We have stayed in Wailea during nearly 10 vacation trips over the past 20+ years, at the former Stouffers Resort...
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    1 / 18
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • Grill
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
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    About this property
    Special Spring 2017 Promo - Book Early Use Promo Code SPRINGSAVER! Wailea Ekahi Village #35B is where you want to be. It is the paradise you have been looking for. Walking through the landscaped grounds, you are surrounded by beautiful orchids, ginger, bougainvillea and hibiscus flowers. Both... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed September 15, 2015
    We stayed at Wailea Ekahi in unit 35B in October and really really enjoyed it. . A favourite happy hour spot was the upper balcony. We loved the ground floor patio and ate our...
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    1 / 80
    5 of 5 bubbles (2) Excellent
    Studio, 3 Bathrooms, Sleeps 6 | Quick View
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    • ?
    • ?
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    • ?
    About this property
    <b>Sea Breeze Suite J405 is located on Maui island, voted #1 best island in the WORLD by TripAdvisor’s 2016 Travelers’ Choice Awards! Maui island was also voted #1 best island in the U.S. by Conde Nast Traveler’s Readers’ Choice Awards published on October 18, 2016.</b> The Wailea Beach Villas is... View all property information
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    Wailea, Maui 96753
    5 of 5 bubbles Reviewed January 16, 2017
    My wife and I along with our 2 sons and their wives, just returned from a week at Wailea Beach Villas J405. From the moment I first contacted Tropical Villa Vacations all the way...
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    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.