Wailea Vacation Rentals – Oceanview Condos & Luxury Villas in South Maui
Wailea is Maui's most refined resort area, offering a curated selection of luxury vacation rentals. Choose from spacious oceanview condos, private beachfront villas, or gated residences-each within walking distance to top beaches like Wailea Beach, Polo Beach, and Ulua Beach. With championship golf, fine dining, luxury spas, and The Shops at Wailea nearby, Wailea is perfect for honeymoons, family vacations, and long-term stays.
Browse Wailea Vacation Rentals by condo/hotel name:
Wailea vacation rentals combine the comfort of home with the indulgence of resort amenities. Whether you prefer a villa with sunset views, a quiet garden retreat, or a beachside condo steps from the surf, Wailea's neighborhoods cater to every kind of traveler.
Top Wailea Vacation Rental Communities
Oceanfront and Beach Access Villas
- Wailea Beach Villas – oceanfront penthouses and beachfront villas
- Polo Beach Club – beachfront condos with panoramic views
- Wailea Point Village – gated luxury with prime oceanfront location
- Mana Kai Maui – beachfront condos on Keawakapu Beach
- Wailea Elua Village – beachfront property with pavilion and pools
Resort-Style Villas & Upscale Condos
- Ho'olei at Grand Wailea – spacious 3-bedroom villas with cascading pool
- Wailea Ekahi Village – low-rise condos with ocean views and tropical gardens
- Wailea Ekolu Village – hillside condos near golf and beaches
- Wailea Grand Champions Villas – golf course condos with pools
- The Palms at Wailea – Mediterranean-style condos with large lanais
Why Stay in Wailea?
- Access to Wailea Beach, Polo Beach, and Keawakapu Beach
- Home to Wailea Golf Club and scenic coastal trails
- Upscale dining and retail at The Shops at Wailea
- Quiet, landscaped communities perfect for long stays
- Consistently sunny weather and calm swimming beaches
Plan Your Stay in Wailea
Wailea offers the best of South Maui-tranquil surroundings, world-class amenities, and stunning natural beauty. Whether you're visiting for a romantic retreat or a long-term tropical escape, Wailea vacation rentals provide the perfect home base for a luxurious island experience.
Wailea Ekahi 33A 1bd/2bth, luxury, remodel, 3 min walk to beach, many amenities
Wailea Ekahi 33A is a beautiful, romantic, family friendly, 1,100 square-foot 1 bedroom, 2 bath condo in a magnificent, lush tropical paradise resort on spectacular Keawakapu beach. Views are of a tropical garden with partial ocean and mountain views. The condo has...
Luxurious 1 BR, 2 BA Wailea- Remodeled Bathrooms.
Our villa is a one bedroom, 2 bathroom on the ground floor with a very large lanai, which features sliding doors that expand the living room into the lanai. This feature expands the already spacious 1022 sq feet into an impressive 1500 sq feet. Hida- couch and single...
Wailea Ekolu 510 - Ocean Views, Private Lanais, Renovated 2-Story with Split AC!
This extra-spacious two-story town-home-styled condo has no common walls and no one above, with a premiere location at Wailea Ekolu unit 510. Enjoy panoramic ocean views from Makena and Molokini to the West Maui Mountains, from the lanai and from the inside of the unit...
Wailea Elua 1401 - Beautiful Ground Floor 1BR Oceanfront Unit on Ulua Beach
Welcome to Wailea Elua Village, a premier gated community nestled in the heart of Wailea. Our ground-floor beachfront condominium (#1401) offers the perfect blend of luxury, privacy, and island living—ideal for two (adults only) seeking a serene getaway.Set within 24...
Beautifully remodeled! Partial Ocean Views! Top Floor! Palms at Wailea 1704
You're sure to have a fabulous stay! This luxury Palms at Wailea unit is located near the spectacular pool and jacuzzi and all the amenities this popular complex affords.This 2 bedroom 2 bath unit is immaculate and beautiful and comes equipped with all the amenities so...
Spacious 2BD/2BA Condo in Wailea Resort Serene Garden and Mountain Views
Fabulous value in Wailea Resort! If you want the perfect and spacious 2-bed/2-bath condo that is tastefully decorated, offers complete privacy and serenity, and features a lanai surrounded by lush shrubbery, this is it! Bright and airy, this unit is located in a quiet,...
Beautifully Remodeled! Top Floor and Near Pool! Palms at Wailea 304
If you are looking for a perfect getaway in paradise, this is it! This luxury Palms at Wailea unit is located near the spectacular pool and Jacuzzi and all the amenities this popular complex affords.This spacious fully air-conditioned two-bedroom two-bath unit is...
Beautifully Remodeled with Central A/C! Top Floor! Palms at Wailea 206
Fabulous condo! This luxury Palms at Wailea unit is located near the spectacular pool and jacuzzi and all the amenities this popular complex affords.This central air-conditioned 2-bedroom, 2-bath unit is immaculate and beautiful and comes equipped with all the amenities...
Fabulous Ulua Beach & Lush Grounds Await: Wailea Elua 807, Groundfloor Gem!
Wailea Elua #807 – Ground-Floor Serenity with Ocean Breezes and Refined ComfortWelcome to Wailea Elua #807, a beautifully appointed ground-floor, 1-bedroom, 1-bathroom condo designed for peaceful and private escapes in one of Maui’s most exclusive beachfront...
Amazing Oceanview! Wailea Ekolu 1BR/2BA - Walk to Golf!
Lesli's luxury Wailea Ekolu Village Condominium is a 900-square-foot, one bedroom, two bath, oceanview condo, occupying the ground floor of a two-story building. Ekolu 107 accommodates up to four adults comfortably. It is fully-appointed and includes phone, radio/iPod...
Golf + Ocean Views | Wailea Ekolu 1205
Wailea Ekolu 1205 is a two-bedroom, two-bathroom ocean view vacation residence that comfortably accommodates four people. The sweeping ocean views beyond the Wailea Blue Golf Course and lush tropical landscaping make this private vacation home feel truly idyllic. The...
Luxurious Wailea Condo | Ocean Glimpses & Modern Living Palms 604
Experience the perfect blend of luxury and comfort in this beautifully updated 2-bedroom, 2-bathroom condo at the prestigious Palms at Wailea. This spacious retreat features a modern open-concept living area, plush king beds in both bedrooms, and efficient ductless AC...
Gorgeous Updated Wailea Condo Walking Distance to Beaches & Near Golf Courses
Address for this Condo: Palms at Wailea 3200 Wailea Alanui Dr. (Unit 2105)Wailea, HI 96753*** Professionally Cleaned Condo, No Contact Check-In/Check Out ****** Newly RENOVATED CONDO!!***Welcome to Palms at Wailea! This is your tropical paradise! This recently remodeled...
Wailea Grand Champion #90 Breathtaking Fairway Views & Serene Surroundings Await
Wailea Grand Champions #90 – Partial Ocean & Fairway Views in the Heart of WaileaEscape to the peaceful beauty of Wailea Grand Champions #90, a spacious two-bedroom, two-bathroom second-floor villa offering partial ocean and fairway views. Tucked between the Wailea Blue...
New Listing! Palms at Wailea 1501! Ground floor with Ocean views!
Welcome to our magnificent Oceanview retreat, nestled within the highly coveted Palms at Wailea. This nicely updated ground floor 1-bedroom, 2-bath unit promises an idyllic Hawaiian escape, complete with all the essential comforts and amenities you could desire.Step...
Wailea Grand Champions Unit 33: Large 2 Br Condo in Wailea Sleeps 6 guests
*New Furniture throughout!! This two-bedroom, two-bath garden-view condo has just been remodeled with all new furniture throughout each room in the condo. The primary bedroom and the guest bedroom both have Cal-King beds plus the living includes a queen sofa sleeper...
Gorgeous Expansive Condo in Wailea with HUGE Lanai & Ocean Views
Address for this Condo: Wailea Ekahi, 3300 Wailea Alanui Dr. (Unit 51A), Kihei HI 96753***Professionally Cleaned Condo, No-Contact Check-In/Check Out*** Welcome to Wailea Ekahi 51A! This beautiful corner unit, located within the tropical oasis of Wailea Ekahi, is a...
Beautifully remodeled ocean view condo in Wailea WE27B
Hawaii Tax ID: TA-072-016-4864-01TMK: 210080600050Enjoy this beautifully remodeled luxury unit at Wailea Ekahi! A short drive to amazing restaurants, breathtaking beaches and all day adventures. You get ocean views while you enjoy your home away from home during your...
Ocean Views + Exquisite getaway Wailea Ekahi 53D!
Special Offer: Book 8 or more nights, get 1 night free or Book 12 or more nights, get 2 nights free. Valid on all new reservations booked on or after 10/17/2024.This exquisite, second floor, 1bedroom, bathroom retreat is the perfect Hawaiian getaway. With gorgeous views...
Wailea Serenity | 2 Bed, 2 Bath
Summary:Wailea Serenity - 2BD - Private, Quiet; the tropical paradise you dreamed about!The Space:This Grand Champions condo (#15 in building #2) is located in the heart of beautiful Wailea, a short walk to the beach, and in the middle of the renowned Blue Golf Course....
Wailea Ekahi 17E | Resort Level Amenities!
Experience the ultimate tropical getaway at Wailea Ekahi 17E, a sophisticated one-bedroom, two-bathroom condo nestled within the prestigious Wailea Ekahi Village in Wailea, Hawaii. This serene escape offers a front-row seat to the beauty of Maui, blending upscale...
Wailea Ekahi #8-B Partial Ocean View, Steps to Beach, Easy access to Pool
1 Bedroom Condo, Steps to Keawakapu Beach, 60 steps to Oceanfront Pool.This ground floor one bedroom two bath has a/c throughout. It boasts a large open floor plan where the floor to ceiling sliders in the master bedroom and in the living area all open up onto the...
Ocean & Garden Views Await at Wailea Ekahi 34B: Spacious 1BR/2BA Ground Floor
Welcome to Wailea Ekahi 34B where lush tropical foliage surrounds you and views of the majestic Pacific await! This updated 1 bedroom / 2 bathroom unit is the perfect setting for your Maui vacation. This ground floor unit boasts incredible ocean and garden views! Enjoy...
Wailea Ekolu #702 Premium 2nd floor 2bd/2ba, Panoramic Ocean Views, Near Pool
Wailea Ekolu 702 is a Premium 2 bedroom, 2 bath top-floor condo ideal for family getaways. This unit was updated in late 2021 with Daikin Split Air-Conditioners in each bedroom and living room. The master suite has a luxurious King bed and the second bedroom has a Queen...
Beachfront, Ocean View, Polo Beach Wailea/Makena #306
Unit 306 is a 2 bedroom and 2 bath condo located on the third floor at the Polo Beach Club. The Polo Beach condo's sleep 6. Please call for very latest openings as there may be a new booking in progress. Polo Beach Club has both ocean front and Prime (on sand) ocean...
Wailea Jewel; near Beaches; SHOPS/5 Star Hotels; Convenient!
ALOHA and welcome to our unit in Wailea Ekolu, A two bedroom, two bath condominium on the ground floor. Our condo is located in the beautiful, lush, and spacious Wailea Ekolu Village. Ekolu is located in the five-star resort area of WAILEA. Our condo sleeps up to 6 and...
KBM Resorts | FREE CAR | Wailea Elua Village | Ocean view | Spacious 2-Bedroom Condo! WEV-2103
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Wailea Beach Villas M311 Seaview Sanctuary Luxury Oceanview Condo
Features of our 2300 sq oceanview condo include: Two full master suites Second bedroom can have two twins or king sized bedA den that closes off completely to sleep up two additional guests (either twin or king sized bed)Private ElevatorWaterworks Bathrooms with large...
Ocean View, Air Conditioned, 2 level Wailea Townhouse
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...
Palms at Wailea 901 - Luxuriously Decorated Spacious Unit w/ Large Private Lanai
Hawaii Tax ID: TA-144-497-4592-01 QUIET PRIVACY IN PARADISE The Palms #901 is a luxurious one-bedroom two-bath ground floor villa tucked away in a private and quiet corner in one of the nicest locations on the property. Often the only sound you will hear is the waves...
Sunny top floor condo, 10 minute walk from Wailea beaches
This spacious, quiet, bright second floor condo has high vaulted ceilings and a large living/dining area that creates a large, bright, and airy feel. Sunlight streams in through the sliding glass doors in the mornings, and you can leave the screens open to enjoy the...
Update: The Maui county council has approved the ban on short term rentals in areas like ours, but with an effective date of 12/31/2030. Hopefully this provides some clarity if you have been following this process and were concerned about booking in the next couple of...
Fully Air-Conditioned and Near the Pool! Come relax at the Palms at Wailea 303!
The name PALMS AT WAILEA aptly describes the feel of this beautiful complex. Located above the pristine shores of Keawakapu Beach, this impeccably furnished home will provide comfort, luxury, and plenty of room to spread out while you explore and enjoy all that Maui has...
Island Luxury at Wailea Elua #302: Expansive Ocean Views and Gorgeous Interior
Wailea Elua #302 – Top-Floor Ocean View Elegance with Artistic Hawaiian TouchesWelcome to Wailea Elua #302, a stunning 1-bedroom, 2-bathroom top-floor end unit located at one of the highest vantage points in the community. This beautifully updated condo features vaulted...
Spacious Ground Floor Revitalized Oasis- Discover Wailea Ekahi #22B
Wailea Ekahi #22B – Ground-Floor Elegance with Ocean Breezes and Garden ViewsStep into comfort, space, and tranquility at Wailea Ekahi #22B, a large and light-filled 1-bedroom, 2-bathroom ground-floor retreat just a 2-minute stroll from Keawakapu Beach, the oceanfront...
Top Floor, Favorite Location, Ocean Views! Palms at Wailea 2104
#2104 is a spacious and recently refreshed 2-bedroom, 2-bathroom condo in Maui with fun tropical accents and cozy comfort. It offers approximately 1500 sq. ft. of living area, including a large lanai. This unit features central air conditioning for your comfort. The...
Palms at Wailea - Fully Air Conditioned
Welcome to our Wailea Condo at the Palms of Wailea. Our condo is a large 1200 square foot newly renovated two bedroom, two bathroom condo that is walking distance to some of the best beaches in the world. For your convenience, we provide beach chairs, beach towels,...
Conde Nast Award Winning Property - Wailea Beach Villas PH504
Wailea Beach Villas Penthouse 504 enjoys 180 degree views of the Pacific Ocean, Kahoâolawe, Molokini crater, and Lanai. This generous two-bedroom, two-bathroom condo provides over 1900 sq. ft. of living space, outdoor lanai, entertaining space, plus a den. Located on...
Spacious Spilt-Level | Wailea Ekahi 3A
For a vacation condo that feels like a private home, select this two story residence with a sunken living room and cascading lanai. Four sets of sliding doors on the first floor provide garden views and invite tropical breezes into the open floor plan. The walk-through...
Wailea Grand Champion Golf Villa 2 Bdr/2 Bath
New, new, new. Upgrades galore. Fresh paint, new tile, new furniture, flooring, electronics, beds, and more!Professional photos pending! Comfortable and spacious 2 Bedroom + 2 Bathroom paradise condominium at the Wailea Grand Champion Golf Villas. A fully stocked...
Wailea Ekolu Village 1406 | Gorgeous Views + Community Pool!
Welcome to Wailea Ekolu Village 1406, your serene tropical oasis nestled in the heart of Kihei, Hawaii. This stunning condo offers a tranquil retreat for up to 4 guests, with 2 bedrooms and 2 bathrooms ensuring ample space and comfort during your stay.As you arrive,...
Majestic Golf Course & Sweeping Ocean Vistas at Wailea Ekolu 312
Wailea Ekolu #312 – Unforgettable Ocean Views & Island EleganceFind your private slice of paradise at Wailea Ekolu #312, a beautifully appointed one-bedroom, two-bathroom upstairs condo offering sweeping ocean views, golf course serenity, and the comfort of home in the...
Tropical setting on the Wailea Blue Golf Course
Ekolu 1602 is a 2-bedroom, 2-bathroom condo on the second floor featuring amenities such as three private lanais, air-conditioning, and a washer/dryer. This unit comfortably accommodates up to 6 guests with a king bed in the master bedroom, a king bed in the guestroom,...
Ekahi Village 1Bed/1Bath - Wailea Beachfront Complex
*Please note Ekahi Village is a non-smoking community. Smoking is not permitted anywhere on property including patio/lanai, and all communal outdoor areas. Located in beautiful Wailea, the complex is just steps from Keawakapu Beach and walking distance to great...
WEK 37C Getaway at Wailea Retreat w AC Pool Near Beach and Golf Course
Wailea Ekahi 37C Experience the Luxury of Wailea at Updated 1Bedroom Condo with Split AC Throughout and Comfortably Furnished and a Short Walk to South Maui Beaches Escape to the natural beauty and serenity of Hawaii at Wailea Ekahi 37C. Located in the exclusive resort...
Dream ~ Exclusive Ocean Front Luxury Home on Wailea Bay, Beach 69 ~ Aina Malia
Summary:Aina Malia, a unique property, is situated above beautiful Wailea Bay on the Kohala Coast of the Big Island of Hawaii, one of the few white sand beaches on the island of Hawaii. Beautiful tropical landscaping abounds with privacy and romance. Custom designed...
Grand Champion Villa: Luxury Stay, Pool, Fast WiFi
Summary:🏖 Prime Location – Walk to beaches & top dining 🛏️ King Suite + Sofa Bed – Comfort & space for all 🌅 Private Lanai – Relax with poolside views 🍳 Fully-Equipped Kitchen – Cook with ease 📺 82” & 65” Smart TVs + High-Speed Wi-Fi 🌬 A/C + Ceiling Fans – Stay cool...
Wailea Grand Champions Condo on Award-Winning Golf Course w/Shared Pool/Hot Tub
Wailea Grand Champions 26Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Wailea Grand Champions Villas 26 is a wonderful, single-level condo in a luxurious, resort community in South...
Prime Wailea: Split AC, Wailea Ekahi 36E
Wailea Ekahi 36E offers the perfect Hawaiian retreat! You will enjoy this second level condo surrounded by tropical foliage. The private lanai offers a relaxing space with floor to ceiling sliding glass doors, indoor/outdoor living is seamless. Wailea Ekahi no longer...
Wailea Ekolu 1403 -1 Bed/2 Bath Vacation Condo
6th night free! discounts applied when booked. offer good until Dec 15th, 2025.Fresh new upgrades - new king bed, new wood flooring, new TVs, kitchen appliances, window blinds, lighting, and two comfortable lanais with an outdoor lawn area. New refrigerator, stove,...