Vacation Rentals in Wailea Hawaii

WAILEA

BOOK DIRECT

Avoid costly fees and gain in service by dealing directly with the Vacation Rental Management Company.

SOUTH MAUI DESTINATIONS

Map of Wailea

Why Vacation in Wailea?

Wailea is a 1,500 acre Resort Community on the beautiful southwest coast of Maui. Known for its crescent-shaped beaches and incedbile layered ocean views. Wailea Beach was named one of the best beaches in the country and many of the beaches in and around Wailea are excellent for bathing, swimming, and snorkeling. Wailea is also home to the Maui Film Festival. 

The Vacation Rental Properties listed below are professionally managed by Vacation Rental Management Companies who know Wailea.


Wailea Hawaii Vacation Rentals

2 Wailea Elua 1508
$649/night
Condo in Wailea Hawaii
2 Beds • 2 Full Baths • Sleeps 6
Ali'i Resorts

Royal Mauian #418
$549/night
Condo in Wailea Hawaii
3 Beds • 2 Full Baths • Sleeps 7
Ali'i Resorts

2 KIHEI SURFSIDE, 608
$209/night
Condo in Wailea Hawaii
1 Bed • 1 Full Bath • Sleeps 3
Ali'i Resorts

Wailea Elua #2201
$549/night
Condo in Wailea Hawaii
2 Beds • 2 Full Baths • Sleeps 6
Ali'i Resorts

2 Royal Mauian 116
$469/night
Condo in Wailea Hawaii
2 Beds • 2 Full Baths • Sleeps 4
Ali'i Resorts

2 KIHEI SURFSIDE, #503
$249/night
Condo in Wailea Hawaii
1 Bed • 2 Full Baths • Sleeps 4
Ali'i Resorts

2 WAILEA ELUA, #2010
$399/night
Condo in Wailea Hawaii
2 Beds • 2 Full Baths • Sleeps 6
Ali'i Resorts

Royal Mauian #416
$369/night
Condo in Wailea Hawaii
2 Beds • 2 Full Baths • Sleeps 4
Ali'i Resorts

Kihei Akahi Resort Unit D605
$199/night
Condo in Wailea Hawaii
1 Bed • 1 Full Bath • Sleeps 3
Maui Vision Properties

Grand Champions 163
$202/night
Condo in Wailea Hawaii
2 Beds • 2 Full Baths • Sleeps 7
Maui Paradise Properties

2 KIHEI SURFSIDE, #211
$209/night
Condo in Wailea Hawaii
1 Bed • 2 Full Baths • Sleeps 4
Ali'i Resorts

Wailea Elua 1402
$639/night
Condo in Wailea Hawaii
1 Bed • 1 Full Bath • Sleeps 4
Ali'i Resorts

Wailea Ekahi 40E
$225/night
Condo in Wailea Hawaii
1 Bed • 2 Full Baths • Sleeps 4
Maui Paradise Properties

Wailea Ekolu 1604
$199/night
Condo in Wailea Hawaii
2 Beds • 2 Full Baths • Sleeps 6
Maui Paradise Properties

2 MAKENA SURF RESORT, #G-204
$699/night
Condo in Wailea Hawaii
2 Beds • 2 Full Baths • Sleeps 5
Ali'i Resorts

Ekolu - 1BR Oceanview
Condo in Wailea Hawaii
1 Bed • 1 Full Bath • Sleeps 4
Hawaii Beachfront Condos

2 KAMAOLE NALU, #605
$339/night
Condo in Wailea Hawaii
2 Beds • 2 Full Baths • Sleeps 6
Ali'i Resorts

2 KAMAOLE NALU, #606
$439/night
Condo in Wailea Hawaii
2 Beds • 2 Full Baths • Sleeps 6
Ali'i Resorts

Wailea Elua #1601
$539/night
Condo in Wailea Hawaii
1 Bed • 2 Full Baths • Sleeps 4
Ali'i Resorts

2 Wailea Grand Champions 148
$229/night
Condo in Wailea Hawaii
2 Beds • 2 Full Baths • Sleeps 5
Ali'i Resorts

Kihei Surfside #411
$239/night
Condo in Wailea Hawaii
1 Bed • 2 Full Baths • Sleeps 4
Ali'i Resorts

Kamaole Nalu #106
$369/night
Condo in Wailea Hawaii
2 Beds • 2 Full Baths • Sleeps 6
Ali'i Resorts

Royal Mauian 517
$399/night
Condo in Wailea Hawaii
2 Beds • 2 Full Baths • Sleeps 4
Ali'i Resorts

Makena Surf F209
$829/night
Condo in Wailea Hawaii
2 Beds • 2 Full Baths • Sleeps 4
Ali'i Resorts


In the realm of vacation rentals in Wailea, Hawaii, a world of luxurious accommodations awaits those seeking a tranquil escape amidst breathtaking landscapes. With an abundance of rental options nestled in this tropical paradise, visitors are spoiled for choice when it comes to selecting their ideal temporary abode. From opulent beachfront villas to cozy condominiums boasting panoramic ocean views, each rental promises a unique experience tailored to individual preferences. But what truly sets Wailea apart as a premier vacation destination lies not only in its diverse lodging offerings but also in the unparalleled experiences awaiting guests beyond their doorstep. A harmonious blend of relaxation and adventure awaits those who choose to immerse themselves in the essence of Wailea's hospitality and charm.

Overview of Vacation Rentals in Wailea

Nestled within the picturesque 1,500-acre resort community of Wailea on the southwest coast of Maui, the vacation rental market boasts 5 reputable vacation rental managers offering a total of 161 unique and inviting accommodations for visitors seeking a memorable stay in this tropical paradise. These vacation rentals come equipped with a range of rental amenities, ensuring guests have a comfortable and convenient experience during their stay. Additionally, visitors have the opportunity to explore the local cuisine, with various dining options showcasing the flavors of Hawaii right at their doorstep. From stunning ocean views to luxurious amenities, these vacation rentals in Wailea offer the perfect blend of relaxation and adventure for those looking to immerse themselves in the beauty of Maui.

Benefits of Booking Directly

Amidst the array of vacation rentals available in Wailea, visitors can enhance their experience by booking directly with the Vacation Rental Management Company to enjoy cost savings and superior service.

Direct Booking Advantages:

  1. Cost Savings: Direct bookings often eliminate additional fees charged by third-party booking platforms.
  2. Personalized Service: Booking directly allows for better communication with the rental management team, ensuring personalized assistance.
  3. Flexible Policies: Direct bookings may offer more flexibility in terms of cancellation policies and special requests.

Vacation Rental Managers in Wailea

Wailea, a renowned resort community on the southwest coast of Maui, is served by 5 vacation rental managers offering a diverse selection of accommodations for visitors. These managers cater to a range of preferences and budgets, ensuring vacation rental pricing options suitable for all travelers. Customer reviews play a crucial role in helping visitors make informed decisions about their stay in Wailea. By assessing feedback from previous guests, potential visitors can gain valuable insights into the quality of accommodations and services provided by each vacation rental manager. Whether seeking luxury villas or cozy beachfront cottages, the vacation rental managers in Wailea strive to meet the diverse needs of travelers, making it easier to find the perfect home away from home.

Accommodation Options in Wailea

Within the vibrant coastal community of Wailea on Maui's southwest coast, a diverse array of accommodation options awaits visitors seeking a memorable stay in this tropical paradise.

  1. Luxury Condos: Wailea boasts an array of luxury condos that offer stunning ocean views, spacious living areas, and top-notch accommodation amenities.

  2. Resort Villas: Visitors can choose to stay in one of the many resort villas that provide upscale comforts, access to pristine beaches, and proximity to local dining options.

  3. Beachfront Hotels: For those seeking the convenience of beachfront accommodations, Wailea offers a selection of beachfront hotels with luxurious amenities and easy access to the area's renowned dining options.

Comparison With Other Maui Destinations

When comparing Wailea to other Maui destinations, visitors will find a distinctive blend of luxury, natural beauty, and diverse accommodation options. Wailea stands out for its upscale resorts, world-class golf courses, and pristine beaches, offering a luxurious vacation experience. In comparison with Kihei, known for its more laid-back and affordable atmosphere, Wailea caters to those seeking an indulgent retreat. Additionally, Makena vacation rentals provide a secluded and exclusive setting for travelers looking to escape the crowds and immerse themselves in the tranquility of Maui. Whether visitors prefer the bustling energy of Kihei or the secluded paradise of Makena, Wailea's unique offerings make it a premier choice for those seeking a sophisticated and memorable vacation in Maui.

Vacation Rental Availability in Wailea

In exploring the vacation rental landscape of Wailea, travelers will encounter a diverse array of accommodations tailored to enhance their stay on Maui's southwest coast.

Key Considerations for Vacation Rental Availability in Wailea:

  1. Rental Pricing: The cost of vacation rentals in Wailea varies depending on factors such as location, size, and amenities offered. Travelers can find options ranging from budget-friendly to luxurious accommodations.

  2. Seasonal Availability: Availability of vacation rentals in Wailea can fluctuate based on the time of year. High seasons, like summer and major holidays, may see increased demand and higher prices, while off-peak times could offer more availability and potentially better deals.

  3. Booking in Advance: To secure preferred accommodations in Wailea, it is advisable to book well in advance, especially during peak seasons, ensuring a seamless and enjoyable vacation experience.

Vacation Rental Options in Hawaii

Amidst the vibrant tapestry of vacation rental options across Hawaii's diverse islands, travelers can discover an array of accommodations tailored to suit their every whim and desire. From luxurious Hawaii beachfront properties offering stunning ocean views to opulent villas nestled in lush tropical landscapes, visitors have a plethora of choices to make their Hawaiian vacation truly unforgettable. Whether seeking a serene retreat by the sea or a lavish escape in a private paradise, Hawaii's vacation rental options cater to every taste and preference. Indulge in the comfort and convenience of a luxury villa, or immerse yourself in the beauty of Hawaii's beachfront properties for a truly magical experience. Explore the possibilities and find the perfect rental to create lasting memories in paradise.

Exploring Wailea's Attractions

Discover the captivating allure of Wailea's attractions, enticing visitors with a blend of natural beauty and cultural richness that promises an unforgettable experience.

  1. Beach Activities: Wailea boasts pristine beaches perfect for sunbathing, swimming, and snorkeling, offering a paradise for beach enthusiasts.

  2. Local Cuisine: Indulge in a culinary journey through Wailea, savoring fresh seafood, tropical fruits, and traditional Hawaiian dishes at local restaurants and food trucks.

  3. Cultural Sites: Immerse yourself in Wailea's heritage by exploring cultural sites like the ancient Hawaiian fishponds or taking a tour of the historical landmarks that dot the region, providing insight into the rich history of the area.

Wailea's attractions offer a delightful blend of relaxation, adventure, and cultural discovery, making it a must-visit destination for those seeking a memorable vacation.

Activities in Wailea Hawaii

Explore an array of captivating activities awaiting visitors in the vibrant paradise of Wailea, Hawaii. Wailea is renowned for its pristine beaches, offering opportunities for sunbathing, swimming, and water sports. Whether you prefer lounging on the soft sands of Wailea Beach or embarking on snorkeling adventures in the crystal-clear waters, there's something for everyone. After a day of beach activities, indulge in the local dining scene, where fresh seafood and Hawaiian delicacies await at charming eateries and upscale restaurants. Experience the unique blend of flavors that Hawaii has to offer while enjoying breathtaking ocean views. From casual beachside cafes to fine dining establishments, Wailea promises a culinary journey that complements the beauty of the surroundings.

Finding Vacation Rentals Near Wailea

Nestled along the southwestern coast of Maui, visitors seeking vacation rentals near Wailea can explore a plethora of accommodation options in this 1,500-acre resort community. When searching for the perfect vacation rental near Wailea, consider the following:

  1. Rental Pricing: Vacation rentals near Wailea vary in price range, catering to different budgets.
  2. Amenities Offered: From luxurious oceanfront villas to cozy cottages, amenities like private pools, beach access, and gourmet kitchens can elevate your stay.
  3. Location: Choose between beachfront properties or those nestled in lush tropical gardens, each offering a unique experience.

With a range of rental pricing options and amenities to choose from, visitors can find the ideal vacation rental near Wailea that suits their preferences and budget.

Frequently Asked Questions

What Are Some Recommended Local Dining Options Near Wailea Vacation Rentals?

When seeking local dining options near Wailea vacation rentals, visitors can indulge in exquisite local cuisine at renowned eateries. For a casual dining experience, exploring food trucks offering authentic flavors is a must. As the sun sets, oceanfront bars provide the perfect backdrop for enjoying sunset cocktails. These dining venues not only offer delicious meals but also provide a memorable experience that complements the beauty of Wailea.

Are There Any Local Markets or Grocery Stores Within Walking Distance of Wailea Vacation Rentals?

Local markets and grocery stores within walking distance of Wailea vacation rentals provide convenient access to fresh produce and essentials. Visitors can explore nearby farmers markets for local delicacies, while convenience stores offer quick snacks and beverages. Additionally, dining options, food trucks, and beach equipment rentals enhance the vacation experience. Water activities, hidden beaches, and scenic hikes are easily accessible, ensuring a vibrant and fulfilling stay in Wailea.

Can Visitors Rent Snorkeling Gear or Beach Equipment Easily in Wailea?

Visitors in Wailea can conveniently rent snorkeling gear and beach equipment for water sports activities. Snorkeling excursions and equipment rentals are easily accessible in the area, allowing guests to explore the vibrant marine life at their leisure. Whether diving into the ocean for a snorkeling adventure or lounging on the beach with the right gear, Wailea offers convenient options for visitors seeking to make the most of their aquatic experiences.

Are There Any Community Events or Festivals That Guests Should Be Aware of During Their Stay in Wailea?

During your stay in Wailea, guests can immerse themselves in cultural celebrations and community gatherings that showcase the vibrant local spirit. Additionally, outdoor concerts and beach parties offer a chance to enjoy music and entertainment in the scenic surroundings of this coastal paradise. These events provide a unique opportunity to connect with the community and experience the dynamic cultural scene of Wailea during your visit.

What Are Some Lesser-Known, Hidden Gems or Off-The-Beaten-Path Attractions Near Wailea Vacation Rentals?

Hidden trails and waterfalls abound near Wailea, offering a serene escape for nature enthusiasts. Scenic drives reveal breathtaking vistas, while encounters with local wildlife add excitement to the journey. These off-the-beaten-path attractions showcase Maui's natural beauty beyond its renowned beaches. Whether exploring lush forests or marveling at cascading waterfalls, visitors can immerse themselves in the island's tranquil landscapes, away from the hustle and bustle of more popular tourist spots.

Restaurant Week Wailea

Restaurant Week Wailea
by Find Rentals





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