Wailea Vacation Rentals

Wailea is one of Maui’s most sought-after destinations, known for its upscale resorts, golden beaches, and beautifully maintained landscapes. Vacation rentals in Wailea include oceanview condos, luxury villas, and spacious townhomes - ideal for couples, families, and groups seeking a refined island getaway. With sunny weather year-round and direct access to world-class beaches like Wailea Beach, Polo Beach, and Ulua Bay, Wailea is perfect for both relaxation and outdoor adventure.

In addition to its scenic beauty, Wailea is home to championship golf courses, luxury spas, high-end shopping at The Shops at Wailea, and a variety of oceanfront dining options. Whether you’re watching the sunset from your lanai or heading out for a paddleboarding session, Wailea offers the perfect balance of serenity and sophistication. Browse our Wailea vacation rentals below and find the perfect home base for your South Maui escape.

Browse Wailea Vacation Rentals by condo/hotel name:

Sort By

Default View Price: Low to High Price: High to Low Bedrooms: Least to Most Bedrooms: Most to Least

• Select Default View Price: Low to High Price: High to Low Bedrooms: Least to Most Bedrooms: Most to Least

List

Map

Makena Surf A204 Oceanfront Condo in Maui

Experience the ultimate Hawaiian retreat at Makena Surf A204, a spacious and luxurious oceanfront condo offering breathtaking views and direct access to Po'olenalena Beach. This 1,600 sq ft second-floor residence features an open-concept design with a generous great room that seamlessly connects living, dining, and kitchen areas, all opening onto a 335 sq ft private lanai perfect for enjoying Maui's famous sunsets.

• 2 bedroom
• 2 bathroom
• Sleeps 6

Hawaii> Wailea

from $952 

View Property   Book Direct

Wailea Elua Village | 107

Located just steps from the beach in the heart of Wailea, Elua Village 107 is a beautifully appointed two-bedroom, two-bathroom ground-floor residence that offers the perfect blend of comfort and island elegance. With a spacious layout and tasteful décor, this vacation rental invites you to relax and unwind in true Hawaiian style.

• 2 bedroom
• 2 bathroom
• Sleeps 4

Hawaii> Wailea

from $943 

View Property   Book Direct

Garden View 1-Bedroom Villa with Full Kitchen & Private Deck

Experience a relaxing getaway in this spacious Garden View 1-Bedroom Villa offering 1022 square feet of comfort. The villa features a full kitchen equipped with stovetop, oven, microwave, refrigerator, dishwasher, coffeemaker, toaster, cookware, and tableware, making it ideal for preparing meals during your stay.

• 1 bedroom
• 2 bathroom
• Sleeps 4

Hawaii> Wailea

from $593 

View Property   Book Direct

Wailea Ekolu #405 Ocean Views on Wailea Golf Course, Wifi, A/C

In the master bedroom is a queen bed, A/C, ceiling fan, and full bathroom. Bedroom 2 queen murphy bed, A/C, and ceiling fan. There is a/c in the living room, a ceiling fan, flat screen TV, and Blu-ray / DVD player. Also enjoy meals on the ocean view lanai!

• 2 bedroom
• 2 bathroom
• Sleeps 4

Hawaii> Wailea

from $438 

View Property   Book Direct

Spacious Ground Floor Hawaii Condo with Private Deck

Experience the comfort of this spacious ground floor condo in Hawaii, offering a 219 sq ft private deck perfect for outdoor dining or lounging. The unit includes a fully equipped kitchen with stovetop, oven, microwave, refrigerator, dishwasher, coffeemaker, toaster, cookware, and tableware, making it ideal for preparing meals during your stay.

• 2 bedroom
• 2 bathroom
• Sleeps 6

Hawaii> Wailea

from $719 

View Property   Book Direct

Spacious 2-Bedroom Hawaii Condo with Deck & Amenities

Enjoy a relaxing stay in this comfortable 2-bedroom condo located on the second floor with a walk-up access. The unit boasts a fully equipped kitchen including stovetop, oven, microwave, refrigerator, dishwasher, coffeemaker, toaster, cookware, and tableware, ideal for preparing home-cooked meals.

• 2 bedroom
• 2 bathroom
• Sleeps 6

Hawaii> Wailea

from $712 

View Property   Book Direct

Wailea Ekahi Village Ocean View 2BR Condo

Discover the perfect tropical retreat at Wailea Ekahi Village, situated above the stunning Keawakapu Beach. This spacious 1,505 sq ft second-floor condo features two bedrooms and two bathrooms, offering breathtaking ocean views from your private lanai.

• 2 bedroom
• 2 bathroom
• Sleeps 6

Hawaii> Wailea

from $699 

View Property   Book Direct

Wailea Beach Villas | PH404

Wailea Beach Villas Penthouse 404 is a stunning two-bedroom plus den, two-bathroom ocean view residence offering over 1,978 sq. ft. of elegant indoor-outdoor living. Situated on the fourth floor, this penthouse enjoys sweeping views of the Pacific Ocean, Kaho'olawe and Molokini, creating the perfect backdrop for your Maui vacation.

• 2 bedroom
• 2 bathroom
• Sleeps 6

Hawaii> Wailea

from $1,512 

View Property   Book Direct

Wailea Ekahi Village | 26D

Escape to paradise in this beautifully appointed one-bedroom vacation rental nestled in the lush tropical gardens of Wailea Ekahi Village. Located on Maui’s sunny south shore, 26D is a tranquil second-floor unit that offers the perfect blend of privacy, comfort, and island charm—just a short stroll from world-renowned Keawakapu Beach.

• 1 bedroom
• 2 bathroom
• Sleeps 4

Hawaii> Wailea

from $530 

View Property   Book Direct

Luxury Maui Condo with Ocean Views and Modern Amenities

Welcome to Wailea Elua Village #2108, a beautifully remodeled and decorated two-bedroom, two-bath residence offering over 1,500 square feet of luxurious living space. Situated on the second floor, this condo provides breathtaking, elevated views of the ocean, off-shore islets, and lush tropical gardens visible from every room.

• 2 bedroom
• 2 bathroom
• Sleeps 6

Hawaii> Wailea

from $895 

View Property   Book Direct

Wailea Beach Villas F202 Maui Luxury Ocean View

Experience the perfect blend of luxury, style, and sophistication at Wailea Beach Villas F202, a stunning Maui retreat perched just above Wailea Beach.
This immaculate villa offers breathtaking blue ocean vistas framed by lush tropical greenery, creating an idyllic island setting that impresses even the most discerning travelers.

• 3 bedroom
• 3 bathroom
• Sleeps 6

Hawaii> Wailea

from $2,420 

View Property   Book Direct

Spacious Ground Floor Condo with Private Deck in Hawaii

Experience a relaxing stay in this spacious ground floor condo located in a beautiful Hawaii resort. The unit offers a large private 473 square feet deck, perfect for outdoor dining and lounging. Inside, the fully equipped kitchen includes a stovetop, oven, microwave, refrigerator, dishwasher, coffeemaker, toaster, cookware, and tableware, making meal preparation effortless.

• 1 bedroom
• 2 bathroom
• Sleeps 4

Hawaii> Wailea

from $658 

View Property   Book Direct

Makena Surf Oceanfront Luxury Condo in Maui

Experience a luxurious beachfront getaway at Makena Surf on Maui, featuring a stunning 2-bedroom oceanfront condo. This exquisite residence offers breathtaking views of the Pacific Ocean and nearby islands like Molokini and Lanai from your private lanai.

• 2 bedroom
• 2 bathroom
• Sleeps 6

Hawaii> Wailea

from $932 

View Property   Book Direct

Luxury Wailea Ekahi 52 Condo Near Beaches

Wailea Ekahi 52 offers a luxurious and spacious one-bedroom condo nestled in the heart of the Wailea resort community on Maui's southern shores. This beautifully appointed second-floor residence provides a perfect blend of comfort, style, and prime location for your island escape.

• 1 bedroom
• 1 bathroom
• Sleeps 4

Hawaii> Wailea

from $541 

View Property   Book Direct

Wailea Ekahi Village 12B Ocean View Studio

Experience the beauty of Maui in Wailea Ekahi Village 12B, a beautifully updated ocean view studio perfect for couples or solo travelers seeking a relaxing retreat. This contemporary, ground-floor condo offers a seamless indoor-outdoor living space, allowing you to enjoy gentle ocean breezes from your private lanai.

• 1 bedroom
• 1 bathroom
• Sleeps 2

Hawaii> Wailea

from $477 

View Property   Book Direct

Walk to white sandy beaches - Palms 501

Enjoy dreamy sunset strolls along the golden sands or start your day with a peaceful jog through paths lined with lush tropical flowers. Dive into the crystal-clear waters for snorkeling, kayaking, or whale watching—it’s all just moments from your door!

• 2 bedroom
• 2 bathroom
• Sleeps 4

Hawaii> Wailea

from $459 

View Property   Book Direct

• « First
• «
• 5
• 6
• 7
• »
• Last »

Showing 7 of 7 pages.