Villas and Beach houses in Wailea, HI

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Wailea, HI villas
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958 Villa rentals in Wailea, HI

Discover Vacation Homes by the Sea in Wailea, HI

Unwind at these welcoming coastal vacation homes in Wailea, HI, ideally located for exploring regional beach-town boardwalks.

Kamaole Sands 1-403 - Spacious 2/2 With Split Ac! - Wailea, HI
9.0 3 reviews

Kamaole Sands 1-403 - Spacious 2/2 With Split Ac!

house, Wailea
This Wailea vacation rental is conveniently located near Kamaole, Keawakapu, and Mokapu beaches, and is 3.4 miles from the Wailea Emerald Golf Course.
This 1180-square-foot property boasts a two-bedroom, two-bathroom layout, accommodating up to 10 guests and featuring a fully equipped kitchen, in-unit fitness center, Jacuzzi, and stunning ocean views.

Our Favorite Vacation Homes with a Pool in Wailea, HI

Having a pool at your Wailea, HI vacation home lets you enjoy a dip to complement a day by the water without extra planning.

Luxury Oceanfront Mana Kai Resort Condo - Wailea, HI
9.7 49 reviews

Luxury Oceanfront Mana Kai Resort Condo

house, Wailea
This oceanfront Mana Kai Resort condo in Wailea, Maui offers stunning sea views and is located 3 miles from the Wailea Emerald Golf Course and a short distance from Keawakapu, Mokapu, and Kamaole Beaches.
This 870-square-foot unit features two bedrooms, a fully equipped kitchen with a dishwasher, a private terrace, free Wi-Fi, and access to a resort swimming pool and fitness center.
Kamaole Sands 9-210 - Wailea, HI
No reviews

Kamaole Sands 9-210

house, Wailea
Kamaole Sands 9-210, a one-bedroom condo in Wailea, offers convenient access to Kamaole, Keawakapu, and Mokapu Beaches, and is 3.4 miles from the Wailea Emerald Golf Course.
This 1-bedroom, 2-bathroom vacation rental sleeps 7, features a fully equipped kitchen, private parking, Wi-Fi, a swimming pool, fitness center, tennis court, and is close to local tour operators.
Kamaole Sands 3-103 - Wailea, HI
10 1 review

Kamaole Sands 3-103

house, Wailea
This Wailea vacation rental is a short walk from Kamaole Beach and less than a mile from Keawakapu Beach, providing easy access to Wailea's attractions.
The 820-square-foot condo features one bedroom, two bathrooms, a fully equipped kitchen, and accommodates up to seven guests, boasting amenities such as a private entrance, free Wi-Fi, and access to an on-site swimming pool and fitness center.
Kamaole Sands 7-404 - Wailea, HI
10 2 reviews

Kamaole Sands 7-404

house, Wailea
This Wailea vacation home, located in the Kamaole Sands complex, offers a two-minute walk to Kamaole Beach and is 3.4 miles from the Wailea Emerald Golf Course.
The 1,180-square-foot property features two bedrooms, two bathrooms, sleeps eleven guests, and includes a fully equipped kitchen, private parking, Wi-Fi, a swimming pool, and a fitness center.

Frequently Asked Questions about villa rentals in Wailea, HI

Popular destinations

Best Wailea, HI villas and beach houses with jacuzzi

Seaspirit 811 Ocean View Luxury Hot Tub Spa - Wailea, HI
10 11 reviews

Seaspirit 811 Ocean View Luxury Hot Tub Spa

house, Wailea
SeaSpirit Villa 811 is a second-floor ocean view villa located within the Andaz Maui at Wailea Resort, steps from Mokapu Beach and the resort's pools and restaurants. The villa has excellent user, location and cleanliness ratings.
The villa has over 3,000 square feet of indoor and outdoor living space and can accommodate up to 8 guests. Enjoy a private patio with a hot tub, a gourmet kitchen, three uniquely decorated bedroom suites, each with a full en-suite bathroom, and access to all resort amenities, including three heated swimming pools, a fitness center, a spa, and multiple dining options.
Spectacular 3rd Row Villa At Ho'olei With Ocean Views - Wailea, HI
10 63 reviews

Spectacular 3rd Row Villa At Ho'olei With Ocean Views

house, Wailea
This Wailea house is conveniently located within walking distance of the Shops at Wailea and Wailea Beach, and within a mile of Wailea Blue Golf Course and Ulua Beach Park.
The 3,980 square foot house features three bedrooms, four bathrooms, and can accommodate up to eight guests, offering amenities like a private pool, jacuzzi, sauna, and a fully equipped kitchen.
Wailea Elua 705 Oceanfront Beach Retreat - Wailea, HI
10 1 review

Wailea Elua 705 Oceanfront Beach Retreat

house, Wailea
Wailea Elua 705 Oceanfront Beach Retreat is a house located in Wailea, offering an oceanfront experience just a 2-minute walk from Ulua Beach and 1.7 miles from the Wailea Emerald Course.
This 1420 sq ft residence accommodates up to 9 guests, featuring a fully equipped kitchen, 2 bathrooms (one with a hot tub), air conditioning, a private patio, an outdoor pool, a fitness center, and free private parking.
5 Star Ocean View, Beach House Chic, Click The Video Tour Below! - Wailea, HI
10 246 reviews

5 Star Ocean View, Beach House Chic, Click The Video Tour Below!

house, Wailea
This Wailea villa is conveniently located near the Wailea Blue Golf Course, the Wailea Tennis Club, and The Shops at Wailea, offering easy access to shopping, dining, and entertainment. It has received excellent user ratings for its comfort and amenities.
The villa features two master suites, each with a private bathroom and separate entrances, providing ample space for families or groups. Guests can enjoy a range of amenities, including a private lanai with ocean and golf course views, a swimming pool, a jacuzzi, and a fully equipped kitchen.

Neighborhoods and points of interest in Wailea, HI

Best Wailea, HI houses with a kitchen

Maui Kamaole C 202 - Wailea, HI
9.5 2 reviews

Maui Kamaole C 202

house, Wailea
This Wailea vacation rental is a six-minute walk from Kamaole Beach and a half-mile from Keawakapu Beach, also near Mokapu Beach and the Wailea Emerald Course.
This 1,310-square-foot house features two bedrooms, two bathrooms, a living room with a flat-screen TV, a full kitchen, and can accommodate up to 11 guests, plus offers a private pool, tennis court, free Wi-Fi, and free parking.
Kamaole Sands 4-306 - New Kitchen & Bathrooms, Ac! - Wailea, HI
8.0 3 reviews

Kamaole Sands 4-306 - New Kitchen & Bathrooms, Ac!

house, Wailea
Kamaole Sands 4-306, a Wailea vacation rental, is a five-minute walk from Kamaole Beach, 3.5 miles from the Wailea Emerald Course, and offers convenient access to other Wailea attractions.
This 820-square-foot one-bedroom, two-bathroom condo sleeps six and features a recently renovated kitchen, a Jacuzzi, a fitness center, a tennis court, ocean views, and on-site parking.
Hale Kamaole 4-334 - Wailea, HI
No reviews

Hale Kamaole 4-334

house, Wailea
This Wailea vacation rental is conveniently located near Keawakapu Beach, a short walk away, and a quick drive from Mokapu and Kamaole Beaches.
This two-bedroom, two-bathroom house sleeps up to 11 guests and features a fully equipped kitchen, private parking, a swimming pool, a fitness center, a tennis court, and a balcony with ocean views; massage services are available.
Kamaole Sands 7-205 - Wailea, HI
No reviews

Kamaole Sands 7-205

house, Wailea
Kamaole Sands 7-205 is a one-bedroom vacation rental in Wailea, Hawaii, a two-minute walk from Kamaole Beach Park and 3.4 miles from the Wailea Emerald Golf Course.
This condo offers two bathrooms, sleeps seven guests, includes a fully equipped kitchen, in-unit laundry, free Wi-Fi, private parking, and access to an on-site swimming pool and fitness center.

Search Luxury Vacation Homes in Wailea, HI

These upscale vacation homes in Wailea, HI provide the perfect blend of premium amenities and a highly desirable prime location.

Haleakala Shores A-308 - Ocean/mountain Views, Stylish 2br/2ba, Lanai, Ac, Wi-fi - Wailea, HI
No reviews

Haleakala Shores A-308 - Ocean/mountain Views, Stylish 2br/2ba, Lanai, Ac, Wi-fi

house, Wailea

Popular Family Vacation Homes in Wailea, HI

These kid-friendly Wailea, HI vacation homes offer plenty of room for the whole family to spread out.

I.p.m Presents: Villa E102 - Private Pool + Yard. Flexible Cancelation Policy - Wailea, HI
9.2 13 reviews

I.p.m Presents: Villa E102 - Private Pool + Yard. Flexible Cancelation Policy

house, Wailea
Exquisite Views, No Detail Spared: Sea Breeze J405 - Wailea, HI
10 24 reviews

Exquisite Views, No Detail Spared: Sea Breeze J405

house, Wailea
Oceanfront 3br Villa W/ Private Lanai And Wailea Beach Access - Wailea, HI
10 3 reviews

Oceanfront 3br Villa W/ Private Lanai And Wailea Beach Access

house, Wailea
Super Chic W/ Ocean Views - Wailea Seashore K507! - Wailea, HI
9.9 28 reviews

Super Chic W/ Ocean Views - Wailea Seashore K507!

house, Wailea

Find the Best Pet-Friendly Vacation Homes in Wailea, HI

Traveling with a pet to Wailea, HI is easy in these vacation homes, featuring dog-friendly amenities.

Fairmont Kea Lani Maui Villa Experience - Wailea, HI
No reviews

Fairmont Kea Lani Maui Villa Experience

house, Wailea

Traveler-Approved Holiday Houses with Wellness in Wailea, HI

Discover spa access at these waterfront vacation homes in Wailea, HI, ensuring wellness by the water is never an afterthought.

Wailea Ekahi Village - Coraltree Residence Collection - Wailea, HI
8.0 2 reviews

Wailea Ekahi Village - Coraltree Residence Collection

house, Wailea

Best Wailea, HI houses with air conditioning

Maui Parkshore 307 - Stunning Remodel, Ocean Views - Wailea, HI
9.0 1 review

Maui Parkshore 307 - Stunning Remodel, Ocean Views

house, Wailea
Kamaole Sands 3-302 - Wailea, HI
No reviews

Kamaole Sands 3-302

house, Wailea
Kamaole Sands 10-214 - Wailea, HI
9.0 2 reviews

Kamaole Sands 10-214

house, Wailea
Summer Sale! Penthouse Ocean Views, Spacious Layout, Beautiful Renovation, Ac! - Wailea, HI
9.3 3 reviews

Summer Sale! Penthouse Ocean Views, Spacious Layout, Beautiful Renovation, Ac!

house, Wailea
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