
Condo vacation rentals in Wailea
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Top-rated condo rentals in Wailea
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100KContemporaryHawaiian Reno in Wailea-Beach/Golf
Stunning 100K Recent Reno+New Decor for a Hawaiian Beach Vibe. Wailea is one of the most sought after resort addresses on Maui.Here you can relax in the luxury of the beautiful grounds+refreshing swimming pool+spa. World Class Golf+Shopping. Ground flr condo with private wrap around lanai. King Master Bed with a contemporary private bath,2 Uber deluxe pull out Queen bed couches.Short stroll to Keawakapu Beach from condo where you can snorkel or take long tropical beach walks.BOOK UP TO 365 DAYS

Spacious S. Kihei Suite New A/C across from Kam 3
This spacious suite is perfect a relaxing stay for two. Brand new split system A/C in bedroom & living room to keep you cool. Peak-a-boo ocean views from the suite with glimpses of Kahoolawe. Located in S. Kihei across from one of the BEST beaches on Maui, Kamaole Beach III and steps from the Kihei Boat Ramp. Walk to shops and restaurants in South Kihei. Keawakapu Beach and Wailea is just minutes away. Choose from 2 pools or play a round of tennis or pickle ball. Large lawns and BBQ areas.

Beachfront Oceanview Wailea Ekahi 16B Studio W/AC
Wailea Ekahi is a luxurious resort fronting onto beautiful Keawakapu Beach with acres of tropical grounds and 4 pools. Unit 16B is a mid property, renovated ground floor ocean view studio unit (500 sq feet) with a King sized bed, walk in shower and full kitchen. Enjoy your morning coffee and meals from the peaceful, shaded lanai which opens onto the lush greenspace and gardens while enjoying ocean views. A short walk to the beach, pools, luxury shopping, highend dining and golf courses.

Romantic, Luxury Retreat w/Ocean View-Couples Only
Luxury 1 bedroom 2 bath condo which has been fully renovated. Our condo has lovely ocean views as well as views of the lush tropical gardens and the pool. It has a fully stocked gourmet kitchen with high end appliances, assorted spices, coffee and tea. Sunset views from the lanai are stunning. If our condo is not available during the days of your travel, please check availability at our other Wailea Palms condo at https://www.airbnb.com/rooms/1728525 Not suitable for children or infants.

Wailea Beauty - walk to the beach & shops
Our locally-owned, newly redesigned 2BD/2BA modern Maui condo is located on the award-winning Wailea Blue Golf Course at The Grand Champions Villas. The Villas are nestled in the heart of tropical Wailea; minutes from shopping, tennis, restaurants and pristine beaches. Stroll to upscale boutiques and restaurants, or take a short walk to some of the most beautiful beaches in the world. Our condo features local Hawaii art and is your perfect home away from home on the beautiful island of Maui.

Luxury condo • 180° Ocean Views • Steps to Beach
Enjoy panoramic ocean, mountain, beach & sunset views year round at Hale Meli (short for "Hale Mahina Meli" or “Honeymoon House” in Hawaiian), a top floor condo with exquisite designer interiors and high-end amenities. Ideally located in Kihei, the condo is right across the street from one of the best beaches on Maui and is walking distance to restaurants, shops and grocery stores. It is also your perfect home base for exploring the rest of Maui, being centrally located on the island.

Upscale and Elegant Vistas
Spacious and elegant condo in the much sought after Wailea area. Fantastic unobstructed ocean and sunset views. Completely remodeled and freshly outfitted. No expense was spared to create our ocean view oasis. This one-bedroom, two-bathroom condo features thoughtful luxurious finishes throughout. Located in sunny and luxurious Wailea, with all of Maui is within reach. Beach chairs, umbrellas, luxury beach towels and a cooler are all provided to enjoy a day at the beach nearby.

Very Comfortable Kamaole Sands Condo Sleeps 4
Very comfortable end unit 1 bedroom condo 2 bathrooms (818 sq ft) with views of the pool, partial ocean view, remodeled kitchen and bathrooms, recently painted, new flooring in living room and conveniently located to everything you need, unit is airy and bright with extra windows. The kitchen is well stocked with all the essentials and cooking utensils. A 5 mins walk to the beach and 10-15 mins leisurely stroll to nearby shops and stores. I take my own photos for my unit.

Escape to Sugar Beach / Ocean Views
Amazing ocean views and breathtaking sunsets in our upgraded one-bedroom, one-bath, air-conditioned condo. Sugar Beach Resort, is just steps away from the 5-mile white sandy beach. Our beach access is excellent for swimming, snorkeling, windsurfing, kayaking, or just relaxing. Central location to all that Maui has to offer. Our unit sleeps 2, with a Cal king-sized bed with luxury linens and a mattress. Fully stocked kitchen with cookware, utensils, etc.

Luxury Condo w/wide Ocean View (Palms at Wailea)!
There is no better location than Wailea to experience your Maui vacation! This quiet and spacious condo has every amenity you could want to make your Maui vacation truly unforgettable. This condo is only a short walk to one of the best beaches (Keawakapu) on Maui and is also in close proximity to the Shops at Wailea. We spared no expenses in stocking this condo with everything you need to make your Maui experience memorable and luxurious.

Wailea Ekolu Village 2/2 with stunning ocean view!
Beautiful, spacious, modern 2/2 condo located in the heart of the Wailea Resort area with gorgeous, far-reaching ocean and island views, and surrounded by brilliant, lush, flowery grounds. Super-close to dining, golf, shopping, and only a short stroll to award-winning Wailea and Ulua beaches! Please note that this Wailea Resort condo has received government approval to operate as a vacation rental for the next 5 years.

Stylish 1 br. gr. floor unit. Steps from the beach
Discover an exceptional South Maui escape just steps from the pristine sands of Kamaole III Beach, one of Kihei’s most celebrated stretches of shoreline. This elegantly furnished 800 sq. ft. residence offers a refined yet relaxed island experience, ideal for up to four guests seeking comfort, convenience, and an unbeatable location. Both short and long terms stays are available.
Popular amenities for Wailea condo rentals
Weekly condo rentals

Fabulous Ocean Views at Ho'okipa at Wailea Ekolu!

Luxury Wailea Beach Condo

Wailea Ekahi Gem |Walk to Beach |May Special!

Gorgeous Condo in Wailea Ekahi Village!

Lovely Ocean View, Great Rates! PA1105

Modern Renovated Palms at Wailea Condo!

Beautiful Kihei Front Row OCEAN View l Top BEACH

Aloha Moon - The Honeymoon Hideaway
Pet-friendly condo rentals

Condo w/ Private Lanai, Ocean View & On-Site Pool!

Steps to Beach & Ocean Views by Bijou Getaways

High-Floor Island Surf | AC | Walk to Beach

The Lava Shack

Breathtaking Location-Sugar Beach #129

Luxury condo 20 steps from beach/pool/hot tub #103

*Rare Find* Quiet Ocean View Condo in Sunny Kihei

Walk to Beach-1BR w/ Full Kitchen/Resort Amenities
Condo rentals with a pool

New Listing! Beautiful 2bd condo in Wailea

Epic View! Lovely 2BR Beach Condo in Kihei/Wailea

Gorgeous Ocean View Condo steps to the beach

Maui Retreat Ekahi 50F -All YOU Need!

Reno 10/2025 Bose Sunrise Sunset view near Resorts

Tropical Wailea Retreat

PURE ELEGANCE*OCEANVIEW Renovated Condo in WAILEA

WBH D225 Aloha Ola – Ocean and Pool View
When is the best time to visit Wailea?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$69,455 GYD | G$72,175 GYD | G$71,966 GYD | G$62,761 GYD | G$54,811 GYD | G$56,275 GYD | G$54,393 GYD | G$52,510 GYD | G$50,627 GYD | G$52,510 GYD | G$61,506 GYD | G$74,685 GYD |
| Avg. temp | 16°C | 16°C | 16°C | 17°C | 18°C | 18°C | 19°C | 20°C | 19°C | 19°C | 18°C | 17°C |
Quick stats about condo rentals in Wailea

Total vacation rentals
Explore 1,460 vacation rentals in Wailea

Nightly prices starting at
Wailea vacation rentals start at G$31,380 GYD per night before taxes and fees

Verified guest reviews
Over 41,430 verified reviews to help you choose

Family-friendly vacation rentals
820 properties offer extra space & kid-friendly amenities

Vacation rentals with a pool
1,400 properties feature pools

Rentals with dedicated workspaces
890 properties have a dedicated workspace

Wi-Fi availability
1,450 of Wailea vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Wailea rentals

4.8 Average rating
Wailea stays are highly rated by guests—averaging 4.8 out of 5!
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- Maui
- Kamaole Beach Park II
- Kaanapali Beach
- Lahaina Beach
- Honolua Bay
- Kapalua Bay Beach
- Polo Beach
- Wailea Beach
- Maui Ocean Center
- Hāmoa Beach
- Ka'anapali Golf Courses
- Old Lahaina Luau
- Ulua Beach
- Big Beach
- Whalers Village
- Black Rock Beach
- Haleakala National Park
- Peahi
- Maui Arts & Cultural Center
- Maui Vista Condominium
- Black Sand Beach
- Kihei Kai Nani
- Kahana Beach
- Maui Sunset




