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.

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Makena Surf | A204 | Beachfront Resort

Makena Surf A204 is a luxurious oceanfront residence offering a serene Hawaiian retreat. This spacious 1,600 square foot condo, located on the second floor, boasts breathtaking ocean views and direct access to the pristine Po'olenalena Beach. The open-concept layout...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

Palms at Wailea Garden Villas 1 Bedroom 2 Bath

Garden View 1 Bedroom 2 Bath Villa- Full kitchen includes stovetop, oven, microwave, refrigerator, dishwasher, coffeemaker, toaster, cookware and tableware- Spacious private deck- 1 king bed or 1 queen bed- Queen sofa bed- 1022 square feet / 95 square meters- Maximum 4...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

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

Introducing the newest unit in our portfolio! Please visit and be our first review with an introductory Special Rate till August 31th! Wailea Ekolu #405 is an ocean view 2 bedroom, 2 bath ground floor unit with air conditioning throughout, a fully equipped kitchen,...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

Palms at Wailea Villa 805 Garden View 2 BD 2 BA

- Ground floor unit- Kitchen includes stovetop, oven, microwave, refrigerator, dishwasher, coffeemaker, toaster, cookware and tableware- Spacious private 219 square feet deck- Master bedroom with 1 king bed- 2nd bedroom with 1 queen bed- Queen sofa bed in living area-...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

Wailea Ekahi Village | 51D

Wailea Ekahi Village tropical vacation condos are situated above Maui's beautiful Keawakapu Beach and close to all the top Wailea resort hotels.  Enjoy easy access from your vacation condo at Wailea Ekahi Village to the restaurants and spas of the Grand Wailea,...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

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...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

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...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

Wailea Elua Village | 2108

Welcome to Wailea Elua Village #2108. This two-bedroom, two-bath residence is fully remodeled and redecorated, features an extra-large floor plan of more than 1,500 square feet, and boasts gorgeous, elevated views of the ocean, off-shore islets, and lush tropical...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

Wailea Beach Villas PH106

Welcome to Wailea Beach Villas Penthouse 106, a luxurious ground-floor retreat in one of Maui’s most prestigious beachfront communities. This stunning 1,899-square-foot villa offers the perfect blend of island elegance and modern comfort, making it an exceptional...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

Palms at Wailea Villa 1103 Ocean View 1 BD 2 BA

- Ground floor unit- Kitchen includes stovetop, oven, microwave, refrigerator, dishwasher, coffeemaker, toaster, cookware and tableware- Spacious private 473 square feet deck- Bedroom with 1 king- Queen sofa bed in living area- 1022 square feet / 95 square meters-...

🛏 1 Bedroom
🛁 2 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

Makena Surf | B204 | Beachfront Resort

Experience the ultimate beachfront getaway at this luxurious 2-bedroom oceanfront vacation rental at Makena Surf, located on the stunning shores of Maui. This exquisite condominium offers breathtaking views of the Pacific Ocean and the nearby islands, including Molokini...

🛏 2 Bedrooms
🛁 2 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

Wailea Ekahi Village | 52D

Wailea Ekahi 52 is a luxurious vacation rental property located in the heart of the idyllic Wailea resort community on the southern shores of Maui. This spacious, one-bedroom, one-bathroom condominium offers guests a serene and indulgent island getaway, with all the...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 4
📍 Wailea, Hawaii

Wailea Point Contemporary 2 Bedroom+Loft/3 Bath Oceanview Condominium

Yes, you can treat yourself and stay in a vacation home at Wailea Point! A premier hospitality destination nestled between the Four Seasons Wailea Resort and the Fairmont Kealani Wailea, featuring an optimal location near beaches, golf, restaurants and entertainment....

🛏 2 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

Wailea Ekahi Village | 12B

Wailea Ekahi Village 12B is a beautiful vacation rental that underwent a complete update in March 2021. Interior designers may want to take notes! This gorgeous ocean view studio is ideal for couples looking for a cozy retreat or solo travelers looking for the perfect...

🛏 1 Bedroom
🛁 1 Bathroom
👤 Sleeps 2
📍 Wailea, Hawaii

Wailea Point 3 Bedroom/3+ Bath Oceanview Condominium #2503

Yes, you can enjoy a holiday and vacation stay at Wailea Point, the iconic red roofs on Maui's wonderful southern shore; and at a rate lower than a suite at the Wailea hotels. 2503 just may be the 'best location in the whole property'; with an expansive outdoor lanai...

🛏 3 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 6
📍 Wailea, Hawaii

Wailea Point Executive 2 Bedroom/3 Bath Oceanview Vacation Home

Welcome home to Wailea Point 2803 - A premier holiday home for you and your family to spread out and enjoy quality time together. A tranquil private lanai for evening BBQs and sunrise breakfast or just sit and enjoy whale watching from your living room during the Winter...

🛏 2 Bedrooms
🛁 3 Bathrooms
👤 Sleeps 4
📍 Wailea, Hawaii

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