Wailea Vacation Rentals
<p>Wailea is located on Maui's sunny southern coast and known for pristine beaches and artfully designed hotels, condominiums, and exclusive residential communities. Golf, tennis, ocean fun and upscale shopping and dining are all hallmarks of the Wailea experience.</p><p><br></p><p><b>Things To Do</b><br>Numerous beaches in the Wailea area offer fine white sands and inviting blue water. Offshore views include Molokini Islet as well as the islands of Lanai and Kahoolawe. During the winter months humpback whales are common in these waters and can be seen from the shore or on a humpback whale watching tour. Golfers will love their choices in the Wailea area with four top-quality courses to choose from including the Blue Course, Emerald Course, Gold Course and nearby seaside Makena Golf Course. Wailea's Blue Course is known for its wide fairways as well as panoramic mountain and ocean views. Lush tropical landscaping makes the Emerald Course and enjoyable experience, while natural hazards, doglegs and narrower fairways provide challenges on the Gold Course which also takes in ocean views. From Wailea you can take a day trip to see the waterfalls of Hana, the scenic Upcountry Maui region or the stunning vistas atop Haleakala Volcano. Boating excursions are also popular including sunset sails, whale watching (during the winter months) and snorkeling and scuba diving trips to Molokini three miles offshore. Wailea also has a state-of-the-art tennis facility. After all the fun pamper yourself at the the Grand Wailea's Spa Grande which is Hawaii's largest spa and offers everything from island-style massage to aromatic mineral baths.</p><p><br></p><p><b>Nearby Beaches</b><br>Wailea Beach and nearby Makena Beach are considered two of Hawaii's finest beaches with white sand and clear blue water ideal for swimming and pleasant days at the beach. Wailea Beach is fronted by the Grand Wailea and Wailea Four Seasons resorts and is the largest and arguably the nicest of Wailea's beac…
70 vacation rentals found. Page 7 of 7 shows 10 properties (10 per page, same as the live site).
Wailea Vacation Rentals
Page 7 of 7 — 70 properties total — 10 per page (matches site listing view).
Floral Gardens Pool Villa G102 at Wailea Beach Villas
Wailea, MauiRating: 5
- 3 Bed
- 3 Full Baths
From $1695.00 / night — Total price: $5085.00
Our collection of Maui vacation residences are HOTEL-Zoned or have LEGAL short-term rental permits. Reserve with Private Paradise Villas with confidence knowing you will be luxuriating in a location legally designated for visitor accommodations and managed by our local on-island professional staff. Photos of updated interior coming soon! Now installed: a gorgeous French Blue velvet sofa, coral and blue dining chairs and stools, new area rug, new 2nd bedroom furniture. New bed frame just added t
Grand Seascape K407 at Wailea Beach Villas
Wailea, MauiRating: 5
- 2 Bed
- 2 Full Baths
From $995.00 / night — Total price: $2985.00
Situated in the centrally located "Penthouse" building on the 4th floor in a west-facing ocean view corner location with breathtakingly beautiful panoramic ocean and sunset views, this 2.5 bedroom (king bed in each bedroom plus 2 twin beds the enclose-able den that can be converted into a king bed) was just beautifully redecorated with stylish furniture from Serena and Lily in calming hues of of blues and whites. There are two bathrooms, a private veranda with a built-in Viking gas grill, a dedi
Royal Ilima A201 at Wailea Beach Villas
Wailea, MauiRating: 5
- 3 Bed
- 3 Full Baths
From $2695.00 / night — Total price: $8085.00
Our collection of Maui vacation residences are HOTEL-Zoned or have LEGAL short-term rental permits. Reserve with Private Paradise Villas with confidence knowing you will be luxuriating in a location legally designated for visitor accommodations and managed by our local on-island professional staff. The Royal Ilima Villa A201 is the only true beach front three bedroom villa offered within the Wailea Beach Villas. Extensively redesigned and redecorated in fall 2023, the Royal Ilima is a three bed
Sandcastles Suite L509 at Wailea Beach Villas
Wailea, MauiRating: 5
- 3 Bed
- 3 Full Baths
From $1525.00 / night — Total price: $4575.00
In all of Hawai'i, Sandcastles Suite L509 is one of the most spectacular private residences available for visitor accommodations in a resort setting. Certainly, L509 Sandcastles Suite is one of the most exquisite of the "Wailea Beach Villas", with its TOP (5th) FLOOR location, exceptionally attractive decor, original elegant oil paintings, and other vintage hand-crafted furnishings. Sandcastles Suite L509 is a 4 bedroom, 3 bathroom, ultra-luxurious ocean view villa residence featuring original w
Sea La Vie L510 at Wailea Beach Villas
Wailea, Maui- 2 Bed
- 2 Full Baths
From $1395.00 / night — Total price: $4185.00
Situated on the 5th TOP FLOOR of the penthouse/tower building of the Wailea Beach Villas Resort, Sea La Vie L510, a fully redecorated and remodeled 2.5 bedroom, 2 bath suite, offers expansive and superlative direct west-facing panoramic views of the Pacific Ocean, Wailea Beach and the Wailea Resort area. Only a few residences on the upper floors of the Wailea Beach Villas offer such exceptional views. This villa is well above the family pool where birdsong and the rustling of palm tree fronds pr
SeaSpirit 811 at Andaz Maui at Wailea Resort
Wailea, Maui- 3 Bed
- 4 Full Baths
From $2495.00 / night — Total price: $7485.00
SeaSpirit Villa 811 at Andaz Maui at Wailea Resort is a contemporary styled, privately-owned and independently-managed luxury 3 bedroom, 4 bath ocean view second floor resort residence. SeaSpirit is set in a prime location within the resort just steps from Mokapu Beach and the resort's swimming pools and dining venues. Experience this tropical paradise on the beach where you can rest and relax within SeaSpirit Villa 811, “Your Own Private Paradise”, with spacious surroundings, exqui
Sun Splash C301 at Wailea Beach Villas
Wailea, MauiRating: 5
- 3 Bed
- 3 Full Baths
From $2195.00 / night — Total price: $6585.00
Our collection of Maui vacation residences are HOTEL-Zoned or have LEGAL short-term rental permits. Reserve with Private Paradise Villas with confidence knowing you will be luxuriating in a location legally designated for visitor accommodations and managed by our local on-island professional staff. Sun Splash Villa C301 was busy this summer with a big makeover! We've installed new hardwood flooring, countertops and other upgrades and updates. The villa is even even prettier and better than it a
Wailea Seashore Suite K507 at Wailea Beach Villas
Wailea, MauiRating: 5
- 2 Bed
- 2 Full Baths
From $1295.00 / night — Total price: $3885.00
Wailea Seashore Suite K507 (2 bedrooms plus additional sleeping area that can be closed off and 2 bathrooms), is set on the top (5th) floor at the beachfront Wailea Beach Villas Resort on Maui Island. K507 was just beautifully redecorated after it was purchased by new owners. The two king size master bedroom suites have gorgeous rich chocolate brown bamboo wood floors with colorful pure New Zealand wool area rugs made exclusively for the Hawai'i market. The den bedroom located off the great r
Wailea Sunset Bungalow
Wailea, MauiRating: 5
- 2 Bed
- 1 Full Baths
From $895.00 / night — Total price: $2685.00
Wailea Sunset Bungalow is a classic 1960's beach bungalow newly renovated, updated, and re-decorated from top to bottom for the 21st century. Annually returning guests and the online reviews speak volumes! The adorable oceanfront 2 bedroom Wailea Sunset Bungalow was completely renovated and is meticulously maintained and managed. Enjoy classy coziness in this iconic oceanfront vintage cottage. Reserve now and enjoy the priceless ambiance of this direct oceanfront home, set on one full acre with
Wailea Sunset Estate
Wailea, MauiRating: 4.8
- 4 Bed
- 5 Full Baths
From $3250.00 / night — Total price: $9750.00
Our collection of Maui vacation residences are HOTEL-Zoned or have LEGAL short-term rental permits. Reserve with Private Paradise Villas with confidence knowing you will be luxuriating in a location legally designated for visitor accommodations and managed by our local on-island professional staff. Wailea Sunset Estate, easily one of our most popular vacation homes, has been lovingly refreshed with upgraded amenities and decor. This exquisite private home is quite possibly the most successful a
