Wailea Vacation Rentals

Wailea & Makena Rentals

Wailea vacation rentals with Maui Condos

Grand Wailea Resort

This luxury resort offers 40 oceanfront acres graced by spectacular water features. Ocean activities are easily arranged through the concierge. The resort is surrounded by Wailea Blue Golf Course, and only minutes away from 5 championship courses — perfect location for a golf getaway.

Contact Jill today for more details on booking at Grand Wailea Resort.


luxury wailea beach rentals

Maui Ho’olei

Ho’olei’s luxurious & private 3-bedroom, 3.5-bath townhouses are perfect for weddings, large party celebrations and extended family vacations. Attractive furnishings, modern kitchens, and private elevators help make each home feel truly upscale — with spacious designs ranging from 3,200 to 4,000 square feet. Enjoy full access to Grand Wailea Resort, including pools, spa, kids activities, etc.

  • Gated entry + 24-hour on-site security
  • Resort shuttle service between residences, rec center, Grand Wailea Resort and Spa, and Wailea Beach
  • Reception services
  • Full concierge services including childcare
  • In room & poolside massage
  • 6 restaurants
  • 9 pools on six levels, connected by a river
  • 4,850 sq.ft. pool with 2 jacuzzis
  • Spa Grande – Hawaii’s largest spa
  • State-of-the-art Fitness Center
  • Wailea Golf Club
  • Wailea Tennis Club
  • Beach Activities: kayak tours, whale watching, scuba diving, snorkeling and windsurfing
  • Extensive art collection throughout the Grand Wailea grounds
  • + more resort perks!

Contact Jill today for more details on booking at Maui Ho’olei.


Wailea vacation rentals with Maui Condos

Four Seasons Resort

On sunny Wailea Beach, this resort combines gracious Hawaiian elegance with uncompromising luxury. The focus on impeccable service and the absolute finest in accommodations and facilities set this luxury resort apart. A wide range of complimentary services, facilities and activities are available.

Contact Jill today for more details on booking a room at Four Seasons Resort Maui.


Wailea condos

Outrigger Palms at Wailea

Located on a scenic bluff within Wailea Resort, Outrigger Palms at Wailea offers privacy and convenience of one bedroom condos and two bedroom condominium suites.

Maui Condo Resort Amenities:

  • 1-bedroom and 2-bedroom villas
  • 2-story walk-up, no elevators
  • Completely non-smoking
  • Complimentary guest parking
  • Complimentary Wi-Fi in guest rooms, lobby, pool deck
  • Full kitchen and washer/dryer in every condo
  • Swimming pool
  • No resort fee
  • + more resort perks!

Contact Jill today for more details on booking a condo at Outrigger Palms.


Wailea Beach Marriott

Wailea Beach Marriott

This beautiful and deluxe Hawaiian-style full-service resort located on the sunny leeward side of South Maui offers guests 22 lush oceanfront acres. Relax in luxuriously appointed guest rooms and enjoy spectacular sunsets.

Maui Condo Resort Amenities:

  • Restaurants: Mala Wailea, MiGRANT, Kai at Wailele Pool, Starbucks, Te Au Moana Luau
  • Air conditioning
  • Smoke-free
  • Wailea Golf Club
  • Mandara Spa (full service spa)
  • Pools, 18+ pool
  • Whirlpool and hot tubs
  • Fitness center
  • Barber & beauty shop
  • Daily housekeeping
  • 21 meeting rooms (27,500 sq ft of space)
  • Biking trail
  • + more resort perks!

Contact Jill today for more details on booking a condo at Wailea Beach Marriott.

maui villas

The Fairmont Kea Lani Villas

Maui’s luxury all-suite & villa oceanfront resort on Polo Beach. Experience luxurious accommodations in a tropical paradise where you’ll stroll hand in hand along the warm white sand beach by day and dine in one of the nearby gourmet restaurants by night.

Contact Jill today for more details on booking a condo at the Fairmont Kea Lani Villas.


Wailea Grand Champions Maui Condo Rentals

Wailea Grand Champions Private Villas

Wailea Grand Champions condominiums are a lushly gardened condominium community in Wailea. Furnished, air conditioned and equipped with large bathrooms, the spacious units feature garden, mountain or ocean views. Each unit has a private lanai, beautiful furnishings and all of the amenities you expect from a luxury condominium resort.

Maui Condo Resort Amenities:

  • Free parking
  • Free wifi internet
  • Free phone calls
  • Air conditioned
  • Private lanai
  • In-unit washer/dryer with detergent
  • 2 swimming pools
  • 2 whirlpool spas
  • BBQ areas
  • Wailea Tennis Center
  • Beach towels provided
  • Fully stocked kitchens
  • + more resort perks!

Contact Jill today for more details on booking a condo at Wailea Grand Champions.


wailea studio 1 2 bedroom condo

Wailea Ekahi Village

Wailea Ekahi Village is a vacation rental for families and friends. Overlooking Keawakapu Beach, the resort offers studios, one and two-bedroom suites with private lanais on 34 acres of beautiful tropical gardens. The resort has four swimming pools, a covered beachfront pavilion near its private beach entrance, convenient beach facilities, shuffleboard, and BBQ areas.

Maui Condo Resort Amenities:

  • Free parking
  • Free wifi internet
  • Free phone calls
  • Air conditioned
  • Private lanai with BBQ grill
  • In-unit washer/dryer with detergent
  • 4 swimming pools
  • BBQ areas
  • Shuffleboard
  • Paddle tennis
  • Beachfront pavilion with ice maker, water, fridge, stove,
  • microwave, BBQ grills
  • Beach towels provided
  • Fully stocked kitchens
  • + more resort perks!

Contact Jill today for more details on booking a condo at Wailea Ekahi.


Makena Resort Condos

Makena Surf

Two bedroom and three bedroom Makena condo rentals amidst lush gardens and white sandy beaches. Makena Surf will be your sanctuary at Po’olenalena Beach, which you can view from the spacious lanai with floor to ceiling glass doors. Every condo features oceanfront views. Check out an ancient cultural site or 2 herb gardens on property.

Maui Condo Resort Amenities:

  • Free parking
  • Free wifi internet
  • Free phone calls
  • Private gated entrance
  • Central air conditioning
  • Private lanai with glass balconies and ocean views
  • 2 swimming pools
  • 2 whirlpool spas
  • 4 tennis courts (2 with lights)
  • BBQ areas
  • Beach towels and beach chairs provided
  • Fully stocked kitchens
  • In-unit washer/dryer with detergent
  • + more resort perks!

Contact Jill today for more details on booking a condo at Makena Surf.

Wailea beachfront condo rentals

Wailea Elua Village

These peaceful and relaxing beachfront Maui resort vacation condos are located along Ulua Beach, known for good snorkeling in the morning and body surfing in the afternoon. Choose from one bedroom, two bedroom, or three bedroom condo suites on 24 acres of scenic gardens and strolling lawns. Upscale boutiques and Wailea’s award-winning restaurants are close-by.

Maui Condo Resort Amenities:

  • Free parking
  • Free wifi internet
  • Free phone calls
  • Air conditioned
  • Private lanai with BBQ grill
  • In-unit washer/dryer with detergent
  • 2 swimming pools
  • 2 whirlpool spas
  • Fitness center
  • Putting green
  • Paddle tennis court
  • BBQ facilities
  • Private beach access
  • Beach towels and beach chairs provided
  • Fully stocked kitchens
  • + more resort perks!

Contact Jill today for more details on booking a condo at Wailea Elua.


weailea beach condos

Wailea Beach Villas

Wailea Beach Villa vacation homes range in size from 1,900 to 3,100-square-feet. Set amid lush gardens and pools on a private 11-acre property offering private pedestrian access to The Shops at Wailea.

Close to everything desirable in Wailea, from golf and shopping to fine dining and world-class spas, this exclusive beachfront Maui resort also makes it easy to jump in the water for swimming, snorkeling, stand-up paddle boarding, sailing, diving or canoeing.

Wailea Resort Amenities:

  • Free valet parking or self parking
  • Car, van and Jeep rentals available
  • Free wifi internet
  • Central air conditioning
  • Large private lanai with BBQ
  • 2 swimming pools
  • 2 whirlpool spas
  • BBQ areas
  • Beach services
  • Fitness facility with locker rooms
  • Business center
  • Activity room
  • Billiards room
  • Beach towels provided
  • Fully stocked European kitchens
  • + more resort perks!

Contact Jill today for more details on booking a condo at Wailea Beach Villas.


polo-beach-club

Polo Beach Club

Luxurious beachfront and oceanfront Maui condos. Enjoy your own oceanfront lanai, beachfront pool, deck, and spa. Prime beachfront Maui accommodations with white water and beach views. Fully appointed, all amenities and close access to golfing.

Contact Jill today for more details on booking a condo at Polo Beach Club.


Wailea Ekolu

One bedroom and two bedroom Wailea luxury condos surrounded by 18 acres of lush gardens

Maui Condo Resort Amenities:

  • Free parking
  • Free wifi internet
  • Free phone calls
  • Air conditioned
  • Private lanai
  • In-unit washer/dryer with detergent
  • 2 solar-heated swimming pools
  • BBQ areas
  • Recreation pavilion
  • Beach towels provided
  • Fully stocked kitchens
  • + more resort perks!

Contact Jill today for more details on booking a condo at Wailea Ekolu.

Wailea / MakenaKiheiLahainaKāʻanapali, Kahana, Napili & HonokowaiKapaluaRoad to Hana

WE ARE UPDATING THIS PAGE – MORE PROPERTIES ADDED SOON

This is not all that we have! Please contact Jill today to match YOU with the perfect Maui condo rental or Maui resort rental for your upcoming trip to Maui.

 

 

 

 

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