Kailua Listings

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Weekly $600.00 - $3095.00

Luxurious Kailua Home w/Pool Oasis & A/C, Near Beaches and Shopping - Maluhia Kailua, Hawaii, Listing ID: 30109

Let the tranquil atmosphere of Maluhia whisk you into vacation mode. A favorite of many celebrities and families for the perfect, peaceful getaway, Maluhia is the definition of island contemporary. Its remodeled, modern interior features nearly 5,000 sq. ft. of living space. The...

  • House
  • 4919
  •  4
  •  4
Weekly $360.00 - $1193.00

Charming Tropical Oasis w/Private Pool & A/C, Walk to Beach - Lanikai Cottage Kailua, Hawaii, Listing ID: 30110

Charming Lanikai Cottage features two dwellings on the same property, providing a total of three bedrooms and two bathrooms. Although separate, the dwellings share a private fenced-in yard with a new pool. Furnished in a beach-chic style, both offer the option of relaxing in air...

  • House
  • 1469
  •  3
  •  2
Weekly $380.00 - $1763.00

Beautiful Tropical Home Close to Beach w/Pool, Yard & AC: Hale Nani Lanikai Kailua, Hawaii, Listing ID: 30113

Nestled in the highly sought after wonderful Lanikai community, this beautiful executive home was newly built in 2014. This home is a perfect vantage point. It boasts 3 bedrooms en suite that are generous in size and more than ample in comfort. Guests will find that the...

  • House
  • 0
  •  3
  •  3 1/2
Weekly $650.00 - $3968.00

Gorgeous Oceanfront Home w/Mokulua Isle Views, Yard & AC: Lanikai Oceanside Kailua, Hawaii, Listing ID: 30128

With front row seats to the ocean and the famous Mokulua Islands of Kailua, Lanikai Oceanside offers the best seats in the house. Newly renovated, this tropical chic and modern oceanfront beach home is open and spacious, yet warm and intimate. Wake up to the sounds of the sea,...

  • House
  • 4880
  •  5
  •  4
Weekly $500.00 - $2918.00

Stunning Secluded Fmaily Oasis w/ Private Pool and Courtyard - Lanikai Breeze Kailua, Hawaii, Listing ID: 30131

This stunning property is now accepting longer-term stays at reduced rates. Please inquire for details. Just steps away from coveted Lanikai Beach, sits our newest luxury rental - Lanikai Breeze. Built in 2017, this brand new construction boasts upgraded appliances and...

  • House
  • 3240
  •  5
  •  4 1/2
Weekly $2300.00 - $12150.00

Expansive Beachfront Kailua Shores Estate w/Pool, Spa, AC & Breathtaking Views Kailua, Hawaii, Listing ID: 30134

One of the largest, most private and secluded vacation rental residences on the island of Oahu, Kailua Shores Estate provides a spectacular beachfront location and all the amenities of a luxury resort, making it ideal for a family reunion, an escape to paradise with a group of...

  • Estate
  • 7500
  •  8
  •  9
Weekly $3000.00 - $13679.00

Luxury Beachfront Kai Moena Estate w/Pool, Spa, AC, Sauna, Tennis Court & More! Kailua, Hawaii, Listing ID: 30136

This luxury vacation rental sits on nearly 60,000 sq. ft. of prime Kailua Beach property with 225+ sq. ft. of linear beach frontage featuring soft sand, blue water and spectacular views of Kailua Bay. Two separate rental houses by award winning architect James McPeak are laid...

  • Estate
  • 8600
  •  9
  •  7 1/2
Weekly $583.00 - $4030.00

Exquisite Oceanfront Retreat w/Mokulua Views, AC & Lush Yard: Lanikai Seashore Kailua, Hawaii, Listing ID: 30143

Experience luxurious coastal living at Lanikai Seashore, a tropical two-story vacation rental just steps away from the renowned Lanikai Beach. This villa’s spacious open floor plan and unobstructed ocean views makes one feel they’re almost on their own private isle; away...

  • House
  • 2100
  •  4
  •  3 1/2
Weekly $334.00 - $2334.00

Elegant Home w/Private Beach Access, Pool & AC: Relaxing Lokomaika'i Kailua Kailua, Hawaii, Listing ID: 30145

Let the relaxing atmosphere of Lokomaika’i Kailua (meaning Gracious Kailua) whisk you into vacation mode. The home includes 2 primary suites that beckon you to the outdoor areas of the pool and garden. There are also 2 additional bedrooms and bonus sitting room located off of...

  • House
  • 2680
  •  5
  •  3
Weekly $470.00 - $1981.00

Bright Kailua Retreat w/hot tub, Lush Pool, Walk to Beach: Hale Ohana Kailua, Hawaii, Listing ID: 30146

Hale Ohana meaning Family House is just that! With multiple lounge areas, pool, hot tub, game room inclusive of a spider man pinball game, ping pong table and much more this home is perfect for a family get away! The home includes 3 bedrooms in the main house and a separate...

  • House
  • 2987
  •  4
  •  3
Weekly $1666.00 - $5500.00

Lavish Oceanview Estate w/Pool, Spa, AC & Mokulua Isle Views: Lanikai Hillside Kailua, Hawaii, Listing ID: 30148

Welcome to Lanikai Hillside Estate, a premier vacation rental nestled on the world’s most isolated chain of islands. While residing here, you’ll delight in the near heaven-like beauty of this small, coastal community which is truly the envy of all paradises. Lanikai Hillside...

  • Estate
  • 6296
  •  5
  •  6 1/2
Weekly $950.00 - $7889.00

Hidden Mountainside Home w/ Private Pool, Ocean Views & soaking tub, Hale Lani Kailua, Hawaii, Listing ID: 30152

Find your next dream vacation here at Hale Lani, situated on the picturesque northern shores of Oahu, Hawaii. Hale Lani in Hawaiian translates to “house in the heavens”, and this heavenly home surely lives up to its name. Nestled atop the lush mountainside of the...

  • House
  • 2888
  •  3
  •  4
Weekly $480.00 - $5000.00

Ocean View Villa w/Beach as Backyard, Walk to Attractions: Kailua Hale Kahakai Kailua, Hawaii, Listing ID: 30160

Let the tranquil atmosphere of Kailua Hale Kahakai whisk you away into vacation mode! Located on one of the most beautiful stretches of Kailua Beach, this spacious villa boasts gorgeous ocean views from four of the six bedrooms. This villa also sits on a quiet flag lot, offering...

  • Villa
  • 4326
  •  6
  •  5
Weekly $1440.00 - $9500.00

Stunning Beachfront Estate w/Private Pool/Spa, Ocean View & AC, Kailua Beach Villa Kailua, Hawaii, Listing ID: 30161

Welcome to Kailua Beach Villa, the perfect luxury Hawaiian home for your next beachfront getaway. This large, 2-level clean and contemporary villa comes with 5 bedrooms (and 1 additional optional bedroom), 5 bathrooms and sleeps up to 12 guests. With a spacious and open-air...

  • Villa
  • 4000
  •  5
  •  5
Weekly $450.00 - $1750.00

Private Luxury Home, Steps from the Beach w/ AC: Ranch Beach House Estate Kailua, Hawaii, Listing ID: 30163

Ranch Beach House Estate is a hidden Hawaiian gem, just steps away from Kailua’s powder white sand beaches. Located on one of Kailua’s most coveted loops, you will find its location ideally accessible to numerous cafés, boutiques and farmers’ markets. A well-manicured...

  • Estate
  • 3800
  •  4
  •  3 1/2
Weekly $667.00 - $7994.00

Oceanfront Luxury Home w/Hot Tub, A/C & Views of Lanikai Beach: Na Makana Villa Kailua, Hawaii, Listing ID: 30165

Welcome to Na Makana Villa, the perfect luxury Hawaiian home for your next beachfront getaway. This expansive villa comes with 4 bedrooms in the main house and a 2 bedroom attached guest cottage, providing enough space to sleep up to 13 guests. With a spacious and open-air...

  • Villa
  • 4098
  •  6
  •  4 1/2
Weekly $300.00 - $1772.00

Peaceful Oceanfront Home Near Downtown Kailua w/ BBQ & AC: Kai Mele Kailua, Hawaii, Listing ID: 30166

Welcome to Kai Mele, your next charming beachfront getaway filled with all the historic charm and character. Nestled on the picturesque Kailua shores of Oahu, this quaint island home with its antique quirks is full of cozy comforts that are sure to relax and revitalize its...

  • House
  • 1690
  •  3
  •  2
Weekly $533.00 - $4408.00

Superbly Designed Home w/ Views of the Mokulua Islands & Ocean: Mokulua Sunrise Kailua, Hawaii, Listing ID: 30173

Enjoy top-tier luxurious living on your next Hawaiian vacation at the Mokulua Sunrise ocean villa, located in the world famous neighborhood of Lanikai on the eastern shores of the vibrant island of Oahu. This 4-bedroom, 3.5 bath home lets you escape to the privacy and...

  • House
  • 4385
  •  4
  •  3 1/2
Weekly $1000.00 - $5006.00

Luxurious Villa w/ Private Pool, Jacuzzi & Stunning Ocean Views: Lanikai Villa Kailua, Hawaii, Listing ID: 30175

Make your tropical fantasy vacation a reality with this seamlessly designed coastal villa just minutes away from the world famous Lanikai Beach. On the eastern shores of Oahu, this luxurious 4 bedroom and 4.5 bathroom home hosts tons of stunning features such as a large...

  • Villa
  • 4800
  •  4
  •  4 1/2
Weekly $400.00 - $3095.00

New to the market! Private Villa w/Pool, AC, walk to beach: Villa Hui Hou Kailua, Hawaii, Listing ID: 30180

The ultimate beach lifestyle awaits you at idyllic Villa Hui Hou on O’ahu’s scenic windward coast. Located off the main strip in the exclusive neighborhood of Lanikai, this recently remodeled five bedroom, four and a half bathroom property boasts a backyard oasis,...

  • House
  • 4920
  •  5
  •  4 1/2

Similar Properties


Monthly $6200.00 - $9340.00

Convenient 2BR Oceanfront 2nd-Floor | Balcony Lahaina, Hawaii, Listing ID: 33066

The Paradise of the Pacific awaits at this oceanfront condo! Equipped with all the comforts of a home away from home and granting you access to an array of shared amenities, this charming condo is the ideal home base to experience everything that Hawaii has to offer. The...

  • Condo
  • 747
  •  2
  •  2
Monthly $4650.00 - $7980.00

1BR Oceanfront 1st-Floor | Pool | Ocean View Lahaina, Hawaii, Listing ID: 33067

Located just steps from the beach and the heated, complex pool, this oceanfront getaway is ready to welcome you to beautiful West Maui. Perfect for a small family vacation or couples retreat, this open and inviting condo features a well-equipped, full kitchen for preparing...

  • Condo
  • 596
  •  1
  •  1
Monthly $6200.00 - $11020.00

Amazing 2BR Oceanfront | Pool | High-Speed WiFi Lahaina, Hawaii, Listing ID: 33068

Step through the door, drop your luggage, and relax at this delightful, second-story condo offering spectacular ocean views off the furnished balcony. Inside, prepare meals in the well-equipped, full kitchen complete with a breakfast bar, dine together at the table, and then...

  • Condo
  • 747
  •  2
  •  2
Monthly $7850.00 - $9920.00

Sugar Beach Resort 415: 1BR Oceanfront | Balcony Kihei, Hawaii, Listing ID: 33161

Snorkel, surf, and swim at this charming Sugar Beach Resort condo! Boasting a prime, walkable location to one of the best beaches in Maui, this resort also offers shared amenities for added fun including a pool, hot tub, sauna, shop, and a grilling area. Wake up the gentle waves...

  • Condo
  • 0
  •  1
  •  1
Monthly $7500.00 - $12400.00

High-End 2BR | Pools | Hot Tub | Tennis | Grill Kihei, Hawaii, Listing ID: 33163

Luxury and privacy meet at this Kihei Condo, located in the condo resort known as Maui Kamaole, and just minutes away from the three sunny Kamaole beaches. Kamaole Beach Park III, located just across South Kihei Road, is one of South Mauis best swimming, snorkeling, and sunning...

  • Condo
  • 0
  •  2
  •  2
Monthly $4650.00 - $7120.00

Maui Kamaole K110: 1BR | Pool | Hot Tub Kihei, Hawaii, Listing ID: 33164

Luxury and privacy meet at this Kihei Condo, located in the condo resort known as Maui Kamaole, and just minutes away from the three sunny Kamaole beaches. Kamaole Beach Park III, located just across South Kihei Road, is one of South Mauis best swimming, snorkeling, and sunning...

  • Condo
  • 0
  •  1
  •  2
Monthly $6200.00 - $10190.00

Maui Kamaole B202: Tropical 2BR | Patio | Pool Kihei, Hawaii, Listing ID: 33165

Luxury and privacy meet at this Kihei Condo, located in the condo resort known as Maui Kamaole, and just minutes away from the three sunny Kamaole beaches. Kamaole Beach Park III, located just across South Kihei Road, is one of South Mauis best swimming, snorkeling, and sunning...

  • Condo
  • 0
  •  2
  •  2
Monthly $4200.00 - $4870.00

Kihei Akahi D613: 1BR Sleeps 4, 2 Pools, private lanai, Tennis & Grills. Monthly Rent: $4,200 - $4,870 Kihei, Hawaii, Listing ID: 33166

Step across the street and enjoy Kamaole Beach Park II, one of Mauis best swimming and stunning beaches. Revel in the spectacular sunsets or stroll along miles of white sandy beach at first light. Kihei Akahi is ideally situated and offers excellent value. This one-bedroom...

  • Condo
  • 0
  •  1
  •  1
Monthly $4200.00 - $4680.00

Kihei Akahi C515: 1BR Oceanview | Pool Kihei, Hawaii, Listing ID: 33167

Step across the street and enjoy Kamaole Beach Park II, one of Mauis best swimming and stunning beaches. Revel in the spectacular sunsets or stroll along miles of white sandy beach at first light. Kihei Akahi is ideally situated and offers excellent value. This one-bedroom...

  • Condo
  • 0
  •  1
  •  1
Monthly $4640.00 - $5890.00

1BR Oceanfront | Pool | Elevator Wailuku, Hawaii, Listing ID: 33168

The Island Sands Resort on Maui is located oceanfront in Maalaea, just a short four miles to Kihei and a scenic 15-mile drive to Lahaina. When you stay in this Island Sands Resort condo, you'll enjoy spectacular sunsets, whale watching in the winter, and walking along the five...

  • Condo
  • 0
  •  1
  •  1