Kailua Listings

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Monthly Rent $ 0

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
Monthly Rent $ 0

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
Monthly Rent $15,000 - $18,000

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
Monthly Rent $ 24,660

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
Monthly Rent $ 15,000

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
Monthly Rent $ 75,000

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
Monthly Rent $ 140,010

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
Monthly Rent $ 28,500

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
Monthly Rent $ 22,050

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
Monthly Rent $ 75,000

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
Monthly Rent $ 188,850

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
Monthly Rent $ 24,990

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
Monthly Rent $ 43,200

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
Monthly Rent $ 17,490

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
Monthly Rent $ 45,000

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
Monthly Rent $ 15,000

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
Monthly Rent $ 22,500

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
Monthly Rent $ 30,000

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
Monthly Rent $ 24,000

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
Monthly Rent $ 0

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

Similar Properties


Monthly Rent $2,138 - $2,594

Remodeled Studio Oceanview 32nd-Floor | Balcony Honolulu, Hawaii, Listing ID: 33043

Open the door and let the amazement set in as you walk into this beautiful studio unit that has been remodeled from top to bottom. The hardwood flooring and quartz counters will upgrade your experience and make your Island Colony stay one of comfort and relaxation. Enjoy a cold...

  • Studio
  • 440
  •  0
  •  1
Monthly Rent $5,572 - $6,355

Relaxing 2BR Near Beach | W/D | Desk | WiFi Honolulu, Hawaii, Listing ID: 33044

Location, location, location! This rare gem, bungalow home in the heart of Waikiki is ideal for a family beach vacation or surfing getaway with friends. Make your way to the world-famous Waikiki Beach and Waikiki surf spots such as Canoes and Queens less than a half-mile away....

  • House
  • 1145
  •  2
  •  2
Monthly Rent $4,192 - $8,099

Zen ocean-view 3BR with balcony & W/D Honolulu, Hawaii, Listing ID: 33045

You're sure to find your zen at this slice of paradise. From a gorgeous lanai to a lush garden, this stunning home offers exceptional outdoor space. Follow the charming stone path to the tropical backyard and spend afternoons reading or simply relaxing to the soothing sounds of...

  • House
  • 1010
  •  3
  •  2
Monthly Rent $2,216 - $4,141

Studio 2 Queen Beds (Sleeps 4), canal and ocean views!! Walk to Shopping/Dining and Waikiki beach | Monthly Rent: $2,985 Honolulu, Hawaii, Listing ID: 33046

Enjoy central living in Waikiki from this beautiful studio. Boasting canal and ocean views, this resort-style condo is within walking distance of great beaches, shopping, and restaurants and offers a bevy of in-home essentials and on-site amenities. The home features...

  • Studio
  • 280
  •  0
  •  1
Monthly Rent $4,983 - $6,475

Luxury 2BR Oceanview 27th-Floor | Balcony | Pool Honolulu, Hawaii, Listing ID: 33047

Luxury living in the heart of Waikiki! Perfect for a family getaway or couples' retreat, this tropical beauty boasts high-end features and resort amenities with central walkability to shopping, dining, and beach access. The bright interior features an elegant, modern design with...

  • Condo
  • 1308
  •  2
  •  2
Monthly Rent $3,640 - $4,320

Ocean-view corner 3BR condo - 90 night min Honolulu, Hawaii, Listing ID: 33048

Admire expansive vistas from this modern corner condo, overlooking the mountains, the city, and the Ala Wai Canal. You'll even enjoy peek-a-boo ocean views from your breezy wraparound balcony! Just a half mile from Fort DeRussy Beach, you'll enjoy a central location with quick...

  • Condo
  • 896
  •  2
  •  2
Monthly Rent $5,050 - $6,058

Upgraded 2BR | W/D | Walk to Waikiki | Lanai Honolulu, Hawaii, Listing ID: 33049

Admire a beautiful view of Diamond Head from this refined, two-bedroom home in Honolulu, where you'll be within walking distance of Waikiki Beach and its many attractions and activities. This gorgeous property is the ground floor of a duplex, offering a fenced yard full of...

  • House
  • 3200
  •  2
  •  2
Monthly Rent $2,871 - $4,991

Prime 1BR Riverfront 20th-Floor | Pool Honolulu, Hawaii, Listing ID: 33050

Spend a spectacular season in the heart of Honolulu at this newly renovated condo on the 20th floor of Island Colony. Enjoy beautiful views, fantastic resort amenities, and a prime location within walking distance of Waikiki Beach and world-class dining and shopping. Island...

  • Condo
  • 570
  •  1
  •  1
Monthly Rent $4,200 - $4,660

1BR Mountainview 24th-Floor | Pool Honolulu, Hawaii, Listing ID: 33052

Welcome to your home away from home at this urban paradise retreat! This gorgeous 24th-floor condo is conveniently located in the financial district of Honolulu, just a few blocks from Hawaii Pacific University, Chinatown, Aloha Tower harbor shops, the State Capital, popular...

  • Condo
  • 575
  •  1
  •  1
Monthly Rent $2,698 - $5,216

2BR second-floor condo with a heated pool Honolulu, Hawaii, Listing ID: 33053

Located within Honolulu's Ala Moana area, this serene, second-story condo puts you and your guests within a couple miles of several popular attractions like the Honolulu Museum of Art, the Children's Discovery Center, and multiple beaches including Kahanamoku Beach and Fort...

  • Condo
  • 902
  •  2
  •  2
Monthly Rent $5,270 - $6,691

Open 3BR Oceanview | Pool | Hot Tub | Patio Kapolei, Hawaii, Listing ID: 33060

Whether you're here for work or for fun, this is the ideal vacation home for your next getaway to the island of Oahu. Inside this gated community of Kai Lani in the Ko'Olina resort area, you'll find beautifully landscaped grounds that lead to an ocean view along with a pool and...

  • Townhouse
  • 1320
  •  3
  •  2
Monthly Rent $4,635 - $6,475

Elegant 2BR 7th-Floor | Pool | Washer/Dryer Kapolei, Hawaii, Listing ID: 33061

Find the ease and comfort of a private home in a beautiful resort setting at this two-story villa within Ko Olina Resort. Beach-goer, golfer, or poolside lounger, you'll be treated to excellent resort amenities and an elegant living space to come home to at the end of each day....

  • Condo
  • 981
  •  2
  •  3
Monthly Rent $6,200 - $9,340

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 Rent $4,650 - $7,980

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 Rent $6,200 - $11,020

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 Rent $7,850 - $9,920

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 Rent $7,500 - $12,400

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 Rent $4,650 - $7,120

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 Rent $6,200 - $10,190

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 Rent $4,200 - $4,870

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 Rent $4,200 - $4,680

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 Rent $4,640 - $5,890

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