Holiday rentals in Waimanalo

Kailua Beach Park - 1 BR Cottage

Kailua Beach was once again been rated as the best beach in the USA for 2019, by Dr. Beach." The cottage is directly across the street from Kailua Beach Park and less than a 2-minute walk to step into the ocean. It is a legal vacation rental, license number 1990/NUC-1758. The property is tucked away one house back from the road into Lanikai, and described by guests as "a little oasis of quiet and calm." The bathroom has been remodeled with a new showers, sinks and plumbing fixtures April 2022!

HawaiianaLuxe_Townhouse at Turtle Bay_Hale LuLu

Come to escape to this newly renovated 1,150SF 2 bedrooms/2.5 bathroom townhouse for a soul comforting Northshore stay! Away from hustling downtown, Hale Lulu sits peacefully a few minutes away from iconic Turtle Bay Hotel and the most beautiful secluded beaches and trails! This unit is the biggest model in Kulima West. We offer 2 king size beds and 1 queen bed in three different bedrooms for your restful stay. The best cleaning crew was hired for your luxurious staying experience in Hawaii.

Beach 6 Min|BBQ|Community Pool+Gym|Peaceful+Gated

Discover your dream vacation, just 2 miles from the world-famous Makaha Beach. This pristine rental is perfect for those seeking an authentic Hawaiian experience! ~Stunning Views: From every room including the backyard! ~Culinary Delights: Create island feasts in our fully equipped kitchen. ~Cozy Comfort: Rest easy in plush bedrooms designed for ultimate relaxation. ~Adventure Awaits: Surfing, fishing, & more are within easy reach. Don't miss out on making memories that will last a lifetime!

Large Kailua Beach Home - Steps To The Beach!

Spacious home for the entire family to enjoy! Just a few minutes walk to the soft sand & clear water of Kailua beach. Spend your days at the beach with your private, air conditioned oasis awaiting you for rest and relaxation. A short bike ride to Kailua Town with restaurants and shops. Lanikai Beach is less than a 5 minute drive away. Hike, bike ride, snorkel, swim, surf, boogie board, kayak, paddle board, kite surf, wind surf, and much more!! Some dates not shown - reach out to confirm avail!

COOL, BREEZY KAILUA ESCAPE *****

Your Home away from Home! Cool, comfy, clean fully furnished 2 bd/1 ba with a complete kitchen, livingroom, separate entry (entire upstairs). New SPLIT A/C's in both bedrooms(very quiet). In nice culdesac. 5-min drive to Kailua Beach and Kailua Town. Enchanted Lake Cntr is only 3 min away... a Safeway, Cinemas, McDonald's, Round Table Pizza, The Shack, Starbucks, etc. Also, Gas Stations, Nail/Hair Salons, Churches, etc! In Kailua Town, a Target, Whole Foods, cute boutique shops.

Sea Cliff House - Oceanfront - 30 Day Stays

Imagine seeing the crystal-clear waters of Laie Bay from nearly everywhere in the house. Eating breakfast out on the lanai so close to the water you feel like you're standing on the ocean. The gentle waves lulling you into a peaceful sleep while the ocean breezes envelope you. This is the Sea Cliff House. This home can only be rented for periods of 30 days or longer. No breakdown in pricing or calendar settings in Airbnb shall suggest that this home can be rented for a shorter period.

Best Kept Secret on Oahu! and WE ARE LICENSED!!!

Hawaii’s Best Kept Secret: The cottage is next to sandy coves, driftwood, shells, and forested pastures filled with polo ponies. The ocean is excellent for snorkeling and fishing; there are two surf breaks within one mile, windsurfers get wind most afternoons, and the mountains behind us offer good hiking trails. The Colony has a nice pool and a large grass chipping green, and a tennis court. We have TV and WiFi. LICENSE NO. 90/TVU-0108. GE-142-964-5312-01. TMK:1-6-8-009-001-0021.

2BR+Den Downtown w/ Ocean Views + Free Parking

Enjoy ocean and city views from this spacious 2BR+Den condo 798 sqft/74 sqm at high floor with floor to ceiling windows. Save $35 a night with secured free parking in the building plus free wifi and fully equipped kitchen. Walk to the best restaurants and bars, China town, and visit historic Iolani Palace. Building has great amenities including a lap pool and hot tub 7 days a week, 24-hour security. Starbucks/711/Paris Baguette/UPS on the ground floor for your daily needs.

Nai‘a Suite at La Bella’s-Walk to Beach-Lic. B&B

La Bella’s B&B is a luxury island retreat on O‘ahu’s beautiful windward side, blending farmhouse charm with beach elegance. Two private suites are available, each with a private entrance, bathroom, kitchenette, AC, luxury bedding Wi‑Fi, and parking. The spacious Nai‘a Suite features a king bed and relaxing atmosphere perfect for couples or small families. Enjoy beautiful gardens, beach gear, nearby shops and eateries, and a short walk to the beach with warm onsite hosts.

Kailua Palm Studio. Walk to Beach! PERMITTED

Licensed, legal (NUC short term rental #1990/NUC-1819, Tax map key: 43073024) *not impacted by Honolulu ordinances banning short term **RECENTLY RENOVATED BATHROOM AND KITCHENETTE (at end of June 2023)** Peaceful retreat in desirable Kailua! An easy 8-10 minute walk to Kailua Beach. Airbnb “Guest Favorite” awardee! Sister Unit: Kailua Pineapple Studio. Walk to Beach! PERMITTED. Property managed by Kupono Services.

60 second walk to Lanikai Beach. 2 Bedrooms w/ AC

Just a 60 second walk from world-famous Lanikai Beach, this unique 2-bedroom setup offers two private 1-bedroom studios. Each studio features its own kitchenette, dining area, sofa, private balcony, and full bathroom. Enjoy cool A/C, fast Wi-Fi, and thoughtful touches throughout. Relax, explore, and soak in the best of Lanikai.

Haleiwa Dream Location

Newly renovated home, excellent location, just 650 feet walking distance to beach and 5-minute bike ride to Haleiwa Town. This is a great getaway for singles, couples, or families wishing to explore without needing to drive. 30-day minimum rental required. Note the beach in the top photo is directly across the street.