Private suite holiday rentals in Kailua

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Top-rated Self-Contained Units in Kailua

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Superhost

Guest suite in Hauula

4.85 out of 5 average rating, 209 reviews

Country Escape with AC + Smart TV + Big Bath

Escape the typical busy touristy areas to experience the real Hawaii in a local country neighborhood🌺 ☕️ Enjoy your morning coffee on the patio surrounded by palm leaves and nature🦎🐓 🌊 You’ll be a block from the ocean and the famous tipping palm tree photo-op. Seals are often seen hanging out here. ☀️ Walking distance from the gorgeous Hauula Loop Trail 🌴Minutes from other local fav beaches, surf spots, food trucks and grocery stores as well as the must visit Polynesian Cultural Center and BYUH

Guest favourite

Guest suite in Kailua

4.91 out of 5 average rating, 352 reviews

Kailua Pineapple Studio. Walk to Beach! PERMITTED

Legal, permitted short-term rental (Permit #1990/NUC-1819, Tax map key:43073024) *not impacted by Honolulu ordinances banning Short-term Rentals Hawaiian style, modern appointments. Beautiful 450 sf suite in the one of the most desirable locations in Hawaii, Kailua! An easy 8-10 min. walk to Kailua Beach, top rated in the world. Private residence at the end of a quiet cul-de-sac. Airbnb “Guest Favorite” awardee! Sister Unit: Kailua Palm Studio. Walk to Beach! PERMITTED Managed by Kupono Svcs.

Superhost

Guest suite in Kailua

4.79 out of 5 average rating, 171 reviews

Kailua - Ocean/Mtn Views - 60' Pool - 2 Decks

Kailua Absolutely Oceanfront Deluxe Vacation Rental One of the few Legal short-term rentals (Less than 30 days) The closest house to the Ocean in Kailua Located in an upscale Kailua neighborhood The quiet uncongested North side of Kailua Only 8 minutes to the center of Kailua Town 60ft salt-sanitized waterfall lap pool 16-foot vaulted skylight ceilings with a loft Two outside covered decks, one overlooking the pool and the mountains. The other has a partial ocean view between the houses

Superhost

Guest suite in Kahuku

4.8 out of 5 average rating, 55 reviews

by the sea

Perfect for a couple or small family that wants to wind down at the end of the day! Away from the noise and city life, you can feel safe outside with the kids! If you are looking for a peaceful place this cottage is for you. 5 min walk to a secluded beach! Very friendly and safe neighborhood. Only 10 minutes away from Hawaii’s number one attraction (PCC). 3 minutes from the famous kahuku food trucks that has a variety of food to enjoy! Located on Oahu’s famous North Shore!

Guest favourite

Private room in Kailua

4.89 out of 5 average rating, 88 reviews

Aloha Suite

NOTE: Temporary construction site is nearby so price has been reduced. Details provided upon booking request so you can make a decision if this works for you prior to confirming. See photos. Only registered guests allowed on property. Welcome to our home! We are a legal vacation rental (TA-188-004-1472-01, 90/BB-0102) hosting guests for more than 30 years. We are an environmentally-conscious family doing our share to "Live Lightly" so our natural resources are protected.

Guest suite in Haleiwa

4.95 out of 5 average rating, 100 reviews

Rocky Point Dream December

Available for the month of December. A rare opportunity to experience North Shore living right next to the ocean at Rocky Point. Our spacious, one-bedroom upstairs apartment is perfectly set for country comfort at its best. Nestled on a private driveway with direct beach access, you'll be steps away from the ocean and iconic Rocky Point surf. Embrace the sights and sounds of the North Shore, with endless waves and sandy shores right outside your door.

Guest favourite

Guest suite in Makaha Valley

4.94 out of 5 average rating, 152 reviews

Slice of Paradise-Studio-Sleeps 4-same$ for 2 as 4

Enjoy this beautiful, private, brand new studio nestled in the mountains of Makaha Valley. This is located in a gated community with 24 hour security. Minutes from year round surfing and golfing. This is a LEGAL vacation rental. Private yard on a perimeter lot with unobstructed ocean and mountain views and just a few minutes drive to many clean, sand bottom beaches. Any combination of 4 guests is okay as long as there is a max of 2 adults.

Superhost

Guest suite in Hauula

4.84 out of 5 average rating, 329 reviews

Hauula Studio

Hauula Hale Studio quietly sits against the mountains in the small town of Hauula, which is just a 5 minute drive from Laie and the Polynesian Cultural Center. Located in the charming country setting of Oahu's windward coast, you can enjoy a quiet and relaxing stay in our comfortable studio. With only a 5 minute walk to hiking trails or the beach or a 20 minute drive to the beautiful North Shore, there is plenty to explore and do.

Superhost

Guest suite in Laie

4.78 out of 5 average rating, 377 reviews

Modern Beach Home Laie North Shore - 30 Day Stays

Beautiful ocean-view unit in a modern "Dwell" style home. This 2-bed 1-bath guest unit sleeps up to six guests. Fully stocked kitchen with high-end appliances. Sandy, crystal-clear beach is just three houses down. Due to local regulations, 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.

Guest favourite

Guest suite in Honolulu

4.84 out of 5 average rating, 289 reviews

DIAMOND ON DIAMOND HEAD

Located on the slope of Diamond Head, our apartment is at a walking distance of Waikiki beach, restaurants, nightlife, public transport. You’ll love my place because of the coziness, the location. I put a special attention on having the mattress spray monthly for bugs and also the apartment for insects. It is very important for me to offer a super clean, cozy, comfy and secure apartment. TA-182-790-8096-01

Top Guest favourite

Private room in Hauula

4.94 out of 5 average rating, 465 reviews

Large Spacious Unique Open Beam Cedar Roof Bedroom

This room is very spacious, open beam, cedar wood ceiling. Your own bathroom. Walk-in closet, King size bed, Fold out double sofa bed, TV, coffee maker, toaster, microwave and small refrigerator. Lanai you can walk out on and see our beautiful mountains which has hiking trails just a short walk away. Gated, on property parking.

Guest favourite

Guest suite in Kailua

4.94 out of 5 average rating, 95 reviews

Quiet, Comfortable Home in Beautiful Kailua, HI

Welcome to your peaceful and safe home-away-from-home in beautiful Kailua, Hawaii! (Approximately 2.5 miles from world-famous Kailua Beach.) **Please note: The City & County of Honolulu has passed a bill that requires a 30-day minimum for all short-term rentals. Our pricing reflects that 30-day minimum requirement. Mahalo!**