Guesthouse holiday rentals in Kailua

The Jungle Bungalow - AC - Smart TV - 30 Day stays

🌺 Escape the tourist crowds and experience the real Hawai‘i in a peaceful local neighborhood. Just a block from the ocean and the famous tipping palm tree—where seals often rest—you’ll also be within walking distance of the Hau‘ula Loop Trail. Minutes from beaches, surf spots, food trucks, PCC, and BYUH. Perfect for families of up to 4 with 2 queen beds, kitchen, AC, Wi-Fi, smart TV, patio, walk-in closet, shared laundry, and 1 parking spot maximum. Absolutely NO smoking. No large van parking.

Value · Family · Parks

Absolutely Oceanfront-60'Waterfall Pool-Legal

Kailua Absolutely Oceanfront Deluxe Vacation Rental The closest house to the Ocean in Kailua Hear waves breaking just outside Located in a quiet uncongested upscale neighborhood 60ft salt-sanitized waterfall lap pool Attached Ocean-View Deck 16-foot vaulted ceilings Wall-mounted Fujitsu air conditioning Tide pooling steps away Dramatic Sunrises Refreshing Tradewinds No Bedbugs here/Bed Bug Protective Queen Mattress and pillow covers Ozone sanitized between rentals NUC: Certificate 90-BB-0060

Location · Family · Access

North Shore Studio Ocean Front

Escape to a peaceful oceanfront studio on Oahu's stunning North Shore. In Hawaii's most beautiful coastlines, this studio is just minutes from world-famous beaches, including Sunset Beach, Waimea Bay, Banzai Pipeline, and Shark's Cove. Whether you're here to surf legendary waves, hike scenic trails, enjoy charming local cafés, food trucks, island markets, and authentic Hawaiian dining. The studio offers an inviting space for couples, solo travelers, or anyone looking to experience North Shore.

Close 2 Beach Entire Guest Suite

Due to local regulations, this home can only be rented once in a 30 day period. *Please reach out to us prior to booking. Availability shown in the calendar is not guaranteed. Recently renovated, this unit is a four bedroom, two bathroom getaway with high speed WiFi internet, washer/dryer and air conditioning. The beach access point is less than a 4 minute walk away! You are also only a 5-10 min walk away from the Polynesian Culture Center, BYU-Hawaii Campus and the Mormon LDS Temple.

Family · Location · Quiet

Private Studio no shared spaces with own entry

Escape to this cozy, intimate studio in Makaha Valley’s exclusive gated resort community The Cottages at Mauna’Olu Surrounded by lush, tropical landscapes, this private retreat offers the perfect blend of comfort and tranquility your area is not shared with the main house it’s private and fenced away from each other. Unwind on famous Makaha Beach, just 4 minutes away, explore nearby hiking trails, or simply relax to the soothing sounds of the mountains. With thoughtful amenities 🌿

Location · Value · Laundry

Studio Nene - Ocean, King bed, Tropical Garden

Aloha! Welcome to Studio Nene, a serene, luxury guesthouse retreat in breathtaking Makaha Valley. Perfect for couples or solo travelers, this stunning space features a plush king bed, high-end finishes, and a private tropical garden. Wake up to stunning mountain views, enjoy your morning coffee surrounded by trade winds, and stargaze at night. Enjoy resort-style community pool, jacuzzi, and gym. Just minutes away from pristine west-side beaches. Guaranteed cancellation in 48 hrs.

Family · Location · Walkability

Aloha Living Near Ko’olina + WiFi/Sleeps 4

Our Guest House sits in a unique & safe neighborhood. You’ll have your own private entrance. Shared entrance will only be through the front gate. We live on the property, but Privacy is always respected. Ko’olina Beach Lagoons & Golf Course is just a 3 minute drive (Free Parking is usually available there for early bird beach goers), Shopping centers, grocery stores, and luaus. A great space for your island get away, especially away from the busy hustle & bustle of town life.

Location · Value · Decor

Beautiful Mountain Studio Retreat

Imagine vacationing in a brand new studio set in a peaceful valley. You're surrounded by Ka’ala & Waianae mountains, towering palms, mango trees, wild peacocks, & famous beaches. You take a sunrise/sunset stroll around the gated neighborhood (w/24hr security) and return home for a peaceful dinner. Studio is fully equipped w/a comfortable queen-size bed, pull-out bed, TV, a kitchenette, mini-fridge, microwave, coffee maker, & bathroom w/ tub & shower.

Location · Family · Hiking

Studio- Ocean View Hideaway

Aloha and welcome to our home away from home in Makaha!! Newly built and luxuriously appointed, this beautiful studio with kitchen and patio area, is the ideal spot on the west side of Oahu. Located in the private gated community, with the amazing views of ocean and mountains. This is the most desirable location to escape, relax and enjoy a rejuvenating and memorable vacation! Kick back and relax in this calm, peaceful space.

Location · Value · View

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.

Value · Location · Wi-Fi

Kailua Beach Cottage - 1990/NUC-1797

WE HAVE PERMIT - 90/TVU-0287 FROM THE CITY & COUNTY WE WERE RATED BY AIRBNB AS A SUPERHOST. KAILUA BEACH RATED #1 BEACH IN AMERICA! This place is good for couples, business travelers, and families. (On the 2nd floor - upstairs) *Additional guest fee of $90 per person per day applies to parties over 4 people. Additional service fee and tax will apply. Visit the 8 Bdrm Villa website for a larger family group.

Family · Value · Quiet

Beach house with Garden stroll to beach

Our unit offers a peaceful home base for families with a young child or couples. Uncrowded beaches, local eateries, are easily accessible, while Haleiwa is close by and provides great dining and activities. We offer all the basic amenities and a calm, private backyard, it’s a comfortable home away from home for respectful guests seeking relaxation and island style living.