Guesthouse vacation rentals in Kailua

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Kailua

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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Superhost

Guesthouse in Haleiwa

4.77 out of 5 average rating, 250 reviews

Walk to Beach Large Studio

1 Block to Beach, Spacious Studio. *Inquire available dates!!* Comfortable, Safe neighborhood. Has queen bed, Hotel style kitchen with toaster/convection oven, microwave, coffee maker, mini fridge/freezer and Outdoor shower. The toilet is inside unit behind carved bali privacy screen. Private Entrance, & FREE off street parking, which is quite a Privilege! (street parking is also an option, if available). It is a very comfortable, clean, affordable place to stay in Most Desirable Location.

Feb 21 – 28

$188 per night

Superhost

Guesthouse in Hauula

4.87 out of 5 average rating, 87 reviews

Ohana Country Cottage

This 2 bedroom 1 bath house features all the amenities of home as well as privacy and a beautiful front lawn, a full size kitchen, washer & dryer, 65in Smart TV w/cable, wifi, A/C. With a king bed in the master bedroom, a queen in the 2nd bedroom and a sofa sleeper in the the living room there is room to sleep five. If more bedrooms or bathrooms are needed, consider renting either the four bedroom main house or adding the studio to this guest house for 3 bedrooms, 2 bath . TA-098-825-1136-01

Jul 3 – 10

$400 per night

Superhost

Guesthouse in Kahuku

5.0 out of 5 average rating, 5 reviews

Spacious King bed studio

This newly-renovated studio, perched on the stunning Kahuku Oahu, is the perfect location for a tropical family getaway with room for up to 4 guests. Walk to the beach in only 5 minutes. The Polynesian Cultural Center, shopping, food trucks, as well as some of the world's most renowned beaches and surf spots (Banzai Pipeline, Sunset Beach, Waimea Bay, Sharks Cove, and Turtle Bay) are all within 5 to 20 minutes by car. Expect an unforgettable 5-star experience at an affordable price!

Feb 23 – Mar 2

$272 per night

Guest favorite

Guesthouse in Waianae

4.93 out of 5 average rating, 56 reviews

Mauna 'Olu Ohana Studio

Kick back and relax in your own private condo with a separately fenced yard and bbq area nestled between the Makaha mountains. Breathtaking ocean views and just a Short 5 min drive to Makaha beach for snorkeling and whale watching. Looking for something bigger the private studio can be rented with the resort home for bigger groups, just message your host for availability. Ask your Hawaiian host about the Jeep rental available to rent @$45 per day $100 Airport pick up and drop off.

Jun 23 – 30

$258 per night

Guest favorite

Guesthouse in Honolulu

4.93 out of 5 average rating, 137 reviews

Hale Wa’a - 2 bed/2 bath - 5 minute walk to beach!

We are located right off the main roadway that circles Oahu. Our neighborhood is peaceful and quiet. You can enjoy ocean views from the master bedroom lanai and there is a secluded beach about a 5 minute walk away; best for taking walks not swimming. Popular attractions such as Waikiki, Hanauma Bay, & Chinatown are within a 15 minute drive away. Stays less than 180 days are subject to our Hale Wa’a Beach Gear Rental Package. Please read our Terms and Conditions for more details.

Feb 13 – 20

$317 per night

Superhost

Guesthouse in Haleiwa

4.92 out of 5 average rating, 13 reviews

Sunset Beach Studio 30 day min

The North Shore is perfect. Truly, this is a destination that engages the spirit and invites the discovery of more than just your surroundings. North Shore is the home to the most powerful waves in the world In the winter time by. And where peaceful bays are perfect for quiet days spent snorkeling and swimming on the summer time. Let Hawaii change your soul and your life making memories that will last for a lifetime. Available for 30 nights or more stays only. Mahalo

Jun 11 – 18

$180 per night

Guest favorite

Guesthouse in Waianae

5.0 out of 5 average rating, 15 reviews

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.

Dec 14 – 21

$311 per night

Guest favorite

Guesthouse in Waialua

5.0 out of 5 average rating, 67 reviews

Serene Mountain Getaway with Ocean Views

Welcome to one of the most unique stays you will find on the North Shore! This guesthouse is located on 4 acres of beautiful property nestled in the hills of Mt. Ka'ala. You will be surrounded by nature while looking at a view of the North Shore and the ocean. We also have very friendly chickens and miniature goats to hang out with if you like animals! Come get away from it all while still only a 15 minute drive to the beach and Haleiwa town.

Apr 12 – 19

$219 per night

Superhost

Guesthouse in Kailua

4.78 out of 5 average rating, 135 reviews

Kailua Beach Cottage - 90/TVU-0287

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.

Apr 23 – 30

$470 per night

Superhost

Guesthouse in Haleiwa

4.33 out of 5 average rating, 12 reviews

Private Room With Private Bathroom and Kitchenette

With the Pacific Ocean lapping at the world-famous Sunset Beach just steps from your door, our Kalihi Ginger Room is much more than a place to stay, it’s a private escape with world-famous vistas at your feet. This special hideaway is tucked back in its own private garden where you can relax on lounge furniture, cook on an outdoor barbecue, and enjoy papayas fresh from the trees on the property.

Jul 7 – 14

$355 per night

Guest favorite

Guesthouse in Kailua

4.85 out of 5 average rating, 333 reviews

Kailua Palm Studio. Walk to Beach! PERMITTED

Licensed, legal 90/BB-0002 short term rental. *not impacted by Bill 41 (2022) **NEWLY 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 Cynthia Rubinstein Real Estate, Inc. (License #RB-16858)

Apr 7 – 14

$323 per night

Guesthouse in Haleiwa

4.74 out of 5 average rating, 392 reviews

Studio Surf Sunset Beach North Shore Oahu

This is a studio that is affordable in an expensive area. The world famous Surf Sunset Beach is a two minute walk away. It is clean, and everything you need for a surf People and comfortable easy stay . We also have a Jeep Wrangler for rent that we can deliver to the Airport upon you arrival. You can rent it for additional days even if you do not stay with us. See the pics.

Oct 13 – 20

$199 per night