Guesthouse vacation rentals in Kailua-Kona

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Top-rated guesthouse rentals in Kailua-Kona

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

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Guest favorite

Guesthouse in Kailua

4.92 out of 5 average rating, 372 reviews

A Piece of Paradise with Ocean Views in Kona

We'd love to share our small piece of paradise with you. Our private studio with ocean views is comfortable, clean and conveniently located. It's decorated with a beach theme to make you feel right at home in Hawaii. The studio is located just above the Wailua Trail in the higher elevation. We get cool nights and ocean breezes but are still only 5minutes to the beach or town. The yard is full of lush tropical vegetation and fruit producing plants such as mangos, avocados, tangerines and lemons.

Mar 12 – 19

G$29,102 GYD per night

Guest favorite

Guesthouse in Kailua-Kona

4.96 out of 5 average rating, 146 reviews

Tiny House in Kona - 5 Minute Walk to the Beach!

Mahalo nui for your Interest! After a year-long break, I am happy to be back hosting this wonderful space ~ Click my profile to check my 1000+ 5-Star Reviews and book with Confidence! This is a real Tiny House on Wheels with an additional connected open air and fully screened kitchen for dining and relaxing. You'll love this "rustic" and private experience in an upscale neighborhood just 4 miles south of downtown Kona! And, you are only a 5 Minute Walk to Magic Sands - the best beach in town!

Jul 19 – 26

G$33,039 GYD per night

Guest favorite

Guesthouse in Kailua-Kona

4.96 out of 5 average rating, 135 reviews

AC | 1 Gig | BBQ | Kitchen | Workspace | Hammock

º 510 sq-ft Ohana (guesthouse) with private entrance, AC, Gig WiFi 6E, BBQ, Laundry, Hammock, Backyard, Patio º 5 min drive downtown, 8 mins to Magic Sands Beach º Fully stocked and equipped kitchenette & bathroom º Desk, chair, 2 monitors, printer, wired ethernet & Wi-Fi; Walk-in closet º Beach equipment (chairs, umbrella, towels, snorkels, kids toys & life jackets, coolers, body boards) º Safe, quiet neighborhood; owner lives on site º Honda Pilot, HR-V, 2 CR-Vs or Kia Sportage SX for rent

May 15 – 22

G$31,686 GYD per night

Guest favorite

Guesthouse in Kailua-Kona

4.98 out of 5 average rating, 321 reviews

Spectacular Views of Kailua-Kona

Aloha and e komo mai to our Ohia Guest House in beautiful Kailua-Kona. Ohia Guest House is your well equipped home away from home, it has everything you will need for a comfortable holiday on The Big Island. We live at a cooler elevation of 1000 feet with pleasant tropical breezes. Our property is on 1.5 acres of tropical landscaping. Ocean views abound, perfect for sunset watching and seeing real-time surf conditions. In the evenings enjoy stargazing and the sounds of the tropics.

Jul 23 – 30

G$36,106 GYD per night

Guest favorite

Guesthouse in Kailua-Kona

4.97 out of 5 average rating, 276 reviews

Cool & Cozy - AC & Wi-Fi - 4 Blocks from Ocean

Our enchanting private guest house is just 4 blocks from the ocean. Sparkling clean & cool. 5 minute drive to beautiful Magic Sands Beach or Kona Town featuring food, shopping & entertainment. Newly built. Air Conditioning & fast fiber optic WiFi. Cool down after a warm day at the beach. Need a rental car? Ask us about our cars available through Turo. A private haven after exploring the many wonders of Hawai’i Island. We are very proud of our reviews & how happy our guests are.

Sep 22 – 29

G$35,868 GYD per night

Guest favorite

Guesthouse in Kailua-Kona

4.99 out of 5 average rating, 142 reviews

Elegant & Peaceful Studio

Tucked away in a friendly, family neighborhood at a cool elevation, this island jewel will provide you with a relaxing place to come home to after a satisfying day of adventures to anywhere on the Big Island. Hale Moa studio is situated next to our family home in a small cul-de-sac. Come enjoy spectacular views of the sun setting over the ocean out front, or relax and fire up the grill in the backyard on your own private patio. We love this spot and hope you will too!

Nov 10 – 17

G$30,376 GYD per night

Guest favorite

Guesthouse in Kailua-Kona

4.97 out of 5 average rating, 524 reviews

Charming Cottage

This quaint & private little cottage is in the Kaloko native Hawaiian forest of Kailua-Kona on the Big Island of Hawai’i. Less than 15 minutes from Kona Airport & less than 15 minutes from town. Not located in town. Elevation is approx. 2200 ft above sea level. Great if you are looking to experience a tropical forest. Due to severe allergies we are unable to host any animals. Not suitable for children. Must use phone navigation to locate as we are in a rural area :)

Nov 1 – 8

G$32,246 GYD per night

Guest favorite

Guesthouse in Kailua-Kona

4.85 out of 5 average rating, 253 reviews

Plumeria; Spacious, Partial Ocean view, Clean

Kailana Cottage includes two separate rental units that share a hallway. These units are freshly remodeled, super clean, fresh and new. This unit is called Plumeria, it is set up like a hotel room; spacious room with King sized bed, large bright bathroom, TV, and kitchenette on the screened in balcony to enjoy tropical sunsets and breezes. The kitchenette has a hot plate, microwave, coffee press, tea/coffee, mini fridge along with utensils, plates, pans, etc.

Dec 3 – 10

G$28,232 GYD per night

Guest favorite

Guesthouse in Holualoa

5.0 out of 5 average rating, 217 reviews

Holualoa Studio Cottage - Incredible Ocean Views!!

BETTER THAN THE REST!!! Our adorable studio cottage is located on the side of Hualalai Mountain in Holualoa, Kona Coffee growing country. We are just above Kailua-Kona town, and only about 12-15 minutes to shopping, and about 15 minutes to the closest beach and only 20 minutes to the airport. You will LOVE our panoramic ocean and coastline view, plus on clear days you can see Mount Hualalai right behind us, plus a beautiful coffee farm too. Read our reviews!

Aug 22 – 29

G$39,109 GYD per night

Guest favorite

Guesthouse in Kailua-Kona

4.95 out of 5 average rating, 317 reviews

Cottage with Ocean and Sunset view

Situated on the western side of the island at a cool 1300ft elevation, this is a small cottage suitable for two people. Privacy is the key word. This is a quiet, clean, peaceful place with A/C, near the airport, town + beautiful beaches located in a safe, affluent neighborhood. After the lava eruption on the other side of the island in 2018 subsided, we are now thrilled to have the best air quality and blue skies since 2007!

Oct 15 – 22

G$23,314 GYD per night

Guest favorite

Guesthouse in Kailua-Kona

4.96 out of 5 average rating, 157 reviews

Our Hawaii Hale: Detached 2 bed ohana with parking

Our Hawaii Hale sits at 1500’ elevation and is 10 minutes from the airport, beaches and downtown Kona allowing for easy access to everything the island has to offer! Our unit features 2 full beds, a kitchenette and large bathroom with walk-in shower. Enjoy parking right outside of unit, beach gear & shared laundry! We are in a residential neighborhood with roosters and coqui frogs. TA-106-058-1888-01

Oct 29 – Nov 5

G$29,804 GYD per night

Guest favorite

Guesthouse in Kailua-Kona

4.98 out of 5 average rating, 197 reviews

Hawaiian Mt. Retreat Suite A

Enjoy a tranquil stay in our well equipped cottage....we tried to think of everything so you can relax. It is centrally located between warm sunny beaches and cool mountain hikes. You're just miles from the popular downtown Kailua-Kona, food, shopping, & ocean sunsets. Come visit Hawaii island style and soak it all in.

Jul 4 – 11

G$30,980 GYD per night