
Guesthouse vacation rentals in Kailua-Kona
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouse rentals in Kailua-Kona
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

Kona Ocean Front Cottage on Keauhou Bay
Waterfront cottage on private, gated 1 acre estate. Close as you can get to an over the water bungalow in Hawaii with direct ocean access to swim, surf, kayak, snorkel and watch dolphins. Walking distance to manta ray, snorkeling, kayak, whale and dolphin tours, golf, restaurants, movie theater, and outdoor art market. Two room suite. Queen bed. Living room with 50 in TV. Bathroom with large shower. Large covered deck with seating area, kitchenette, dining table, lounge chairs. Outdoor shower.

Romantic Cabin Treehouse in Hawaii Cloud Forest
Stay in a unique cloud forest at a 2500 foot elevation, yet minutes to airport, beaches, restaurants, bars and shops. Extraordinary lodging, perfect for a honeymoon, writers retreat or meditation vacation. Surrounded by native forest, with tree fern and Hawaiian song birds. Afternoon rains end in grand sunsets. Nights are cool for sleeping with windows open. State forest hiking trails are at your doorstep. Great bird watching, including a local flock of cockatoos that visit in the morning!

Private Kona Oceanview Retreat with parking
Escape to a private oceanview retreat in North Kona! This cozy guesthouse offers breathtaking views from your private deck, surrounded by lush tropical plants. Enjoy your morning coffee while soaking in the serene ocean scenery, and unwind in a tastefully decorated interior with all essentials, a well-equipped kitchen, modern bathroom with a luxurious shower, and convenient laundry facilities. Perfect for couples or solo travelers and easy access to Kona’s attractions! Tax ID W01822068-01

KoKo Cottage: Adorable 2-Bedroom Ocean View/Lanai
Enjoy our beautiful cottage all to yourself at a cool and breezy 1400' elevation just 10 minutes from town and minutes up the mountain from the Kona International Airport. Relax at the end of a fun day of adventure with a glass of wine on the spacious lanai while you watch the sunset. Our cottage is a perfect base for exploring, whether you want to have fun in beautiful Kailua-Kona or head north to some of the world's most spectacular beaches we're located conveniently between the two.

Kealakekua Bay Bali Cottage -steps from Bay
This hidden jewel is at Kealakekua Bay. Private setting in our lower backyard. Walk to nearby Manini Beach. We are located 4 miles down at the bottom of Napoopoo Rd Fully equipped outdoor kitchen. Gas stove, under counter refrigerator/freezer. Living/Dining area and bedroom/vanity area enclosed with open area at roofline where a large ficus tree limb goes through. Outdoor shower/ wc area. Very Private. Daily pricing includes Hawaili State taxes, 10.25% TAT and 4.25% GE .

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.

Kona Guesthouse ❤ Ocean Views | Kitchen | Patio
Enjoy all the comforts of home with sweeping views of Kailua Kona. Start your day with a brisk morning walk in our friendly neighborhood walking trail. When you are ready to get out and explore, you are minutes away from attractions that bring people to the island. Snorkel amidst turtles and reef fishes in Kahaluu Beach. Try night diving among Manta Rays in Keauhou Bay. Drive south to Kealakekua Bay and snorkel in one of the best spots known for its spectacular coral reefs.

Kona Paradise Ohana Studio
Enjoy epic sunset views over the ocean while surrounded by lush jungle foliage. The scent of plumeria and the gentle calls of tropical birds will never let you forget you're in paradise. While you're here you'll be a stone's throw from many wonderful places to snorkel, as well as Place of Refuge National Park. This is a terrific base camp to explore Volcanoes National Park, Mauna Kea Observatories, the most southern point of the U.S., a black sand Beach and much more!

Plumeria Studio; Garden Balcony, Close to Airport
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.

Hale Kamalei in Kailua Kona
Enjoy all the comforts of home in this stylish guesthouse in the heart of Kailua Kona. This detached one bedroom ohana is centrally located - just minutes from the airport, shops, restaurants and some of the best beaches on Hawai'i Island. Experience Hawaii away from the hustle and bustle of resorts and overcrowded condominiums and stay where the locals live! The designated parking space is just steps from the front door. Private, clean, and convenient.

The Banyan House
Offering a newly renovated & private 1 bed, 1 bath guest suite conveniently located in a friendly residential area in Kona, close to beaches and restaurants. You have your own separate entrance to the unit, although we do share a wall, as this Ohana is connected to the main house. Please note that there are stairs and a pathway coming up to the property, guest should be comfortable walking up the path with their belongings and bringing them up stairs.

Cottage with Ocean and Sunset view
Situated on the island's western side at a cool 1300ft elevation, this small cottage is suitable for two people. Privacy is the keyword. This is a quiet, clean, peaceful place with A/C. It is near the airport, town, and 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!
Popular amenities for Kailua-Kona guesthouse rentals
Family-friendly guest house rentals

Kona Hale Ohana

Sunset House by the Sea

Serenity and Comfort Just off Main Road

Paniolo Place (taxes included)

Oceanview Zen Luxury Coffee Estate Home

Cozy Hawaiian studio just minutes from the beach

Sunset Orchard, Upcountry / Beach!

Hale Moana Breeze - Ocean View/AC/Close to Airport
Guest house rentals with a patio

Sea View Studio Getaway

Tranquil Tropical Retreat

All About The View!

I'o Hale on Wings of Aloha: 180° Ocean Sunset View

Ohana With Private Pool & Jacuzzi

Fresh & Bright Tropical Getaway- Ocean View

Bright Island Hideaway | King Bed + Ocean Views

New 2-Bedroom Guesthouse w/ Mountain & Ocean View!
Guest house rentals with a washer and dryer

Private Ohana w/ AC, Fast WiFi, BBQ & Hammock

Mango Hale Cottage

Kimo’s Getaway

Lani Wai Ka Napo'o

Big Lanai w/ outdoor living! Ocean view & breezes!

Look No Further Hale Nai'a Pink Cottage Kealakekua

Holualoa Ekahi -Country guest house,Taxes included

Holualoa Country Home
When is the best time to visit Kailua-Kona?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ602 | ﺩ.ﺇ661 | ﺩ.ﺇ584 | ﺩ.ﺇ558 | ﺩ.ﺇ573 | ﺩ.ﺇ555 | ﺩ.ﺇ525 | ﺩ.ﺇ518 | ﺩ.ﺇ533 | ﺩ.ﺇ595 | ﺩ.ﺇ566 | ﺩ.ﺇ621 |
| Avg. temp | 6°C | 6°C | 6°C | 7°C | 9°C | 10°C | 9°C | 9°C | 9°C | 9°C | 7°C | 6°C |
Quick stats about guesthouse rentals in Kailua-Kona

Total vacation rentals
Explore 40 vacation rentals in Kailua-Kona

Nightly prices starting at
Kailua-Kona vacation rentals start at ﺩ.ﺇ367 per night before taxes and fees

Verified guest reviews
Over 4,670 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
40 of Kailua-Kona vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Kailua-Kona rentals

4.9 Average rating
Kailua-Kona stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Honolulu Vacation rentals
- Oahu Vacation rentals
- Kauai Vacation rentals
- Island of Hawai'i Vacation rentals
- Waikīkī Beach Vacation rentals
- Kona Vacation rentals
- Kihei Vacation rentals
- Kaanapali Vacation rentals
- North Kona Vacation rentals
- Princeville Vacation rentals
- Hilo Vacation rentals
- Wailea Vacation rentals
- Family-friendly rentals Kailua-Kona
- Apartment rentals Kailua-Kona
- Villa rentals Kailua-Kona
- Beach condo rentals Kailua-Kona
- Beachfront rentals Kailua-Kona
- Condo rentals Kailua-Kona
- Smoking-friendly rentals Kailua-Kona
- Rentals with beach access Kailua-Kona
- House rentals Kailua-Kona
- Rentals with breakfast Kailua-Kona
- Rentals with a hot tub Kailua-Kona
- Waterfront rentals Kailua-Kona
- Cabin rentals Kailua-Kona
- Private suite rentals Kailua-Kona
- Rentals with a fireplace Kailua-Kona
- Townhouse rentals Kailua-Kona
- Luxury rentals Kailua-Kona
- Pet-friendly rentals Kailua-Kona
- Hotel rooms Kailua-Kona
- Rentals with a kayak Kailua-Kona
- Rentals with a washer and dryer Kailua-Kona
- Beach house rentals Kailua-Kona
- Rentals with pools Kailua-Kona
- Fitness-friendly rentals Kailua-Kona
- Serviced apartment rentals Kailua-Kona
- Rentals with outdoor seating Kailua-Kona
- Resort rentals Kailua-Kona
- Rentals with a fire pit Kailua-Kona
- Rentals with a patio Kailua-Kona
- Guesthouse rentals Hawaii County
- Guesthouse rentals Hawaii
- Guesthouse rentals United States
- Hapuna Beach
- Pahoa Beach
- Mauna Kea Golf Course
- Kohanaiki Private Club Community
- Waikōloa Beach
- Kaunaoa Beach
- Ke‘EI Beach
- Mauna Lani Golf
- Volcano Golf and Country Club
- 49 Black Sand Beach
- Kuki’o Golf & Beach Club
- Kealakekua Bay State Historical Park
- Kona Dog Beach
- Nanea Golf Club
- Waikoloa Beach Golf Course
- Hapuna Golf Course
- Kona Country Club
- Makalawena
- ʻAlula Beach
- Mauumae Beach
- Honokohau Beach
- Pololū Beach
- Kukio Beach
- Wawaloli Beach
- Things to do Kailua-Kona
- Things to do Hawaii County
- Art and culture Hawaii County
- Nature and outdoors Hawaii County
- Food and drink Hawaii County
- Sports activities Hawaii County
- Things to do Hawaii
- Nature and outdoors Hawaii
- Food and drink Hawaii
- Entertainment Hawaii
- Tours Hawaii
- Wellness Hawaii
- Sightseeing Hawaii
- Sports activities Hawaii
- Art and culture Hawaii
- Things to do United States
- Sightseeing United States
- Entertainment United States
- Art and culture United States
- Sports activities United States
- Wellness United States
- Nature and outdoors United States
- Tours United States
- Food and drink United States






