
Guesthouse holiday rentals in Kailua-Kona
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Top-rated Guesthouses in Kailua-Kona
Guests agree: These guesthouses are highly rated for location, cleanliness and more.

Garden Cottage Ohana
Welcome to your small slice of paradise! Newly redone kitchen, LR, and bathroom! The garden cottage is surrounded on three sides by dense forest. Enjoy coffee and sunsets on your private porch overlooking our tropical fruit farm, the ocean, and stargazing skies. Birds singing, a chorus of frogs, and a wild rooster’s crow are just some of the “sounds of the jungle” that will surround you. The cottage sits between two beautiful bays that host some of the best snorkeling of the Hawaiian Islands.

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

Tiny House in Kona - 5 Minute Walk to the Beach!
Mahalo nui for your Interest! After a short break, I am happy to be back hosting this wonderful space ~ Click my profile to check my 1400+ 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!

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.

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!

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
Popular amenities for Kailua-Kona guesthouses
Family-Friendly guesthouses

Lovely Kona Island Getaway (Gazebo, 2bed/1 bath)

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

Modern Condo. Large Lanai. Amazing Ocean View!

Kona Ohana Retreat – Pool, Cabana & Island Living

Naniloa Studio by Magic Sand Bch

Sunset Orchard, Upcountry / Beach!

New Guest Home in Kona with Ocean Views

Waimea Honu Cottage- Cozy & Relaxing
Guesthouses with a patio

Sea View Studio Getaway

Tranquil Tropical Retreat

Ocean View Guesthouse, Kona!

3-min walk to beach | King bed | Newly Renovated!

Ohana With Private Pool & Jacuzzi

Cozy Vintage Inspired Hawaiian Guest Cottage

Fresh & Bright Tropical Getaway- Ocean View

Bright Island Hideaway | King Bed + Ocean Views
Guest house rentals with a washing machine and dryer

Kimo’s Getaway

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

Lani Wai Ka Napo'o

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

Amazing Sunset / Ocean View, Beautiful New Home

Look No Further Hale Nai'a Pink Cottage Kealakekua

Holualoa Ekahi -Country guest house,Taxes included

“Special Rate” Private, Waimea Ohana (Guest House)
When is the best time to visit Kailua-Kona?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $292 NZD | $320 NZD | $283 NZD | $270 NZD | $277 NZD | $268 NZD | $254 NZD | $251 NZD | $258 NZD | $288 NZD | $274 NZD | $300 NZD |
| 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 holiday rentals
Explore 40 holiday rentals in Kailua-Kona

Nightly prices starting at
Kailua-Kona holiday rentals start at $178 NZD per night before taxes and fees

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

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
40 of Kailua-Kona holiday rentals include Wi-Fi access

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

4.9 Average rating
Kailua-Kona stays are highly rated by guests—averaging 4.9 out of 5!
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- Hapuna Beach
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