We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

Holiday rentals with a pool in Holualoa

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Holualoa

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Apartment in Kailua-Kona

4.87 out of 5 average rating, 102 reviews

Downtown Kona Condo / Vintage Hawaii / Fast WiFi

The sweet golden era of Hawaii – that’s what awaits you in this stylish centrally located condo. Nestled in the heart of Kona town, literally a coconuts-fall from world-famous All’i Drive, just walking distance to beaches, oceanfront bars/restaurants, and shops (but don’t forget our farmers market, shave ice or local breweries!). Or maybe stay-in, play our vintage Hawaiian vinyl records, enjoy the lanai catching a peek-a-boo oceanview. Practical too: excellent WiFi, smart TV, and a full kitchen.

Guest favourite

Apartment in Kailua-Kona

4.91 out of 5 average rating, 115 reviews

True Oceanfront, Top-Floor, Downtown, A/C, Parking

Get away from it all right in the heart of Kona! Feel the ocean spray as you watch for turtles on the lanai, or gaze at the tropical paradise through your bedroom window. While only steps away from the active downtown, this top-floor unit is on the ocean side of a boutique complex, meaning no noise from the street or guests above. After a busy day at the beach and a night on the town, you'll appreciate the peace and quiet of your own space with only the sound of the ocean to lull you to sleep.

Guest favourite

Guest suite in Hōlualoa

4.91 out of 5 average rating, 354 reviews

Monkey Pod Villa- Guest Suite w/ Pool & Patio

Perched on the cool hillside above Kona, escape to this private retreat on a country estate. Located off the beaten path and away from tourist areas but a 7 mile scenic drive to town & pristine beaches. Awaken from a peaceful night’s sleep to a symphony of the island’s delightful birds. Enjoy a cup of coffee on the garden patio under the shade of a majestic monkey pod tree. After a day of Big Island adventures, unwind with a dip in the sparkling pool and savor the breathtaking Hawaiian sunset.

Guest favourite

Home in Kailua-Kona

4.98 out of 5 average rating, 108 reviews

Private tropical villa: Pool, Hot Tub & Ocean view

Kona House of Palms sits on a very private half acre lot in a gated community. Enjoy ocean views and resort-style backyard with pool, waterfall and hot tub. 3-bedroom, 2-bathroom house comfortably sleeps 8 with the sofa bed in the common area. Lush greenery keeps yard, pool and hot tub very private. Fast Internet, smart TVs, plenty of linens, well-stocked kitchen, beach chairs, pool toys and much more is provided. Everything you need to enjoy you stay is HERE. Fully licensed: STVR-19-365351

Guest favourite

Home in Kailua-Kona

4.94 out of 5 average rating, 103 reviews

Tropical Private Oasis, Heated Pool & OceanView!

3 bedroom/2.5 bath, Sleeps 8 with Private Solar Heated Pool with Waterfall, Lanai, Gazebo with Ocean View, Tropical Yard. 5 min to downtown Kona along the water. This "model home" sits in a gated community of Kahakai with breathtaking views. It has all upgrades throughout the house for ultimate luxury. A pathway on this 1/2 acre plus property leads to an elevated private gazebo for that amazing romantic evening dinner or relaxing with your special one while looking at an amazing ocean view.

Guest favourite

Rental unit in Kailua-Kona

4.94 out of 5 average rating, 255 reviews

Ocean View Pool Home. Kona Tropical Oasis.

READ THIS BEFORE YOU SEND A MESSAGE / REQUEST TO BOOK. Welcome to Ka-Iwi-Pele, the backbone of Pele. This is a hosted location - we live on site. NO INFANTS/TRAVELERS UNDER 30 accepted. Apartment is not a walk out to pool patio. It is 14 steps from your door to pool. We do not accept more than two travelers. Rate does not include HI St taxes or Airbnb fees charged to traveler which we do not control. DO NOT request an exception to our minimum age or total head count or pet/smoking policy.

Apartment in Kailua

4.81 out of 5 average rating, 102 reviews

Kailua Kona Downtown Condo Walk to Pier & Beaches

In the center of Kailua Kona Village, a new wall to wall renovation has succeeded in bringing beautiful accommodations at a reasonable price to the heart of Kailua Kona Village. This top floor [2nd] air-co unit located in the historic Kona Kai complex has a peek-a-boo view of the coastline. Inspired by the Hawaiian Paniolo, there are unique one-of-a-kind features, and a gentle country-like appearance. Two blocks to beautiful beaches around the Kailua Pier and access to many ocean activities!

Guest favourite

Home in Kailua-Kona

4.99 out of 5 average rating, 108 reviews

Stunning Serene Bali Retreat [Pool/AC/Ocean View]

Experience true island living! This 2,000 sq ft home features indoor/outdoor living, Thai and Balinese architecture, and ornate, hand-carved wood. Floor-to-ceiling windows and skylights showcase the beauty of the Big Island. The kitchen and living rooms connect to spacious bedrooms with a covered dining lanai stretching back to the private pool. Perched on a hill with 180º ocean views, this secluded retreat enjoys a cooler breeze than busy downtown while not being far from the action.

Guest favourite

Apartment in Kailua-Kona

4.9 out of 5 average rating, 408 reviews

Plantation Hale

Step back in time to old Hawai'i at our Plantation Hale, located just steps from the beautiful beaches and shoreline of Ali’i drive where you'll discover all the best restaurants and shopping in Kona. Ever wonder what it might have been like to live back in the days when sugarcane was king, and everybody had a ukulele? Not only will you be delighted inside, but the atmosphere at Kona Islander, with all of its beautiful landscaping and meandering pathways, is just as enchanting.

Guest favourite

Apartment in Kailua-Kona

4.82 out of 5 average rating, 110 reviews

Oceanview condo walking distance to Kona Town

Location! Location! Location! Welcome to our centrally located studio condo #345 in the heart of Kona Town! Nestled between Ali’i Drive and Kuakini Hwy, you’ll be within walking distance of Kona’s best restaurants, shops, beaches, and bars. Enjoy swimming & snorkeling at the nearby pier, just a short walk away. Unwind by the pool or hot tub, take an evening stroll for a nightcap, or start your day with a morning walk for a cup of Kona coffee. Your perfect getaway awaits!

Guest favourite

Guest suite in Kailua-Kona

4.96 out of 5 average rating, 118 reviews

1-Bedroom Suite with Private Pool and Garden Lanai

🌬AC included in price! ☀️We invite you to stay with us at our peaceful 1-bedroom studio `ohana unit in the heart of Kailua-Kona, Hawai`i. We offer a private bathroom, kitchenette, and coffee station to fulfill your traveling and exploring needs. 💦Or stay in and hang out poolside by your own private pool that comes with a comfy seating area, lounge chairs, and a grill. 🌿Whatever you choose, we hope to create a relaxing environment for you to unwind and feel at home.

Guest favourite

Rental unit in Kailua-Kona

4.86 out of 5 average rating, 469 reviews

☀ Modern, Tropical and Oceanside + AC & Free Pk ☀

Enjoy waking up to cool breezes and swinging palm trees in this newly remodeled modern ground floor condo just steps away from the warm pacific ocean. Offering breathtaking sunsets from the oceanside pool and the convenience of being less then a mile from downtown Kona and white sandy beaches. One dedicated parking spot located right outside the condo. Family owned and managed and dedicated to providing a great place to stay in Kailua-Kona!

Holiday rentals for every style

Get the amount of space that is right for you

Flats

Convenient locations with everyday essentials

Houses

A space that's all yours, with room for everyone

Hotels

Stylish accommodation and amenities

Popular amenities for Holualoa rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Guest favourite

Home in Keauhou

5 out of 5 average rating, 74 reviews

Mollie’s Paradise Resort Home - No Cleaning Fee!

Guest favourite

Home in Kailua-Kona

4.99 out of 5 average rating, 82 reviews

Exceptional Oceanview Home - Pool & Stunning View

Home in Kailua-Kona

4.93 out of 5 average rating, 14 reviews

Kona hale

Guest favourite

Home in Keauhou

4.9 out of 5 average rating, 134 reviews

Tropical Oasis Home with Pool and Steps to Beach

Home in Keauhou

4.89 out of 5 average rating, 89 reviews

Honu Kai Hale - Oceanfront home

Guest favourite

Home in Captain Cook

4.97 out of 5 average rating, 174 reviews

Tiny House Hawaii

Guest favourite

Home in Kailua-Kona

4.94 out of 5 average rating, 224 reviews

Classic Kona 🤙🏻 \\ Epic Ocean View 🌊 \\ Pool 🏊

Guest favourite

Home in Kailua-Kona

5 out of 5 average rating, 8 reviews

Ocean, Sunset, Pool, King's Luxury experience

Apartment rentals with a pool

Guest favourite

Apartment in Kailua-Kona

4.98 out of 5 average rating, 223 reviews

Inna's Downtown-Walk to Beach and to Supermarket!

Guest favourite

Apartment in Kailua-Kona

4.94 out of 5 average rating, 232 reviews

DT Kona Beach Plumeria Condo: Private, quiet

Guest favourite

Apartment in Kailua-Kona

4.93 out of 5 average rating, 182 reviews

Blissful paradise with epic view- Hale Mahana

Guest favourite

Apartment in Kailua-Kona

4.93 out of 5 average rating, 158 reviews

Hawaiian Vacation Starts Here!

Guest favourite

Apartment in Kailua

4.93 out of 5 average rating, 148 reviews

Renovated Oceanfront Penthouse in Kona with AC

Apartment in Kailua-Kona

4.82 out of 5 average rating, 188 reviews

Cozy Kona Condo on Ali'i drive Ocean View Pool

Apartment in Kailua-Kona

4.82 out of 5 average rating, 142 reviews

Air Conditioned Beach-Front Gem in Kona Town!

Guest favourite

Apartment in Kailua-Kona

4.99 out of 5 average rating, 263 reviews

Best Location Hawaiian Charm W/Modern Amenities

Quick stats about holiday rentals with a pool in Holualoa

Total rentals
1.8K properties
Nightly prices starting at
$66 SGD before taxes and fees
Total number of reviews
58K reviews
Family-friendly rentals
860 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
1K properties have a dedicated workspace

Destinations to explore