
Holiday rentals with a pool in Kalaoa
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Top-rated rentals with a pool in Kalaoa
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Aloha Paradise! Remodeled with A/C & Ocean View!
Best unit at Kailua-Kona’s popular Sea Village and one of the only with A/C! Captivating ocean views, breezes, tropical sights and sounds greet you in this easily accessible ground floor unit. Start your day on the private lanai watching the spinner dolphins and end it with a glass of wine watching sunset over the ocean. This fully updated, turn-key condo boasts open concept living and is 5 minutes to downtown. An ideal base for an individual, couple or small families to explore the Big Island!

Cozy Couples Retreat- Guest Suite w/ Pool & Patio
Perched above Kona on a serene hillside, the Monkeypod Villa offers a peaceful escape on a private country estate. Nestled off the beaten path & away from tourist crowds, you're just a scenic 7-mile drive from downtown Kona and pristine beaches. Wake to the gentle chorus of birds and sip your morning coffee beneath the shade of a magnificent monkey pod tree. After a day of exploring the Big Island, take a refreshing dip in the pool & unwind as the sky transforms with a stunning Hawaiian sunset.

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!

Discounted KonaReef D33 OceanFront* AC* Park Free*
The Kona Reef is being renovated in 2026. Check out our special construction rates. Reno hours 8a-5p Mon-Sat while you are out at the beaches, volcano etc. You’ll love this condo! Absolute Ocean Front. 5 minute walk to downtown. Free parking! Completely remodeled! Fresh, clean, stylish & comfortable. NEW Full A/C, Stocked Kitchen & Beach & Golf Equipment. ATTENTION GOLFERS! 2 sets of Callaway Clubs! Check out our 2 other Kona Reef condos A35 & B31 TA-109-936-6880-01 STVR-19-352037

Oceanfront Gem, Walk to Beach/Town, AC, Elevator
Right-on-the-ocean, newly renovated, spacious, upscale condo in a gated boutique complex. Unbelievable views from the lanai, living room and bedroom. Close to everything! 1-2 blocks to Honl's beach, farmers market, restaurants, bars, and shops in Kailua Village. New king bed and queen sleeper sofa with memory foam mattress for up to 4 guests. Heated, ocean-front salt water pool with outdoor shower and community BBQ. Quiet; no noise from Ali'i Drive. Reserved parking spot. A/C. Elevator.

Updated condo with ocean views & air conditioning
Kick back and relax at this renovated condo with partial ocean views, an oceanfront saltwater pool, and lusciously landscaped grounds. This air-conditioned unit boasts a central location just 1.3 miles from the heart of downtown Kona. Conveniently located between downtown Kona and the world-famous Magic Sands beach, this is the perfect home base to explore everything Hawaii Island has to offer. Enjoy the shared BBQs and private sandy beach area as you soak up Kona's sensational sunsets.

Suite Magic Sands Beach
Save money & time! Ho'omalu located just off of Alii drive "Ironman Route" is only an 11 minute walk to magic sands beach and many more hot spots. In a private and tranquil gated community this modern day Villa awaits where sophistication meets relaxed Hawaiian living. The inviting pool enveloped with mature tropical landscaping is the centerpiece to this compound and features upscale finishes and flooring. The apartment is on the second level. Ask about our car rental fleet discounts.

Keauhou Garden - Ocean view - Walk to Harbor
Stunning ocean views, walking distance to the harbor and shopping center. Keauhou Garden is a clean and cozy stay at the heart of Keauhou, one of the best neighborhoods to stay on Big Island. Peaceful and quiet place, yet just a short drive from Kona downtown. A perfect place to unwind and relax while admiring beautiful views of the ocean and the golf course. Keauhou Resort is nestled next to the Kona Country Club, a spectacular public golf course with breath-taking ocean views.

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.

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.

Halia Hale
Escape to your own private Kona retreat, perfect for couples or friends. This gated and fully fenced home sits among 500+ mature Kona coffee trees and seasonal fruit like mango, papaya, banana, tangerine, orange, and avocado. Relax by the lap pool, detox in the commercial-grade sauna, or sip fresh coffee on the lanai. Just minutes from Kona’s beaches, shops, and dining, yet peaceful and secluded—an ideal spot to recharge and enjoy the spirit of Hawai‘i.

Blissful paradise with epic view- Hale Mahana
Serenity in Kona- with epic ocean views! Wake up with the ocean waves crashing below. Hang out on the lanai with some Kona coffee from the Green Flash cafe next door. You have a front row seat for whale watching during whale season. Or, hang out and enjoy the sunsets- at times with our local manta ray! We have a queen sofa bed, and AC. Close to town- an 18 minute walk. Quiet, very little road noise here. You can rent bikes too across the street.
Popular amenities for Kalaoa rentals with a pool
House rentals with a pool

Mollie’s Paradise Resort Home & Private Pool

Exceptional Oceanview Home - Pool & Stunning View

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

Kahaluu Bay Get-Away

Tropical Oasis Home with Pool and Steps to Beach

Tiny House Hawaii

Huge Kona Home • Ocean View • Pool • 4 bdrms • AC

HAVEN: Poolside Sanctuary with Heavenly Views
Apartment rentals with a pool

Longboard Studio at Kona Magic Sands Beach

Ocean Views~by Honl's Beach~Heart of Kona~AC

Lovely studio condo with kitchenette and pool

Condo with A/C, Pool, Spa & Golf Course Views

The Olena at Keauhou Bay

*Oceanfront Penthouse in Kona with AC!*

Beautiful Villa ... walk to most everything!

Hawaii Retreat with Beautiful Ocean View and AC
Other holiday rentals with a pool

Gorgeous Unit, Stunning Views!

Spacious Fairways 2BD townhome. Pool/Beach Club!

Comfortable, Relaxing Poolside Retreat

Luxury couple’s retreat w ocean view/AC/king bed

Downtown 1BR Condo AC, Pool, BBQ & Walk to Beach

Clean Stocked Relaxing Kona Home • AC • Pool • BBQ

NEW! ADORABLEbungalow in Kona

1BR Kona Condo w/ Chef’s Kitchen & Tropical Lanai
When is the best time to visit Kalaoa?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $570 SGD | $698 SGD | $699 SGD | $699 SGD | $647 SGD | $641 SGD | $588 SGD | $679 SGD | $633 SGD | $602 SGD | $641 SGD | $1,235 SGD |
| 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 holiday rentals with a pool in Kalaoa

Total holiday rentals
Explore 90 holiday rentals in Kalaoa

Nightly prices starting at
Kalaoa holiday rentals start at $165 SGD per night before taxes and fees

Verified guest reviews
Over 2,000 verified reviews to help you choose

Family-friendly holiday rentals
80 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wifi availability
90 of Kalaoa holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Kalaoa rentals

4.9 Average rating
Kalaoa stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
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- Hapuna Beach
- Waikoloa Beach
- Waikōloa Beach
- Kohanaiki Private Club Community
- Kona Country Club
- Makalawena
- Spencer Beach Park
- Mauna Kea
- Mauna Lani Beach Club
- Big Island Retreat
- Magic Sands Beach Park
- Pololū Valley Lookout
- Manini'owali Beach
- Waialea Beach
- Sea Village
- Kaloko-Honokohau Nat'l Hist Park
- Puʻuhonua o Hōnaunau National Historical Park
- Hapuna Beach State Recreation Area
- Captain James Cook Monument
- Kua Bay
- Kona Farmer's Market




