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

HAVEN: Poolside Sanctuary with Heavenly Views
HAVEN Where the changing colors of the heavens melt into the sea. This is a place where dreams are born and special moments of your life unfold. Tranquility, privacy, and stunning beauty await you. A masterclass of design in harmony with nature, this exquisite and inspired home beckons you; a salve for body and soul. Whether you are submerged in the saltwater pool or lounging inside one your deluxe bedroom suites, the views will enchant you, providing an ever-changing patina of color & light.

Spectacular View, Direct Oceanfront Kona,Top Floor
ALOHA, WE INVITE YOU TO RELAX AT SEA VILLAGE Our lovely top floor condo is perfect for you! Sit back and take in the spectacular view from the lanai as you watch dolphins and whales (in season) during the day and beautiful sunsets in the evening! Lose yourself in the never ending sound of waves throughout the condo. Enjoy a closet full of essentials for visiting gorgeous beaches on the island. Downtown Kailua-Kona is a short mile walk from the condo, or relax at the oceanfront pool and hot tub!

Ocean Views~by Honl's Beach~Heart of Kona~AC
ENJOY OCEAN VIEWS from a newly renovated Stylish condo in one of Kona's most desirable locations. Condo is an apx 6 to 8 min walk to a variety of Ocean Side Restaurants, entertainment and a quick walk to Honl's Beach. No rental car is needed, you are a short walk to town. The condo looks directly out to the Pacific Ocean and is on the ground floor so (no long stairs to climb). FREE dedicated parking spot! Free parking is so IMPORTANT in KONA now! 65" SMART TV, AC, our SOFA folds to a 2nd bed.

The Olena at Keauhou Bay
Discover the calm of The Olena, a contemporary 1-bedroom ground floor apartment with A/C, nestled in a quiet complex at the heart of Keauhou in Kailua-Kona. Designed with natural accents and thoughtful details, it is an ideal getaway for 2 guests to enjoy easy walking access to Keauhou Bay and the shops at Keauhou Shopping Center. Enjoy a shared pool, savor sunsets on the expansive lanai with a picturesque view of the Kona Country Club, and immerse yourself in the laid back lifestyle of Hawaii.

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!

Longboard Studio at Kona Magic Sands Beach
Welcome to LongBoard Studio – Kona’s premier direct oceanfront escape at Magic Sands Beach! This stylish, film-featured studio offers stunning ocean views, a brand-new lanai with teak furniture, and full-width NanaWall doors for seamless indoor-outdoor living. Enjoy a gourmet kitchen, AC, queen bed, in-unit laundry, and the sound of waves at your doorstep. Perfect for relaxing, writing, or watching dolphins & whales from your lanai. Steps to the beach, serenity, and aloha! TA-005-037-8752-01

Bungalow Bliss Ocean & Pool View
Your home away from home after exploring the island’s many beaches, coffee farms, snorkeling/diving spots, & downtown Kailua-Kona! Sun-kissed ocean & pool views await you in this cozy, stylish space. A perfect budget-friendly, clean, cool place to rest between your island adventures! Located near downtown Kailua-Kona and 500 ft above sea level, this property offers cooler temperatures and breezes that delight guests. This suite best fits solo travelers or couples who like to be cozy!

Right-on-Ocean; Renovated; Walk to Beach/Town, A/C
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.

Downtown Kona Plaza Condo w/AC
Visit all the Big Island has to offer and lay your head to rest at this comfortable, renovated condo located in the heart of downtown Kona. Situated on historical Ali'i Drive, we are just steps from shops, restaurants, coffee houses, and beaches. Take in the breathtaking sunsets and hear the nightly luau from the enclosed lanai. Enjoy the newly refinished pool, and head up to the sunset deck for a bbq or cocktail. Catch charters, sunset cruises, and snorkel tours off of Kailua Pier.

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 Kailua-Kona rentals with a pool
House rentals with a pool

Exceptional Oceanview Home - Pool & Stunning View

Kini Kini Pua – Private Retreat in Paradise!

Tropical Oasis Home with Pool and Steps to Beach

Private Pool - 180° Ocean View - Minutes to Beach

Tiny House Hawaii

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

Clean Stocked Relaxing Kona Home • AC • Pool • BBQ

Big Family Home, Pool, Views, Yard, Lanai, Clean!
Apartment rentals with a pool

Magic Reef 306 Oceanfront

Direct-On-Ocean/Walkable inTown/Quiet/PoolElevator

Downtown | AC | Pool | Kitchen | WFH | 1 Gig | BBQ

Keauhou Garden - Ocean view - Walk to Harbor

Ali'i Dr w/ Ocean Sunsets next to Farmer's Market

O/F View, on ocean 1 Bdrm, Casa De Emdeko Ironman

Hawaii Retreat with Beautiful Ocean View and AC

Honua Studio *Ocean Views on the Golf Course!
Other holiday rentals with a pool

Gorgeous Unit, Stunning Views!

Centrally Located Downtown Kona Condo

WAVES! WAVES! ON THE OCEAN! BOUTIQUE COMPLEX

Brand NEW Oceanfront Retreat! Steps to Beach!

Hawai'i paradise at Kona Isle

Stunning Oceanfront Beach Condo!

Ocean Front Corner Condo in Paradise

1BR Kona Condo w/ Chef’s Kitchen & Tropical Lanai
When is the best time to visit Kailua-Kona?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $322 SGD | $344 SGD | $311 SGD | $301 SGD | $280 SGD | $283 SGD | $274 SGD | $250 SGD | $258 SGD | $300 SGD | $285 SGD | $307 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 Kailua-Kona

Total holiday rentals
Explore 1,940 holiday rentals in Kailua-Kona

Nightly prices starting at
Kailua-Kona holiday rentals start at $65 SGD per night before taxes and fees

Verified guest reviews
Over 73,110 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
1,050 properties have a dedicated workspace

Wifi availability
1,920 of Kailua-Kona holiday rentals include wifi access

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

4.8 Average rating
Kailua-Kona stays are highly rated by guests – averaging 4.8 out of 5!
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- Hapuna Beach
- Pahoa Beach
- Mauna Kea Golf Course
- Kohanaiki Private Club Community
- Kaunaoa Beach
- Waikōloa Beach
- Ke‘EI Beach
- Mauna Lani Golf
- Volcano Golf and Country Club
- 49 Black Sand Beach
- Kuki’o Golf & Beach Club
- Nanea Golf Club
- Waikoloa Beach Golf Course
- Kealakekua Bay State Historical Park
- Hapuna Golf Course
- Kona Dog Beach
- Kona Country Club
- Makalawena Beach
- Mauumae Beach
- Honokohau Beach
- ʻAlula Beach
- Pololū Beach
- Wawaloli Beach
- Mahaiʻula Beach
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