Holiday rentals with a pool in Kailua-Kona

Ocean, Sunset, Mountain & Celestial Views

🌴 Guest Favorite - Top 10% on the Big Island Enjoy stunning ocean, mountain, sunset, and starry views from nearly every room in this cozy, family-friendly three-bedroom, two-bathroom Waikoloa Village, Hawaii home. The house includes everything you'll need on your paradise escape including a fully equipped kitchen, beach gear such as boogie boards, snorkels, coolers, umbrellas, towels and Wi-Fi. We also provide bath towels, bed linens, soaps/shampoos, coffee, children's toys, and a BBQ grill.

Location · Value · Getting around

Seahorse Luxury Suite at Seaspray Ocean View

A private oasis across from the desirable Kahaluʻu Beach Park. This two bedroom luxury suite is bright & airy with a private lanai & your own KOI pond. A private guest only pool deck includes a barbecue and dining area for outside entertainment. The living room is a great place to relax with ocean views and the sounds of ocean waves. The chef of the family will appreciate a fully stocked modern kitchen. The whole group will enjoy everything Kona has to offer from this centrally located Oasis.

Family · Value · Outdoor spaces

Private Pool - 180° Ocean View - Minutes to Beach

WOW! That’s what guests always say when they arrive at Kona Heavens Hideaway — Surrounded by lush tropical gardens, exotic fruit trees, and vibrant birds, this 1-acre property offers total privacy, stunning 180° ocean views, and comfortable breezes at 900 ft elevation. Just 4 miles from Kona town and close to beaches, it's the perfect blend of quiet country living and convenient access to everything you need. Spacious, serene, truly special — with reallyFast WiFi Hawaii Tax ID: W01435344-01

Value · Family · Outdoor spaces

Ocean-front penthouse, sunsets, whales, surfers!

*Gorgeous views from oceanfront lanai *See whales, surfers, turtles from lanai *Beach/snorkel/surf right outside *4th Floor Penthouse w/ A/C *Stocked kitchen incl air fryer *Covered parking *Oceanfront Gas grill *Da Poke Shack in complex *Pack 'N Play/High Chair *Shared Pool w/ hot tub *Completely remodeled w/ split air unit & double vanity in master

Value · Family · Air conditioning

Tropical Oasis: Heated Pool, Waterfall, Ocean View

Welcome to Nakukui Hale, your own private Hawaiian sanctuary — a beautifully designed estate for up to 8 guests in a gated community. A resort-style waterfall spills over lava rock into a blue-tiled heated pool. Wander the lush landscape, listen to colorful birds sing, and unwind in the spa or relax in the private gazebo as the sun sets over the Pacific. Just minutes from Ali'i Drive, Magic Sands Beach, Ironman Pier and the best restaurants in Kona. This is Hawaii living at its absolute finest.

Location · Family · Accuracy

Exceptional Oceanview Home - Pool & Stunning View

Exceptional quality, unobstructed panoramic Oceanview, three-bedroom home with AC and a heated pool located in Kailua-Kona. As you walk through the door and see the deep blue ocean, you have arrived in Hawaiian paradise! The home features wide pocket doors that seamlessly expand the living space out to a large balcony (lanai). Relax in your own private oasis swimming pool, lounge in the shade under a poolside gazebo, unwind in your own hot tub! All just minutes from restaurants & shopping.

Family · Value · Kitchen

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.

Value · Family · Nearby

OCEANFRONt 3+2.5 FREE AC BeachGear

OCEANFRONT Kanaloa 3Br 2+1/2 Ba AC SPACIOUS 2000 sq ft. FREE Parking. FREE Resort Fees. FREE AC. Enjoy Meals Out on your Oceanfront Lanai. King Beds. Twins avail. Walk to Keauhou Harbor (Snorkel Tours, Manta Ray Boats), Secret Cove (Hee'eia), Movies, Market, Restaurants 5 min drive to Kahaluu 3 Pools, Hot Tubs, BBQs, Clubhouse, Oceanfront walkway, 16 Acres of tropical grounds. 15 Stairs 2 night min $298 cleaning & 17.96% Hawaii tax is shown on your Airbnb quote.

Value · Location · Hiking

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.

Value · Family · Getting around

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.

Value · Family · TV

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

This luxurious condo with custom interior design is located in historic downtown Kona from where you can walk to sandy Kailua Bay beach just 2 blocks away, restaurants, supermarket, shopping and entertainment. The condo features: pool with BBQ deck, private laundry, full kitchen with dishwasher and ice maker, two zoned ultra quiet AC, Cal. King bed, a screened-in Lanai with peekaboo view of the ocean, fiber optic internet, and a 65” 4K smart TV!

Value · Family · Parking

Mollie’s Paradise Resort Home & Private Pool

Welcome to Mollie's Paradise! This gated resort vacation home features a beautifully crafted outdoor paradise with a private pool and spa. Your host, Mollie, has curated a vacation home experience that will exceed your expectations. Her attention to detail, quality amenities and extra clean home is loved by guests.

Value · Family · Nearby