Vacation rentals in Captain Cook, HI with a pool

Explore 6 vacation rentals, homes, and villas with pools in Captain Cook, HI for your next getaway or business trip. Step outside to your own private or shared pool and into a home filled with premium amenities such as Homes with Free Parking, Homes with hot tub and Air Condition Homes. Throughout your stay, unwind poolside, soak up the sun, and enjoy an outdoor space designed for relaxation. With options starting as low as $117 per night and homes offering up to 5 bedrooms and 6 bathrooms, it's easy to book a comfortable, personalized stay. You'll also have access to high-speed Wi-Fi and 24/7 local support, creating a more secure, connected atmosphere for your trip. Marriott Bonvoy members enjoy the added benefit of earning points on every stay, so each trip's more rewarding than the last. Book your next poolside escape with Homes & Villas by Marriott.

6 Homes with Pools in Captain Cook

Holua Kai #26

Kailua-Kona, HI, US
3 Bedrooms 10 Guests
Aug 28 - 31
$1,094 night

Holua Kai #26 is a two-story, plantation-style retreat in the gated Holua Kai at Keauhou community, overlooking the 2nd hole green of the Kona Country Club’s Makai Golf Course with glimpses of the Pacific from its expansive covered lanai. This 2,685-square-foot residence blends refined indoor comfort with vibrant outdoor living, complete with a private infinity-edge pool, spa, and sunset views that turn every evening into an event. What You’ll Love About Holua Kai #26 * Golf course and ocean views from the lanai and upstairs suite * Private infinity-edge pool and spa for year-round enjoyment * Gourmet kitchen with Bordeaux Dream granite and GE Pro appliances * Primary suite with soaking tub, dual vanities, and private balcony * Access to tennis and pickleball courts, day or night (fee applies) Living & Dining Floor-to-ceiling sliders frame a view of swaying palms and manicured greens, drawing you to the lanai where plush seating invites lingering. Indoors, the open-plan living area features coastal-inspired décor, ample seating, and a Smart TV for relaxed evenings. A formal dining space near the kitchen captures natural light and lush garden views. Chef-Ready Kitchen The kitchen is a showpiece, with Bordeaux Dream granite countertops, solid wood cabinetry, and stainless steel GE Pro appliances, including a wine fridge. A generous island with bar seating is ideal for casual breakfasts before a day on the water or course. Outdoor Oasis The covered lanai extends into a private backyard anchored by an infinity-edge pool and spa, set against golf course greens and the Pacific beyond. Multiple seating areas—some shaded, others sun-kissed—create spaces for quiet reading or lively group meals. The outdoor dining table seats eight, and a built-in grill makes hosting effortless. Sleeping Quarters * Primary Suite – King bed, ensuite bath with soaking tub, walk-in shower, split vanities, private lanai, ocean and garden views * Guest Bedroom 2 – Queen bed, mountain view, shared bath * Guest Bedroom 3 – King bed, ensuite bath, garden view * Office – Double daybed * Upstairs Living Room – Three twin beds Extras Central A/C, high-speed Wi-Fi, washer/dryer, beach gear, wine fridge, and private garage parking. Resort / Community Highlights Guests have access to 7 private tennis courts (5 lighted) and 20 pickleball courts (8 lighted), with court rentals and open play available for a fee. Membership options are offered for extended access. Nearby Walk to the Kona Country Club’s Makai Golf Course and Holua Kai’s racquet facilities. A short drive takes you to Keauhou Bay for boating and manta ray night dives, Kahaluʻu Beach Park for snorkeling, and Kona’s shops, dining, and historic sites. Scenic drives along Ali‘i Drive await. Good to Know * Tennis/pickleball court rentals: $25/hour per court for non-members; drop-in pickleball play $10/person per session. Membership options available. For Saturday Round Robin pickleball, sign up by Friday 7 PM at the Big Island Rogue Pickleball Hui site. Pickleball Update (Effective September 15) To help us keep Holua Kai’s racquet facilities in great condition for everyone, a few updates are being introduced this fall: * Open Play Sessions: Non-member drop-in rates will adjust from $10 to $15 per person, per session. Punch Cards: * 7-punch card: $90 (saves $15). * 10-punch card: $120 (saves $30). * Punch cards are valid for Open Play only (not reservations). * Court Reservations: Tennis and pickleball reservations remain unchanged at $10 per person, per hour. * Sign-In: For smoother check-ins, all guests will use a quick QR code sign-in. * Members: simply enter your name. * Non-members: name plus phone number (and email if requested). These updates allow Holua Kai to maintain vibrant, well-managed facilities — ensuring you and fellow players can enjoy high-quality courts and a thriving pickleball community year-round. * This property does not have the capability to charge electric vehicles. Guests with electric vehicles will need to plan their own charging arrangements during their stay. * Tax ID: TA-024-144-9472-01 * STVR#: 21-458833 * TMK: 780230260000 Reserve your dates now and experience Holua Kai #26’s blend of island elegance and modern comfort.

Bay View Farms Estate House

Captain Cook, HI, US
5 Bedrooms 20 Guests
Aug 24 - 27
$2,454 night

Paradise at Bay View Farms w/ Private Infinity Pool, Hot Tub & Incredible Views Retreat to a gentler, slower-paced era in this beautifully decorated “Estate Home”, offering 6400 sq. ft. with 3 bedrooms, 3 bonus sleeping quarters, 6.5 bathrooms, 6400 sq. ft. surrounded by 18 acres on one of the most pristine working coffee plantations on the Big Island of Hawaii. Just a short drive to the beach and local restaurants. This home has endless unobstructed views of Mokuakae Bay and the ocean beyond - from the infinity pool/hot tub and a beautifully furnished poolside deck/patio - you will not find a more a relaxing place to lounge, barbecue, or dine al fresco any time. The main entrance presents an expansive lanai with beautiful pool and ocean views and easy access to the patio. Enter the great room with the main living area with a wet bar, a large flat screen TV, and lots of cluster seating from which to enjoy the TV and the sweeping views - all at the same time - accompanies the formal dining area that seats 8. The beautiful expansive kitchen has a large island and everything you need to satisfy your culinary desires including a dining nook with seating for 6. Just add the food and the fun and create memories that will last a lifetime. The ocean-view king bedroom, next to the great room, has a vaulted ceiling, a seating nook, a flat screen TV, as well as slider access to the well-furnished view pool/patio. Its elegant, expansive en suite bath has both a large walk-in shower and spa tub. The 2nd king suite has an expansive en suite bath with a large walk-in shower, a king bed, direct pool/patio access, a seating area, and a flat screen TV. The 3rd suite, has a king bed, direct pool/patio access, a seating area, a flat screen TV and an en suite bath with a shower. In addition to the 3 suites, there are 3 additional sleeping quarters, with two located on the second floor, equipped with king beds, full sized pull-out couches, flat screen TV ‘s and balcony access with plantation views. Each en suite bath has a walk-in shower. This home comfortably sleeps 20 in beds and all bed and bathrooms are furnished with an ample supply of premiere linens for your ultimate comfort. Each room has an Air Conditioning unit to customize for your individual needs. Additional amenities include a ½ bath near the entrance, WIFI and cable, a washer and dryer, and parking in the driveway for up to 10 vehicles. Come enjoy this versatile, unique slice of paradise where you can relax, recharge and connect as you create beautiful memories that will last a lifetime. <b>THINGS WE LOVE ABOUT THIS HOME:</b> • Spectacular setting – on a working coffee plantation with sweeping views of Mokuakae Bay and the shimmering Pacific Ocean. • Easy access to pool/spa and patio from so many rooms. It is truly easy to experience the best of indoor/outdoor living here. • Each of the suites has it’s own beautiful en suite bath, TV, and nooks for reading or relaxing, so it easy to get some private time amongst all of your happenings. <b>THINGS TO KNOW</b> • This home is very private (at least 150m from the nearest structure). • The expansive grounds of the Bay View Farms coffee plantation are equipped with a gift and sundries store. The staff is wonderful and available to assist with any recommendations and/or souvenirs for purchase. • This home is equipped with air conditioning. • No smoking inside or outside the property – NO EXCEPTIONS! • Please note: reservations for this home will not be refunded if cancelled within 60 days of arrival. • This property is managed by Heavenly Vacations. • All guests shall abide by Heavenly’s good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m. License number: 830080010000,19368592

Kona Blue Vacations Holua Kai

Kailua Kona, HI, US
3 Bedrooms 6 Guests
Aug 24 - 28
$665 night

Kona Blue Vacations Holua Kai is a refined single-level retreat tucked within the private gates of Holua Kai in Kailua-Kona, perched along the manicured fairways of Kona Country Club. Blending island warmth with resort-inspired comfort, this 3-bedroom, 2.5-bath home features a private heated pool & spa, high-end finishes, and a seamless indoor-outdoor flow—just minutes from Keauhou Bay and Big Island adventures. What You’ll Love About Kona Blue Vacations Holua Kai * Private heated pool & spa framed by lush gardens and golf course vistas * Chef’s kitchen with granite counters, stainless appliances, & central island * Fully stocked adventure gear—kayaks, paddleboards, surfboard, snorkel sets * Central A/C, vaulted ceilings, and thoughtfully curated coastal décor * Close to Keauhou Bay, pristine beaches, shopping, dining, & boat tours Living & Dining The open-concept great room welcomes you with soaring ceilings, soft neutral tones, and comfortable seating that invites conversation and relaxation. Glass sliders open wide to the shaded lanai, letting in gentle breezes and garden views. A formal dining area seats six for shared meals, while the lanai’s dining table is perfect for sunset BBQs under the stars. Chef-Ready Kitchen Polished granite surfaces, rich wood cabinetry, and top-tier stainless steel appliances make cooking a pleasure. The large island doubles as a breakfast bar, perfect for morning Kona coffee or chatting with the chef as dinner sizzles. Outdoor Oasis Your private pool & spa are framed by swaying palms, vibrant tropical plantings, and golf course greens beyond. Loungers offer a sunny perch, while the shaded lanai provides cushioned seating for lazy afternoons. A private BBQ grill completes the alfresco experience. Sleeping Quarters * Primary Suite – King bed, lanai access, pool view, ensuite with soaking tub & walk-in shower * Guest Bedroom 2 – King bed, ceiling fan, central A/C * Guest Bedroom 3 – King bed, ceiling fan, central A/C Extras * Adventure gear: 2 kayaks, 2 paddleboards, 1 surfboard, snorkel sets, boogie boards, cooler, beach chairs & umbrella * Fitness items: free weights, yoga mat, foam roller * Indoor entertainment: board games, books, DVDs * Laundry room with washer & dryer Resort / Community Highlights Guests enjoy access to Holua Kai’s community pool and hot tub, plus nearby tennis & pickleball courts at Holua Racquet & Paddle (fee applies). Nearby Walk to Keauhou Bay for calm-water swims, paddleboarding, or boat excursions. A short drive takes you to Kua Bay and Makalawena Beach, Keauhou Shopping Center’s grocery, dining, and cinema, or historic Kona town. Don’t miss manta ray night dives and scenic coastal drives. Good to Know * Pickleball Update (Effective September 15) To help us keep Holua Kai’s racquet facilities in great condition for everyone, a few updates are being introduced this fall: * Open Play Sessions: Non-member drop-in rates will adjust from $10 to $15 per person, per session. Punch Cards: * 7-punch card: $90 (saves $15). * 10-punch card: $120 (saves $30). * Punch cards are valid for Open Play only (not reservations). * Court Reservations: Tennis and pickleball reservations remain unchanged at $10 per person, per hour. * Sign-In: For smoother check-ins, all guests will use a quick QR code sign-in. * Members: simply enter your name. * Non-members: name plus phone number (and email if requested). These updates allow Holua Kai to maintain vibrant, well-managed facilities — ensuring you and fellow players can enjoy high-quality courts and a thriving pickleball community year-round. * A mid-stay cleaning fee of $235 applies to stays of 14 nights or longer * This property does not have the capability to charge electric vehicles. Guests with electric vehicles will need to plan their own charging arrangements during their stay. * Short-Term Vacation Rental License: STVR-20-399603 * Tax ID: TA - 177-167-8208-01 * TMK: 780230140000 Reserve your dates now and enjoy Kona’s sunshine, style, and island adventures in the comfort of your own private retreat.

Holua Kai #32

Kailua Kona, HI, US
3 Bedrooms 6 Guests
Aug 24 - 28
$665 night

Holua Kai #32 offers a refined Big Island escape in Keauhou’s exclusive gated oceanfront community. Steps from championship golf and a short stroll to Keauhou Bay, this plantation-style home blends breezy indoor-outdoor living with panoramic coastal views, warm sunsets, and private resort-style amenities. What You’ll Love About Holua Kai #32 * Private pool and gated backyard oasis * Short walk to Keauhou Bay to snorkel or swim with manta rays * Spacious open floor plan with soaring ceilings * Pocket doors opening to a shaded lanai for seamless indoor-outdoor flow * Gourmet kitchen with granite counters and solid wood cabinetry * Access to tennis, pickleball, and community pool facilities Living & Dining An airy great room anchors the home, framed by high ceilings, elegant island-inspired décor, and floor-to-ceiling pocket doors that open to the lanai. The living area features plush seating and a 52" 4K TV with Blu-ray/DVD player, perfect for relaxed evenings. The adjacent dining space seats eight at a rustic wood table, ideal for lingering meals after a day of adventure. Chef-Ready Kitchen The gourmet kitchen offers generous counter space, granite surfaces, a breakfast bar for three, and stainless steel appliances. A full suite of cookware and small appliances makes home dining effortless, from fresh Kona coffee at sunrise to late-night snacks by the pool. Outdoor Oasis Step onto the covered lanai for morning coffee beside your private pool. The gated backyard provides a lush setting for sunbathing, al fresco dining, or simply listening to the palms sway in the ocean breeze. Sleeping Quarters * Primary Suite – Cal King bed, ceiling fan, central A/C, garden and pool views, ensuite bath with soaking tub, walk-in shower, and dual vanities * Guest Bedroom 2 – Queen bed, ceiling fan, central A/C, ensuite bath with shower/tub combo * Guest Bedroom 3 – Queen bed, ceiling fan, central A/C, ensuite bath with walk-in shower Extras Central A/C throughout, washer/dryer, 4K TVs in every room, Blu-ray/DVD player, Wi-Fi, and private parking. Resort / Community Highlights Enjoy Holua Kai’s outdoor lounge areas, ocean/sunset lookout, community pool and hot tub, and access to 7 tennis courts (5 lighted) and 20 pickleball courts (8 lighted). Nearby * Walk: Keauhou Bay, Keauhou Shopping Center (restaurants, movie theater, shops) * Short Drive: White Sands Beach Park, Kona Town shopping and dining, championship golf, snorkeling, diving, hiking, and the Ironman World Championship course Good to Know * Please note that 7 private tennis courts and 20 pickleball courts are available for guest use for an additional fee. Of those facilities, 5 tennis courts and 8 pickleball courts have lights. Court rentals are $25/hour per court for non-members. If you’d like to become a member of the Holua Kai community, the court rental fee will be waived. To book a private tennis or pickleball court, guests may call or text Holua Kai’s shop phone and share the day and time you plan to play. A member of Holua Kai’s community team will confirm availability. * Drop-in, Open Pickleball Play Schedule @ Holua Racquet and Paddle: Every drop-in play is open to members and non-members alike. Non-members pay $10 per session (increasing to $15 starting September 15, 2025). For example, if you join the 8 AM play and pay the session fee, an additional fee applies for the afternoon play. Weekly, monthly, and longer membership rates are available through Holua Kai’s shop. Schedule: * Sunday: 8 AM * Monday: 8 AM and 4 PM * Tuesday: 4 PM * Wednesday: 8 AM * Thursday: 4 PM * Friday: 8 AM * Saturday: 8 AM Round Robin Play (with The Big Island Rogue Pickleball Hui) * For more information or to sign up, please visit the Big Island Rogue Pickleball Hui website. Sign-up for Saturday play must be completed by Friday at 7 PM. Pickleball Update (Effective September 15) To help us keep Holua Kai’s racquet facilities in great condition for everyone, a few updates are being introduced this fall: * Open Play Sessions: Non-member drop-in rates will adjust from $10 to $15 per person, per session. Punch Cards: * 7-punch card: $90 (saves $15). * 10-punch card: $120 (saves $30). * Punch cards are valid for Open Play only (not reservations). * Court Reservations: Tennis and pickleball reservations remain unchanged at $10 per person, per hour. * Sign-In: For smoother check-ins, all guests will use a quick QR code sign-in. * Members: simply enter your name. * Non-members: name plus phone number (and email if requested). These updates allow Holua Kai to maintain vibrant, well-managed facilities — ensuring you and fellow players can enjoy high-quality courts and a thriving pickleball community year-round. * This property does not have the capability to charge electric vehicles. Guests with electric vehicles will need to plan their own charging arrangements during their stay. * Tax ID: TA-075-222-0672-01 * This property is a licensed short-term vacation rental. STVR-19-378017 * TMK: 780230320000

Holua Moana Hale

Kailua Kona, Hawaii, US
3 Bedrooms 6 Guests
Nov 17 - 22
$1,303 night

Nestled within the private, gated community of Holua Kai in Kailua Kona, Holua Moana Hale offers a seamless blend of modern comfort and barefoot island luxury. Overlooking the rolling greens of Kona Country Club and the endless Pacific beyond, this two-story residence spans nearly 2,700 square feet of thoughtfully designed living space. Whether you’re here for golf mornings, coastal adventures, or slow afternoons by the pool, every detail is crafted for an inviting Big Island retreat. What You’ll Love About Holua Moana Hale * Private saltwater pool and spa with panoramic ocean views * Jack Nicklaus–inspired putting green for practice or play * Chef-ready kitchen with quartzite counters and wine fridge * Expansive covered lanai for sunset dining and lounging * Primary suite with soaking tub, ocean-view lanai, and ensuite bath * Whole-home water filtration and reverse osmosis system Living & Dining Open-concept interiors flow effortlessly between living, dining, and outdoor spaces. Gather in the great room, where custom pocket doors invite in natural light and sea breezes, or settle upstairs in the lounge for a cozy movie night. The dining area, set for eight, extends to the lanai where twilight meals unfold against Kona’s fiery sunsets. Chef-Ready Kitchen Designed for both beauty and function, the kitchen showcases quartzite counters, stainless appliances, a wine fridge, and thoughtful touches like a coffee bar and tropical tile backsplash. Spacious and fully stocked, it’s perfect for cooking together or indulging in takeout feasts from nearby Kona favorites. Outdoor Oasis Step outside to your private saltwater pool, bubbling spa, and outdoor shower, framed by tropical landscaping and wide ocean horizons. The covered lanai sets the stage for alfresco dining, while Sonos sound and ambient lighting create an easy evening rhythm. The putting green adds playful competition with the Pacific as your backdrop. Sleeping Quarters * Primary Suite – King bed, ensuite bath with soaking tub and walk-in shower, dual vanities, private lanai, ocean view * Guest Suite – King bed, ensuite bath, garden view * Guest Bedroom – King bed, mountain view, shared bath * Bonus Room – Two twin beds, ideal for children or extra guests Extras Enjoy the convenience of whole-home water filtration, reverse osmosis drinking water, Sonos speakers, dimmable lighting, and a full-size laundry room. Beach chairs, towels, and gear are included for island outings. Resort / Community Highlights Set within Holua Kai’s plantation-inspired enclave, guests have access to a community pool, hot tub, and shaded recreation areas. Tennis and pickleball are available nearby for a nominal fee, and the home sits adjacent to the Kona Country Club for world-class golf. Nearby * Walk: Kona Country Club golf, Holua Racquet Club, shoreline trails * Short Drive: Keauhou Bay for snorkeling and water sports, Kona dining and shopping, farmers markets, historic sites, hiking trails Good to Know * Community pickleball/tennis access requires a small fee * This property does not have the capability to charge electric vehicles. Guests with electric vehicles will need to plan their own charging arrangements during their stay. * This property is a licensed short-term vacation rental (STVR #21-460902) * TA-039-641-1904-01 * TMK 780230170000 Reserve your dates now and let Holua Moana Hale be your private gateway to Big Island living at its most spectacular.

Holua Kai #8

Kailua-Kona, Hawaii, US
3 Bedrooms 6 Guests
Sep 3 - 6
$707 night

Holua Kai #8 invites you to unwind in style within the private gated community of Kona Country Club Ocean Course. This elegant single-level home blends open, light-filled interiors with a private heated pool and lanai framed by lush golf course greens and distant mountain views. Just minutes from Keauhou Bay and Big Island adventures, it’s a serene retreat for up to six guests. What You’ll Love About Holua Kai #8 * Private heated pool with bench jets and golf course backdrop * Spacious lanai with outdoor dining &; lounge areas * Chef’s kitchen with premium appliances &; granite countertops * Luxurious primary suite with freestanding tub &; dual vanities *Access to community pool, hot tub &; racquet facilities Living &; Dining The open-concept great room welcomes you with rich wood tones, vaulted ceilings, and plush seating oriented toward sweeping golf course views. A large Smart TV anchors cozy movie nights, while sliding glass doors invite the island breeze. Adjacent is a bright dining space for six, perfect for leisurely breakfasts or candlelit dinners. Chef-Ready Kitchen Outfitted with stainless steel appliances, wide granite counters, and a central island with bar seating, the kitchen is ready for everything from quick smoothies to full-course feasts. Thoughtful touches like a rice cooker, blender, and coffee grinder make it easy to recreate your favorite island flavors. Outdoor Oasis Step onto the covered lanai to find multiple seating areas for lounging and dining. The heated pool shimmers beside manicured grass, offering a refreshing dip after a round of golf or a morning at the beach. Sleeping Quarters * Primary Suite – King bed, ensuite bath with freestanding tub &; shower, dual vanities, golf &; mountain views, lanai access * Guest Bedroom 2 – Queen bed, ensuite full bath * Guest Bedroom 3 – Queen bed, shared half bath Extras Central A/C, washer/dryer, Wi-Fi, beach towels, and secure parking are all included. Resort / Community Highlights Enjoy the community pool, hot tub, and access to 7 private tennis courts &; 20 pickleball courts (fees apply). Drop-in play and memberships available through Holua Kai’s racquet program. Nearby Keauhou Bay’s manta ray dives, snorkeling spots, and ocean tours are minutes away. Short drives bring you to Kona’s shops, restaurants, golf, and island trails. Good to Know *Court rentals are $25/hour for non-members; drop-in pickleball is $10/person per session. See Holua Kai’s shop for availability &; membership details. Pickleball Update (Effective September 15) To help us keep Holua Kai’s racquet facilities in great condition for everyone, a few updates are being introduced this fall: * Open Play Sessions: Non-member drop-in rates will adjust from $10 to $15 per person, per session. Punch Cards: * 7-punch card: $90 (saves $15). * 10-punch card: $120 (saves $30). * Punch cards are valid for Open Play only (not reservations). * Court Reservations: Tennis and pickleball reservations remain unchanged at $10 per person, per hour. * Sign-In: For smoother check-ins, all guests will use a quick QR code sign-in. * Members: simply enter your name. * Non-members: name plus phone number (and email if requested). These updates allow Holua Kai to maintain vibrant, well-managed facilities — ensuring you and fellow players can enjoy high-quality courts and a thriving pickleball community year-round. * This property does not have the capability to charge electric vehicles. Guests with electric vehicles will need to plan their own charging arrangements during their stay. * TA-064-122-6752-01 * PL-STVR-2022-000523 *TMK 780230080000 Reserve your dates now and experience Big Island living at its most effortless.

Vacation Rentals in Captain Cook by Amenities & Features

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Vacation Rentals Near Captain Cook

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