TOP 30 Best Holiday retreats in Kailua-Kona, Hawaii

Kona Sugar Shack Villa is a charming real estate and travel agency located at 77-6483 Ali‘i Drive in the beautiful town of Kailua-Kona, Hawaii. Our agency specializes in luxury vacation rentals and real estate properties in the stunning Hawaiian Islands. Whether you are looking for a dream vacation rental or interested in investing in a piece of paradise, our dedicated team is here to assist you every step of the way. Experience the magic of Hawaii with Kona Sugar Shack Villa.

Big Island Retreat is a serene and peaceful lodging located at 78-226 Kahalu'u Road in Kailua-Kona, Hawaii. Surrounded by lush tropical gardens and just a short distance from the beautiful beaches of the Big Island, this retreat offers a tranquil escape from the hustle and bustle of everyday life. Whether you're looking for a relaxing getaway or a rejuvenating retreat, Big Island Retreat provides a comfortable and inviting atmosphere for guests to unwind and recharge. With cozy accommodations, friendly staff, and a convenient location, this retreat is the perfect place to experience the beauty and tranquility of Hawaii.

Located in a scenic cove on the west side of Hawaii's Big Island, Aston Kona by the Sea is a charming oceanfront condo resort offering a peaceful retreat for guests. The spacious accommodations provide stunning views of the coastline, perfect for relaxing under swaying coconut trees or exploring the nearby town of Kailua-Kona with its shops, restaurants, and nightlife. The resort is also a great starting point for snorkeling, surfing, and exploring must-see attractions like Hawaii Volcanoes National Park and Kona coffee farms. Each suite at Aston Kona by the Sea features a full kitchen and a private balcony with either partial or full ocean views. Guests can enjoy lounging by the saltwater pool, cooking meals on the outdoor barbecue, and watching breathtaking sunsets from the oceanfront lawn. Special promotions, packages, and membership discounts are available to help guests make the most of their stay.

Kona Magic Sands is a beachfront institution located at 77-6452 Ali‘i Drive in Kailua-Kona, Hawaii. This stunning property offers guests a magical experience with its pristine white sandy beach and crystal-clear turquoise waters. The resort features luxurious accommodations, top-notch amenities, and breathtaking ocean views. Guests can enjoy swimming, snorkeling, sunbathing, and beachcombing right outside their doorstep. With its convenient location near popular attractions, restaurants, and shopping, Kona Magic Sands is the perfect destination for a relaxing and unforgettable Hawaiian getaway.

Kona Shores is a beautiful institution located at 75-6008 Ali‘i Drive in Kailua-Kona, Hawaii, United States. This idyllic location offers stunning views of the ocean and is just steps away from the beach. The institution provides a tranquil and relaxing atmosphere for visitors to enjoy their stay in Hawaii. With comfortable accommodations, friendly staff, and convenient amenities, Kona Shores is the perfect destination for a peaceful getaway in paradise.

Kona Surf House is a unique institution located in the beautiful town of Kailua-Kona, Hawaii. As a real estate agency and travel agency, we specialize in helping clients find their dream vacation home or investment property in this stunning coastal paradise. Our team of experienced agents is dedicated to providing personalized service and expert guidance to ensure a smooth and successful real estate transaction. Whether you're looking to buy, sell, or rent a property in Kailua-Kona, Kona Surf House is here to help you every step of the way. Contact us today to start your journey towards owning a piece of Hawaiian paradise.

Kona Bed and Breakfast is a charming lodging establishment located at 74-4920 Palani Road in Kailua-Kona, Hawaii. Situated in the heart of the beautiful Big Island, this cozy bed and breakfast offers guests a relaxing and comfortable stay with a touch of Hawaiian hospitality. The rooms are tastefully decorated and equipped with modern amenities to ensure a pleasant stay. Guests can enjoy a delicious breakfast each morning and relax in the peaceful surroundings of the property. With its convenient location and warm atmosphere, Kona Bed and Breakfast is the perfect choice for travelers looking for a memorable stay in Hawaii.

Paint in Hawaii is a premier art institution located at 75-6129 Ali‘i Drive in Kailua-Kona, Hawaii. Offering a unique and immersive experience, Paint in Hawaii provides a variety of painting classes and workshops for artists of all skill levels. Whether you are a beginner looking to explore your creativity or an experienced painter wanting to enhance your techniques, Paint in Hawaii has something for everyone. With the beautiful backdrop of Hawaii's stunning landscapes and vibrant culture, this institution provides the perfect setting for inspiration and artistic growth. Come join us at Paint in Hawaii and unleash your inner artist in paradise.

Located on Ali‘i Drive in Kailua-Kona, Hawaii, Native Surf.co is a unique institution offering a variety of services including an art gallery, lodging, store, and travel agency. This exclusive surf school, established in 1998, is the only Native Hawaiian surf school on the Big Island. With private classes available for all skill levels, Native Surf.co provides an all-exclusive surf experience for its students. Rashguard tops and water shoes are included in the classes, or students can shop for top gear picks at the store. The institution offers 2.5-hour exclusive surf school courses with all equipment included, and 100% private VIP classes for a personalized experience. The instructor ratio is 1:1, ensuring individualized attention and coaching. Classes are exclusive, with only one booking per time slot, so it is recommended to book early. Customers have praised the patient and knowledgeable instructors, highlighting the safe and enjoyable experience provided by Native Surf.co. In addition to surf lessons, the institution partners with non-profits such as Special Olympics West Hawaii and Make A Wish Foundation to grant surf wishes and make memories for those in need. Experience the thrill of surfing in the beautiful waters of Kona with Native Surf.co, a family-owned Hawaiian surf school dedicated to sharing the waves and creating unforgettable moments.

Ohia Kona Estates B&B is a charming bed and breakfast located in the beautiful town of Kailua-Kona, Hawaii. Situated at 73-4671 Kahualani Road, this cozy establishment offers a peaceful and relaxing retreat for guests looking to experience the true spirit of Aloha. With comfortable accommodations, friendly staff, and stunning views of the surrounding landscape, Ohia Kona Estates B&B is the perfect choice for travelers seeking a unique and authentic Hawaiian experience. Whether you are exploring the nearby beaches, enjoying local cuisine, or simply relaxing on the property's grounds, this bed and breakfast is sure to provide a memorable stay for all who visit.

Kona Condo is a luxurious accommodation located at 75-5657A Kuakini Highway in Kailua-Kona, Hawaii. This stunning property offers guests a peaceful and relaxing retreat with breathtaking views of the ocean and surrounding landscape. The condo features modern amenities, spacious living areas, and a private balcony to enjoy the tropical breeze. Guests can also take advantage of the on-site swimming pool, fitness center, and barbecue area. Whether you're looking for a romantic getaway or a family vacation, Kona Condo provides the perfect home away from home in paradise.

Paint in Hawaii is a unique art institution located in the picturesque town of Kailua-Kona, Hawaii. Situated at 74-5567 Pawai Place, this creative hub offers a variety of painting classes and workshops for artists of all levels. Whether you are a beginner looking to learn the basics or an experienced painter wanting to hone your skills, Paint in Hawaii has something for everyone. With its stunning tropical surroundings and expert instructors, this institution provides the perfect setting for unleashing your creativity and exploring the vibrant world of art. Come join us at Paint in Hawaii and let your imagination soar!

Kahaluu Beach Villas at Kahaluu Beach offers a luxurious and relaxing lodging experience in the beautiful town of Kailua-Kona, Hawaii. Located at 78-6721 Ali‘i Drive, this institution provides guests with spacious villas just steps away from the pristine Kahaluu Beach. Enjoy stunning ocean views, comfortable accommodations, and easy access to a variety of water activities such as snorkeling and surfing. Immerse yourself in the natural beauty of Hawaii while staying at Kahaluu Beach Villas.

Elite Pacific Vacations is a prestigious real estate and travel agency located in the beautiful town of Kailua-Kona, Hawaii. Situated at 75-5865 Walua Road, this institution specializes in luxury vacation rentals, property management, and personalized travel services. With a team of experienced professionals, Elite Pacific Vacations offers unparalleled expertise in helping clients find the perfect vacation home or investment property in Hawaii. Whether you're looking for a relaxing beachfront villa or a high-end condo in a prime location, Elite Pacific Vacations has the resources and knowledge to make your dream vacation a reality. Contact them today to start planning your next unforgettable Hawaiian getaway.

Bears' Place Guest House is a charming lodging located on Pu'ukala Road in the picturesque town of Kailua-Kona, Hawaii. This cozy guest house offers a peaceful retreat for travelers looking to experience the beauty of the Hawaiian islands. With comfortable accommodations and a warm, welcoming atmosphere, Bears' Place is the perfect home away from home for your Hawaiian vacation. Enjoy the stunning views, relax in the lush garden, and experience the true spirit of aloha at Bears' Place Guest House.

Ali’i Breeze is a charming lodging institution located on the beautiful island of Hawaii, specifically in the town of Kailua-Kona. Situated at 75-5782 Kuakini Highway, Ali’i Breeze offers a relaxing and comfortable stay for guests looking to experience the beauty and tranquility of the island. With its prime location near the ocean, guests can enjoy stunning views and easy access to the beach. The institution provides a range of accommodations, from cozy rooms to spacious suites, all designed to make guests feel at home. Whether you're visiting for a romantic getaway or a family vacation, Ali’i Breeze is the perfect place to unwind and enjoy the Aloha spirit of Hawaii.

Foster's Ohia Hale is a charming lodging located in the beautiful town of Kailua-Kona, Hawaii, United States. This cozy institution offers a peaceful and relaxing atmosphere, perfect for those looking to escape the hustle and bustle of everyday life. With comfortable accommodations and a convenient location near local attractions, Foster's Ohia Hale is the ideal choice for travelers seeking a memorable stay in paradise. Whether you're exploring the island's stunning beaches or enjoying the vibrant culture of Kailua-Kona, this institution provides a welcoming home away from home.

Aloha Sailing LLC is a premier sailing institution located at 72-4019 C Road in the beautiful coastal town of Kailua-Kona, Hawaii. Our experienced crew offers a variety of sailing experiences, from leisurely sunset cruises to adventurous snorkeling excursions. Whether you're a seasoned sailor or a first-time visitor, Aloha Sailing LLC provides a unique and memorable way to explore the crystal-clear waters of the Pacific Ocean. Join us for an unforgettable journey on the open sea and experience the true spirit of aloha.

My Hawaii Vacation Rental is a premier real estate and travel agency located at 75-5958 Ali‘i Drive in Kailua-Kona, Hawaii. We specialize in providing top-quality vacation rentals in the beautiful Hawaiian Islands. Our properties range from cozy beachfront cottages to luxurious oceanfront villas, ensuring that we have the perfect accommodation for every traveler. With personalized service and attention to detail, we strive to make your Hawaiian vacation a truly unforgettable experience. Contact us today to book your dream vacation rental in paradise!

Silver Oaks Ranch is a charming lodging institution nestled in the picturesque surroundings of Kailua-Kona, Hawaii. Located at 73-6039 Mauka Road, this tranquil retreat offers a peaceful escape from the hustle and bustle of everyday life. Surrounded by lush greenery and serene landscapes, Silver Oaks Ranch provides a cozy and comfortable accommodation for guests looking to unwind and relax. With its warm hospitality and inviting atmosphere, this institution is the perfect destination for those seeking a rejuvenating getaway in the heart of paradise.

A.S.K. About Travel is a unique institution located in the beautiful city of Kailua-Kona, Hawaii. Specializing in both health and travel services, this agency offers personalized assistance and guidance for individuals looking to plan their next adventure while prioritizing their well-being. Whether you're seeking a relaxing beach vacation or an active outdoor excursion, the knowledgeable staff at A.S.K. About Travel is dedicated to helping you create unforgettable experiences. Visit us at 73-4430 Holoholo Street to start planning your dream getaway today.

Hale Wailele is a charming lodging located at 78-7102 Walua Road in the beautiful town of Kailua-Kona, Hawaii. This tranquil retreat offers a peaceful escape surrounded by lush tropical gardens and stunning ocean views. The accommodations at Hale Wailele are cozy and comfortable, providing guests with a relaxing home away from home during their stay in paradise. Whether you are looking for a romantic getaway or a family vacation, Hale Wailele is the perfect choice for those seeking a serene and unforgettable experience in Hawaii.

The Pyramid House is a unique institution located at 76-6322 Kaheiau Street in Kailua-Kona, Hawaii. This stunning architectural masterpiece draws inspiration from ancient Egyptian design, featuring a striking pyramid-shaped structure that stands out amidst the lush tropical surroundings of Hawaii. The institution offers a one-of-a-kind experience for visitors, with a focus on wellness, relaxation, and spiritual rejuvenation. Guests can enjoy luxurious accommodations, holistic therapies, and breathtaking views of the island. The Pyramid House is a hidden gem in Hawaii, perfect for those seeking a truly unforgettable retreat.

KonaHome Ali’i Hale Vacation Rentals offers luxurious and comfortable lodging in the heart of Kailua-Kona, Hawaii. Located at 78-6620 Ali‘i Drive, this institution provides a perfect getaway for travelers looking to experience the beauty and tranquility of the Hawaiian islands. With a range of vacation rental options to choose from, guests can enjoy spacious accommodations, stunning ocean views, and convenient access to local attractions and activities. Whether you're looking for a romantic retreat or a family-friendly vacation, KonaHome Ali’i Hale Vacation Rentals is the perfect choice for your stay in paradise.

ResorticaHawaii.com, Inc. is a real estate and travel agency located at 69-1020 Keana Place in Waikoloa Village, Hawaii, United States. Specializing in vacation rentals on the beautiful Big Island of Hawaii, ResorticaHawaii offers a range of properties in popular resorts such as Waikoloa Beach Resort, Mauna Lani Resort, Mauna Kea Resort, and Kailua-Kona Town. With a team of passionate locals who have been serving the island since 2006, ResorticaHawaii provides exceptional service and attention to detail to ensure a memorable vacation experience. Whether you're looking for adventure or relaxation, ResorticaHawaii has the perfect rental for your stay in paradise. Contact them at 808-881-8222 or [email protected] to book your dream vacation today.

Swim Free Hawaii is a premier travel agency located in Kailua-Kona, Hawaii. Our experienced team specializes in organizing unforgettable swimming adventures in the crystal-clear waters of Hawaii. Whether you're a beginner looking to improve your technique or an experienced swimmer seeking a new challenge, Swim Free Hawaii offers personalized trips and tours to suit every level of ability. Join us at 77-6451 Leilani Street and dive into the beauty of Hawaii's ocean with Swim Free Hawaii.

Hale Kai O'Kona is a charming oceanfront vacation rental located at 75-6204 Ali‘i Drive in Kailua-Kona, Hawaii. This tropical retreat offers stunning views of the Pacific Ocean and is the perfect place to relax and unwind. The property features spacious accommodations, a private lanai, and easy access to the beach. Guests can enjoy the beautiful sunsets, swim in the crystal-clear waters, and explore the nearby attractions. Hale Kai O'Kona is a peaceful oasis in the heart of paradise, where guests can experience the true spirit of Hawaii.

Falling Waters Vacation Villa is a luxurious and secluded retreat located at 6493 Akai Street in Kailua-Kona, Hawaii. This stunning property offers a range of vacation rental options, including spacious villas and cozy cottages, perfect for families, couples, or solo travelers looking for a peaceful and relaxing getaway. As both a lodging and real estate agency, Falling Waters Vacation Villa also offers the opportunity to own a piece of paradise in Hawaii. With a dedicated travel agency on-site, guests can easily book excursions, activities, and explore all that the beautiful island of Hawaii has to offer. Experience the ultimate Hawaiian vacation at Falling Waters Vacation Villa.

VI Resorts at Sea Village is a stunning lodging destination located on Ali‘i Drive in Kailua-Kona, Hawaii. Situated right along the beautiful coastline, guests can enjoy breathtaking ocean views and easy access to the beach. The resort offers spacious and comfortable accommodations, perfect for a relaxing getaway. With a range of amenities including a pool, hot tub, and BBQ area, guests can unwind and soak up the tropical atmosphere. Whether you're looking for a romantic escape or a fun-filled family vacation, VI Resorts at Sea Village is the perfect destination for your Hawaiian holiday.

Ahi Hale is a charming lodging located at 73-1013 Ahikawa Street in Kailua-Kona, Hawaii. This cozy institution offers a peaceful and serene atmosphere for guests to relax and unwind during their stay in the beautiful island of Hawaii. With comfortable accommodations and convenient amenities, Ahi Hale is the perfect choice for those looking for a peaceful retreat in a stunning tropical setting. Experience the true essence of Hawaiian hospitality at Ahi Hale.