The Best Vacation Rentals In Hawaii: Highly-Rated & Hidden Gems
By Megan McDonald|Published October 30, 2023
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Megan McDonald
Author
Megan McDonald is a writer, photographer, and owner of humu media, an Alaska-based digital media agency. She spends her free time traveling with her husband and daughter around the US and the world.
As local travel experts, we know what travelers are looking for when it comes to finding the perfect accommodations for their next trip. To compile our lists, we scour the internet to find properties with excellent ratings and reviews, desirable amenities, nearby attractions, and that something special that makes a destination worthy of traveling for.
With its stunning beaches, lush landscapes, and vibrant culture, Hawaii is a dream destination for many travelers. Whether exploring the city’s bustling streets and staying in the best hotels in Honolulu, enjoying the serene beauty of Kauai County, or relaxing on the charming beaches of Kihei, finding the perfect place to stay is crucial for a memorable vacation. I’ll guide you through a curated selection of highly-rated hotels and hidden gem vacation rentals across these exquisite locales. From luxurious resorts with all the amenities to quaint bungalows steps from the beach, we’ve uncovered the best accommodations Hawaii has to offer, ensuring your stay is as splendid as the islands themselves!
Best Vacation Rentals In Honolulu
Honolulu, Hawaii, offers a vibrant and diverse experience, combining the best urban living with stunning natural beauty. Honolulu is teeming with activities as the state’s capital and largest city, from visiting historic sites like Pearl Harbor and Iolani Palace to indulging in its thriving food scene featuring various local and international cuisines. The world-famous Waikiki Beach is a must-see, offering a fun atmosphere and opportunities for surfing, sunbathing, and enjoying the famous Hawaiian sunset. The city has many shopping options, from high-end boutiques to unique local shops. Nature enthusiasts can hike up Diamond Head for the panoramic city and ocean views. Honolulu’s mix of cultural attractions, outdoor activities, and relaxation opportunities provides a well-rounded vacation experience for all types of travelers. If you’re wondering where to stay in Honolulu, Hawaii, I’ve got a great round-up of places you’ll want to visit!
1. Ocean View Diamond Head Kahala Slope / Honolulu, Hawaii
The Ocean View, Diamond Head Kahala Slope residence is a stunning gated property on the Diamond Head Crater slope, offering ocean and mountain views from every room. With a contemporary design, the home integrates indoor and outdoor living, featuring travertine stone floors, a pool, a heated spa, and a covered lanai.
The 4,000 sq ft space includes four bedrooms, a gourmet kitchen, and multiple living areas under 15' vaulted ceilings. Positioned less than a mile from the beach and two miles from Waikiki, it accommodates up to eight guests, providing a luxurious yet serene experience in Honolulu.
Book a night at this dream stay on their VRBO listing.
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2. New Modern Urban Hillside Home / Honolulu, Hawaii
Indulge in contemporary living in this fully furnished 3 bedroom, 2 bath Mid-Century-inspired house, aptly described as "The incredible lightness of Being." Perched just above downtown Honolulu and the vibrant Arts District, the residence offers convenient access to restaurants, Kakaako, and the Pali Highway, leading to more beaches. It is low on the hillside and boasts a spectacular 180-degree panorama of mountains, city, and coastline.
The home embraces indoor-outdoor living, featuring a dream kitchen with black stainless appliances, perfect for hosting gatherings. The open-plan living and dining area flows seamlessly onto a lanai, offering a private outdoor retreat. The split bedroom plan ensures privacy, with the main suite presenting a tropical rainforest bathroom, complete with a soaking tub, 12" rain shower, double vanity, and a spacious walk-in closet.
Two additional guest bedrooms share a bathroom with another soaking tub and rain shower. Other highlights include oak wood flooring, split a/c units for zoned comfort, solar hot water, whole-house water filtration, and a separate laundry room with full-size appliances.
Book your stay at this modern dream on their VRBO listing.
Situated on the 10th floor of Waikiki Sunset, this newly renovated condo with central AC comfortably sleeps 6, featuring a well-appointed bedroom, an expansive living area with a high-quality sofa bed, and a fully-stocked kitchen. Guests can enjoy stunning mountain and city views, dine on the outdoor patio, and access free parking and Wi-Fi.
The building offers ample amenities, including a pool, gym, mini-mart, and laundry. Located just a block from Waikiki Beach, when you stay here, you are close to world-class dining and shopping, as well as local attractions, ensuring an incredible stay!
Stay a night at this gorgeous condo and book it on their VRBO listing.
4. Aston Waikiki Beach Tower: 2 Br with Ocean Front Views & Full Kitchen / Honolulu, Hawaii
Located in the Aston Waikiki Beach Tower, this gorgeous spot offers a luxurious two-bedroom suite with captivating ocean views, a full kitchen, and immediate access to Waikiki Beach. This vibrant condo resort combines condominium privacy with premium resort services, placing you in the heart of Waikiki’s incredible shopping, dining, and nightlife.
This spacious and elegantly furnished suite offers a gourmet kitchen, in-suite laundry, and a private lanai with stunning ocean vistas. Enjoy the resort’s amenities, including a recreation deck, outdoor grilling area, pool, fitness room, and jet spa.
Start your vacation off right when you book a night on their VRBO listing.
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Best Vacation Rentals In Kauai County
Kauai County offers a compelling blend of lush natural beauty, tranquil beaches, and adventurous outdoor activities, making it an ideal destination for travelers seeking a diverse Hawaiian experience. Known as the “Garden Isle,” Kauai is home to stunning landscapes, from the dramatic cliffs of the Napali Coast to the expansive Waimea Canyon. Visitors can explore the island’s lush rainforests, cascading waterfalls, and pristine beaches. Beyond its natural allure, Kauai also boasts a rich cultural heritage and a variety of local markets and restaurants serving fresh, authentic Hawaiian cuisine. With its laid-back atmosphere, Kauai provides a perfect escape from the hustle and bustle of more tourist-heavy destinations, offering a chance to experience Hawaii’s beauty and culture at a slower, more relaxed pace. Here are the best areas to stay in Kauai County, Hawaii:
1. Hale Lani at Poipu Kai By Parrish Kauai / Koloa, Kauai
Located in Poipu Kai Resort amidst lush greenery, this spacious 4-bedroom, 3-bath Kauai vacation home combines privacy with accessibility. The open layout with central air conditioning encourages indoor-outdoor living, opening to a serene backyard and covered patio. Guests can enjoy communal spaces or seek solitude within the home, and nearby attractions are easily accessible, including beaches, the Grand Hyatt, and resort amenities.
The home boasts a variety of amenities, including a swimming pool, spa, modern interior, and a well-appointed backyard with a BBQ area, ensuring a memorable and enjoyable stay in this tropical paradise. It’s one of the best places to stay in Kauai County!
Stay the night at this garden oasis when you book on their VRBO listing.
Situated directly on the ocean, this boutique second-floor studio condo is surrounded by tropical gardens and offers direct beach access. Enjoy stunning ocean views and the serene sounds of waves and trade winds from your lanai. The condo has a full kitchen, beach amenities, cable TV, free WiFi, and communal facilities like a pool, grill, and laundry. Nearby, you’ll find wonderful shopping, incredible dining, and a delicious coffee shop.
Book your vacation at this cozy spot on their VRBO listing.
3. Home Of The Cherished Seacoast By Parrish Kauai / Koloa, Kauai
Located just steps from Poipu Beach and across from Brennecke Beach, the cottage, Hale Kahakai Punahele (The House of the Cherished Seacoast), offers a prime beach location in Poipu with unobstructed oceanfront views. This popular Kauai vacation rental features quaint island-style furnishings and a comfortable two-level floor plan with air-conditioning in the master bedroom.
Guests can enjoy the expansive ocean views from the wrap-around covered lanai, surrounded by lush tropical gardens. This oceanfront property provides a serene and deluxe retreat for your Kauai vacation.
Book your vacation today on their VRBO listing.
Best Vacation Rentals In Kihei
Kihei, located on the sun-soaked shores of Maui, is the perfect destination for travelers seeking a blend of relaxation and adventure. Visitors can enjoy snorkeling in the clear blue waters, exploring local shops and restaurants, or simply lounging on the sandy beaches. The area boasts a range of accommodation options, from budget-friendly vacation rentals to luxurious resorts, ensuring travelers can find a place that fits their needs and preferences. With its laid-back atmosphere and breathtaking natural beauty, Kihei is a top choice for those looking to experience the best of Maui. The best places to stay in Kihei, Maui are these lovely spots:
1, Oceanfront, Exceptionally Remodeled, Split A/C, King bed, OH the sunsets / Kihei, HI
The newly renovated one-bedroom, one-bathroom oceanfront condo at Hale Kai O Kihei offers a luxurious and comfortable stay with direct beach access. The unit features modern amenities on the second floor, including a top-grade split air conditioning unit, a fully equipped kitchen with stainless steel appliances, and a living area with a memory-foam pull-out sofa and a 50” Smart TV.
Guests can enjoy stunning ocean views, whale watching, and breathtaking sunrises and sunsets from the private lanai, equipped with an electric sunshade and new glass sliding doors. The bedroom boasts a king-sized bed and an option for privacy with a barn door. Beach essentials are provided for enjoying the secluded beach just a short 60 feet from the unit! Restaurants, shopping, and a grocery store are conveniently located only a block away. This spot is a dream location!
Stay at this oceanfront beauty and book a night on their VRBO listing.
2. Luxury Cottage w/ Private Pool. Under The Warm Maui Sun / Kihei, HI
Right at the entrance of Wailea Resort, Villa Paola offers a tranquil Italian-inspired retreat, combining artistic design with master craftsmanship in marble, woodwork, and more. This one-bedroom, one-bath cottage captures the elegance of a Tuscan villa, surrounded by lush tropical foliage and a stunning saline pool.
The villa is adorned with Italian-themed paintings and complemented by modern amenities like 4K TV screens and high-speed internet. The fully-equipped kitchen and outdoor terrace provide perfect settings for dining, while the luxurious bedroom and bathroom ensure a restful and indulgent stay.
Just minutes away from Maui's renowned beaches, including Keawekapu, Wailea, and Makena, and world-class dining and shopping, Villa Paola is a prime location for exploring the island's diverse attractions! It’s one of the best places to stay in Kihei, Maui.
Reserve a night at this oasis on their VRBO listing.
Have you ever stayed in any of the best vacation rentals Honolulu? Let us know in the comments below! And if you’re looking for more great places to stay, we love VRBO for vacation rentals at every price point!
