Hawaii Vacation Rentals – Island Condos, Beachfront Homes & Luxury Villas
Welcome to your guide for Hawaii vacation rentals, where tropical luxury meets everyday comfort. From sunrise-facing lanais on Maui to private bungalows near the lush valleys of Kauai, each rental is handpicked for quality, location, and local charm.
Why Book a Vacation Rental in Hawaii?
Unlike traditional hotels, vacation rentals provide full kitchens, private lanais, and dedicated living space—ideal for families, couples, or long stays. Many homes are steps from the beach, offer high-speed Wi-Fi, and include perks like pools, BBQ areas, or resort access.
Popular Vacation Rental Locations
- Waikiki, Oahu – High-rise condos near beaches, shops & nightlife
- Kihei, Maui – Walkable, affordable, and family-friendly
- Princeville, Kauai – Scenic cliffs, golf, and luxury condos
- Kailua-Kona, Big Island – Oceanfront escapes with sunset views
Rental Types Available
- Beachfront Condos with resort amenities
- Private Beach Homes with full kitchens
- Luxury Villas with pools & panoramic views
- Studios & Bungalows for solo travelers or couples
What Makes To-Hawaii.com Rentals Stand Out?
- Verified properties across all major Hawaiian islands
- Detailed descriptions, amenities, and photo galleries
- Helpful internal links to top Hawaii activities and Hawaii rental cars
- Flexible booking options, from weekend getaways to long-term stays
Plan Your Dream Island Escape
Explore the beauty of the islands with confidence. Whether you're whale watching on Maui, snorkeling on Oahu, or enjoying a peaceful sunrise on Lanai, our vacation rentals offer the perfect base for unforgettable memories. Start planning your Hawaiian adventure today.
100-4 Island living at its best!!
Puamana 100-4 is a beautifully remodeled 3-bedroom, 4-bathroom townhome offering partial ocean views in a prime location, directly across from the beach access. Unfortunately, the historic clubhouse and some amenities were lost to the fire. Despite this, Puamana still...
Luxury Big Island villa steps away from the best beach, sleeps 10!
Located in a prime position, within the gated, luxury enclave of Pauoa Beach, in the Big Island’s Mauna Lani Resort, the Pauoa Beach Oceanfront Villa delivers a 5-star vacation rental experience. Travelers seeking elegant surroundings, access to private Club amenities,...
Experience Paradise Summer Special: Updated Kapalua Golf Villa 5-Star Ocean View
Our condo, 26T8 Kapalua Golf Villas, has everything you need for a perfect vacation:COMFORT: Central air conditioning, remodeled kitchen, new furniture, newly carpeted and painted, king bed upstairs, and new sleeper sofa with a memory foam mattress downstairs. VIEW: Our...
Amazing views from this ground floor, corner unit steps from the beach!
Enjoy a piece of heaven from this ground floor corner unit with quartz counter tops, tile flooring, washer and dryer, and a fully furnished kitchen with everything you need to cook gourmet meals. The condo sleeps 4 comfortably. The master bedroom has a king size bed...
Hale Oka Nunu: Oceanfront Private, Spacious Paradise North Shore Home w/ Hot Tub
Hale Oka Nunu is a four-bedroom, three-bath oceanfront retreat on O’ahu’s North Shore, where the Pacific is just steps from your lanai. Designed for both relaxation and connection, this single-level home blends open living spaces, gourmet amenities, and sweeping views...
Newly Renovated Waikiki Beach 1 Bedroom/1 Bath Condo
Just 2 blocks from the world-famous Waikiki Beach. Short-term 1 to 6 month rental (28 day minimum). Completely renovated 1 Bedroom, 1 Bath condo at Waikiki Lanais with a private lanais with golf course and mountains views. Unit features all new kitchen with granite...
Private cottage above Kona surrounded by coffee farms.
Experience living in Hawaii lush garden property. Very private fully remodeled 1bed/1bath cottage on 2 acre property in Holualoa, just above Kailua Kona. Cooler elevation, surrounded by coffee farms. Hike to a famous Kona Coffee farms like : Heavenly Hawaiian and...
Stunning Ocean View at Kapalua Bay Villas
Kapalua translates to "arms embracing the sea" in Hawaiian. Enjoy one of the most special places on Maui at this 1-bedroom 1-bath Kapalua Bay Villa. Enjoy expansive views & the fresh island breeze from this second level unit with large bay windows & two patios. At the...
Kolea 14K ~ Immaculate, Luxurious, Special Rate+ Lava Lava Beach Cards!
Kolea 14K Current Special Rate $550/nt+tax$100 Lava Lava Beach Card Emailed to you upon arrival!The perfect vacation rental awaits you! This 3 bedroom, 2 bath condo is centrally located in the beautiful oceanfront neighborhood of Kolea. It is one of those versatile...
Romantic Suite with AC, walk to 2 Beaches and 1 Hotel Resort and restaurants
Property Description:Tropical Elegance Meets Modern ComfortThe moment you step inside, the height of the soaring vaulted ceilings—beautifully finished in natural bamboo—creates an immediate sense of island luxury and breathability. This bright, stylish suite is designed...
Located in the closest two-bedroom stack to the ocean at the entire resort, Hokulani 405 boasts gorgeous views of the turquoise-hued Pacific and lush interior courtyard. Treat yourself to a getaway surrounded by the luxury of upgraded modern mahogany wood furniture and...
Welcome to our slice of Hawaii paradise! This fully updated and remodeled unit offers a taste of luxury in every corner. From the tiled entrance, kitchen, and bathrooms to the hardwood floors that grace the remaining spaces, you'll find comfort and style throughout.Sink...
Hale Mahina: Gorgeous Remodeled Pupukea Home with Private Hot Tub & Ocean Views
Welcome to Hale Mahina by Gather, a serene four-bedroom, three-and-a-half-bath sanctuary set in the emerald hills of Pupukea on Oʻahu’s North Shore. Blending panoramic coastline views with refined modern design, this single-level estate spans 3,798 square feet and...
Nalu Hanalei - Stunning Hanalei Home Right by the Beach!
Nalu Hanalei – your ultimate Hawaiian getaway! Located just steps away from the world-renowned Hanalei Bay, this luxurious 4-bedroom, 3-bathroom property offers the perfect combination of comfort, convenience, and breathtaking ocean views.As soon as you step into this...
Spacious unit located in Maui Hill Resort+Netflix&more
Welcome to an upscale neighborhood. Aston Maui Hill in the heart of Kihei right next to Wailea. We offer you an entire place. There's one bedroom with king bed the master bed has an attached bathroom and balcony and there will be another queen bed in the living room...
Olivine Surf Lodge - Corner Unit w/ Ocean Views & Amazing Sunsets
Newly updated, light-filled condo on the North Shore of Kauai! This modern, tranquil retreat has a wide-open floor plan and a lanai with stunning ocean and golf course views. Superb location, close to walking paths and the Princeville town center, with great cafes,...
Enjoy Perfect Vacation at Luxury Beach Front Resort.
Welcome to the paradise in Kauai, Waipouli Beach Resort. G-205 with 2 suite bedrooms and 3 full bath is equipped with high end luxuries to provide a comfortable, memorable vacation experience. Wake up to the sound of the ocean and prepare for a full day of leisurely fun...
Amazing Hotel Zoned Beach Front Condo on Sugar Beach. Reserve with Confidence!
Ready for a beach vacation in paradise?!? Beach front complexes on the south shore of Maui are generally not this close to the shoreline and most are apartment zoned and may be subject to recent proposals to convert to longer term housing rentals. Nani Kai Hale is hotel...
Comfortable House close to beaches with Peloton Bike+ and 4 New Trek bikes
Very cute, Newly-remodeled cottage with a modern garage that has been turned into home gym with mat, weights, peloton bike+, and home office table, chairs and monitor. The interiors have completely been redone with new flooring, furniture, new kitchen countertops and...
KKSR#7303 Remodeled Top Floor Unit With Loft, Golf Course Views
Welcome to Keauhou Kona Surf & Racquet Club #7-303!This Gorgeous top floor unit truly is special, a lot of custom features one can enjoy. This spacious premium unit has an impressive 1,384 interior square feet, featuring 3 bedrooms & 2 bathrooms. The property has...
Kolea Landing Modern Beach House w/ Double Suite and Third Bedroom Option
Aloha and Welcome to Kolea LandingA short walk (less than 400 steps to be exact) and you will be relaxing at Lanikai Beach! Our 2,200 sf guest house is the perfect blend of island and modern living. Our guest house has a master bedroom (king bed) with an en suite...
Comfortable, Classy Farmstay Studio, walk to secluded world-class Kahili Beach
Book a stay on an operating Sugarloaf White Pineapple and Tropical Fruit Farm. Stay in a luxurious accommodation within walking distance to a lovely world-class Kahili (Rock Quarry) beach, a white sand beach with lots of exploration possibilities.It is a 15 minute...
Waikiki Banyan Condo With Panoramic 37th Floor Ocean Views by Koko Resort Vacation Rentals
Panoramic 37th Floor Ocean Views, Free parking & Wi-Fi The pool and all associated amenities will be closed starting April 7, 2025,for an estimated duration of 10 to 14 months to accommodate the RecreationDeck renovation project. Enjoy panoramic views of the ocean and...
Beautiful 2-BR Villa at Four Seasons Hualalai
**Please note that the Chairman's Club Event takes place each year at Four Seasons Resort at Hualalai from approx December 2 - December 7th. . This event will result in limited access to resort amenities. Details at end of listing!. **Enjoy the quintessential Hawaiian...
Oceanfront ground level recent remodel at Kona Isle
Direct oceanfront, ground level, recently remodeled D4 at Kona Isle. Enjoy beautiful ocean views and breezes. Steps to the beachfront area with lounge chairs to relax in. Or swim in the solar heated pool. BBQ grills and picnic tables make for cooking out a breeze and a...
Aston Maui Kaanapali Villas A405 Ocean View 1 bedroom on N. Kaanapali Beach
Maui Ka’anapali Villas #A405: One bedroom ocean view on N. Kaanapali Beach with Pool and Beach Access. Maximum occupancy: 3This condominium is located in the Aloha Tower, the central hub of the property. Situated on the 4th floor, this unit boasts magnificent ocean...
Aston Maui Ka’anapali Villas A109: Ground floor w/2 Br on N. Kaanapali Beach
Maui Ka’anapali Villas #A109: Ground floor 2 bedroom on N. Kaanapali Beach with Pool and Beach AccessThis condominium is located in the Aloha Tower, the central hub of the property. Situated on the coveted ground level, this unit boasts a full lanai, and affords easy...
Luxury Estate with Panoramic Honolulu views. Steam room, Sauna, Spa, Heated Pool
The ultimate contemporary estate to de-stress, unwind and recharge your well-being. Luxury hotel and spa experience without the crowd and traffic. It can accommodate multiple families and corporate retreats, providing private and shared spaces, allowing guests to come...
Welcome to Molokai Shores luxury condo Ka Hale Kealoha A215! This beautifully updated (and freshly painted Sept 2021!!) 526 sq ft condo boasts high end appliances as well as a fully equipped kitchen with everything you would ever need. Sleeps 4 in a brand new (9-2021)...
Waimanalo 4 Bedroom / 3 Bathroom Private Home
This home includes ocean views, a rooftop deck, and a heated pool. Enjoy breathtaking views of the majestic lava-formed Ko'olau mountain range and only steps to the # 1 rated beach In the world (2015), Waimanalo Beach, famous for the filming of Magnum PI, Baywatch,...
Hale Hau'oli ~ House of Happiness
This one bedroom, one bathroom condo was completely renovated in 2020 and has everything you need to relax and enjoy your time on the island. It is the perfect space for solo travel, couples or escaping with your best friend. All of the furnishings are brand new and...
Hapuna Modern House – Sleek Oceanview Luxury at Mauna Kea Resort
vrKCV - Hapuna Modern House, Professionally Managed by Kona Coast VacationsHapuna Modern House – Hawaiian Luxury Resort LivingPerched on the highest point in the coveted High Bluffs at the Mauna Kea Resort, Hapuna Modern House is a home like no other in Hawai'i. Unlike...
Luxury Villa Steps to Ocean w/ 3+ Bedroom Sleeps 8
This gorgeous ocean view Luxury Estate is in a gated community right on the 5th hole of Mauna Lani Resort South Course with breathtaking views of fairways, ocean and mountains. Experience the exclusive lifestyle just minutes away from the beach - with 3,600 square feet...
Cute and quaint little cottage on a homestead.
This quaint country cottage in Anahola sits on acreage surrounded by fruit trees and tropical foliage. If you are looking for an authentic local experience, this is it. Far from resort vibes, Banana Hideaway is as real Kaua'i as you can get. Wake up to incredible...
Elegant Giant Oceanfront Estate - steps to Magic Beach with pool, sub zero
Gorgeous and High end 4 bedroom plus bonus (sleeping) loft home. Located in a prime gated community, sleeps 12. Sleeping cots available if needed. The home has a Tropical landscaped yard, fantastic ocean view from both lanais, central A/C, plunge pool with a water...
Pristine End Unit, Mauna Lani Golf Villas, Beach Club+Golf Pkg savings!
STVR-21-559570Seeking a flawless, worry-free spot for your next get away? Look no further….Come, relax and make yourself at home in our well-appointed, high-end furnished, corner villa inside the Mauna Lani Beach Resort. Take advantage of our Kings Club membership at...
Newly Remodeled, Ocean View, Beachfront Paradise at Lae Nani
Lae Nani Condo unit 435 is a 2-bedroom, 2-bathroom Penthouse unit with two ocean view lanais from the main living area and the master bedroom suite. Our remodel in late Spring 2024 included a full kitchen remodel, new flooring throughout and an update to both bathrooms....
Glorious ocean and Bali Hai views from this ground floor, air conditioned home
This immaculate luxury condo, perched on an emerald bluff overlooking the Pacific Ocean, offers spectacular views of the surf and the famous Bali Hai mountain range. On Kauai's North Shore, near Hanalei Bay, this 1700-square-foot, ground-floor unit is found in the...
Gated 2-story beach house with big yard
Hoku Lani, or “Heavenly Star” is a two story air conditioned 3 bedroom, 2.5 bath home with lofty ceilings, concrete construction and gorgeous details throughout. You’ll love the mahogany and kiwi custom cabinetry and granite countertops in our gourmet chef kitchen. Fine...
Poipu Luxury Farmhouse: NEW Estate with Access to Pool & Pickleball
Welcome to our Luxury Farmhouse, perfect for large groups or families. Just a half mile from the beach, this property features 5 bedrooms, 4 baths, 2 family rooms, and 1.5 kitchens. Enjoy open shared spaces, private lanais, well-equipped kitchens, spacious baths, A/C...
*NEW Poipu 2BR Retreat|Pool|AC & Athletic Club
Discover luxury in the serene Poipu Beach Estates with our charming 2br/1ba cottage. Enjoy farmhouse-inspired design, full kitchen with KitchenAid appliances, and quartz countertops. Relax in A/C-cooled bedrooms or on the lanai. Exclusive access to Poipu Beach Athletic...
Hale Kai O Kihei Condo w/ Ocean View, Shared W/D-Waves Await
Hale Kai O Kihei 216Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This Hale Kai O’ Kihei condo offers a breathtaking ocean view from every room and includes a private lanai that...
MODERN HAWAII ⛳️ Luxe Remodel, Closest 3BR Kapalua Golf Villa to Beach & 4th Tee!
Modern Luxury at Kapalua Welcome to your luxury Kapalua Golf Villas retreat located in the heart of Kapalua Resort on Maui’s beautiful West Coast. This elegant ocean-view condo is just minutes from Kapalua Bay Beach, Montage Kapalua Bay, and the world-famous PGA Golf...
Holua Moana Hale: Spectacular Oceanfront Home with Private Pool & Spa
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...
Garden View Room - Oceanfront Hilo Beach House Inn
Welcome to the Hilo Beach House - A Unique Boutique Inn located in the quiet tropical oceanfront setting of Onekahakaha Beach Park. Stay at this upscale 4 room Inn. Rest, Relax, and Rejuvenate at this Tropical Oceanfront Retreat.If the Garden view Plumeria Room is...
New Aloha Ilikai 1Free Parking<br>(1777 Ala Moana BLVD)
ALOHA! Fully Renovated in June of 2025 / 1 free parking(There is a top-quality water purifier inside the unit, so there is no need to buy bottled water.)Perfect for couples, families, solo travelers, or business stayWe offer the ultimate Waikiki experience, combining...
Monthly Discovery Bay 1713 Ocean/City Views 1 Bd 1Ba
WAIKIKI / OCEAN VIEWS, 5 Minute Walk to Beach, Remodeled, Furnished and Fully Appointed. No smoking condo. Parking, Pool, Utilities, WIFI, BBQ, Gym, Sauna, Security, Washer/Dryer Included. Monthly.Excellent Views from Breezy Lanai, Tasteful and Clean. Monthly / contact...
DAZZLING OCEANFRONT! Stunning views and steps to Sugar Beach, vacay awaits!
🌴 Oceanfront Maui Getaway – Kanai A Nalu #319 🌊Wake up to the sound of the ocean and panoramic views of Ma’alaea bay! Take a stroll along Sugar Beach, Maui’s longest sandy shoreline. This true oceanfront condo offers uninterrupted views of Ma’alaea Bay, Haleakala, and...
Stunning Ocean Front Views, Wailea, Polo Beach Club Condo - unit 303
Welcome to your tropical escape at Polo Beach Club, our cherished slice of paradise! Having fallen in love with this magical location years ago, we are thrilled to be able to share our beautiful condo with you. Nestled at the tranquil south end of Wailea Beach Walk,...
Five bedroom log cabin near Waipi'o Valley
The Log Cabin, a licensed 'inn', is located in lush and peaceful Ahualoa, just an 8 minute drive up the mountain from historic Honokaa town. The Log Cabin is a great setting for families, groups, weddings or other special events.You can enjoy a stroll around the yard or...