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.
OCEANFRONT High Floor RENOVATED Maui Kai 806 Condo Private OPEN Lanai KING BED
OCEANFRONT High Floor RENOVATED Maui Kai 806 Condo Private OPEN Lanai KING BEDExperience true oceanfront at low welcome back pricing!Recent Cal KING bed and appliances!MK806 is an oceanfront studio condo apartment with a perfect ocean view that has been completely...
Dog-friendly condo with furnished lanai & washer/dryer plus pool & tennis
Hale Kamaole 249Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This second-floor retreat is a bright and open oasis located just steps from the ocean! Enjoy evenings watching...
Hawaiian Elegance – 5BR Retreat Steps from Mauna Kea & Hapuna Beaches
Welcome to Hawaiian Elegance! From sunrise to sunset, beautiful views surround this exquisite five en-suite bedroom estate in the prestigious Kauna'oa gated community in the heart of the Mauna Kea resort. Hawaiian Elegance is a brand new home just completed in March...
King Bedroom Beachfront Sans Souci 1104
You'll find bicycles, golfing, and more on site at this beach apartment. There's convenient covered onsite parking, so you can leave your vehicle behind and head out to Waikiki Beach and Kaimana Beach, just a short walk away. Relax on the porch or lanai (enjoy the...
Keauhou Punahele B-308 Top Floor, Ocean Views, 3 bedrooms, 3 Bathroom!
A True Beauty at Keauhou Punahele: New Rental in 2024! Keauhou Punahele#B-308 is a gorgeous top floor rarely available 3 bedroom, 3 bathroom condo with approximately 1594 interior sq. feet with an additional 234 square foot lanai! It sits right on Keauhou Country Club...
ICC 18 Remodeled Cottage w Pool AC Beach
International Colony Club 18 Beautifully Remodeled Air Conditioned Hawaiian Plantation Style Cottage Across the Street from the Beach Welcome to your dream Hawaiian getaway at our beautifully remodeled plantation cottage in the heart of Kaanapali, Maui. Nestled across...
Direct oceanfront Studio in Kaanapali, Maui
Welcome to Maui Kai – a unique boutique complex boasting a pool, spa, and BBQ area, nestled as a hidden gem along the renowned Kaanapali Beach. Our penthouse is on the 9th floor and offers uninterrupted panoramic views of Lanai and Molokai islands, seasonal whale...
Free parking marinesurf Comfort central Waikiki
Aloha our unit have free reserve parking ,5-10 minutes walk to the beach , heart of Waikiki, International market, DFS , Royal Hawaiian shopping center. You stay in a very convenient and comfortable place .
Ocean Escape
Routine Spray Pest Control 2025 Dates : 5/2, 8/1 & 11/7 between 8am-8:30 am for 15 to 30 minutesGreetings from Maui, and a warm welcome to your very own Maui condominium nestled within a sought-after complex in the vibrant heart of sunny Kihei. We're thrilled to share...
Ocean, Sunset, Pool, King's Luxury experience
Summary:Tucked away on a quiet cul-de-sac, this villa offers expansive ocean and sunset views. Nested on a 1/2 acre lot, refreshing pool, central A/C. Features: Vaulted ceilings, 10ft ceilings, TV & high end cotton linen in each bedroom. Open floor plan with large,...
🏖️Renovated Ocean Front | Concierge Included |vrKCV
vrkcv - Alii Villas 134, Professionally Managed by Kona Coast VacationsAlii Villas Unit 134 – Oceanfront Serenity in KonaExperience true oceanfront living at Alii Villas Unit 134, a beautifully renovated 2-bedroom, 2-bathroom retreat designed to accommodate up to 4...
Honolulu Condo w/ Private Lanai: Walk to the Beach
Experience the perfect blend of beachside relaxation, outdoor adventure, and city exploration when you stay at this 1-bedroom, 1-bath vacation rental. Complete with modern amenities, a private lanai with sweeping mountain views, and a central walkable location, this...
Sky Ala Moana 43rd fl PENTHOUSE Ocean & Diamond head view 1 Parking
-Luxurious Penthouse Retreat in the Heart of HonoluluIndulge in the ultimate urban oasis with our luxurious 43rd-floor penthouse condo, perfectly situated in the vibrant Ala Moana Center area between Waikiki and Kaka'ako. This prime location offers unparalleled...
Gorgeous Ocean & Park Views! Full Kitchen! Steps to Beach!
Waikiki Shore #605 – 2161 Kalia Rd.Waikiki Shore is the only condo in Waikiki where you can step directly from the building onto the sands of Waikiki Beach! This 6th-floor beachfront studio is a favorite with return guests! You'll feel right at home in this cozy rental...
The Westin Kāanapali Ocean Resort Villas- Studio
Summary:Explore the summit of a dormant volcano. Or hike through a rainforest to a 400-foot waterfall. There’s no better place than Maui for a once-in-a-lifetime experience. The Westin Kā‘anapali Ocean Resort Villas maintains relationships with the top tour operators on...
Stunning Ocean View Gem with AC: Kamaole Nalu 504 - Your Island Getaway!
Kamaole Nalu #504 – Direct Oceanfront Luxury in KiheiKamaole Nalu #504 places you just steps from the golden sands of Kamaole Beach Parks I and II with unobstructed oceanfront views. This two-bedroom, two-bathroom fifth-floor condo has been designed for both comfort and...
Lae Nani 531-Oceanfront View Top Floor with AC
Welcome to Lae Nani Oceanfront Penthouse Unit 531, where paradise awaits! This exquisite two-bedroom, two-bathroom condo promises an unforgettable vacation experience in the heart of Kauai's Coconut Coast. As you step into this Royal Hawaiian-inspired penthouse, you'll...
Beachfront-AC-W/D-Ocean view-Pool-Open Concept #9
This is the perfect tropical resort in Kauai nestled among the palm trees on 35 acres of lush lawns and fragrant flowers. The unit is ocean front on the beach which has beautiful view of the beach/ ocean and sunsets from the upstairs deck (rare). It has a new...
Hawaiian Serene Paradise Oasis at the Pool
Indulge in the serene ambiance of Maui Kamaole C-106, a sparkling clean condo conveniently located right next to the pool and just steps away from the stunning Kamaole III Beach. Featuring two tranquil garden patio lanais, including a completely private one, this ground...
11th Floor 2 Bedroom Sans Souci condo w/ incredible bay views
Luxurious Monthly Rental Property:Relax in the comfort of this high floor Sans Souci condo with stunning ocean and bay views.Condo Features:2 King Size Beds, Full Kitchen, Free Wifi, Ocean Front, Ocean View, One complimentary dedicated Parking Stall is...
Front Row Eclectic Updated Oceanview S Kihei 1 bedroom 1 bathroom condo
Welcome to Maui Vista 1312. This eclectic updated partial oceanview 1 bedroom condo is located in the heart of South Kihei. This condo can accommodate 4 people & has everything needed to feel at home. Cross the street & end up at Charley Young beach which connects to...
Aloha Pearl - Kona Home with Ocean Views, Pool & Hot Tub
Discover the ultimate retreat for relaxation and rejuvenation in our stunning private home, discreetly located just off the iconic Alii Drive in Kailua-Kona, Hawaii. This exceptional property, designed with an eye for luxury and a touch of island charm, promises an...
Large Luxury Home w/ pool and Ocean Views. Special discounted rate March 2025
This magnificent architectural masterpiece - a luxury home that captures an unobstructed 180-degree vistas of the Pacific Ocean, stretching from the iconic Diamond Head to Koko Kai awaits you. Enjoy ever-changing views, from sunrise to sunset, a daily spectacle. Nestled...
Kona Penthouse 2 Bedroom: Relax and Unwind Aloha Style
Top-floor Kona retreat with stunning ocean views!This 2,000 sq. ft. unit features one king-size and one queen-size bed, hosting up to 4 guests. Perfectly located near downtown Kona's restaurants, shops, and farmers market, tucked in a family-friendly neighborhood. Fully...
Maui Resort Rentals: The Whaler 707 - Luxuriously Remodeled 7th Floor 1BR/2BA w/ Stunning Ocean and Mountain Views!
Situated in the first column of suites directly back from the oceanfront, Whaler 707 delivers spectacular ocean views that extend to Maui's neighboring island, Lanai, in addition to gorgeous vistas of the lush West Maui Mountains. This luxurious 1BR/2BA 7th-floor suite...
Ka'anapali Vista: 4BR Home with Pool, AC, BBQ & Outdoor Shower
This is a legally permitted vacation rental according to the County of Maui ordinances.Heavenly Ocean Views with Your Private Saltwater Pool & Lanai at KAANAPALI VISTAAloha e komo mai—welcome to your Maui paradise, where the spirit of aloha embraces you in every moment....
Luxury 2 bedroom in Waikiki!
Welcome! We hope you enjoy the newly renovated and spacious 2 bedroom/2 bathroom. This high-floor unit has an amazing wrap-up lanai deck featuring 180 views of Diamond Head, the ocean, the mountains, the sunrise, sunset, and metro Honolulu. You’ll be a 10-minute walk to...
ICC 22 Beautiful 2BD Cottage Perfect Tropical Vacation
International Colony Club 22 Beautifully Designed 2Bedroom Cottage For the Perfect Tropical Vacation. Private, Next to the Pool, and Close to the Beach FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*:...
Maui Resort Rentals: The Whaler 1015 - Gorgeously Remodeled 10th Floor Interior Courtyard Studio, Spectacular Ocean and Mountain Views!
Boasting breathtaking ocean views in addition to lush vistas of the West Maui Mountains, this luxurious 10th-floor interior courtyard residence is one of the finest studio suites on offer at the acclaimed Whaler Resort. Its fully remodeled interior features several...
Oceanfront Kihei Paradise Vistas
Summary:Spacious and elegant. Completely remodeled in April 2024, no expense was spared to create our gorgeous oceanfront oasis. This one-bedroom, condo features luxurious touches paired with oceanfront serenity. Located in sunny Kihei, all of Maui is within reach....
MRR Presents Kaanapali Ali'i 292 - Renovated 9th Floor Corner 2BR w/ Partial Ocean AND Mountain Views!
Boasting stunning partial ocean views in addition to lush vistas of the West Maui Mountains, this luxurious, fully renovated 2BR/2BA 9th-floor suite features a highly sought-after corner location nestled high above the palms. The space is further elevated by its...
Maui Resort Rentals: Honua Kai Konea 705 - Upgraded 7th Floor Interior 2BR Suite w/ Unobstructed Ocean Views!
Konea 705 is a luxurious 7th-floor "penthouse" interior courtyard two-bedroom suite boasting unobstructed views of the stunning blue Pacific from its prime vantage point high above the palm canopy. In addition, this suite has one of the rare Honua Kai two-bedroom...
REMODELED Tropical Paradise 1BR unit in Princeville with AC & assigned parking!
Beautiful TOTALLY REMODELED 1 br/1 ba unit with living room, full kitchen washer/dryer and spacious lanai in heart of Princeville.ASSIGNED PARKING SPACE!Great views of Princeville golf course and mountains!Unit furnished with portable A/Cs in the bedroom and the living...
𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 Beachfront Maui Ocean Club Resort+Amenities. 2BR Villa
Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢🌴🌺 Ideally located in the heart of Kaanapali Beach along the famous Kaanapali Beachwalk. It is right next to Kaanapali Point and mere minutes from the shops and restaurants of Whaler’s Village.Additional $500-$1000 SAVINGS available for 𝐅𝐢𝐧𝐝𝐢𝐧𝐠...
Waiulu Villa 119A – Bright & Updated | Includes Onsite Staff & Daily Housekeeping
Recently Updated! Located in the popular Waiulu Villa neighborhood, this luxurious 2 bedroom, 2 bath single-level lower floor corner villa was just updated with new furnishings and decor in the living room, dining room and lanai. Accommodating up to 4 guests, this light...
Watermark Waikiki Unit 901: Luxe Condo w/ Pool, Resort Amenities & Oceanviews
Step into refined island living at Watermark Waikiki Unit 901, a spacious two-bedroom, two-bathroom corner residence in Honolulu’s iconic resort district. From the ninth floor, your lanai frames sweeping views of the ocean, marina, city, mountains, and fiery sunsets—a...
Kolohala in Haena is a tranquil place to enjoy your tropical vacation!
Kolohala in Haena is a peaceful place to enjoy your tropical vacation. Great for honeymooners! It faces a beautiful meadow with horses and cows. You can walk to a string of white sand beaches in 5 mins. Close to Ke'e beach, Tunnels beach, Kalalau hiking trails, Napali...
Country Club Villas#326 Top Fl Corner, Incredible Oceanview,Spacious Lanai,AC
Country Club Villas, Unit#326 is a phenomenal new addition to the Vacation Rental Market that Knutson & Associates Property Management is proud to represent. This top floor corner unit is completely remodeled, with soaring ceilings & lots of extra windows for natural...
❤️PiH❤️ House of Manta ★ Hilton Waterslide & Pool Passes ★ Bikes ★ Golf Clubs
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to House of Manta, a part of our Hawaiian Luxury Collection. House of Manta at KaMilo is a wonderful new single level 3 bedroom home. We pride ourselves on provide some of the most sought after homes on the...
Remodeled #56, New owner discount rates, AC, grnd flr end unit, ideal location!
Newest addition to our Kiahuna Plantation condos! We just purchased and started renting #56. For additional accommodations, please look up our other units - VRBO 1300156, 1587209, 3511146, and 2160974Brand new dual AC in living room and bedroom.Kiahuna is a beachfront...
Ocean view condo near beach & dining, beach chairs & gear provided
Kapa'a CaptivationOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Promotional rate of $169 a night until the end of 2025! Make the most out of your time in Hawaii at this Kapa'a...
Glam Condo Located in Central Waikiki, Panoramic Ocean View, & Full Kitchen!
♨ Glam Condo Located on the 42nd Floor With Panoramic Ocean View ♨Enjoy this fully equipt kitchen including a full-size fridge, wall oven, stovetop & dishwasher.✔ Located in Central Waikiki✔ 5 Min Walk From Shops, Restaurants, & The Famous Waikiki Beach✔ Public...
Hale Cassia: New Listing! Home w/ Lanai, Outdoor Dining, Near Shops, Restaurants
Hale Cassia welcomes you to the heart of Princeville, a lush corner of Kauai where mountain peaks meet tropical gardens. This detached, single-level residence blends modern comfort with island ease, offering three bedrooms and two bathrooms across 1,700 square feet....
2 Bed 2 Bath Surfing & Snorkeling in Kahaluu Bay
Aloha! Come and stay at the Hale Hamoa created for everyone with everything we love about Hawaii. Only 1 minute walk to one of the best snorkel beaches on Kona Side and the Surf school next door. The condo comes with all the essentials you need for an awesome vacation...
Tropical paradise with pools, hot tub, BBQ, lanai, washer/dryer, AC
Plantation Hale C1Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This well-appointed condo has everything you need for a breezy and tranquil stay! This spacious, end-unit condo is...
Kapalua's Finest: Luxe Villas with White Sand Beach Access
Nestled in lush gardens and beside pristine beaches, our secluded sanctuaries offer tranquility. Enjoy world-class golf, snorkeling, award-winning spa treatments, and farm-to-table dining. Experience luxury in our fully-equipped villas, with stunning sunsets from your...
Luxury Golf Front Home with Pool and Spa
Constructed in 2019, this one-story luxury residence is nestled in Holuakai's exclusive gated community. A modern island retreat, it seamlessly combines sophistication with tranquility, boasting contemporary amenities for the ultimate luxury experience. Crafted by...
Ke Aloha Villa - 3BR Princeville Paradise with Lanai, Pool & Golf Views
All reservations require the main guest to review and sign a rental agreement to stay at Ke Aloha Villa.**Dearest Future Guests,**Welcome to your very own slice of paradise at Ke Aloha Villa in beautiful Princeville! As you prepare to embark on this adventure, we want...
Contemporary Chic Comfy - 2Bed 2Bath Condo, Steps to Charley Young Beach
We are happy to invite you to our beautiful & stylish vacation condo - AquaMaui. Our family is grateful to have experienced the magic of Hawaiian living and we would love others to experience this. Our condo is a 3 minute walk to one of the most beautiful beaches in...
Na Hale 3: Exclusive Family Retreat with Private Pool and Resort Privileges
3BD Na Hale 3 at Pauoa Beach Club at Mauna Lani Resort by Gather is a single-level retreat designed for effortless indoor-outdoor living within the gated Pauoa Beach community. Surrounded by lush landscaping and steps from the immaculate Fairmont Orchid shoreline, this...