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.
Stunning waterfront condo with WiFi, shared pool/hot tub, & amazing ocean views
Pali Ke Kua 224Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Enjoy the awe-inspiring views of the Pacific Ocean and the north end of Hanalei Bay with Mt. Makana in the background....
Comfortable & Spacious North Shore Home - AC in Both Bedrooms!
Puamana 25A is a well-maintained, spacious vacation home offering 1200 square feet of comfort, privacy, and a fantastic location on Kaua'i’s North Shore! With its charming vintage character, this home provides everything you need for a relaxing stay, including the...
Remodeled Ocean View Condo with Beach Access, Resort Pool & Hot Tub
Kahana Villa E610Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Stay in this recently-remodeled, family-friendly, air-conditioned condo with ocean views and enjoy shared on-site...
Kaanapali Shores 544 60%Off May & June Deals at Tropical Escape with Ocean Views
The Stice Team — Powered by Gather Vacations. Maui Born and Raised Professionals. Your Local Experts in Crafting Unforgettable Stays.Welcome to Kaanapali Shores 544, a newly refreshed 1-bedroom, 1-bath condo perched on the fifth floor of this beloved North Ka'anapali...
Halii Kai 15D True Ocean Front. Watch Dolphins and Whales (in season) from your Very Private Lanai
This highly desirable upper floor, corner unit is in one of only three buildings at top-rated Hali'i Kai resort that are directly on the oceanfront. This top level corner unit is located near the Ke Kailani grotto, avoiding some of the noise and activity from the...
Perfect Maui Beach Home: Penthouse, Great Views, From $195
This is our Maui home, a 4th floor penthouse. We recently put in new furniture, carpet and paint. This condo has been a part of our family since it was new in 1974 and we have carefully remodeled it for maximum comfort and enjoyment. There is a new flat screen (4K, HDR)...
Stunning Ocean and Mountain View | Kauai North Shore
Hanalei Bay Resort, #3105Spacious studio unit with stunning ocean and mountain views of Kauai's north shore. This is a fully air-conditioned, ground floor condo that overlooks Hanalei Bay, Bali Hai, and is located at the beautiful Hanalei Bay Resort. The spaceStudio...
Ocean-Sunset Views Home in Gated Makaha Community w/Great amenities
Book with confidence! This property is professionally managed by Ali'i Beach Rentals, an award-winning property management company.May 2025 the Community Pool, Jacuzzi, and Gym are now OPEN!!Discover the peace and beauty of your own secluded retreat nestled in the...
Explore Kauai & Relax in Luxury - Pool - Grills
Adventure & Luxury Awaits You - Explore the Island of Kauai: Swim, Snorkel, Hike, Surf or Read Under a Shade Tree. Then return to this High-End Luxury Suite with a Resort Pool, Jacuzzi and BBQ grills just steps away. This well appointed suite is Ideal for Special...
Classic Kailua Beach House – Oceanfront Bliss in Windward Oahu
This property is professionally managed by Private Homes Hawaii, LLC and is licensed as a short term vacation rental, 1990/NUC-1780 and is compliant with Hawaii State Legislation (HB2078) for vacation rental accommodations, TA-179-906-2528-01. TMK.Welcome to "Kailua...
Beautiful - Palms at Wailea 1802
Located in the Kihei/Wailea area, in the world-famous Wailea Resort community, The Palms at Wailea complex boasts a beautiful pool, hot tub and is conveniently located close to the Shops of Wailea, luxury hotels, stylish boutiques, great restaurants, tennis, the Wailea...
Beautiful penthouse suite with stunning ocean view, pool, hot tub & beach access
Sugar Beach Resort PH05Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Treat yourself to the unmatched beauty of Maalaea Bay from Sugar Beach Penthouse 5. You'll be situated mere...
COZY CONDO, JUST STEPS FROM THE OCEAN, LOW DENSITY PROPERTY!
MAUI SANDS SEASIDE IS A SMALL COMPLEX WITH LESS DENSITY FOR THOSE WHO WISH TO PRACTICE SOCIAL DISTANCING OR JUST PREFER TO BE AWAY FROM LARGE CROWDS IN GENERAL. THIS IS A GREAT LOCATION FOR A FAMILY VACATION OR FOR A COUPLE'S RETREAT. THIS IS THE PERFECT LOCATION TO...
❤️PiH❤️ Seashell Villa ★ Bikes ★Free Hilton Resort Passes ★Free Private Beach Club
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to the newest home in our Hawaiian Luxury Collection. Seashell Villa is a wonderful almost new exquisite 3 bedroom home in the gated Kulalani community with high end finishes with pool and recreation center...
Oceanfront Condo with 180-degree penthouse views
Sealodge G9Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Perched atop the oceanfront cliffs in the community of Princeville, this unit offers unbelievable views from every room....
Modern Ocean View Studio - Waikiki Paradise!
Thoughtfully appointed studio with modern decor. Fully renovated in February 2022! Includes FREE high speed Wi-Fi, cable TV, and various TV apps for streaming services.Check in and out at your convenience with a lock box. Check in after 3pm and check out before 11am....
Poipu Koloa - 2 br unit Ocean/Garden view in Kauai
We can book Ocean Front/OV/Garden view unit if they are available.Price from the system is for Garden View unit. If you like OV, please request it.This is timeshare resort, per policy, unit number floating. Don't know exact unit be assigned until check in, but the view...
Palm-lined condo with easy beach access, pools, hot tubs, & tennis courts
Tropical Oasis at Poipu Kai 514Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Say aloha to your next favorite vacation when you book a stay at this newly remodeled first-floor Poipu...
Views! Beaches and Shopping Right Next Door! A308
Discover your perfect Maui escape at Kihei Alii Kai A308, a stunning 2-bedroom, 2-bathroom oceanview condo that seamlessly blends comfort and tropical luxury. Recently refreshed with fresh paint, new living room furnishings and crisp white linens, this spacious retreat...
Daydream Believer, House, 4 bed, 3 bath, sleeps 13
DAYDREAM BELIEVER AT KOLOA KAI VACATION RENTALSMountain Views, Steps from Shipwreck Beach, and Room for the Whole OhanaWelcome to Daydream Believer, where the spirit of aloha and family come together in a spacious, mountain-view retreat just a five-minute walk from...
Private Waterfront House AC & Fast Wi-Fi 30 Day
This house is all about being right on the water. A seawall provides protection from waves at high tide. A North Shore Beach House with the comforts of a nice home ideal for long term stays. Local pickle ball played right down the street. 30 Day Minimum ContractIncluded...
Spectacular Views 1 BR / 1 BA condo in Poipu
A lovely condo overlooking the blue Pacific. Fully equipped and furnished by the owners with much attention to detail. The fully equipped kitchen is both lovely and very convenient for preparing meals and snacks. You will want to visit the local Sunshine Markets for...
TCNC # 1161 All Cedar Home - Breathtaking Hanalei Bay and Mountain Views
TVNC # 1161 Waterfall laced mountains and Hanalei Bay views through a tropical prism. These will be your first impressions and lasting memories of this welcoming home. The Hanalei Vista House is an all cedar home built 15 feet off the ground to enhance the spectacular...
Naia Hale, Spacious A/C home for a relaxing visit
Spacious A/C two-story home, perfect for families and friends to spend quality time together. Have a wonderful family reunion here, come during the holidays for a relaxing visit with loved ones, or celebrate a special occasion at this elegant home. You will create...
Pacific Ocean views & newly renovated kitchen
For the same price as a hotel room (i.e. 1 bedroom), you get a home that fits 6 people with beautiful scenic ocean views & a newly renovated kitchen! This bright & airy 3 bedroom, 2 bath home features a large outdoor deck that fits the entire family overlooking the...
Weneki's Island Paradise; Oceanfront complex, Updated, Wi-Fi, Unit 103
Weneki's Island Paradise is an oceanfront complex, ground floor condo with a garden/pool view and just steps from access to the ocean. Located in Honokowai, just 5 minutes from Lahaina. It is a 1 bedroom without A/C, fully furnished with a Cal-King bed, 1 bath with...
🏖️Spacious Property! | Tranquil Location | Concierge Included | vrKCV
vrKCV - Mauna Lani Islands M3, Professionally Managed by Kona Coast VacationsWelcome to Mauna Lani Islands M3—your home away from home on Hawaii's stunning Kohala Coast.Located within the prestigious Mauna Lani Resort and Golf Course, this beautifully appointed...
Pali Ke Kua #110 Paradise! Panoramic Ocean and Bali Hai Views!
This beautiful ground floor condo has undergone a COMPLETE REMODEL! The beautiful remodel features Quartzite counters. All new cabinets, Kitchen Aid stainless steel oven and dishwasher, along with a Café refrigerator. Beautiful new tile flooring, all new furniture, and...
Breathtaking Anini home with guesthouse & steps away from beach
Ka Hale Olu at Anini Beach TVNC#4218Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Find a true escape in the luxe comfort of this exclusive property steps away from Anini Beach and...
Hibiscus Hale in the Heart of Downtown Kona
1 Bedroom, 1 Bath, kitchen, bottom level town house. We have a BBQ area and a laundry room for you as well. This is a vacation you will never forget! The house is located just minutes walking distance to all restaurants, sports bars, shops and beautiful beaches in the...
"Island Time" at Plantation Hale D4* New to our Management**Special Rate**
"Island Time", a freshly updated, ground-level condo at Plantation Hale, offering comfort, style, and space just steps from Kauai's Coconut Coastline. With two full size beds in the bedroom and a full size sofa sleeper, this unit is perfect for families or friend groups...
Car Available! 180 degree Ocean Front Unobstructed View. Sleeps 8
OCEAN VIEWS! OCEAN frontage FAMILY GETAWAY!4 bedroom/4 full baths SLEEPS 8Live the true Hawaiian experience of peace, beauty and relaxation. Sleep with the gentle sound of the ocean and cool breeze. This ocean bluff condo offers it all! Why go to Kauai and not stay on...
Beautiful 1BR, Steps to Waikiki Beach + Parking
Aloha from Midway Vacations! Our team of local hospitality experts is dedicated to turning your Hawaiian getaway into a reality. When you stay at one of our properties, you can count on a professionally cleaned and meticulously maintained experience. We're even...
150-3 Superior Oceanfront Gold Coast Location.
This beautifully appointed 3-bedroom, 2-bath oceanfront unit on Puamana’s “Gold Coast” remains a peaceful retreat amidst the recovery efforts following the Lahaina fire. Located in a tropical oasis at the south end of Lahaina, this luxurious townhome offers the...
Papaikou Escape < 3 Mi to Botanical Garden!
Bask in the paradise of the Big Island at this gorgeous Papaikou home! This 3-bedroom, 2-bath vacation rental features an updated interior, a spacious kitchen, and a location in proximity to captivating beaches and parks. Grab those surfboards and ride the waves of...
Quiet Condo on the Kona Country Club Golf Course
This spacious 1,200 SF 2-BR 2-Bath condo is in a quiet and relaxing spot at the south end of Ali'i Drive. Adjacent to the 8th teebox of the Kona Country Club, it's a beautiful setting whether you're a golfer or not. It sleeps 4 Adults max, and up to 6 total including...
Hidden Island Getaway
Hidden gem awaits your arrival. Newly renovated condo just minutes from one of Oahu’s many beautiful beaches, Makaha Beach. A welcoming family retreat 2 bedroom, 2 full bath, AC and full kitchen facility. Spacious living and dining providing ample space to plan your...
Turtle Bay East 1 Bedroom with Loft SLEEPS 4-6
Turtle Bay Retreat with Loft | Sleeps 4–6 | Golf Course ViewsNewly refreshed and now under new management! Enjoy laid-back island living in this spacious and clean 1-bedroom + loft unit, ideally located on the stunning North Shore of Oʻahu. Nestled beside the Arnold...
Waterfront Home near Beach. Peaceful Community w/ Swimming Pool and Boat Dock
Experience Oahu like a Kama'aina (local) in this 3 bedroom, 2 1/2 bath waterfront home. Safe community. Views from every room. Private lanai, BBQ grill, community pool, and boat dock. Walk to dining, shopping, bars, farmers market, hiking, beaches. 5 minutes drive to...
KKSR#197 Direct Oceanfront Air Conditioned Townhome, Extended Lanai & Yard
Welcome to this spectacular very popular oceanfront townhome in the heart of historic Keauhou! This 2-bed, 2-bath townhome offers the perfect blend of privacy and convenience sleeping a maximum of 4 guests.Townhome#197 is very unique, you'll notice an extended lanai,...
Spacious Townhome at Mauna Lani Resort - Close to Beach!
This newly renovated 2-bedroom condo at the Mauna Lani Resort is now available for your next vacation. This condominium/townhome is bright and airy and spans two floors with large windows to allow in the natural light. This popular floor plan features a second floor...
Lovely, spacious private estate, 300 ft to Sunset Beach TA#083767910401
30 DAY RENTAL*****A beautiful, peaceful, private north shore estate, 300 ft from sunset beach. The main house has 4 bedrooms and 4 bathrooms and sleeps 8 in beds. You may rent the cottage for an additional 2 people-check availability-it's called the plantation cottage;...
Kihei Kai Nani - 1BR Unit, Just Steps Away From Kamaole Beach!
This 1BR/1BR, 2nd floor corner/end unit features a beautiful garden view and a remodeled tropical interior. The extra windows in the living room and bedroom create openness, ventilation and light. The trade winds and the peaceful garden setting make it one of the best...
Luxury condo next to Disney Aulani Resort and Marriott's KoOlina Beach Club
Beach front condo on lagoon #2 at Ko Olina shoreline. Only steps away to the white sandy beach where you can explore Hawaii vacation. Very convenient for eat-out, golfing, luau show and shopping. The unit is large enough for 3 couple's and even with kids. The oversized...
⛱ Ocean Escape🌴 Your Perfect Spot! Ocean View, Upscale, Clean, Cozy, Prkg, WiFi
Welcome, 'E Komo Mai'CALENDAR IS ALWAYS CURRENT... Please check the availability and if it is full check out our other unit 'Mountain Retreat' VRBO listing https://www.vrbo.com/382565haAloha Hideaway offers a high quality unit at a reasonable price. The Views are...
Kihei Surfside #508: Gorgeous Oceanfront Escape with Mesmerizing Views
Kihei Surfside #508 – Oceanfront Escape with Split-Duct AC and Breathtaking ViewsWelcome to Kihei Surfside #508, a beautifully situated 1-bedroom, 1-bathroom oceanfront condo offering unobstructed views of Maui’s stunning coastline. Perfect for two guests, this...
Maui Family Owned/Managed - Keawakapu Beauty
A mere four minute walk from the lavish Keawakapu beaches will find you in the serenity of our peaceful condominium. Our quiet first floor unit has a partial ocean view where guests can enjoy the vibrant colors of a Maui sunset at the closing of the day on the patio....
Oceanview #202 at Hana Kai Maui - Lofted Studio Upper Floor, Panoramic View!
"Alau” – Unit 202 – is an upper-floor, lofted, ocean-view studio located in Hana Kai’s Mauka Building. The unit accommodates up to 4 guests with 1 queen bed on the main floor and another queen bed in the loft. *Note* SLEEPING IN THE LOFT JUNE THROUGH OCTOBER OS...
Napili Shores E-243 - Upgraded, steps to ocean and pools. Napili Bay - ideal location for vacation
E Komo Mai - Welcome to Napili! Attention to detail in this One Bedroom / One Bath Fully Renovated Condominium with air conditioning. Napili Shores Resort is adjacent to the gorgeous sandy beach of Napili Bay. Not only are the accommodations ideal, you are just steps...
Kihei Beach #404- Serenity by the Shoren
Kihei Beach #404 – One-Bedroom Beachfront Condo with Two BathroomsWelcome to Kihei Beach #404, a one-bedroom, two-bathroom beachfront condo offering panoramic views of the Pacific Ocean and Maui’s neighboring islands. Located in a six-story beachfront property with...