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.
🏝️SUMMER-Booking Now Beautiful Oceanview, Great Location Across the Beach🏝️
This beautifully renovated condo boasts a stunning ocean view and is situated across one of the best beaches in Kihei, Kamaole 3 Beach Park. Enjoy the daily sunset from the lanai, whale-watching from December to April while sipping coffee, cocktails, and savoring...
Stunning Ocean View 1BR Suite – Upper Floors, Hyatt Kaʻanapali
Experience breathtaking ocean views and refined island luxury in this 1-Bedroom Ocean View Suite (Upper Floor Band: Floors 5–10) at Hyatt Vacation Club at Kaʻanapali Beach, perfectly located on Maui’s world-famous Kaʻanapali Beach. This elegant villa offers the...
Maui Bay Villas by Hilton Grand Vacations Club - 1 Bedroom Penthouse Premiere
*** Sanitation/Cleaning Update ***We understand that our guests’ expectations for hotel cleaning and disinfecting have changed. That’s why we’ve taken additional measures beyond our industry-leading cleaning standards by partnering with RB, maker of Lysol &...
Royal Kahana Maui 917 Ocean View Studio
- 9th floor condo with balcony- Updated kitchen with granite counters and stainless steel appliances includes stove, oven, refrigerator, microwave, coffeemaker, toaster, coffee starter kit, blender, tea kettle and complimentary tea- Tile floors in entry, kitchen and...
Royal Kahana Maui 1008 Oceanfront 1 Bedroom
- 10th floor condo with balcony- Updated open kitchen with granite counters and stainless steel appliances includes stove, oven, refrigerator, microwave, coffeemaker, toaster, coffee starter kit, blender, tea kettle and complimentary tea- Tiled entry, dining room,...
Cozy Aloha Suite with AC in charming Kailua
Welcome to our home! We are a legal vacation rental (TA-188-004-1472-01, 90/BB-0102) hosting guests for more than 30 years. We are an environmentally-conscious family doing our share to "Live Lightly" so our natural resources are protected.**PLEASE NOTE: As of November...
Honua Kai | 2 Free Rental Cars | KBM Resorts | Extra Large Lanai | 2 Units, 3 Bedrooms | HK ML-1460
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Lani Paradise Oceanfront Cottage
Discover paradise in our 2 bedroom cottage overlooking Maui’s North Shore, featuring a pool surrounded by breathtaking oceanfront scenery.This exclusive property offers waterfront views of the sought-after surf break, Tavares Bay, with sandy beaches within a 3 minute...
North Shore Oahu | Turtle Bay - Hale Kahakai
Welcome to Hale Kahakai, located in the gated Turtle Bay community in North Shore. You're just a 5 minute walk to a beautiful white sand beach in a cove protected by a natural reef- perfect for children. Arnold Palmer Golf Course, Turtle Bay Resort, and Roy's Beach...
Direct Ocean View Condo | Lahaina Shores #313 | Beachfront Bliss
Lahaina Shores 313 – Great ocean views!Lahaina Shores is a charming boutique resort located directly on the oceanfront in the heart of historic Lahaina Town. Unit 313 is a 3rd-floor oceanfront studio offering privacy and comfort for 2 guests. Step onto the private...
Maui Eldorado C203 Peaceful Paradise Adjacent to C202
Step into your own slice of paradise at Maui Eldorado C203, a spacious one-bedroom, two-bathroom condo surrounded by tropical gardens and island serenity. Recently updated and thoughtfully appointed, this relaxing retreat offers sweeping views of the island of Lanai,...
Kanaloa at Kona Oceanfront 2 Bedroom + Loft
- Oceanfront condos with loft located on 2nd floor- Kitchen features stovetop, oven, refrigerator, microwave, dishwasher, coffeemaker, blender, disposal, cookware and tableware- Private balcony with wet bar- Master bedroom with 1 king bed or 1 queen bed and private...
Kaanapali Alii 132
Welcome to Kaanapali Alii 132, a luxury vacation rental that promises an unforgettable stay in Lahaina. This meticulously designed unit offers a perfect blend of modern elegance and coastal charm, making it an ideal short-term rental for families and couples seeking a...
Kaanapali Alii Unit 2105
Welcome to Kaanapali Alii Unit 2105, a luxurious vacation rental nestled in Maui's exclusive Kaanapali Alii Resort. This stunning property offers breathtaking views of the Pacific Ocean, white-sand beaches, and the meticulously maintained grounds of Kaanapali. With its...
Tropical Elegance Top Floor
Welcome to your relaxing island vacation! This stunning condo is conveniently located right on the golf course of a luxury resort community and within a few minutes of the beach. Featuring a private lanai with sweeping views and access to resort amenities, like a pool...
Awesome access to Beach 1min!Studio in Hotel&Condo
【Basic Info】This is a private studio unit in Waikiki!!You can enjoy your stay by yourself, friend or partner. The condominium is located east area in Waikiki.This area is really closed to the Diamond Head, Kapi olani Park.You can enjoy a walk while feeling the...
Royal Kahana Maui 215 Ocean View 1 Bedroom
- 2nd floor condo with balcony- Tile & Vinyl plank flooring throughout- Fully equipped kitchen with– fridge, stove/oven, microwave, cookware, tableware- Tiled bathroom with walk-in pebble shower with grab bar- Queen sofa bed in living area- Central Air Conditioning-...
9th Fl Waikiki Banyan | Parking | AC | Partial Diamond Head View
The SpaceEnjoy your Waikiki stay in this modern 9th-floor corner unit with views looking toward Diamond Head. The open layout makes it easy to relax after a day at the beach, with a queen bed in the bedroom and a pull-out sofa in the living room for added...
Napili Point | 2 Free Rental Cars | KBM Resorts | Ocean View 1-bedroom Villa At Napili Point Maui | 2 Units, 3 Bedrooms | NAP ML-1556
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Wailua Bay View 105 Oceanfront Condo
Kapaʻa is waiting for you at this lovely 1-bedroom condo. This adorable property comes equipped with all the essentials you need for a comfortable stay, including WiFi, a washing machine, and AC in the bedroom. We'll be available to answer any questions while you stay...
Makaha Vista Villa - Pool, Amazing Views
Welcome to your private Hawaiian escape on the beautiful west side of Oahu—a stunning 4-bedroom, 3.5-bath estate offering 4,000 square feet of beautifully designed living space. Set in a quiet, upscale neighborhood where homes are generously spaced for maximum...
Kapalua Bay Villa 36B4 Oceanfront 1 Bedroom
- Villa closest to Oneloa Beach- One level condo with no stairs between parking and the front door- Travertine tile floors in living room, dining room, kitchen; porcelain tile in bathroom and carpet in bedroom- Updated white kitchen with granite counters includes...
Hana Hou Hale: Poipu Oceanfront Villa and Guest House
Poipu Hana Hou Hale & Ohana is THE vacation home of your dreams. Situated in sunny Poipu, with first-class views of the sparkling Pacific, this picturesque home is equipped with everything you need for an unforgettable stay on Kauai. Enjoy uninterrupted sunrise and...
Stunning Ocean View Unit at Marriott's Ko Olina Beach Club on Oahu
Find your bliss in this luxurious space, where unequaled comfort provides an intimate refuge. There are too many amazing things about the island of Oahu to list them all but let’s just run through some highlights: world-class beaches and surfing, premier golf,...
Stylish 1BR Mountain View Suite – The Grand Islander Honolulu
Enjoy contemporary comfort in the heart of Waikiki with this 1 Bedroom Mountain View Suite at The Grand Islander, a Hilton Grand Vacations Club, located within the famed Hilton Hawaiian Village® Waikiki Beach Resort. Perfect for couples or small families, this modern...
Wailea Ekolu Village 1203 - 1 Bedroom Ocean View Condo
Wailea Ekolu Village condo #1203 is an exquisite one-bedroom, two-bathroom ocean view retreat designed for discerning travelers seeking the best of Wailea. This sanctuary offers a seamless indoor-outdoor living experience, allowing guests to enjoy breathtaking panoramic...
NEW LISTING! Offering limited time introductory rates! Luxury Remodeled Townhouse with Breathtaking Golf, Mountain & Partial Ocean Views
Property Highlights • Luxury remodeled townhouse offering sweeping golf course, mountain and partial ocean views from every window • Large lanai, ideal for whale watching and outdoor living at its very best • Close walk to three world-class beaches, including...
Ocean View 2BR Middle Floor Villa – Hyatt Kaʻanapali Beach Resort
Experience the perfect balance of elevated ocean views and relaxed island comfort in this 2-Bedroom Ocean View Villa (Middle Floor Band: Floors 5–8) at Hyatt Vacation Club at Kaʻanapali Beach. Perfect for families or two couples traveling together, this spacious...
Royal Kahana Maui 912 Oceanfront 1 Bedroom
- 11th floor condo with balcony- Vinyl plank flooring throughout- Fully equipped kitchen with– fridge, stove/oven, microwave, dishwasher, cookware, tableware- Tiled bathroom with walk-in tiled shower- 1 king bed and twin sofabed- Washer/dryer in unit- Central air...
Ocean View Bliss: 1-Bedroom Premium Villa at Westin Ka’anapali Ocean Resort
Indulge in the ultimate Hawaiian escape with a 1-Bedroom Premium Ocean View Villa at Westin Ka’anapali Ocean Resort Villas, where breathtaking Pacific vistas meet unmatched luxury and family-friendly fun. Nestled along the pristine sands of Ka’anapali Beach, this...
'Olina NEW (PKC 106) ~ 3 BR ~ Ground Floor ~ Pool
Summary:'OLINA, Puako Condo 106 is a ground floor unit that was designed with great attention to detail for a clean modern style and high quality feel throughout. The unit stays cool with two A/C units (one in the main bedroom and one for the living room kitchen) and...
Royal Kahana Maui 606 Ocean View 1 Bedroom
- 6th floor condo with balcony on the north side of the building- Updated open kitchen with granite counters includes stove, oven, refrigerator, microwave, coffeemaker, toaster, coffee starter kit, blender, tea kettle and complimentary tea- Tile flooring throughout-...
Royal Kuhio 1707 - Spacious Studio w/ Diamond Head and City Views in Waikiki
Heart of Waikiki - Royal Kuhio (17th Floor)Address: 2240 Kuhio Ave., #1707, Honolulu, HI 968151 Bed | 1 Bath | Sleeps 4Beds: 2 Full-size beds + 1 Queen sofa bedSize: 436 sq ft + 80 sq ft lanaiKitchen: Fully equipped with oven, microwave, modern appliances, cookware, and...
Mystic Mermaid Island Retreat! Entire Home
This home is not your typical VRBO, this home is designed for guests who appreciates CLEANLINESS, COMFORT, CARE, SAFETY AND QUALITY! Escape to Your Mystic Mermaid Island Retreat, your private, spacious oasis near Oʻahu’s majestic mountains! NO neighbors behind the...
Kaanapali Alii | 333
Welcome to Kaanapali Alii 333, your luxury vacation rental in the heart of Lahaina, Maui. Nestled on the third floor, this oceanfront residence offers unparalleled views of the Pacific Ocean and Kaanapali Beach, making it the perfect short-term rental for families and...
Kaanapali Alii Unit 161
Welcome to your dream Maui getaway at Kaanapali Alii Unit 161, a luxury vacation rental that offers a serene island escape with partial ocean views. This one-bedroom residence is perfect for a family-friendly short-term rental, providing a comfortable and inviting...
Charming Glamping Getaway
Unwind at this enchanting getaway. Immerse yourself in the serene sounds of nature at this exceptional retreat. Experience glamping in a picturesque garden that provides fresh, seasonal fruit. A peaceful haven for one or two guests, featuring a full-size bed, a modern...
Big Island, HI Kona Hawaiian Resort- 2 bdrm suite
About this spaceRelax in this fabulous 2 bed/2bath suite on the Big Island’s west coast, Kailua-Kona. Beautifully designed to capture the traditional Hawaiian feel, you’ll want for no modern amenity. Outdoor pools and the nearby beach are waiting for you.This...
Waterfront studio with mountain view, rooftop pool, hot tub, sauna & central AC
Honolulu Horizon Haven-30 night minimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Perched high above the bustling city of Honolulu in Waikiki, this stunning condo offers a...
Wailea Beach Villas PH508 - 3 Bedroom Ocean View Penthouse
Experience Wailea at its absolute best in Penthouse 508, a spectacular 2,893-square-foot residence that stands apart with a totally unique layout—perched at the top of the Wailea Beach Villas with sweeping ocean views, soaring ceilings, and a spacious design...
Sunset Shores - UNIT B Kauipoho
Summary:Relax with the Escape to serenity in this shared Kailua Kona space. Embrace the tranquil island ambiance and inviting interiors.With convenient beach access, this is an ideal location for a peaceful coastal getaway. Immerse yourself in the beauty of Hawaii and...
Honua Kai | 2 Free Rental Cars | KBM Resorts | Extra Large Lanai | 2 Units, 5 Bedrooms | HK ML-1913
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Views on the Kaanapali Coast!
Prepare to be completely swept away by the breathtaking beauty and boundless excitement that awaits you on the island of Maui, your best vacation yet! At the beachfront retreat of Paki Maui, the azure waters of the Pacific Ocean gently caress the golden sands just steps...
Hale O Ka La – Luxury Villa at Mauna Kea Resort
MEET THE VILLAHale 'O Ka La on the Big Island defines Hawaiian luxury. Developed by Laurance S. Rockefeller in the 1960s, Mauna Kea Resort was the Kohala Coast's first luxury destination and remains an icon of island elegance.This stunning 5,358 sq. ft. estate features...
Kamaole Nalu 506 - Ocean Front
Book with us and come to Maui to explore everything we have to offer!Stunning ocean views from the lanai of your oceanfront condo. Just steps away from beautiful Kamaole I & II beaches, a wide range of restaurants, shops and activities make this convenient location a...
Kapalua Ridge Villa 124 Gold Ocean View 1 Bedroom
- Villa is closest to Oneloa Beach- Second floor unit with 15 stairs from parking to the villa- Tile flooring in kitchen, bathroom and carpeted in living room and bedroom- Fully equipped kitchen with stainless steel appliances includes stovetop/oven, microwave, and...
Golf Discount in Village, Gorgeous Views, 2 Pools
Welcome to your peaceful island retreat overlooking Waikoloa’s golf course & ocean sunsets - perfect for couples, friends & small families:- Sleeps 4 | 2 bedrooms | 2 beds | 2 baths- Access to 2 pools, hot tubs & tennis courts- Private lanai w/ panoramic views- Fully...
Gorgeous 5 br for 12 in Kapaa - Beachfront!
Listing provided by "The Vacation Rental Experts". Contact directly for more options!The fabulous 5 bedroom, 4 bath oceanfront for 13, is made up of a 3 bedroom and 2 bedroom oceanfront townhome, just steps apart! Fabulous beachfront pool and sundeck onsite! Beautiful...
Wailea Ekolu 1608 | 1 Bedroom | Prime Wailea Location with Golf Course Views
Experience the beauty and convenience of Wailea from this tastefully appointed 1-bedroom, 2-bath condo at Wailea Ekolu 1608. Perfectly situated along the fairway of Wailea’s prestigious Blue Golf Course, this ground-level home offers comfort, privacy, and stunning...
Modern Family Beach Villa near shops and dining
Choose to spend your days on the Ko Olina Championship golf course or at the Marina; relax at one of four breathtaking sandy lagoons, pamper yourself at the award winning Four Seasons Resort and Spa; spoil the kids at Au’lani Disney Resort or explore the rich culture...