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.
Kaimana Breeze by Gather: Luxe Oceanfront Condo w/ Beach & Fireworks Views
Property is currently for sale. The property manager will contact you to make arrangements to schedule showings at a convenient time. This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies...
Sunset Hale: Spectacular Oceanview Home w/Private Pool & Spa, AC & Lanai
Sunset Hale by Gather | Private Kona Retreat w/ Ocean Views, Pool & Lanai – 30-Night MinimumSunset Hale welcomes you to elevated island living on the sunny slopes above Kailua-Kona, where distant Pacific blues, fragrant palms, and a private stone lap pool create an...
3 Story Ocean Luxury House - Sleeps 16! Whole House - steps to the Beach-Shore!
Welcome to Hale Mauna & Moana! (House of Mountain & Ocean) This 3 Story house is steps to beach-shore access. Listen to the sounds of the ocean and enjoy ocean views from the second and third-floor rooms and lanais! Boasting over 4,000 finished square feet. Living in...
Charming 3br Cottage w AC, Ocean Views
New Listing! Welcome to Kukuiula Vacation Home #2, a charming ocean view beach cottage located in the heart of Poipu's desirable Kukuiula neighborhood. This single-story plantation-style home beautifully combines vintage Hawaiian charm with modern luxury, offering a...
Oceanfront Condo & Pool, Beautiful views & Sunsets
***Professionally Cleaned Condo, No-Contact Check-In/Check Out*** Welcome to Hale Hui Kai 309! This beautiful condo is located within a beach-bungalow style oceanfront Complex, situated on the long span of golden sand that is Keawakapu Beach in Kihei. This 2 bedroom/2...
On Wailea Blue Golf Course ⛳️with Ocean View. 🌊
Hawaii GE & TA Tax ID # G/T 006-824-3456-01 Taxes on total amount is 17.42%. Not included in the vrbo quote. Required is a signed rental agreement between guest and owner.This rental agreement is in addition to the deposit. After you initial and sign the agreement, it...
MAKAI SUNSETS, Waikoloa Vista A202, LUXURY CONDO ⭐️⭐️⭐️⭐️⭐️ 58+ 5 STAR REVIEWS
A LUXURIOUS VIEW CONDO CLOSE THE THE BEACH AT VISTA WAIKOLOA - THE ENTIRE CONDO HAS BEEN COMPLETELY RENOVATED AND UP TO DATE! THIS 2ND FLOOR CONDO IS IN ONE OF THE BEST LOCATIONS ON THE ISLAND! WALK 8 MINUTES TO A BEAUTIFUL WHITE SAND BEACH! OVER 1400 SQ. FT. AND A WRAP...
SPACIOUS LUXURY - OWNER DIRECT - OCEAN peek-a-VIEW
Aloha! Welcome to our Maui paradise and your personal getaway to relax and regenerate. Whether this is your first trip to the Valley Isle or you’re a regular visitor, thank you for giving us the opportunity to host your special vacation. Bougainvillea-109 is one of...
Beautiful 1 bedroom/2 bath condo centrally located
Enjoy the lush beauty of Maui from this single level one bedroom, two bathroom condo located at Kamaole Sands in Kihei. Take a swim at the resort pool or at Kamaole Beach Park just across the street!At Kamaole Sands 8-203, you can relax on your beautiful lanai while...
Koa Lagoon- Beachfront - Spectacular Location with Incredible Views
The top floor ( 6th floor) Corner unit makes this a prime location! A beachfront location with a panoramic views of the gorgeous Pacific Ocean. This property is upgraded and updated with an open floor plan and two bedrooms and two bathrooms. The decor is tasteful and...
Ocean Front, Edge Of Cliff - Feel & See Every Crashing Wave From All Room
Full Ocean Front On Cliffs Of North Shore!Beautiful 2 bedroom/2 bath, ocean views from every room! Lay in bed from either bedroom & watch the crashing waves roll into the cliffs directly below unit! Both beds in each bedroom are Westin Heavenly beds!! Upgraded condo,...
Beachfront / Corner / Renovated / 2nd floor condo unit: F-204
Literally sitting at the waters edge, this elegantly furnished and tastefully designed ocean front condo is so close to the shore you almost feel like you can reach out and touch the water. It has an ocean view from every room except the guest bedroom which overlooks...
Kaanapali Alii | 241
Welcome to Kaanapali Alii 241! This fourth floor ocean view residence showcases the beauty of Ka'anapali Beach. Visit during whale season for a glimpse of humpbacks breaching, enjoy the epic Maui sunsets with your favorite beverage, or simply relax and appreciate the...
MK- D106: Convenient 1BR Condo, Lush Tropical Views
Embrace island living in this conveniently located, ground floor 1-bedroom, 2-bathroom condo at Maui Kamaole D106. The spacious open-concept layout features bedroom with a plush King bed with en-suite bath and a sleeper sofa for added sleeping flexibility. Enjoy your...
Unique self sufficient ocean view Eco Village in Hawaii 15 minutes from Hilo
Welcome to the Hawaiian Wildlife Eco Village, which is part of the responsible tourism effort to take care of the Aina (Mother Nature in Hawaiian).We offer an individual detached self contained bedroom (hexagon) with full bathroom and a kitchenette. To start your day at...
Escape to your private oasis perched on a cliff with a jungle view
Private island retreat with an awesome jungle view. Situated in an upscale Hilo neighborhood. Close to downtown, delicious restraunts, and a fun farmers market. This unit is a completely separate guest room that has a private entrance and private bathroom. Plus a...
Islander on the Beach ONE-BEDROOM unit #308, Top floor, incredible Ocean Views
NO RESORT FEE, FREE WIFI in the condo and FREE DEDICATED PARKING.Unique Top floor One-Bedroom unit #308 is one of the only two truly one-bedroom units available in the Islander on the Beach resort. It features a separate bedroom with a California King bed; living room...
Hale Nani: New Poipu Villa - Pool / Spa + Ocean Views
Breathtaking, sensational, divine. It’s impossible to overstate the appeal of this exceptional villa, with its spacious, elegantly appointed rooms and gorgeous grounds set against a dazzling backdrop of palm-fringed golf course, dramatic mountains, glittering ocean,...
Ocean view house, short walk to beach, lots of extras!
10 out of 10, Traveler Award winner for 2024. Hanalei Bay Villa 26 is one of our most popular Kauai vacation rentals with its great views, short walk to beach, and updated interior. Bali Hai sunset views are just steps away. This luxurious 2br/2ba home at Hanalei Bay...
PURE ELEGANCE*OCEANVIEW Renovated Condo in WAILEA
For travelers seeking luxury and an escape from life in the resort town of Wailea, this complex is one of the most exclusive sanctuaries. The newly renovated 1536 square foot condo is a spectacular beachfront vacation rental with panoramic ocean views and extensive...
Alii Villas#303 Fully Remodeled Top Floor unit with Ocean Views
Alii Villas 303 – Top Floor Remodeled Retreat with Ocean ViewsStep inside to find a bright, open-concept living area with updated vinyl plank flooring, tropical furnishings, and a spacious private lanai offering partial ocean views—perfect for guests to enjoy...
*Ocean View * Newly Remodeled *A/C * Beach Access
Stylishly remodeled, comfortable unit with split system a/c and incredible ocean view from the private lanai, kitchen, and master bedroom.Each bedroom features a king bed, private bathroom w/walk-in shower, Toto toilet, and custom vanity. Designer Poggenpohl kitchen...
Kailua-Kona Oceanfront Home
Welcome to our exceptional oceanfront property, a luxurious home in one of Kona's most exclusive neighborhoods off Kailua-Kona’s scenic Ali’i Drive. With stunning views of Holualoa Bay and breathtaking ocean sunsets, this architectural marvel seamlessly blends...
Exquisite Renovated Beachfront Haven - Experience Sugar Beach #329
Welcome to Sugar Beach Resort #329– Exquisite Renovated Beachfront HavenExperience the serene beauty of North Kihei at Sugar Beach Resort, a picturesque beachfront condominium resort offering breathtaking Pacific Ocean views. Two six-story buildings, equipped with...
Maui Resort Rentals: Honua Kai Konea 416 - 4th Floor 1BR w/ Mountain Views
Konea 416 is a luxurious one bedroom mountain view suite that enjoys expansive vistas of the West Maui Mountains. The suite is ideally suited to take advantage of some of the most beautiful sunrises anywhere. Coupled with frequent afternoon rainbows, you will cherish...
Westin Kaanapali Oceanview - Christmas & New Years Weeks - Studio
We own a 2-bedroom unit that is available as a 2-bedroom, 1-bedroom, or studio. This listing is for the studio unit.While most guests do not know which unit they will be assigned to until their arrival, this is a fixed unit, 7569. This unit is located on the 5th of 6...
Tropical Beach Vacation Home
Enjoy the beach life from this renovated and stylishly furnished apartment right on world famous Makaha Beach. Stroll on the beach. Swim with turtles. Snorkel with colorful reef fishes. Surf or just watch the surfers.Registration number840010050035, 304,...
Mauna Lani Islands Townhouse - Private location - Walk to Beach and Shops!
Welcome to Paradise! We hope to host your stay!B2 is located within the Mauna Lani Resort at The Islands at a private, gated community situated along the famed fairways of Mauna Lani golf course. Handsome townhomes set within gardens of flowering plumeria, hibiscus and...
Stay in our Private Recently Updated Home in The Villages-Closest to The Shops!
OUR HOME IS CLOSEST TO THE SHOPS YET GUESTS LOVE THE SPACIOUS GROUNDS AND PRIVACY OF OUR UNIT.We continue to update and refresh our home to ensure it's the optimal space for your stay in paradise including:*All new comfortable beds *Brand new quartzite kitchen...
Ali'i Kai 1-202 · Beautiful Mountain View Condo in Princeville
Recently remodeled 2-bedroom, 2 bath condo close to many amazing beaches. This unit features great mountain views and you can even peek at the ocean from the dining area to check out the swell. Close to restaurants, spas, shops, golf, and tennis this is the perfect...
KBM Resorts | FREE CAR | Mahana | Oceanfront | Gorgeous 2-Bedroom Condo! MAH-301
Stunning Oceanfront, 2-Bedroom Villa, Direct Ocean Views, Includes Rental Car!*Special Offer - Book any KBM rental Home in Hawaii for 6 nights or more with an arrival date between Jan 1 - Dec 31, 2025 & receive a complimentary 4-door rental car from Hertz, Alamo, Avis,...
Wailea Beach Villas | PH502
Wailea Beach Villas Penthouse 502 boasts a panoramic ocean vista, ideal for whale watching in the winter, and with spectacular sunset views all year long. This top floor penthouse has been exquisitely redecorated with an elegant, casual décor.Your private elevator...
Professional Design: Ocean View: Private Apartment
Summary:Designed by Twin Islands Interior Design Group - Escape to Big Island and indulge in the tropical paradise of Hawaii with this charming 1 bedroom, 1 bathroom Airbnb property. Enjoy an ocean view from your breezy porch and sleep peacefully in a comfortable...
❤️PiH❤️SPARKLING WATERS ★ Hilton Passes ★ Large Pool & Waterfall Spa ★
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to the newest elegant home, Sparkling Waters, in our Hawaiian Luxury Collection.Sparkling Waters is a wonderful new large single level 4 bedroom, 3 bathroom home. This home has one of our largest private heated...
Napili 1st-level serene and peaceful retreat
Welcome to Napili Shores E135, a stunning ground-level 1 bedroom 1 bathroom condo nestled in the heart of Napili featuring a garden view and split AC system. This condo sleeps up to 4 guests. This resort does not have elevators. The living room is enhanced by an...
Puu Poa Ocean Bluff Condo, Incredible Views, Walk to Beaches
Are you looking for the absolute perfect condo for your once in a lifetime vacation to Kauai? Do you want breath taking views from almost every room? Do you want to be within walking distance to multiple beaches? How about be close to shops and dining? Do you want...
Coconut Villa Entire home in KoolinanWalking distance to the shops and beaches
Enjoy your morning coffee or evening cocktails out on our lush tropical lanai with the tranquil backdrop of the Ko Olina golf course. Take in the stunning sunsets from this perfect vantage point.Our villa is located in an ideal location; everything is within walking...
Kuhio Shores 217 Superior Air Conditioned Condo at Kuhio Shores
New mini split Air Conditioning system just installed to make your Kuhio Shores 217 cooling experience perfect. Open windows, trade winds, fans to hear the soothing sounds of the ocean. And now if none of the above works you have use of a quiet, efficient air...
Private and Quiet Luxury Beach House 5 minute walk to beach TVNV#5151
Live like a local in this professionally designed two bedroom, two bath retreat, offering the perfect blend of luxury and laid back Hawaiian charm. The area is known for its slowed down pace and ocean-centric lifestyle to escape the hustle and bustle of city life.The...
Big 3BR / 4BA (3056sq ft) Kona Home with Pool/Jacuzzi, OceanView (Sleeps 16 max)
BEFORE BOOKING, PLEASE THOROUGHLY READ ALL ITEMS LISTED BELOW ...Three bedroom HOSTED property (Main House; 3056 sq ft / 284 sq m) sitting on a single level with a panoramic view of the ocean. We are fully Hawaii County bill HB 108 COMPLIANT; our General Excise Tax...
KBV 35G2 Best Rate LUXE OceanFront Villa w Oceanview | Lanai | AC
Welcome to our spacious one-bedroom, one-bathroom condo nestled along the coast in the luxurious Kapalua Bay Villas. This oceanfront location offers breathtaking views of the Pacific, inviting you to immerse yourself in the beauty of West Maui. Situated on the ground...
Kaanapali Alii -11th Floor - Ocean & Mountain View
Spectacular Ocean and West Maui Mountain views can be enjoyed from this luxurious 11th floor newly remodeled condominium. This family owned 2-bedroom vacation home offers vacation privacy in one of the most desired upscale resort locations in Hawaii. Kaanapali Alii is...
Ko Olina Beach Villas B301: Serene Beachfront Luxury w/ Pool Views
Welcome to the captivating Ko Olina Beach Villas B301 by Gather, a luxurious three-bedroom, three-bathroom beachfront vacation rental with unbeatable views and space for up to eight guests. This third floor unit, adorned with direct ocean and poolside views, provides a...
2Bd/2Ba Condo at Lagoon Tower Hilton Hawaiian Village Sleeps 6
Nestled within the renowned Hilton Hawaiian Village, this spacious 1,025 square foot, two-bedroom, two bath condo offers the ideal retreat for families seeking relaxation and adventure.Step into the expansive living room, where ample seating invites you to unwind after...
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...
Kaanapali Alii | 255
This two-bedroom, two-bath residence with an open floorplan offers sweeping ocean views and features a warm and inviting contemporary design. This spacious vacation rental can comfortably accommodate up to six guests.The primary bedroom has a king bed, a flat-screen...
COMPLETE REMODEL | Central AC | WIFI | vrKCV
vrKCV - White Sands Village 220, Professionally Managed by Kona Coast VacationsExperience Island Living at Its BestWelcome to your perfect Hawaiian retreat! This beautifully appointed 2-bedroom, 2-bathroom condo is located directly across from White Sands Beach—also...
Trendy Hawaiian Monarch Studio | Ocean View | Pool
Relax in this beautifully renovated, modern studio at the Hawaiian Monarch building. Located at the beginning of Waikiki, this unit offers ac, smart tv, wifi and cable. It is a short walk from Fort DeRussy Beach Park, Hilton Hawaiian Village, Ala Wai Canal and more. The...
MRR Presents Kaanapali Ali'i 465 - Renovated 2BR Corner Suite w/ Gorgeous West Maui Mountain Views!
Luxuriously renovated and meticulously maintained, suite 465 boasts epic views of the majestic West Maui Mountains and the Kaanapali Royal Golf Course from its 6th-floor vantage point. Its stunning interior has been beautifully updated with modern tile flooring, custom...
North Shore Condo Rental at Kuilima
Relax to swaying palms, stunning seas and a tropical breeze! You deserve it! Step right out the lanai onto fairway one of the Fazio golf course. Swaying Palms is an end unit, situated within the complex to provide lots of natural light, privacy, and a more spacious...