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.
ULTRA LUXURY OCEANFRONT 2Bd/ 2Ba Fully Renovated!
This sixth floor, oceanfront, luxury unit opens up onto your very own private patio with stunning, FULL ocean views. Complete with lounge chairs and outdoor seating, just steps from the turquoise waters of the Pacific Ocean, your paradise awaits.Relax in your king sized...
Honua Kai H825 Luxurious Kaanapali Beach 3BD Condo with Beautiful Ocean Views
The Stice Team — Powered by Gather Vacations. Maui Born and Raised Professionals. Your Local Experts in Crafting Unforgettable Stays.Welcome to Honua Kai Hokulani 825, an eighth-floor 3-bedroom, 3-bath penthouse style residence that sleeps up to 10 guests and frames...
New! Hale Aloha with Ocean Views - steps to beach
This beautiful, airy open floor plan home has white water ocean views on one side and a lush jungle on the other making it the perfect location for an epic family vacation. If you’re looking to escape the crowds and enjoy your own piece of paradise overlooking one of...
Villa On The Ocean - One Of Largest Condos On Alii Drive. Directly Oceanfront.
This is an absolute Oceanfront Villa. Watch the dolphins while you have breakfast.This wonderful Villa offers oceanfront amenities including the fragrance of the ocean spray and warm tropical breezes truly distinctive to Hawaii!Welcome to this two bedroom, two and...
Stunning, spacious home with VIP access to private Mauna Lani Beach Club!
AMAZING PROPERTY!! VERY PRIVATE & VERY SPACIOUS HOME, INCLUDES VIP PASS TO PRIVATE BEACH CLUB.This Phase One Maile plan with its direct west facing view and end of cul-de-sac location is a gem. Immaculately maintained with many developer and custom upgrades. The custom...
Discovery Bay-Resolution Ocean View Condo
Oceanview 1 Bedroom, 1 Bathroom Sleeps Up to 4 Condo DescriptionLooking to travel to the island for business or extended vacation? This large newly renovated 1 bedroom unit has everything you need that will make you feel at home while reminding you that you are on a...
Private1BR @Waikiki Max 6! near Ala Moana Center!
【Basic Info】This is a 1BR room in Waikiki!!You can stay with you friends, partner, family. You can spend your time with a reasonable price.This condominium is located west area in Waikiki.You can walk to Hilton village lagoon and beach and Kahanamoku beach in...
Pono Pearl Villas | Beach Access + AC In Every Room
Just a short walk from the beach, this spacious home is ideal for family reunions, retreats, or groups looking for space, privacy, and easy shoreline access. This listing represents one of several similarly appointed homes in the Windward area. All units share the same...
5 Star Luxury Beach Villa ~ Mountain, lake and golf views. BBQ on the lanai!
Indulge In Quality And Comfort In Our Tropical Condo For Your Island Get Away, Perfect For Unwinding After A Day Of Exploring. We Are Directly Across From One Of Two Lagoon Style Pools And BBQ Areas And Right On The 8th Fairway Of The Beautiful Waikoloa Beach Golf...
Wailea Beach Villas | PH410
Wailea Beach Villas PH410 is a fourth floor penthouse suite that overlooks the central swimming pool with spectacular views of the Pacific Ocean and Wailea Beach, along with views of Kaho’olawe, Molokini and Lana'i.From your private elevator landing, the suite opens...
Paia beach house with huge ocean view and only one minute walk to Kuau beach
Maui County Rental permit - STPH 2018/0003 (this is a legal, permitted Maui vacation rental)TA-066-523-9552-02 / GE-066-523-9552-02 TMK-260090240001It's a Beach House! A place to relax, unwind, listen to the breeze through the palm trees, absorb the ocean views. Start...
Steps to Beach. Stunning View. Lovely 2BR Condo near Wailea
Enjoy paradise at one of Maui's premier beaches. Our air-conditioned retreat features a clean and bright interior, offering stunning views from the main living area. Enjoy cooking in a well-equipped kitchen and relax with beach chairs, umbrellas, and boogie boards...
Panoramic Ocean View B&B on Kohala Coast-Holiday/Winter/Summer Rate 285.
This lovely private Big Island bed and breakfast, just four miles from Hawaii's most beautiful white-sand beaches, continues to be one of the most sought-after locations. Free parking on property, includes daily breakfast and AC. The consistently sunny skies,...
Monthly Discovery Bay 2810 Studio Ocean / Sunset / Marina Views King Bed, Sofa Bed
PANORAMIC Ocean VIEWS, 5 Minute Walk to Beach, High Floor, Remodeled, Furnished and Fully Appointed. No smoking room. Parking, Pool, Utilities, WIFI, BBQ, Gym, Security, Washer/Dryer Included. 1 Month Minimum / contact Agent.Sweeping Ocean Views from High Rise, Tasteful...
Waipouli Beach Resort Courtyard View 2 BD 3 BA
This well-appointed two-bedroom condo overlooks a beautifully landscaped courtyard, creating a soothing atmosphere. Perfect for a Kauai getaway, it offers plenty of space to unwind and enjoy island life.Courtyard View 2 Bedroom 3 Bathroom• Kitchen features granite...
Hale Alaula, Elegant Hawaiian Home at exclusive Sunset Drive
Hale Alaula, Princeville Welcome to Hale Alaula, a stunning high-end plantation style home located on golf course greens in Sunset Drive, Princeville. Alaula, meaning "Sunset Glow" in Hawaiian, is just that. Hale Alaula is situated in the exclusive Sunset Drive...
WOW!! - WHALER's BEST STUDIO - Posh Remodel-10th Fl.- PANORAMIC Ocean Views!!!!
Unit 1064 is the ABSOLUTE nicest studio at The Whaler !!! Unit 1064 has been completely remodeled and professionally decorated just a few years ago... Unit 1064 has EXPANSIVE & PANORAMIC views of the OCEAN, the island of Molokai, the Kaanapali beach Boardwalk, Blackrock...
Spacious Beachfront 1 BR + Loft (sleeps up to 5)
When the developer built this 18 unit condominium in 1973, he saved this unit for his family. One look will tell you why. It is the largest unit in the complex and is wonderfully spacious and open. Decorated in seaside colors, our unit provides a roomy, calm...
Kehena Black Sand Beach House: 2 BR Eco-Retreat with Ocean View & Swim Spa
The ultimate eco-retreat. Timeless design for indoor-outdoor relaxation, dining and sleeping. Experience ocean views and crashing waves from wide-open bifold doors. Walk nextdoor to Kehena black sand beach, or drive the Red Road to Hawaii's only hot springs at Pohoiki....
Aloha Condos, Na Hale O Keauhou, Townhome L-6, Ocean View, AC
Welcome to Aloha!! Listen to the crashing surf from gorgeous Na Hale O Keauhou L-6. Spacious 2-story luxury air-conditioned Townhome with Panoramic Ocean Views. This wonderful remodeled and upgraded unit features 3 Bedrooms, 3 Baths, well-appointed kitchen and full...
Oceanfront Puu Poa Condo 311 AC thruout best Bali Hai View & Sunsets Princeville
Our Oceanfront, Mountain and Sunset view is THE most famous on all of Kaua'i!!!Newly renovated with A/C throughout unit. 4 split Mitsubishi units: one in each bedroom , one in kitchen/dining area and one in living room/atrium area.If you are looking for the most...
Ohana Retreat - The Real Hawaiian Experience
Experience the Beauty of Hawaii at Ohana RetreatOhana Retreat is the ultimate getaway for large families looking to embrace the breathtaking beauty of Hawaii. Our spacious island-style home features eight luxurious bedroom suites, each complete with a private bath, wet...
Experience Tropical Tranquility: Luxury Studio Home in Hilo!
Experience convenient and comfortable living staying at our studio in our newly built duplex home. Located centrally in Hilo. You will be just 3 miles from Hilo airport, Liliuokalani Park and Garden, Carlsmith Beach Park, and many other popular attractions and...
Wailea Elua Village | 804
The Wailea Elua 804 vacation rental is a true gem nestled within the picturesque Wailea resort community on the island of Maui. From the moment you step inside this stunning, 1,700-square-foot condo, you're enveloped in a sense of luxury and tranquility. The...
Wailea Grand Champions | 73
Wailea Grand Champions Villa 73 is a recently renovated vacation rental that offers a perfect blend of luxury, comfort, and stunning views in the heart of Wailea, Maui. As you enter the villa, you're greeted by a bright and spacious great room, ideal for relaxation...
Hololani Resort #A104 - Vacation West Maui - Oceanfront at Kahana
Hololani Resort A104 is a stunning resort condominium featuring spacious and elegant designs, offering panoramic views of the Pacific Ocean and the nearby islands of Molokai and Lanai. The condo comes equipped with all the modern amenities you need for a comfortable and...
A Beautiful View Beach House at Kahalu'u Bay! Snorkeling & Surfing ~ Steps Away!
This is a very special property within a treasure of history, located across the street from Kahalu'u Bay & Beach Park on the mauka side of Ali'i Drive. Known for world class snorkeling with beautiful coral reefs, bright fish, sea turtles & a super fun ~ surf break....
FREE Auberge/Mauna Lani Fitness Club Access @ this nearby Palm Villas Condo
E KOMO MAI TO THE PALM VILLASThis 2BR/2Bath ground-floor Palm Villas unit is private and secluded, surrounded by 6 acres of lush landscaping. As our guest you have full access to the Auberge/Mauna Lani Fitness Center, located across the street. Play tennis and...
180 Degree Ocean View in Wailea! WE204
Welcome to Wailea Ekolu Village, unit 204! This is a top floor, FRONT LINE, two bed, two bath condo with a 180 degree ocean view! Overlooking the Wailea Blue Golf Course course, this unit boasts dramatic ocean views! The interior has been extensively remodeled and...
Lavish Premier Beachfront Townhouse W/ Unrivaled Views Wailea Elua 1305
Wailea Elua #1305 – Premier Oceanfront Townhouse for Elevated Maui LivingWelcome to Wailea Elua #1305, a luxury 3-bedroom, 3-bathroom oceanfront townhouse designed for travelers seeking the finest in comfort, privacy, and sophistication. Meticulously remodeled and...
1 Block to Heart of Hilo: Fully Renovated Home
Family Friendly | At-Home Laundry | 1 Block to Shops, Eateries & OceanWelcome to this 2-bedroom, 1-bath townhome boasting a walkable location near Historic Hilo. The vacation rental is ideal for tourists or business travelers, allowing anyone to easily access popular...
Hale Waima Lani - Luxury Oceanfront Estate in Puako
Modern luxury and old Hawaii charm meet and beckon from one of the largest oceanfront lots in Puako. With 350+ feet of beachfront access and ocean views from every room, this unique and meticulously maintained home is a vacation dream—the main hale with a luxury...
Walk to Kalapaki Beach: Condo w/ Ocean & Mtn View!
Banyan Harbor | Saltwater Pool Access | Near Shopping & DiningSay hello to a prime location with 24-hour security and an easy drive to the North and South shores at this Lihue vacation rental. This single-level unit features 2 bedrooms, each with a private full...
Ocean Front Beach House located only steps from the water!
E Komo Mai!At Nalu Hale (surf house) we welcome you to emerse yourself in surf culture. Wake up to the waves crashing on the shore of Kahalu'u Bay and never miss a sunset. Whether you like to surf, sup or snorkel, Nalu Hale puts you just steps from your next ocean...
Stunning Beachfront - Hale Kai O Kihei 112
Welcome to your perfect escape in Kihei! This bright and beautifully updated oceanfront ground-floor one-bedroom condo is just steps away from the beach, offering breathtaking views and modern comforts. Ideal for couples or small families, this inviting retreat features...
Charming 2BR Home near Ewa Beach, Fully Equipped, Free Parking
PERFECT FOR:Family | Couples retreats | Digital nomads | Pet ownersSPACE HIGHLIGHTS:- 2BR w/ queen beds- Sleeps 4 guests- Full kitchen- Living area w/ smart TV- Private entrance- In-unit washer & dryer- High-speed WiFiUNBEATABLE LOCATION:- Walking distance → Ewa...
Fairway Villas-2 Bed/2 Bath Lots of updates! Close to golf, shopping, and ocean
Welcome to our family’s piece of paradise. We’ve been travelling to Hawaii for twenty years, and our condo is the fulfillment of a dream to call the Big Island our second home. Our goal is to provide you with that same sense of aloha.Our 2BR/2 BA condo has a king in...
PINEAPPLE HILL KAPALUA-SILVERSWORD-4 BEDROOM-4.5 BATHS-PANORAMIC OCEAN VIEWS
Nestled in the luxurious KAPALUA RESORT, this custom home is located in the prestigious gated community of Pineapple Hill. The 4-bedroom, 4.5 bath residence, encompassing over 3500 square feet, has 1 Master Suite, 3 Bedroom Suites (2nd Floor) and 2 smaller rooms that...
**Fairways Mauna Lani #1606 - Luxurious 2-Bedroom Retreat: 2 King beds, Remodele
**Fairways Mauna Lani #1606 - Luxurious 2-Bedroom Retreat: 2 King beds, Remodeled with Spa-Like Bathrooms, Steps from the Pool!**PLEASE NOTE: The swimming pool will be closed for Maintenance Mon-Fri from 8:30am-4:30pm Oct 6-27, 2025. Dates may be subject to change due...
Ko Olina Beach Villa Ocean View 3BR/3BA - B907
Penthouse Beach Tower 9th Fl (B907) - Steps from the Ocean. Escape to a Hawaiian Paradise at the Beach Villas Palekaiko on Oahu! Sleeps up to 8.The Palekiko welcomes you to paradise from the moment you walk in the door with all you need to relax and rejuvenate during...
Hualalai Palm Villa 140C
The spacious floor plan includes a downstairs primary bedroom suite with king bed and luxury spa-like bath. Just off the master is a large living room with queen sized sofa pull out that opens to the downstairs lanai, leading to the lawn and golf course. Guests enjoy...
Ground-Floor Retreat W/Ocean Views-Kiahuna 2166
Kiahuna Plantation unit 2166: This modern tropical one-bedroom ocean view unit on the ground floor is a rare find and provides the utmost comfort with cool flooring and decorative carpeting, two cooling ceiling fans, and floor-to-ceiling windows allowing for plenty of...
Maui Resort Rentals: Westin Kaanapali Ocean Resort 1 BR Oceanview Villa
1 Bedroom Ocean View Villa at the Westin Kaanapali Ocean Resort South This one bedroom, one bathroom luxury villa is nearly 900 square feet and features a large balcony set off the primary bedroom. The villa affords delightful views of the Pacific Ocean. The villa is...
Summer Special Rates! Oceanfront 4BR Puamana 9-2
Summary:4 Bedrooms • 4 Bathrooms • Sleeps 8Oceanfront | Gated Community | Private Lanai | Steps to the BeachThe Space:Welcome to Puamana 9-2 - Enjoy our introductory summer rates when you select your dates on the calendar. E Komo Mai (Welcome) to your oceanfront...
LUXURY PENTHOUSE 2 BDRM OCEANFRONT BUILDING: Just steps from the beach!
"Aloha Kai" Completely Renovated 2-bedroom (King Bed in each) Oceanfront at Menehune Shores with A/C in every room (hard to find). Many of these condos have no A/C or just one mini-split in family room.Fantastic 6th Floor Ocean Views!! Pack your suit...Aloha Kai has...
Honu Hale at Kukui'ula: Elegant Poipu Home w/ Pool, Spa & AC
Welcome to Honu Hale at Kukui'ula, where modern luxury meets the tranquil charm of old Hawaii. This stunning Poipu vacation rental offers a plantation-style main home and a separate ohana (guest house), designed to provide the ultimate in relaxation and comfort. With...
Palms at Wailea Spectacular Ocean Views with Exceptional Star Rating
Aloha and welcome to our retreat in Wailea, Maui, the heart of paradise. Your Hawaiian vacation will be nothing short of spectacular when you stay in Unit 1510, Palms of Wailea ocean view condo. There are many reasons our guests consider our luxurious, world-class...
Kaanapali Alii Resort 346
Welcome to the Kaanapali Alii Resort! This Executive condo unit is Top of the line Luxury and very fitting for the Hawaiian word " Alii" with its meaning of Royalty. It is Luxury at its Best and the condo unit is much more. When we say DIRECT Beach front ,...
Big Island Hawai'i Hali'i Kai 22A Quiet Relaxation or Family Adventure
Aloha! Hali’i Kai #22A is located in beautiful Waikoloa Beach Resort on the Kohala Coast. Our villa welcomes you with the serenity of a retreat and beautiful view from the lanai of the Coconut Grove, Kohala Mountains, Hapuna Bay and Mauna Kea. The two bedrooms are...
Direct Ocean Front, Top Floor Studio Paradise
Aloha and welcome to our tropical paradise in beautiful Kauai, Hawaii!Indulge in an extraordinary couples' getaway at our top floor ocean and beachfront studio condo in Kapa'a. Just 150 steps from our condo's front door, the beach awaits! Offering breathtaking,...