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.
M.Vista Bldg. 2-Immaculate Updated Quiet Classy- across from Charley Young Beach
Located in prime S. Kihei in highly desirable Maui Vista Bldg. #2 (Quiet, no traffic noise), up on 3rd floor (no car headlights). Directly across from famous Charley Young Beach. Condo is posh, remodeled a few yrs. ago with decorator paint, Granite counters, Rainfall...
Maalaea Kai 307 Maui Prime Oceanfront nKing Beds w/ ensuitenDedicated Workspace
Welcome to our nicely remodeled 3rd floor unit featuring gorgeous views throughout the unit of Maalaea Bay, the grand volcano Haleakala and the sparkling Kihei lights at night. The unit is tastefully decorated with the spirit of Aloha and has a large split air...
Spacious MAUI ground floor condo for 5, full AC, 2 min walk to Kamaole 3 beach
Welcome to your slice of paradise at Hale Kamaole unit 111! This spacious ground floor unit in South Maui offers the perfect blend of comfort, convenience, and island charm. Immerse yourself in the relaxed vibes of this low-density complex, boasting 2 pools, a tennis...
B209: Ocean Views from every room of this Ko Olina Beach Villa!
Beach Tower villa 209 has a spectacular view of the sunset! Its location is superior to all other units in the complex because it is truly beachfront. Beautifully decorated with high end furnishings, two very comfortable sofas and a beautiful dining area. The master...
KRV 1423 2BD Kapalua Villa w Ocean Views AC Relax
Kapalua Ridge Villas 1423 Experience Kapalua, Maui from our Spacious 2Bedroom, 3Baths, Ocean View Villa! A Tropical Retreat to Relax and Recharge FREE daily activities included with your stay value up to $1035! Complimentary admission, every day of your stay*: Lu'au,...
Awesome hi-rise ocean view, On-Beach, Lanai, Salt Pool, Sauna, Spa, Gym, Parking
💖 A Romantic Retreat for TwoWelcome to your dream couples’ getaway in the heart of Waikiki! Perched high inside the iconic Foster Tower, directly across from Waikiki Beach, our ocean‑front condo delivers sweeping Pacific views, modern comforts, and the perfect...
POOL & OCEAN VIEW | LUXURY | Snorkel With Turtles!
Summary:We invite you to relax in the private and peaceful Honokeana Cove with breathtaking views of the Pacific Ocean. You will be very impressed with this direct oceanfront, luxury, vaulted-ceiling townhome with gorgeous views of the ocean and the island of Molokai...
Sky Ala Moana 2908: 2 BR, 2 BA Condominium in Honolulu, Sleeps 4
This stunning 2BR/2BA condo is located in the brand-new Sky Ala Moana building, offering breathtaking ocean views and luxurious amenities. The unit features a spacious living room, a fully equipped kitchen with modern appliances, and two elegant bedrooms with...
Beautiful Ocean-view Kailua-Kona Condo! 5 min walk to the beach!
**Please note, effective Jan 1st. 2026, Hawaii's Transient Accommodations Tax will increase from 10.25% to 11% for all stays with an arrival in 2026 forward. We will need to collect the tax difference to secure and finalize your booking. We will contact you to confirm...
Seaside Splendor: Immerse Yourself in Luxury with this Stunning Oceanview Condo!
Oceanview bliss awaits! This condo not only boasts mesmerizing ocean views but also pampers you with luxury amenities. Enjoy a fully-equipped kitchen, spa-like bathroom, high-speed Wi-Fi, and beach equipment. Elevate your vacation - book this seaside sanctuary for the...
KBV 35G2 Best Rate LUXE OceanFront Villa w Oceanview | Lanai | AC
Kapalua Bay Villas 35G2 Fabulous OceanFront Getaway on the Kapalua Coast. Updated Luxury 1Bedroom Condo with Expansive Ocean Views for Sunsets FREE daily activities included with your stay value up to $1035! Complimentary admission, every day of your stay*: Lu'au, Golf,...
Banyan Tree 301: DIRECT OCEANFRONT 2/2 REMODELED WITH AIR CONDITIONING!
WOW! That's what you'll say when walking into Banyan Tree, Unit#301, a third floor fully remodeled condo in a secure and private building with an elevator, pool, spa and barbecue! You'll find floor to ceiling glass showcasing the beautiful ocean almost at your feet! ! A...
Hale Ho'okipa: 2 Homes/2 Pools in Poipu-Sleeps 16
Gathering of the clan? Extended-family reunion? Or just an amazing shared adventure? Whatever the occasion, this beautiful 7BR/5+BA compound, with ample space for 16+ guests, offers blissfully comfortable accommodations for a large, congenial group. Two impeccably...
Top Floor Maui Vista with Ocean View, AC, 5min Walk to Beach
Welcome to your dream tropical paradise! Bask in the glory of gorgeous sunsets right from your own living room or lanai. Centrally located in the heart of Kihei, this 2bd/2ba top floor, 2-story loft condo is across the street from Charley Young/Kamaole 1 beach and...
New home in quiet neighborhood, amazing views, minutes from top resorts.
This beautiful, custom built home was completed last year and has never been rented before. Outdoor living is a premium with a 700 square foot deck and a 700 square foot lanai facing west that capture the entire Kohala coast line. Enjoy views of the ocean, sunsets,...
KaMilo at Mauna Lani Condo w/ Resort Pool Access!
Experience the perfect blend of oceanfront adventure and tranquil relaxation when you stay at this 4-bedroom, 3.5-bath vacation rental in KaMilo at Mauna Lani. Complete with several private lanais, a large chef's kitchen, and unbelievable views of the golf course and...
Support LOCAL: NEW! Makaha Valley Home
Mahalo (thank you) for choosing to support LOCAL!We know you have many options available to you in this neighborhood from big corporations, but we promise that you will be pleased with your decision.We are new to VRBO so check out our multiple 5-STAR reviews on Google...
Ewa Beach Apartment ~ 1 Mi to Puʻuloa Beach Park!
Life is a breeze when you stay at this Ewa Beach vacation rental! Located less than a half-mile from the beach, this 3-bed, 2-bath apartment makes it easy to soak in the sunbeams. Practice your swing at Kapolei Golf Club one day, satisfy your inner adventurer at Coral...
Unique, Top of the Line Ocean View in Makaha
Locally owned and operated. Newly renovated with upcycled local accents and eco friendly products. All new premium wood cabinets combine with one of a kind solid cement coulter tops, stainless steel appliances, and mango wood shelving in the kitchen. A premium sofa...
Valley Isle 304 Beautifully Decorated OceanFront Condo
Valley Isle 304 Direct OceanFront Condo in Kahana, Maui with Stunning Ocean Views From the Lanai and Bedroom for a Romantic Tropical Island Getaway. Relax, Reconnect Aloha, and welcome to our beautifully renovated 1-bedroom condo in Kahana, Maui, nestled directly on the...
Wai Lani: Ocean View Home, AC & Lanais
Wai Lani by Gather offers an elevated Princeville escape where breathtaking ocean views, cooling trade winds, and thoughtful modern comforts come together in perfect harmony. Perched at the end of Albert Road and surrounded by lush tropical beauty, this serene retreat...
Hidden paradise with a hot tub, wood fireplace, large lanai, & jetted tub
Anthurium CottageOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Wake up to the melodic serenade of native birds and step out onto your private lanai to behold the lush, natural...
Bright & modern dog-friendly oasis on two lush acres with generous patio & W/D
Orchid Land | 31-Day MinimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Escape to paradise in this charming, newly built home in Keaau, Hawaii available for long-term stays....
Hale Ho'ouluulu: New Poipu Villa w/Pool/Ocean View
Wherever you look, this stunning Kukui'ula villa inspires admiration, and sparks delight. First, there’s the expansive view: an enchanting parfait of rolling hills and verdant orchards in the foreground, the glittering sea beyond, and impossibly blue skies overhead....
Luxury Oasis Palm Villas at Mauna Lani - Golf/Beach/Shops/Restaurants
Luxury Oasis at Palm Villas in Mauna Lani Resort on the Big Island of HawaiiWelcome to your dream Hawaiian getaway at the Palm Villas located in the Mauna Lani Resort, where paradise meets perfection! Nestled within the prestigious Palm Villas community, our luxurious...
3 bedroom Villa with golf discounts
Aloha! Welcome to our 1800 sqft Hawaiian style 3 bedroom, 3 bathroom villa at the Waikoloa Beach Resort Fairway Villas. Situated on the 4th hole of the Lakes Course overlooking Kings' Lake, Kings' Shops, with sunset skies and moonlit nights.The Resort has a beautiful...
Splendid 2BD w/ One FREE Parking
This lovely 2 bedroom unit is a rare find in Waikiki. With 1,000 sq ft of spacious living, 2 bath, 2 balconies, 1 free parking, split AC, 4 beds, 8 guests, this unit is one you can't go wrong with. We are centrally located making restaurants, Friday night fireworks,...
Includes Hilton Waikoloa Pool Pass for 2026. 101 Waikoloa Colony Villas
Waikoloa Colony Villas 101.Please scroll down for detailed informationHilton Pool Pass: Valid for stays now through December 31, 2026. Maximum 6 persons per pass (children under the age of 5 are not counted towards the 6 person max). Use of the Hilton Waikoloa Pass is...
True Oceanfront, Top-Floor, Downtown, Central A/C, Free Parking
Get away from it all right in the heart of Kona! Feel the ocean spray as you watch for turtles on the lanai, or gaze at the tropical paradise through your bedroom window. While only steps away from the active downtown, this top-floor unit is on the ocean side of a...
Chameleon Suite Ocean Views Kitchen Volcano NP
About this spaceSee our 5 star reviews! Looking for a unique stay w Ocean Views, cool nights, beautiful sunsets, & Chameleons? We are centrally located between Hilo & Kona 50 minutes from the Volcano. Perfect for exploring the South End of the Island. Chameleon Suite is...
Kapaa Shore Resort A307, Oceanfront, Walk to Shops, Restaurants, Beaches
Discover unparalleled luxury in this oceanfront haven, Kapaa Shores A307. This top-floor condo (walk-up) provides an exclusive experience with two bedrooms and two bathrooms, 909 square ft of living space, Accommodates up to 4 guests, including children and infants. The...
AMAZING OCEANFRONT MAUI - Watch the whales right from the balcony
WELCOME to Our Beautiful Ocean Front Condo at Kanai A Nalu, on the quiet side of Maui. Our ocean front unit, located on the third floor overlooks the grounds Lush Tropical Garden as well as the Crystal Blue Waters of Maalaea Bay. Kanai A Nalu is a beautiful beachfront...
Fantastic Ocean View Unit- close distance to the beach, lagoon, mall, and more
Experience the elegance and comfort of this ocean-view one-bedroom unit, featuring two queen-size beds and a refined renovation. You can walk to the famous Ala Moana Shopping Center, the stunning beach park, and the lagoon. Many restaurants are nearby, and an ABC store...
Dancing Volcano Estate - sleeps 8 Near Hawaii Volcanoes National Park
Dancing Volcano Estate in Volcano, Hawaii is a fantastic place to stay and visit Hawaii Volcanoes National Park just a few minutes drive from our property. Our main house has 3 bedrooms and 2 bathrooms, full kitchen, large dining area, large living area with SMART TV,...
Ocean View Estate w/AC & Pool, Close To Beach
Looking for a unique and luxurious Kauai getaway with incredible views, a pool, and air conditioning? Would you like something that feels private and secluded yet close to some of Kauai's most amazing beaches? Escape to this bluff estate overlooking Anini Beach and...
Prime ground-floor location with many extras
Papakea B102 is a 1-bedroom, 1-bathroom condo featuring amenities such as a washer/dryer, 1 window air-conditioning and more! The condo can accommodate up to 4 guests with a California King-size bed in the bedroom and a queen sleeper sofa in the living space. The...
Aloha Breeze by AvantStay | Amazing Ocean Views, Game Room, Modern Design
Kick back in the heart of Makaha Valley at Aloha Breeze, a 4BR retreat that puts you 10 minutes from the beaches of Oahu. With a stunning view of tropical mountains and the ocean from your backyard, this modern Hawaiian escape blends style, space, and a beautiful...
Best Ocean Views at Kihei Kai Nani #206nSteps to the beach 1 Bdrm / 1 Bath
Looking for the best view at Kihei Kai Nani? It is unit #206! This updated, corner penthouse boasts stunning beach and ocean views from the living room and lanai (patio). Relax to the sounds of the ocean and enjoy sunset views every night from the lanai or living room....
Includes Beach Gear! F1 Na Hale o Keauhou
Na Hale O Keauhou #F1 on the Big IslandThis vacation rental is professionally managed by ResorticaHawaiiPlease scroll down for detailed informationBedroom Configuration:Master Bedroom: King BedGuest Bedroom: Queen BedGuest Bedroom: Two Twin BedsAmenities:Beach...
Hale Makala - Luxurious Hanalei Home TVNC #5093
Hale Makala, Luxurious Hanalei Home Renovated to PerfectionEscape to Hale Makala and experience ultimate luxury. Immerse yourself in the perfect fusion of traditional Hawaiiana style and modern design at Hale Makala, a recently renovated luxury home that promises a...
A Cozy Cabin in the Country
Welcome to our haven of tranquility nestled in Hawi's breezy back country. At an elevation of 1800ft, our stylish retreat offers a refreshing escape from the ordinary. Start your day with a fresh cup of coffee and immerse yourself in the soothing symphony of wind...
NEW LISTING Kailua-Kona 3-bedroom, 2-bath single-family home Ocean & Sunset View
Immerse yourself in the enchanting allure of Kailua-Kona at our 3-bedroom, 2-bath single-family haven, offering you panoramic views of the endless ocean horizon. Every detail has been meticulously attended to, including newly installed split AC units in every room, new...
Steps to the Beach, Calming Ocean Sounds & Views, Amazing Sunsets, Remodeled
Beachfront living at its finest. This recently remodeled condo offers it all! Incredible oceanfront views, quiet complex, breathtaking sunsets, whale watching during the season, steps to the beach, great restaurants, grocery store, coffee shops and convenience stores...
Pool & Beachside—NEW Kailua Luxury Beach House - Direct beach access!
Indulge in an Unforgettable Stay at Our BRAND-NEW Luxury Beach House at Kailua BeachEscape to our newly built, luxurious rental home, perfectly nestled in the heart of the most sought-after location by the world-renowned Kailua Beach. This contemporary haven is designed...
2 BR Luxury Oceanview Condo in Kukuiula
Kainani #1 is a 2-bedroom, 2-bathroom villa nestled in the heart of paradise, offering an unparalleled experience of comfort, convenience, and tranquility.As you step through the ground-level entry, you'll be greeted by the seamless fusion of indoor and outdoor living...
Hawaiian Retreat w/ Ocean Views in Captain Cook!
Indulge in the ultimate Hawaiian getaway at this stunning 3-bed, 3-bath vacation rental house in Captain Cook. Upon arrival, you’ll be greeted by 3 manicured acres of mature fruit trees. Past the front door lies access to the ocean-view lanai, which is the perfect spot...
2021 Toyota Tacoma with a Rooftop Tent and all the camping gear!
2021 Toyota Tacoma TRD Sport with a Pop up tent! Our camper truck comes with all the amenities! Travel around the lush island of Maui and stay in a different part of the island every night!! Book your adventure today!! We provide everything you need from bedding &...
Close to Everything, Stunning Palms at Wailea Condo, Full A/C, Upper Floor
Welcome to Palms at Wailea 2304. Come to Wailea to enjoy the most beautiful beaches and best restaurants Maui has to offer. Get ready to make long-lasting memories while relaxing at this recently updated two-bedroom condo at the beautiful Palms at Wailea. This second...
Book Maui Vista NOW for whale seasonn Relax-Work-Play in this tropical getaway!
Book 7+ days receive 10% discount, 30+ days receive 15% discount.Perfect location! Newly remodeled 1 bedroom/1 bathroom corner unit that sleeps 4. Ideally located with ocean and mountain views. Stay in style with everything you need for work and play. Start your day...
Waikoloa Beach retreat! Top floor, walk to beach+shopping+golf, saltwater pool
Welcome to our happy place, Vista Waikoloa D301! Centrally located in Waikoloa Beach Resort on the Big Island, your condo features:- Spacious 350 sq ft. wrap-around lanai (with peek-a-boo views of Anaeho'omalu Bay)- Gorgeous views of Mauna Loa and Hualalai- Walk to...