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.
NEW LISTING!! Kapalua Ridge Villa #1722 with views that are simply spectacular!
With views that you thought were only made for dreams, this villa will surely take your breath away. Located in the world-class Kapalua Resort, the vistas this unit has to offer are truly jaw dropping. Your windows are filled with a panorama composed of the sparkling...
High Floor Ocean View Wyndham Waikiki Resort
Aloha! Enjoy the boutique-hotel ambiance of the Royal Garden Hotel and the beautiful Hawaiian tropical setting. It’s the perfect spot for your vacation, business trip, or a refreshing getaway.Our condo is located in the heart of Waikiki, just a short walk from the main...
Kona Plaza 301, Ocean Views and Renovated
Kona Plaza 301! Your Ideal Hawaiian Getaway! Welcome to Kona Plaza 301, where modern comfort meets tropical paradise! This beautifully updated condo features brand new floors and is designed to provide you with a relaxing retreat during your stay in the heart of...
~New~ Hale Kai at Turtle Bay Golf Course
Brand New Listing! Relax in this bright and beautiful getaway on the North Shore and be the first to review this 5-star guest favorite listing that is new to our portfolio! Please note that the living room and patio have been updated with new tile floors and beautiful...
New Listing! Peaceful island living with a view
Welcome to Kaanapali Shores Unit 733! This comfortable 1-bedroom, 1-bath condo is located on the 7th floor and can easily accommodate up to 4 guests. Stay cool with central air conditioning or step out onto your private lanai to enjoy the ocean breeze and relaxing views...
Kona Coast, BEST Oceanview&Pool, Yoga/Meditation Space, Pickle Ball&Basket Ball
Welcome to Halani — Your Serene Sanctuary on the Big IslandEscape the busyness and crowds of the resort scene and discover Halani, meaning “heavenly breath”—a peaceful retreat perched above the South Kona coast, offering one of the most unparalleled ocean views on the...
4 Star Beachfront Resort. King Bed. Lanai. AC. Restaurant. Pool. Gym. Spa.
Welcome to Kauai, Hawaii! We are delighted to welcome you to Outrigger Kauai Beach Resort, a hidden gem nestled on the sandy shore of an exclusive east-side oceanfront property. Our resort offers a blend of luxury, convenience, and affordability, providing a serene...
Rare Penthouse Ocean View Unit 3bd/2bth Upgraded
Welcome to one of Kihei's best-kept secrets- a top-floor, corner-unit penthouse at Kamaole Beach Royale, now available.3Bd/2Bth luxury condo offers unmatched privacy, panoramic ocean views, and exclusive developer upgrades. Perched on the 6th floor, this spacious...
New Listing! Luxurious 4BR/3BA House with AC
Discover Elegance at Poipu: The Leilani House hosted by BlueTideVillasWelcome to The Leilani House, a beautifully designed 2,100-square-foot retreat set on a private half-acre just minutes from Poipu Beach and local dining. Celebrated as one of Poipu’s most desirable...
Wailea Elua 808 - Scenic Ocean Views, Classic Wailea Charm, Central AC, Wi-Fi
Welcome to Wailea Elua 808, your ideal Maui retreat. This spacious 2-bedroom, 2-bath condo offers the perfect setting for a relaxing getaway or a family vacation. With a thoughtfully designed floor plan, stylish furnishings, and ample natural light, you'll feel at home...
Jungle Retreat in Kona Cloud Forest Sanctuary, An unforgettable Cloud Forest Sanctuary retreat exper...
Wake up in your cozy private jungle retreat nestled in the lush serenity of the Kona Cloud Forest Sanctuary. All stays include a private guided Sanctuary tour. Enjoy yoga, sound baths, and other experiences on site, take a morning walk for fresh brew and coffee tours at...
Pili Mai 06L By Parrish Kauai
Nestled among a championship golf course, Pili Mai is set in an ideal location on the island of Kauai’s south shore in Poipu Beach. This is Kauai's newest resort development and has a choice of two, three, and four bedroom luxury condominiums.This central Poipu location...
Kaanapali Shores 435 By Parrish Maui
Kaanapali Shores offers the best of oceanfront resort living on Maui’s renowned West Side. Each spacious vacation rental includes a full kitchen, private lanai, and thoughtfully designed interiors that blend comfort with island style. Guests enjoy access to two swimming...
Surf, Sand & Serenity- Kihei Akahi D213 Ocean View
Aloha and Welcome to Your Maui Escape at Kihei Akahi D213!We're new owners and offering great prices. Discover your perfect island getaway at our beautifully updated one-bedroom, one-bathroom condo in the heart of South Kihei. Just steps from Kamaole Beach Park II and...
Kauai Oasis - Luxury 6 BR Kukui'ula Estate with Infinity Pool
Magnificent, spectacular, and amazing describe Kauai Oasis, a brand-new 2024 Kukuiʻula retreat. This luxurious home offers sweeping views of the ocean, Kukuiʻula golf course, Hđupu mountains, sunrise, and full moonrise. Watch the Milky Way and meteor showers from the...
Dazzling Waikiki Apt Sleeps 7-excellent A/C & PARKING included
Stylishly, modern and comfortable apartment perfect for your stay in Waikiki. Perfect for a family/group. There are 2 separate bedrooms one king bed/one queen bed. The living room has a queen sofa bed. The kitchen is stocked with necessities to cook your meals & a...
Tropical Bamboo Retreat in Upcountry Maui! Bamboo Heaven Maui LLC BBPH 2012/0003
Consider this bed & breakfast your home away from home while you visit Haiku Maui! This tropical property offers a peaceful retreat in the country with fruit trees, rainbows, and night skies filled with stars and galaxies! My unique bamboo home welcomes you to unwind...
Private KÅloa Retreat | Pool + Golf Course Views | Near PoÊ»ipÅ« Beach
Discover this lovely 3-bedroom gem in Kōloa. This awesome house features two king beds and two queen beds perfect for families or friends looking for a relaxing island retreat. With three full bathrooms including walk-in showers, a soaking tub in the master suite, and a...
Cozy suite just 1 block from beautiful Waikiki Beach! FREE parking nearby!
Ni'ihau Apartments #902 – 247 Beach WalkThis cozy suite with peak-a-boo ocean view is just a quick 1-block stroll to the white sandy beaches of Oahu's south shore! FREE Wi-Fi and parking at nearby lot. Secured building/elevator. Located in the newly revitalized Waikiki...
Oceanfront Condo: Stunning Sunrise & Ocean Views
'Lele's by the Sea' | Oceanfront Vintage Hawaiiana Getaway | Balcony | Pool + Gym | Beach GearAloha and welcome to your ultimate island escape! Retreat to this 1-bed, 1-bath vacation rental on Oahu’s lush, tropical side. Swim or snorkel at the sandy beach, relax and...
Kona Koa House by Gather: Oceanview 3BR Estate w/ Heated Pool & BBQ
Escape to Kona Koa House by Gather, a stunning 3-bedroom plus bonus room, 3-bath vacation home set within the prestigious Keauhou Estates gated community in Kailua Kona, Hawai‘i. Perched 500 feet above sea level, this luxurious single-level retreat spans nearly 3,000...
Hale Kai - Brand New Kukui'ula Luxury Home with Pool & Spa
Nestled in the exclusive Kukui'ula neighborhood in Poipu, this stunning, brand new luxury home offers the perfect blend of comfort, elegance, and island charm. With 4 bedrooms and 4.5 bathrooms, this meticulously designed residence comfortably accommodates up to 10...
Ohia Lehua Hale-Hot Tub-Fireplace-Fire Table-3-Bed, 2-Bath Newly Renovated Home
Welcome to Ohia Lehua Hale, located just 6 minutes from Hawaii Volcanoes National Park. Escape to our recently renovated vacation home; we recently added many upgrades to enjoy a relaxing stay.*New Built-in Gas Fireplace *New Smart TV*New Outdoor Hot Tub *New Outdoor...
Cozy ground floor condo, lush lanai, dining nearby
Welcome to Maui Kamaole F101 – your perfect island retreat! This beautifully appointed ground-floor condo features 1 bedroom and 2 full bathrooms, comfortably accommodating up to 4 guests. The dual-bathroom layout is ideal for families or couples traveling together. The...
Streaming with Sunlight 2+2 Hawaiian Villa
2 bedroom, 2 bath Villa with ocean views nestled in picturesque Kona Coffee Villas. Higher elevations, and mountainside complex presents an ideal setting for your Hawaiian Life Style. After a day at the beach, sink into one of two comfortable sofas in the living room...
Maui Kamaole #C-203 - Remodeled Upstairs Retreat with AC and Resort Pools!
Maui Kamaole #C-203Maui Kamaole #C-203 is a beautifully remodeled two-bedroom, two-bathroom upstairs unit offering a peaceful setting, modern comfort, and a fantastic location near some of South Kihei’s best beaches. This updated condo features island-inspired décor,...
North Shore Bali Style Home on Waialua Beach with Mesmerizing Ocean Views!
. "Hale Ohana", our secluded, luxury beach house has stunning 180 degree views of the breathtaking Haleiwa coastline and tranquil countryside. 45 minutes from Honolulu, but it feels like you're a world away in your own little piece of paradise. Relax on outdoor deck or...
Relaxed Suite Near Shipwreck Beach + Parking & Pool Access + Kitchen
Experience oceanfront serenity with stunning views, spacious rooms, full kitchen, private balcony, and in-room laundry—ideal for couples and families. Snorkel nearby, hike the Mahaulepu Trail, or spot turtles at Poipu Beach. Relax in our large outdoor pool. Whether you...
View of Mauna Kea in Gated Community across from Golf Course
Quiet & Private 1 King bed/1 Twin daybed/1 bath kitchenette (attached to main house) w/ separate entrance & patio ~600 sqft in secluded & gated community at a cool 2400 ft elevation. Wake up to beautiful views of Mauna Kea. Located 30 min by car from Kona Airport,...
KÄÊ»anapali Ocean View Condo with Beachfront Cabana for Guests
This charming studio places you in the heart of KÄÊ»anapali, one of Maui's most iconic destinations. Enjoy ocean and golf course views from your private lanai and inside you'll find a fully equipped kitchen, A/C, king bed, and Wi-Fi for a comfortable stay. Guests have...
Quiet Studio Vacation Rental on the Beautiful Puna Coast
This private studio and thoughtfully equipped with everything you need for a comfortable stay. You’ll have your own entrance, a comfortable (new) queen bed, and bathroom. The space also features an outdoor shower — perfect for tropical climate. The studio includes a...
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 morning...
1-Bedroom Condo near Kahana Beach | Pool + Hot Tub
Discover serenity and convenience in this 1-bedroom condo at Kahana Falls Resort. Located just steps from Maui's picturesque Kahana Beach, this unit is ideal for couples or solo travelers seeking a restful escape. Enjoy a queen bed, fully equipped kitchen, modern...
🏖️Ocean Front - Direct View of Kailua Bay | Concierge Included | Nicely Renovated
vrKCV - Alii Villas 329, Professionally Managed by Kona Coast VacationsWelcome to Your Kona Home Away from Home at Alii Villas!Discover the perfect island escape for families or couples seeking relaxation, adventure, and unforgettable sunsets. This beautifully upgraded...
Corner Oceanfront 1BR Condo w/ Panoramic Views
Enjoy a serene beachfront experience at this 1-bedroom condo in Waianae’s Hawaiian Princess Makaha. Perfect for couples, this peaceful escape offers a private lanai with ocean views, direct beach access, and all the comforts of home. Wake up to the sound of waves and...
Wailea Elua 2007 – Oceanview Luxury Condo in the Heart of Wailea
Welcome to Wailea Elua 2007, a stunning 1-bedroom, 2-bath vacation retreat with gorgeous ocean views, a spacious private lanai, and upscale island furnishings throughout. Perfectly positioned within the prestigious Wailea Elua Village, this beautifully appointed condo...
Hanalei Bay Villas #2, Beautiful Free-standing Hawaii Villa, walk to beach
Welcome to your tropical retreat at Hanalei Bay Villas #2 in Princeville, Kauai.Unwind at the adorable and comfortable free-standing 2-story villa located in the prestigious community of Princeville! This spacious, fully furnished 2 bedroom and 2.5 bath stand alone...
New Listing: Boutique-Inspired Tropical Décor
Shores of Maui 123 is a beautifully updated one-bedroom condo featuring an open-concept living space and tile flooring that flows seamlessly out to the private lanai. This ground-floor unit comfortably accommodates up to four guests, with a king bed in the bedroom and a...
Gorgeous Ocean View w/ Full Kitchen, Lanai, Steps to Beach!
Waikiki Shore #606 – 2161 Kalia RdGorgeous ocean views & epic tropical sunsets make this contemporary suite that sleeps 4, a favorite of those craving a blend of Waikiki energy & private relaxation! Wall-to-wall sliders, and windows let the beautiful Pacific Ocean flow...
New Listing 🏊 Private Pool 🚶♂️ Walk to ML Beach Club 💰 Discounted Intro Rates
Summary:Dreaming of sun, sand, and serenity? Hale Linaka offers it all. This 4BR/3.5BA home in Mauna Lani Resort is just a 5-min stroll to the Beach Club with turquoise waters and Napua restaurant. Enjoy indoor-outdoor living with sliding doors, plantation shutters,...
Let's Do Sunset On Maui! 1 Minute Walk to Beach and Sunsets
Close to the beach without the beachfront price tag! Located just a 1 minute walk from white sandy beaches, stunning sunsets, & turtles on the beach daily, this island retreat is an ideal getaway. Your dream condo is centrally located in the heart of Kihei, Maui. This...
Direct Oceanfront Condo – Chasing Life On Maui - AC, Heated Pool & Hot Tub
Escape to Maui and settle into your freshly remodeled, ultra-stylish condo perched right on the shimmering edge of Maʻalaea Bay. In Unit 205 at Maʻalaea Banyans, you’re treated to true ocean-front living—imagine starting each morning with coffee on your private lanai...
Luxury Hawaii Getaway Close to the Beach & Ocean!
Discover the very best of the Big Island from the comfort & convenience of this upgraded private retreat! Perfectly situated near Hilo just minutes from Haena Beach, experience the majesty of Kilauea in Volcanoes Park, stunning black sand beaches or the fresh flavors of...
Emmalani Hale, High-end, Luxurious, Tranquil retreat, AC in Princeville
Welcome to Emmalani Hale, your perfect retreat in Kauai!More than just a vacation rental, Emmalani Hale offers a luxurious and welcoming island escape designed for relaxation and comfort. This beautiful 3-bedroom, 3-bathroom home with large spacious living space,...
Ocean View Escape, Walk 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...
Canoe Palms Waikiki Pool, Gym, WiFi, AC
It’s a legally zoned cute studio in the heart of Waikiki. Short walk to the best locations, famous beaches, restaurants, and shopping.Easy 24/7 self check in and check out.Studio has a comfortable Queen bed, a kitchenette with cook top for preparing basic meal....
Kanaloa at Kona 3201, Oceanfront
Welcome to Your Oceanfront Escape –Hale Moana Kai.Experience island living at its finest in this beautifully appointed ground-floor condo, offering 1,486 square feet of refined comfort and uninterrupted views of He’eia Bay, and the vast Pacific Ocean. Located in the...
Stunning Ocean Views, Ground Floor Lanai
Wake up to stunning vistas from the king bedroom and cozy daybed, or step outside onto your private ground-floor patio (lanai) that flows into a lush grassy bluff with panoramic ocean views. Just outside your front doorstep, a moderate half-mile hiking trail begins,...
Renee's Poipu Paradise! Oceanfront Views & A/C!
SPECTACULAR Oceanfront Views and A/C! Enjoy the sunrise, turtles and whales in season directly off your private lanai! Kauai's best snorkeling? A 5 minute walk to Lawai Beach. Kid-friendly beach? "Baby Beach" a 5 minute walk the other way. Surfing? 30 feet to the water...
2 Mi to Hawaii Volcanoes Nat'l Park: Tranquil Home
Furnished Gazebo | BBQ Ready | Near Hiking & GolfingDiscover breathtaking natural beauty with this Volcano vacation rental as your launching pad! Boasting peaceful surroundings and convenient proximity to Hawaii Volcanoes National Park, this 3-bedroom, 2-bath home makes...