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.
Hokulani 542 is an expansive 2BR/1BA suite boasting views of what West Maui is most famous for, the blue Pacific Ocean and lush West Maui Mountains. With its den converted to a second bedroom, this rare offering provides the space and privacy of an additional bedroom...
Wyndham Kauai Beachboy Resort | King Bed Studio
Summary:Wouldn’t it be fun if Jurassic Park were real? This resort is the next best thing (think luscious jungle without the ferocious dinosaurs). The island of Kauai provided the background for the iconic Hollywood film, but this resort is all sun, swimming, and spa...
Top Floor Ocean Front Molokai 1 Bedroom Condo
Our condo is located in east end of island of Molokai. It is “NOT” on Maui. Recently totally renovated.Has spectacular views of the ocean and of west Maui coast. Watch whales from lanai during mid Dec-early April Book now don’t miss out everything is filling fast. Check...
Tiki Tiki - A Gorgeous Boho Beach Hideaway!
Fall in ALOHA with Tiki Tiki!! This special studio is truly a piece of Paradise!A magical retreat that will have you feeling zen & refreshed. Tiki Tiki is the perfect home for honeymooners, girlfriend getaways, or any adults looking for a tropical stay in the the heart...
Dlx Oceanview Waikiki1Br Condo...Stunning Ocean/Marina Views!
Welcome to your own 1br Oceanview Condo in Waikiki...ideally located on the Marina side of Waikiki...near the famous Hilton Hawaiian Village.. Enjoy great ocean & marina views from the privacy of your own lanai from your Waikiki beach vacation condo rental ...just...
Beautiful Oceanfront Estate with heated saltwater pool, Hamakua Coast Acreage.
Summary:You found a perfect balance of comfort, style, and location. This home blends natural finishes with calming treehouse vibes, offering a peaceful escape just minutes from Hilo on the Hamakua Coast. Enjoy a kitchen, lux bathroom, smart TV, and cozy seating for...
*Hono Kai A11* Maui condo steps to the sand!
In the beautiful ground floor Hono Kai A11 garden-view unit, you will be immersed in rich tropical foliage from your spacious private lanai only steps from the complex beach access! Remodeled and decorated with the spirit of Aloha, this unit features a primary bedroom...
★O‘ahu Perfect Vacation • Million Dollar Views, Pool, Near Beach, 4BR Sleeps 14★
Why guests love our cozy Makaha Valley home, The Ohaha Paradise!Free parking for up to 3 cars (hotels charge $40–$100 per car)Full kitchen—cook your own meals and save on dining out4-stage reverse osmosis drinking water—no need to buy bottled waterPrivate backyard with...
VIP Maui - Amazing Ocean Views at the Royal Kahana
Vincson's Island Paradise (VIP) located at the Royal Kahana Resort in beautiful West Maui, is a newly remodeled studio that boasts all the amenities you need to make this your home away from home. Centrally located in quiet picturesque Kahana, we are 4 miles from the...
Puako Beach Getaway - Luxury Vacation Home with Old Hawaii Charm
Tucked along the pristine shoreline of Puako Beach, Puako Beach Getaway is a luxurious 3-bedroom, 3.5-bath oceanfront home that combines elegant contemporary design with the timeless warmth of Old Hawai‘i. Framed by sweeping views of Maui, the Kohala Mountains, and...
Luxury, oceanfront condo. Newly renovated; best location! Sunset views! #404
Aloha! Welcome to Sugar Beach Resort, #404! This luxury renovated unit has all you need for your perfect Maui vacation: incredible ocean sunset views and just steps from crystal clear Sugar Beach. During whale season (Nov-April), you will see humpback whales from the...
Breathtaking Golf Course Views, Home "B", Modern-Clean-New, Unwind in Paradise!
Welcome to Hillside Perfection on the Greens at Golf Ridge Homes!Discover your ideal fully furnished, 5 bedroom, 4.5 bath, 2 car enclosed garage, air conditioned executive home located in central Honolulu. Perfect for savvy business travelers and visiting construction...
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...
Experience Unmatched Comfort with Magnificent Panoramic Views and AC!
**Kapalua Golf Villas 21T 5-6**This newly remodeled, ground-level 927 square foot residence offers a spacious master bedroom with a king-size bed and a remodeled full bath. The master vanity area features excellent lighting, perfect for makeup and hair. The guest bath...
Elua 1310 Ocean Front Condo - Family Managed - 50 Steps to the Beachfront/Walk!
(9/17/25) We just wrapped a full condo remodel of our oceanfront home and am bringing the unit back online!Elua 1310 is in the closest building to the beach with 120 degrees of unobstructed ocean views and sits next to the famous Wailea Beach walk.You are just steps...
Take it easy at this unique and tranquil getaway. Who doesn’t dream of coming to Hawaii and staying in an original built Hawaiian home set on an acre surrounded by coffee, mango, avocado, papaya, passion fruit trees and much more! Surrounded by Kona coffee farms and...
Unquestionably one of Honua Kai's best values, Konea 308 is a rare 2BR/1BA suite that offers the space and privacy of an additional bedroom without the price tag of a standard 2BR/2BA. Enjoy beautiful partial ocean views from its spacious lanai, as well as those of the...
Relaxing Gardens - Peaceful Retreat w/Panoramic Ocean Views
Welcome to our private, peaceful retreat on Hawaii Island's Hamakua Coast - Relaxing Gardens. Unwind and enjoy the panoramic ocean views from our home atop a hill in Laupahoehoe, Hawaii. Our lush gardens will delight your senses with color, fragrance and even a few...
Maui Sunset A203 - Perfect for Families and Couples - Beach, Pool, Hot Tub+More!
Clean, private, updated, one-bedroom condo perfect for couples and families. Condo has additional queen-size Murphy bed.Located in the desirable Maui Sunset complex in Kihei, on the leeward, sunny side of Maui. The condo comes fully furnished with supplies for 4 people...
LUXURY/MOST POPULAR SNORKELING & SURFING BEACH! Turtles!
Wow! The perfect beach home w/ beautiful ocean views, Kona sunsets, newly renovated Hawaiian style home, "Kahalu'u Gem" is located right across Kahalu'u Beach Park and next to a surf shop!Total renovation by Kona Architect, Ali Ghalamfarsa, with Ohi'a wood, Opiuma wood,...
Summary:Completely remodeled. Our new Wailea luxury condo is immaculate and offers direct ocean views. Airy, comfortable, and with stylish decor, every amenity a Maui visitor could hope for is provided. Guests will fall in love with Wailea's beautiful lushness while...
Oceanside-Spectacular View and Poolside Oasis!
Summary:With a sprawling ocean view, this little island oasis is the epitome of the dream vacation home. Wood beam ceilings and rich grainy finishes contribute to the "island beach house" character. Poly Shores is minutes from world famous Kaanapali beach and Kaapalua...
Breathtaking Part. Ocean View in Kauai!
The Point at Poipu is a dream vacation destination on the southernmost tip of Kauai. The resort overlooks the sands of Shipwreck Beach & is secluded among lush landscapes. After a day of exploring, return to the resort to relax in the spacious two-bedroom accommodations...
Modern Oceanfront Condo with Stunning Views, Perfect for Any Getaway #705
Spectacular Maui condo! This bright and beautifully, modern condo is perfect for honeymooning couples, anniversary stays, family getaways, and those just looking to escape to their own tropical retreat. Mana Kai Resort is a favorite oceanfront community among travelers...
Cotton Candy Sky Kona Pacific Condo
Enjoy ocean and garden views from this third floor, corner unit condo in Building C of Kona Pacific! Located in a prime location in the heart of Kailua Kona on the Big Island of Hawaii, this 1-bedroom, 2-bathroom condo has been completely remodeled. It also offers...
Hale Joli: Historic Typical Hawaiian Home w/Ocean Views, Lanai & BBQ Area
Welcome to Hale Joli, a private hillside retreat in Kailua-Kona where panoramic ocean views, warm wood architecture, and the natural beauty of the Big Island come together. Set on historic royal lands once belonging to King Lunalilo, this single-level home blends old...
Steps from Stunning Moloaa BAY
Formerly "Hale Houston" Moloaa Beach Hideaway is a 2 bedroom, 2 bath home situated just steps away from beautiful Moloaa Bay on the northeast shore of Kauai. Walk up a flight of stairs to enter this 1200 sq.ft. spacious, air conditioned well appointed home with an open...
Montage Kapalua Bay - Grand 3BR Oceanview Villa 2206
** 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...
Dramatic Ocean Views, Wailea Ekolu 407, Perfect for Couples, Renovated, Split AC
Experience the essence of Maui at Wailea Ekolu 407, a luxurious 1-bedroom, 2-bathroom condo that offers breathtaking panoramic ocean views from the spacious living area, kitchen, primary suite, and oversized lanai. Nestled in the heart of Wailea, this elegant...
NEWLY REMODELED! Partial Ocean View condo along the golf course
This newly remodeled 3 bedroom 2 bath condo located in the heart of Wailea is the perfect vacation oasis for your island getaway. This condo comfortably sleeps 6 and has amenities such as 2 outdoor pools each with a hot tub, a full kitchen, wireless internet, air...
Coastal Paradise 🏝️ Private 3 Bedroom - AC, Pool, Spa, Beach, WFH
Your private paradise awaits just steps away from Kahana beach. This newly remodeled 3 bedroom townhouse was designed by us with laidback, rustic accents and clean, thoughtful designs to welcome you to your luxury coastal stay.The spaceAll bedrooms feature exposed...
Beautiful Ocean Views 5 Bedroom Sleeps 14 Walk to Beach, Pool, AC, & Game room
The "Akai Beach House" is a beautiful 5 bedroom 4 bath home that sleeps 14 with ocean views, a pool, air conditioning and a large game room in the garage. Enjoy ping pong and foosball, or relax on the couch and watch TV in the game room. Magic Sands Beach - the best...
TOP Floor-Stunning Ocean Views-Well Equipped-All NEW Furnishings
Book with confidence, this remodeled top floor unit at The Royal Mauian with stunning ocean views. This 2 bedroom, 2 bathroom condo offers an exceptional vacation experience and is fully equipped with everything that you need to have a great vacation. It has been...
Makaha Ocean View - 2 bedroom, 1 bath - family friendly
Hawaii License # 031-420-0064-01This property may not be rented for fewer than 30 consecutive days. Rental prices will not be reduced or adjusted based on the number of days the rental is actually used or occupied.ABOUT THIS CONDO: Meticulously clean! This is a...
Hoku Hale – Ainamalu at Waikoloa Beach Resort
***Luxury Golf Course Estate with Private Pool, Daily Hilton Waikoloa Pool Access, Concierge Services & Game Room | Sleeps 10+ in Waikoloa Beach Resort***Hoku Hale is a luxury five-star vacation home located in the heart of Waikoloa Beach Resort on the Big Island of...
Aolani Coffee Cottage | #1 AirBnb | Condé Nast | AC
Peaceful Holualoa Farm Retreat | 12 Minutes to Kona & BeachesAbout This SpaceWelcome to Aolani Coffee Cottage, a private, design-forward retreat tucked into Kona’s lush coffee belt. Set on a working farm with sweeping ocean views, this serene hideaway blends refined...
Aolani House+ Cottage | #1 AirBnb on Big Island | Condé Nast
Aolani House & Coffee Cottage – Your Private Hawaiian SanctuaryNestled in the serene coffee farms of Holualoa, Aolani House & Coffee Cottage offers an exclusive retreat for relaxation and rejuvenation. Perched on 5 private acres of Kona Coffee and Macadamia Nut farms,...
Ocean front 180° Ocean Views! Kapalua Bay Villa 22G2!! Quam Properties Hawaii
Experience the epitome of island luxury at Kapalua Bay Villa 22G2, a ground-level retreat offering sweeping 180° ocean views and effortless indoor-outdoor living. This spacious two-bedroom, three-bathroom villa welcomes you with an open floor plan and expansive lanais...
Bright & Airy Beach House w/ Oceanfront Views
Balmy days and breezy nights await at this 2-bedroom, 2-bath vacation rental in Kailua-Kona. With the Pacific Ocean as your backyard, you won't have to travel far for some vitamin D and 'sea,' whether you'd prefer to surf and swim or snorkel and sunbathe. When hunger...
Kolea 7F - 3 Bedroom Front Row Penthouse
Kolea 7F is located in one of the most popular buildings within Kolea. The location offers expansive ocean views as well as easy access to the Kolea Beach Club and the white sand beach at A'Bay. Throughout the villa you will also find nice Hawaiian artwork! The moment...
NEWLY remodeled Modern Maui condo across the beach.
Enjoy a stylish experience at this centrally located Maui Vista condo steps to popular Charley Young beach. Beautiful sunsets and a relaxing breeze on the lanai overlooking lush lawn and tropical plants. Beautifully renovated (2021) modern design. This 1bd 1 bath is...
Chic and Central Ocean Dream Vista
Summary:Upscale remodel with high-end furnishings 1br oasis situated directly across from Kameole Beach. Fantastic lanai with direct ocean views. Experience the resorts many amenities such as tennis courts, pool and jacuzzi and grills. We provide everything from beach...
Impressive Wailea Ekahi 1 Bd+2Ba Condominium 20G-Adjacent to Keawakapu Beach
Don't miss the best that Wailea Ekahi has to offer. Ekahi 20G - newly remodeled as of August 2025. Full kitchen and bathroom remodel, with all new appliances, Gorgeous! Stay with Wailea Rentals at Wailea Ekahi Village 20G and you and your guests will enjoy premier...
Halana Maile - Ocean Views, A/C, Beautifully Furnished Halana Maile Sleeps 8, 3200 sq. ft
Summary:Elegant ocean-view home with A/C, 3 bedrooms and spacious living areas, sleeping up to 8 guests. Perched along Poipu’s crater ridge with sweeping views and easy access to Shipwreck Beach and the Poipu Kai Greenbelt. Features a gourmet kitchen, expansive lanai,...
Beachfront top-floor unit on Oahu's north shore!
10% OFF FOR MAY 2025! ONLY $180/NIGHT.This remodeled condo is on the top floor of a beachfront complex on Oahu's north shore. Experience the North Shore lifestyle, including breathtaking sunsets, world-class surfing, snorkeling, and hiking. The view of the blue ocean...
Maluhia Wai - Modern 2 Bd Condo w/Pool, A/C, Wi-Fi
Wai Maluhia awaits! FIRST TIME OFFERED This newly renovated condo is like no other in Hilo. IF you are looking for the best East Hawaii experience look no further. New furnishings, modern decor, and upscale luxury are all features you will appreciate. This corner condo...
Includes Hilton Waikoloa Pool Pass thru June 2025! Waikoloa Colony Villas 1605
This vacation rental is professionally managed by ResorticaHawaiiWaikoloa Colony Villas 1605 Please scroll down for detailed informationHilton Pool Pass: Maximum 6 persons per pass (children under the age of 5 are not counted towards the 6 person max). Use of the Hilton...
Marriott's Waiohai Beach Club 2BR Islandview Villa
Tucked along the pristine Poipu beach in the heart of Kauai's South Shore, Marriott's Waiohai Beach Club invites travelers to step away from the hurried pace of daily life and ease into the soothing tempo of island living. Flanked on both sides by world-class resorts,...
Marriott's Waiohai Beach Club 2BR Oceanview Villa
Tucked along the pristine Poipu beach in the heart of Kauai's South Shore, Marriott's Waiohai Beach Club invites travelers to step away from the hurried pace of daily life and ease into the soothing tempo of island living. Flanked on both sides by world-class resorts,...
NEWEST! California Coastal Inspired in Maui 2 BR
Welcome to Maui Eldorado G106, a beautifully designed 1,440 sq ft California coastal-inspired retreat in the heart of Kaanapali. Located within the sought-after Maui Eldorado resort, this spacious ground-floor condo comfortably accommodates up to six guests and is just...