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.
Hale Kamaole #309 Spacious Ocean View Family Vacation Condo Near Kamaole Beaches
This outstanding condo, situated in the Kihei Hale Kamaole Resort, features ocean views from every room! Watch the whales from our lanai. The two bedroom plus loft, split level unit has over 1300 square feet of living area. Completely furnished in a casual, comfortable...
Plantation Hale Suites H15, Top Floor, AC, Walk to Beach
NOTE: Rates Automatically Discounted from September 15 through December 2025 due to construction repairs on various H-building decks during this time. We apologize for the inconvenience. Work Hours: Monday–Friday, 9:00 AM–5:00 PM.Plantation Hale Suite H15, Top/2nd...
Aloha Hale-Tranquil Ground Floor w/AC Near Beach!
Welcome to our tranquil Maui condo just steps from the beach! We are centrally located in Kihei, only 20 minutes from the airport and minutes from the best beaches, shops, and restaurants that South Maui has to offer!If you decide to prepare your own meals, our...
🏖️Updated Townhome | Ocean View | vrKCV🏖️
vrKCV - Na Hale O Keauhou D3, Professionally Managed by Kona Coast VacationsWelcome to Your Perfect Home Base in Na Hale O Keauhou!Experience the charm of this beautifully updated townhome in the serene and highly sought-after Na Hale O Keauhou complex. This gated...
Oceanfront Remodeled Condo! Can't Beat Views!! Air Conditioning
Premium 2 Bedroom/2 Bath ocean front condo with amazing ocean views and the best location in Central Maui (half way between Lahaina and Kihei). Enjoy the best views of Maalaea Bay from your large, private Lanai -- see the whales jumping, and enjoy beautiful sunrises and...
Ocean View Villa in Kahana, Maui
Experience the ultimate comfort and relaxation in our beautifully adorned Maui haven, Kahana Villa F404. This exquisite condo boasts an array of personalized touches that will leave you feeling right at home. Indulge in the breathtaking vistas of the Pailolo channel and...
Sea Village Oceanview Condo
Unwind with modern comforts, including a flat-screen TV with cable, high-speed WiFi, and a fully equipped kitchen perfect for preparing island-inspired meals. Step outside to soak up the sun in the oceanfront complex, where you can lounge by the pool, take a dip in the...
City-View Waikiki Beach Condo - Free Parking!
Who needs an ocean view when you can have majestic green mountains, blue skies, and lively street views from the 17th floor of Ilikai condo? Plus, you might even catch a rainbow or two! This cozy 500 sq. foot condo may not have a wall separating the bedroom from the...
Luxury Cottage w/ Private Pool. Under The Warm Maui Sun Pmt #BBKM\2016\0004
Under the Warm Maui Sun - Permit#BBKM\2016\0004 Due to cancellation last moment special forMon, Oct 31 - Thu, Nov 10, 2022 $350/nightRegular rates 2022: April 1 - December 27 2022$410/nite for 2 personsWinter rates 2023: January 3 - March 31 $490/nite for 2...
BEAUTIFUL! Cooks Landing at Hali'i Kai 18H
Welcome to Cooks Landing! A 3 bedroom 2 bath ground floor luxury villa (18H) in the prestigious Hali'i Kai gated condominium community of Waikoloa Beach. Includes gourmet kitchen, full sized washer and dryer, detached garage plus another reserved parking space. Access...
1 Bedroom at Oceanfront Resort Kapaa
This spacious one-bedroom resort suite measures approximately 628 square feet. You will enjoy a queen bed in the master bedroom and one queen Sleeper Sofa/Murphy bed in the living area.. Additional amenities include a full kitchen and dining area and a balcony. Maximum...
Kiahuna Plantation Oceanfront Renovated Ground floor Steps to ocean W/D in unit
Guest to pay onsite management Castle Resorts direct at check in/out for required cleaning. Full check out cleaning for 1 bedroom units for 2025 is $268.00 plus 18.712% tax effective 1-1-26 Any stays over 10 nights also require a full mid stay cleaning at a cost of $110...
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities
Our Maui home is quiet vacation escape. The upstairs has a master bedroom with a California King mattress with a bathroom having a Jacuzzi tub separate from shower. The secondary bedroom also has a California King mattress with a 3/4 bath. The kitchen has all amenities...
Na Hale 3: Exclusive Family Retreat with Private Pool and Resort Privileges
Welcome to Na Hale 3 at Pauoa Beach Club, an embodiment of exquisite indoor/outdoor living nestled in the Mauna Lani Resort, Hawaii's premier destination. This single-family haven is a symphony of luxury and natural beauty designed to offer an unparalleled vacation...
Makana Nui - Beachfront Home on Hanalei Bay
Welcome to the Makana Nui, located on the famous Weke Road in Hanalei. This home sits directly on the beach and is just a short walk through your private lawn to the sand. The picturesque Hanalei coastline remains relatively undeveloped and provides breathtaking views...
Relax, with breathtaking ocean views. Makaha 1-bedroom condo near Ko Olina
Nestled in the town of Makaha, our 1-bedroom condo offers a tranquil retreat for your Hawaiian getaway. As you step inside, you'll be greeted by a gorgeous ocean view! A kitchenette, complete with a stove, oven, refrigerator, and all the necessary appliances and...
Maui Resort Rentals: Honua Kai Konea 613 - Upgraded 6th Floor Ocean View 2BR w/ Deluxe Corner Floor Plan
Konea 613 is amongst a class of the most sought after 2 bedroom floor plans at Honua Kai. What distinguishes this column in the Konea interior are the direct ocean views from virtually every interior vantage point of the suite. This premier two-bedroom boasts a spacious...
Luxury Panoramic Ocean Views!
Summary:This beautiful and stylish remodeled home is perfect for group or couples vacations! You will be very comfortable in this large and upscale 2 bedroom 3 full bath home that is completely renovated!We are located in the Kapalua Ridge Villa Community. Only a 6 min...
Heart of Princeville w/AC minutes from everything!
Escape to our North Shore Kauai retreat in Princeville! A haven of beauty awaits you, with leisurely walks along Makai Golf Course offering breathtaking mountain and waterfall views. Experience mesmerizing sunrises, stunning sunsets, and starry nights in the tranquil...
Oceanfront Vacation Rental in Kihei Maui
Looking forward to relaxing on the lanai, enjoying the most beautiful view - morning, noon and night? Want to enjoy incredible sunsets, watching the sky burst with a fiery glow of mesmerizing color? Would you like to open all the windows and hear the sound of the waves...
Luxury Waikiki condo - 28th floor! Stunning views, convenient location, parking
Allure is one of the most luxurious private condominiums in Waikiki. The grounds, pool, and other amenities rival the resort hotels, but you get even more space, privacy and freedom. This property is ideal for couples or families seeking to feel at home in Waikiki for...
Turtle Bay Hale Lani by RedAwning
This lovely 1 bedroom w/loft upgraded unit has new kitchen cabinets &appliances, ceramic tile floors and granite countertops. The living room has aflat-screen TV, internet and WIFI, and ceiling fan. Window a/c in the livingroom and the bedroom. Reserved parking spot,...
Maui Eldorado K-106 - April Specials!
Centrally located in the heart of Ka'anapali, Maui Eldorado Kaanapali is the perfect place to enjoy your Maui Vacation. This ground-floor end unit with an elevated garden view is very close to the front desk and outdoor parking - handy for unloading luggage and...
Kailua Beachfront Vacation Home with Pool
This property is professionally managed by Private Homes Hawaii, LLC and is licensed as a short term vacation rental, Non-Conforming Use Permit Number 1990/NUC-1783. It is compliant with Hawaii State Legislation (HB2078) for vacation rental accommodations,...
KaMilo #503 by Gather: Luxury Mauna Lani Retreat Near Golf & Beach
Nestled in KaMilo at Mauna Lani Resort, this three-bedroom, three-bathroom villa offers elegant island living with resort-style amenities. The open-concept design features vaulted ceilings, Cumaru wood flooring, and a gourmet kitchen with high-end appliances and a...
Maui Resort Rentals: Honua Kai Hokulani 506 - Spacious 5th Floor 2BR Corner Suite w/ Direct Ocean & Mountain Views!
Maui Resort Rentals is proud to bring you this 2BR Partial Ocean View Suite at the Honua Kai Resort, newly launched on May 7th, 2025 to start taking reservations for check-ins on June 7th, 2025!Just two stacks from oceanfront, this highly sought-after 2BR/2BA corner...
Beautiful Ocean View on Quiet Side of Honua Kai
NO RESORT OR PARKING FEES WHEN BOOKING WITH US!Honua Kai is a Four Star resort with four pools, five spas, a fitness center, Aina Gourmet Market, and beachfront Dukes Restaurant on premises. Our one bedroom condo (unit 514 in The Hokulani Building) has a partial ocean...
Lovely Palms at Wailea condo, spacious, large lanai, close to beach! Full A/C
Located in the highly desirable Palms at Wailea, this delightful condo offers a relaxing retreat for guests. This spacious condo sleeps 4 with 1 bedroom featuring a king bed and a queen size sofa bed in the living room. It also has two full bathrooms. It's upstairs...
Maui Resort Rentals: Honua Kai – 6 Total Bedrooms, Ocean Views, 3300 Combined Sq Ft, Sleeps up to 18!
This one-of-a-kind 6 bedroom offering combines one 2br ocean view suite with two 2br partial ocean view suites located directly across the hall to create a tandem package with 3300 sq ft of interior living space and the capacity to accommodate up to 18 guests. Enjoy the...
Luxury Ko Olina Beach Rental Panoramic Ocean View 3BR 3BA 8th floor 2 parking
Imagine yourself in a world-class Oahu, Hawaii oceanfront resort in Ko Olina beach rental bliss with exotic woods, natural stone, and an expansive lanai. Imagine as you lie down on a bed of total luxury. You sink down into silky softness that cuddles you as you are...
🏖️NEW LISTING | Brand New Renovation! | Professionally Managed | vrKCV
vrKCV - Mauna Lani Fairways 1601, Professionally Managed by Kona Coast VacationsFeel the Aloha Spirit and relax in tropical paradise at Sandy Feet Retreat! Newly renovated in the summer of 2022, enjoy the modern Hawaiian vibe in this two-bedroom, two-bathroom townhome...
~ This Is Wailea Living ~
This is Wailea Living!Nestled in a private and secluded enclave between the Wailea Blue Course and the Wailea Tennis Club, the Wailea Grand Champions Villas are where travelers can golf, play tennis, be pampered at the Wailea Grand Spa, whale watch or turtle spot, or...
Happy Place Bungalow, 2-Minutes to the Beach! TVNC #4339
Hanalei Happy Place Bungalow Permitted Vacation Rental Property - TVNC#4339Transient vacation rental is located in the tsunami evacuation zoneCharming bungalow studio with jungle views close to the beach!Nestled between the verdant mountains and golden beaches of...
Hanalei Bay Villas #22 - a 2br / 2.5BA, mountain and golf course view condo
Hanalei Bay Villas #22 is a spacious two bedroom, two and a half bath, two story stand-alone condominium. With an additional queen size sleeper sofa, this unit sleeps six comfortably. Beach access is available past the 1 Hotel Hanalei Bay next door. Views include the...
Come spend some time at Our Kohala Ranch House!
From our covered lanai you have expansive views of the ocean, the sprawling Kohala ranchland and Haleakala on neighboring Maui. There really is no better way to start your day!And what you do with the rest of your day is completely up to you: Feeling a bit lazy? Relax...
Halii Kai 12H - 3 Bedroom Deluxe Ocean View Hali Kai Vacation Rental
Sit back, relax and enjoy the best view of the Waikoloa Beach Resort! The view from this villa is nothing short of breathtaking. From this villa you overlook the signature hole of the golf course and onto the blue waters of the Pacific Ocean. The view from this villa is...
Maui Resort Rentals: Honua Kai Hokulani 1034 – Expansive Top Floor Corner 2BR w/ Gorgeous Mountain Views!
Perched high above the palms on the top floor of the Honua Kai Resort, this exquisite 2-bedroom, 2-bathroom corner penthouse showcases stunning views of the lush West Maui Mountains, complemented by peekaboo glimpses of the sparkling blue Pacific.With nearly 1,300...
Ko Olina Beach Villas B103: Spacious Elegance & Oceanfront Views
Welcome to Ko Olina Beach Villas B103 by Gather, a ground-floor beachfront villa offering a breathtaking oceanfront getaway in the heart of Ko Olina. This three-bedroom, three-bathroom retreat is the perfect blend of luxury and comfort, designed to provide an...
Front Row Eclectic Updated Oceanview S Kihei 1 bedroom 1 bathroom condonn
Welcome to Maui Vista 1312. This eclectic updated partial oceanview 1 bedroom condo is located in the heart of South Kihei. This condo can accommodate 4 people & has everything needed to feel at home. Cross the street & end up at Charley Young beach which connects to...
AlohaCation - Oceanfront Work and Family Time
Work from Paradise or Enjoy Family Time by the BeachImagine waking up to breathtaking ocean views, working remotely with the sound of waves in the background, or spending quality time with your little ones on a peaceful, safe beach. Our oceanfront apartment blends...
Includes Hilton Waikoloa Pool Pass for stays in 2025! Includes Golf Package.Wai
This vacation rental is professionally managed by ResorticaHawaiiWaikoloa Beach Villas E23Please scroll down for detailed informationHilton Pool Pass: Valid for stays through December 31, 2025. Maximum 6 persons per pass (children under the age of 5 are not counted...
Modern Renovated Maui Kamaole Condo Near Main Pool, Beach Across Street
***Summer Discounts now available for July and August 2025! 15% off plus an extra 5% for weekly rentals and 10% for monthly! Quote calculates the lower rates!***This 1050+ square foot 2BR/2BA condo is in the highly desired Maui Kamaole complex, one of the newer condo...
❤️🏖BEAUTIFUL LARGEST 1BD, OCEAN VIEW ONE OF THE CLOSEST TO OCEAN 120 REVIEWS❤️
🏖 LARGEST ONE BEDROOM WITH OUTSTANDING REVIEWS. UPDATED! Newly Painted interior and lanai. COMPARE OUR FLOOR PLATE TO SEE OUR LOCATION COMPARED TO OTHERS ON VRBO.🌺 You are renting directly from the owners. We would love to have you stay with us. As our guest, you...
Ocean Views/Private Swimming Pool. Mauna Kea High Bluffs Home
This vacation rental is professionally managed by ResorticaHawaiiMauna Kea High Bluffs #9. Stunning Private Home with swimming pool and ocean views. Mauna Kea Resort Amenity Program add on optionPlease scroll down for detailed informationPLEASE NOTE: There is ongoing...
New Remodeled Kuaui Escape! 1/1 condo in charming Kapaʻa with WiFi, AC
Welcome to our charming one-bedroom condo by the beach in the heart of Kapaa next door to Coconut Marketplace. This newly remodeled one-bedroom offers a fully equipped kitchen,a furnished lanai,a king-size bed, and a sofa sleeper that can accommodate up to four guests....
Hale Honu - 5 Star Oceanfront Home Overlooking Turtle Cove!
Perched above historic Koloa Landing, also known as Hanaka’ape Bay, Hale Honu boasts dominant bay and ocean views. Just off your private lanai is some of the best snorkeling and scuba diving the island has to offer. Giant sea turtles can be seen below swimming and...
BEAUTIFUL CONDO WITH AWESOME SUNSET VIEWS
Beautiful two bedroom two bath luxury condo. Kitchen with granite counter tops and all stainless steel appliances. Bathrooms with granite counter tops and beautifully tiled bath/showers. This condo is located in Maui Kamaole One of Kihei best first class resort...
nPrivate, Walk to Beach, Golf, Shopping and Restaurants!
Located in Waikoloa Beach Resort at Vista Waikoloa.. Beach, Golf, Snorkeling, Seasonal Whale Watching, Shopping, Restauants, all minutes away!Our beautiful ground-floor condo, on the sunny/dry side of the island, is located in the luxurious resort of Waikoloa Beach. We...
Kahala Oceanside – Coastal Sanctuary with Panoramic Views
Kahala Oceanside is a private paradise retreat that comfortably sleeps 14. This luxurious ocean front hideaway on the South Shore of Oahu, known for its spectacular sunsets, is just minutes away from fine eateries, world-famous hikes, and the endless attractions of...
Professionally designed and remodeled in 2021! 2 master bedrooms, spacious plan
2025: New appliances (French door refrigerator with filtered cold water and ice dispensers, ultra quiet dishwasher) and outdoor sofas.2024: (2) New sofabeds!2021: Professionally designed and newly remodeled! No expense has been spared to make this a comfort. All brand...