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.
Maui Resort Rentals: Honua Kai – Incredible 6 Bedroom Oceanfront Gem, Over 4200 combined Sq. Ft. w/ Built-in Viking B.B.Q.!
This 6BR offering combines one of the finest 3BR oceanfront residences at Honua Kai, with a neighboring 3BR oceanview residence to create an epic gathering space, perfectly suited to larger groups and families. Each residence boasts stunning ocean views, abundant living...
3 BDR/3BTH Oasis | Dual Suites + Outdoor Kitchen
Modern Hawaiian Oasis with Dual Primary Suites, Outdoor Showers & Outdoor Kitchen – Waikoloa Beach ResortWelcome to your Big Island getaway!This luxurious 3-bedroom, 3-bathroom retreat in the exclusive Ainamalu community of Waikoloa Beach Resort is designed for...
2 BEDROOM @ Marriott's Maui Ocean Club
Conveniently set in the Kaanapali Beach Resort district of Lahaina, Marriott's Maui Ocean Club - Lahaina & Napili Towers is located a 8-minute walk from Kaanapali Beach, half a mile from Hanakaoo Beach Park and a 18-minute walk from Alii Kahekili Beach. The property is...
Kuleana Club #608 Oceanfront - 1 bd 1 ba - Gated
Summary:Located on Maui's tropical west coast, the Kuleana Club has a panoramic view of the Pacific and the lovely offshore islands of Molokai and Lanai. This unit is a ground floor oceanfront condo, only steps to the ocean, and surrounded by a plush Hawaiian garden....
Kaanapali Alii 136
Welcome to your dream luxury vacation rental in Lahaina! Kaanapali Alii 136 is a stunning two-bedroom Ocean Front condo that offers breathtaking ocean views from every room. Whether you're relaxing on the lanai, dining at the glass table for six, or enjoying a drink at...
Fully Remodeled Oceanfront Condo MAKENA SURF RESORT, #F-206
Makena Surf #F-206Discover the beauty of Maui’s southern coastline at Makena Surf #F-206, a luxurious 2-bedroom, 2-bathroom oceanfront condo that sleeps up to 4 guests. Set within a gated community of lush tropical gardens and pristine beaches, this retreat combines...
Honua Kai | 3 Free Rental Cars | KBM Resorts | Gorgeous Inner Courtyard | 3 Units, 5 Bedrooms | HK ML-1613
** 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...
Honua Kai | 2 Free Rental Cars | KBM Resorts | Most Stunning Views | 2 Units, 4 Bedrooms | HK ML-1850
** 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...
We are OPEN welcome back 536 GORGEOUS Studio Partial Ocean views from lanai
Welcome to Kaanapali Shores #536Located in beautiful and fabulous Kaanapali Shores, a AAA, triple diamond rated resort, on world famous Kaanapali Beach. The condo has a king size bed and a double sofa sleeper, central air conditioning, a fully equipped kitchen, an LED...
Relaxing 1BR Suite at WorldMark Kona — Your Big Island Base
Escape to Hawaii with this comfortable one-bedroom suite at WorldMark Kona in Kailua-Kona. Designed for up to four guests, it’s perfect for couples or small families seeking both convenience and island charm.Inside you’ll find a master bedroom with a king bed plus a...
Family-friendly 2BD 2BA 2 Parkings Honolulu Home
Summary:Newly built 2bd 2ba home. This charming unit offers all the essentials, including a convenient washer & dryer, making your adventure hassle-free.Prime location—just minutes away from popular attractions! Explore the famous Waikiki Beach or indulge in shopping...
Tantalus Glass House by Gather Modern Honolulu Retreat
Welcome to Tantalus Glass House by Gather, an architectural masterpiece perched high above Honolulu. This five-bedroom, five-and-a-half-bathroom estate combines modern design with lush tropical surroundings, offering a rare blend of privacy, sophistication, and...
Golf Villas Gold Partial Ocean View 1 Bedroom at The Kapalua Villas Maui
Nestled in lush gardens and beside pristine beaches, our secluded sanctuaries offer tranquility. Enjoy world-class golf, snorkeling, award-winning spa treatments, and farm-to-table dining. Experience luxury in our fully-equipped villas, with stunning sunsets from your...
PRIVATE OCEAN FRONT ESTATE ON TURTLE COVE, NAPILI - MOST SPECTACULAR LOCATION
THE MOST MAGICAL PLACE ON MAUI! SNORKEL WITH TURTLES,WATCH SURFERS FROM YOUR LANAI AND ENJOY EXQUISITE DIRECT OCEANFRONT DINING,TRULY A TROPICAL PARADISE!!Jacuzzi, Pool Table, Dry Sauna ....Locals tell us Papaua Paradise is the best location on Maui. We are located at...
Beach Getaway! Relax on Waikiki Beach, 3 Amazing Units, Restaurant
Looking for a beachfront getaway in Waikiki? Look no further than this convenient property! Just minutes from the most popular attractions, the excitement of Waikiki is all around you! And with comfortable amenities and authentic Hawaiian hospitality, you'll have...
Central Island Living | AC, Parking, Kitchen, W/D
Located in the vibrant community of Waipahu, this 2-bed, 2-bath condo offers convenient island living. Situated near shopping centers, local eateries, parks, and easy freeway access, this location makes exploring Oahu a breeze. The neighborhood is known for its...
Puka Pa 8 – 4BR Hualalai Estate with Ocean Views, Pool & Golf Carts
This thoughtfully designed 4-bedroom, 4.5 bath home is the ultimate in modern design and construction and just 6 minutes to resort amenities. All four designer-appointed bedrooms are under one roof and ample outdoor space invites activities such as cooking, TV...
Maui Ka’anapali Villas #273: One bedroom ocean vie
Maui Ka’anapali Villas #273: One bedroom ocean view on N. Kaanapali Beach with Pool and Beach Access. Maximum occupancy: 2Bright, open and spacious one bedroom loft condo with ocean views. The lanai is perfect for relaxing and enjoying the cool trade winds. The bright...
Wailea Elua Village 1509 - 2 Bedroom Garden View Condo
Wailea Elua Village offers tropical vacation condos set amid Wailea’s resort hotels, making it a perfect luxury destination. Enjoy easy access from this vacation condo at Wailea Elua Village to the restaurants and spas of the Wailea resorts via the picturesque...
Cabin in Kealakekua with kitchen
Enjoy indoor/outdoor living Hawaii style! The Bamboo Cabin offers a cozy room that opens onto a private veranda with its own kitchen. Your senses will delight at all the beauty which surrounds you. Take a nap in the hammock or catch some rays on your lawn. Explore the...
19th Floor Condo with Lanai & Sea Views - FREE Parking! by Koko Resort Vacation Rentals
Deluxe Ocean View Waikiki Condo - 1908-2, Free parking & Wi-Fi The pool and all associated amenities will be closed starting April 7, 2025,for an estimated duration of 10 to 14 months to accommodate the RecreationDeck renovation project. Watch the surf from your lanai...
Paradise Beach Estate: 6BR Oceanfront Villa w/ Pool, Spa & Views
Wake up to the sound of surf and the shimmer of the Pacific at Paradise Beach Estate, a six-bedroom, five-and-a-half-bath beachfront sanctuary in Honolulu’s coveted Diamond Head enclave. With 4,705 square feet of airy interiors, resort-style outdoor living, and...
Brand New Remodel, July 2016! Luxury Getaway With Stunning Ocean Views At the Ilikai Hotel
1 Bedroom Deluxe Yacht Harbor View on the 14th Floor!Enjoy stunning sunsets from your private lanai. This beautifully renovated condo has just finished renovations (with brand new stainless steel appliances and high-end finishing throughout the condo) & it desirable by...
H2-Seaview-6BR/3BTH-OceanView-Sleeps 12
Aloha! Welcome and relax with the whole family at this peaceful Kona Islander home. Enjoy a nice cup of Kona coffee, while looking out to the beautiful view of the ocean by day and sleeping to the sound of nature by night. Immerse yourself in nature and get the perfect...
Spacious 4 Bedroom Honolulu Stay 30 Night Minimum
Honolulu 30+ Night Island Retreat – Spacious 4BRHonolulu Monthly Rental – 4BR Extended-Stay Home Near Waikiki & Ala MoanaLive in comfort like a local in this bright 4 Bedroom, 2 Full Bath Honolulu retreat just minutes from Waikiki. Designed for comfort and...
On The Beach! Kahana Sunset C2 Stunning 2BR/2BA Beautifully updated Condo w/AC
Escape to this beautifully updated 2-bedroom townhome just north of Lahaina in Kahana. This inviting townhome features a primary suite with king bed and updated ensuite bathroom with shower. The guest room also has a queen bed (with an extra futon in the closet you can...
2 bdrm deluxe suite at Kauai Beach Villas, HI
Welcome to the paradise in Kauai Beach Villas 2 bedroom deluxe suite and 2 full bath is equipped with high end luxuries to provide a comfortable, memorable vacation experience. Wake up to the sound of the ocean and prepare for a full day of leisurely fun within the...
Beachfront Oasis- Walking Distance to Everything in S. Kihei!
November Special! Walk to everything in S. Maui!Kihei was unaffected by fires and everything is open! We have a special discount for November due to last minute cancellations!!Our condo is 45 minutes away from the disaster zone and is completely unaffected by the...
Marriott's Kaua‘i Beach Club | Three Studio Villas
Summary:Discover paradise at Marriott's Kauai Beach Club, nestled on the stunning Kalapaki Beach. Enjoy breathtaking ocean views from your villa, perfect for a relaxing getaway. This resort offers access to a beautiful beach, swimming pool, and various amenities....
Kapalua Bay Villa 19G4 Gold Oceanfront 1 Bedroom
- Villa closest to Oneloa Beach- One level condo with 19 stairs between parking and front door- Tile flooring throughout- Updated white kitchen with granite counters includes stovetop/oven, microwave, and refrigerator with ice maker, coffeemaker, cookware, tableware-...
New Listing | Maui Oasis at The Grand Champions unit 53
Forget your worries in the spacious and serene space. This recently refreshed bright, 1 bedroom, 2 bath condo is perfect for up to 4 guests to enjoy all of Maui's luxury establishments within walking distance. Retreat to the ground floor lanai where you will soak in...
Poipu Modern Luxury Home - Lo'i Hale
Escape to Kaua’i’s sun-drenched South Shore and experience island living at its finest in this beautifully designed 3-bedroom, 3.5-bath retreat just minutes from world-famous Poipu Beach. Nestled on a quiet cul-de-sac and surrounded by lush tropical landscaping,...
Charming 1BR Premium Villa with Island Views – Westin Ka‘anapali Ocean Resort
Step into island comfort in this 1-Bedroom Premium – Island View villa at The Westin Kāʻanapali Ocean Resort Villas. These villas typically span around 800–900 square feet, offering generous space for couples or small families to unwind in style. Inside, you’ll...
Kamaki House 4bed/3.5bath in Holualoa
Welcome to Kamaki House – your peaceful retreat in the heart of Holualoa, Hawaii. This beautiful 4-bedroom, 3.5-bath family home blends comfort, island charm, and stunning ocean views. Perfectly situated in Holualoa’s lush countryside, Kamaki House invites you to...
Luxurious KoOlina 2-bedroom, 2 bath beach villa located just outside of Honolulu
Discover comfort at our Oahu vacation resort. Pamper yourself at our premium vacation ownership resort, Marriott Ko Olina Beach Club, surrounded by clear blue waters and a picturesque lagoon. Our Oahu vacation resort is nestled within a beautifully landscaped, gated...
3 BedroomSuite, The Grand Islander Resort
Enjoy the glamour of this stylish, upscale place. Situated in one of the most desirable locations in Waikiki, The Grand Islander is an elegant 38-story tower soaring high above the area's legendary coastline. The Grand Islander offers access to 22-acre Hilton Hawaiian...
Maui Kamaole D211: Bright and open two bedroom condo in S. Kihei across fro
PROPERTY PROJECT: The upper pool will be closed from November 11th through November 21st 2025 to re-coat the upper pool deck. Bright and open two-bedroom garden view Condo. The master bedroom and bathroom are up in the loft which opens up to the living and dining areas....
The Lodge at Kukui‘ula - Cottage 1
The three-bedroom cottages at The Lodge at Kukui'ula on Kaua'i offer luxurious accommodations and exclusive access to the award-winning private club facilities and amenities of The Club at Kukui'ula, including the 18-hole Tom Weiskopf designed golf course, sprawling spa...
Beautiful central kihei two bedroom (MBG309)
Hawaii Tax ID: TA-156-046-3872-01**Charming 2-Bedroom Condo Across from the Ocean in the Heart of Kihei, Maui**Stay in this delightful 2-bedroom, 2-bathroom condo, perfectly located just steps from the beautiful beaches of Kihei. Situated across the street from the...
Maui Ka’anapali Villas #148: Studio garden view condo
Maui Ka’anapali Villas #148: Studio garden view condo at Beach Front Resort on N. Kaanapali Beach.This newly remodeled condominium is located on the ground floor, giving quick and easy access to the pool. This luxurious studio is furnished with a king-sized bed and a...
Maui Resort Rentals: Honua Kai - 5 Total Bedrooms, Ground Floor Interior Courtyard, Steps to Pools, Beach, BBQs!
Comprised of two adjacent ground-floor 2BR suites and a neighboring 1BR suite, this luxurious five-bedroom offering is the perfect gathering place for large groups and families. Each suite features an expansive interior, a private lanai with a large adjoining lawn area,...
Honua Kai | 3 Free Rental Cars | KBM Resorts | Mountain Views | 3 Units, 4 Bedrooms | HK ML-1838
** 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...
Royal Garden @ Waikiki Studio
Unwind in a tranquil setting near Waikiki Beach at Royal Garden at Waikiki, your ideal vacation retreat. Situated along the Ala Wai Canal, this European-style resort boasts a prime location for exploring Honolulu. From cultural sites and golf courses to hiking and...
New Listing, Oceanfront Paradise, Kona Isle D3, 1BR
Oceanfront Paradise – Kona Isle D3 | 1BR Retreat with Stunning Views!Welcome to Kona Isle Unit D3 – Your Perfect Oceanfront Escape on the Big Island! Ground floor unit, so no stairs! Located just steps from the Pacific, this beautifully updated 1-bedroom, 1-bath...
Kapalua Bay Villa 25G2 Gold Oceanfront 2 Bedroom
- Villa closest to Oneloa Beach- 1st floor villa accessible by 16 stairs from parking lot- Large oceanfront lanai off living and dining areas with direct lawn access- Tile floors throughout- Updated kitchen with granite counters and high end appliances – fridge with...
Discover Island Bliss in a Studio Villa at Westin Ka'anapali Ocean Resort
Escape to paradise with a Studio Island Villa at Westin Ka’anapali Ocean Resort Villas, the perfect retreat for couples or small families seeking luxury and adventure on Maui’s iconic Ka’anapali Beach. With its prime location, family-friendly amenities, and...
Wyndham Bali Hai Villas | 5 2BR Villas Sleeps 30!
Summary:This listing is for five 2BR/2BA suites at Club Wyndham Bali Hai Resort in Princeville, HI. Live Suite guests will have access to all resort amenities. Each suite sleeps up to 6 guests. - Photos are stock photos provided by the resort. Your suite may vary...
Lovely 2-bedroom Hawaiiana near historic Pāhoa Town close to Black Sand Beaches
Experience East side of the island in this 2-bedroom house near Pahoa. The cozy atmosphere and comfortable furnishings make it a nice retreat for guests. The home is newly renovated with brand new appliances, ensuring a pleasant stay. You're sure to make fantastic...
Seaside Sanctum: Work and Play
Step into a world where magic meets comfort at our unique and delightfully family-friendly condo. Here in Kai Lani, you have access to all the perks of the the Koolina resort with the creature comforts and space in your home away from home. We are community within a...
Waikiki high-rise Ocean view with free parking
Your home away from home in Honolulu with 1 bedroom. See the million-dollar ocean view room you've been dreaming of! Your room windows offer direct ocean views, allowing you to witness the sea, surfers, whales, sunsets, and more.This beachfront property is just minutes'...