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.
Honua Kai | 2 Free Rental Cars | KBM Resorts | Exceptional Value | 2 Units, 3 Bedrooms | HK ML-1439
** 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...
Kapalua Bay Villa 27B2 Gold Oceanfront 2 Bedroom
- Villa closest to Oneloa Beach- Split level loft style villa with no stairs between parking and front door- Tile floors throughout- Updated kitchen with granite counters, farmhouse sink includes – fridge with ice maker, stove/oven, microwave, dishwasher, cookware,...
New Home!+Napali Views+Pool/spa+Cold plunge+Sauna
Experience the essence of modern island luxury at Napali Sunsets, a stunning new home in Princeville. Designed with sophistication and comfort in mind, this retreat offers a heated pool, spacious covered outdoor lounge, and sweeping views of the Hanalei mountains and...
Tropical Bliss in Kailua
Welcome to your dream retreat in Kailua, a sun-drenched haven where tranquility meets convenience. This charming unit is part of a thoughtfully designed duplex, offering a perfect balance of privacy and community. Whether you’re here to relax, explore, or work, this...
Hilton Grand Vacation Club Resort/Spa Lagoon Tower
This 1 bedroom, 1 bath villa features a king bed in the master bedroom. The spacious living area includes a separate dining area, large television with cable and DVD player, and a queen-size sleeper sofa. Our 1-bedroom plus suite features all the comfortable features of...
Relax in Your 2 Amazing Units w/Partial Ocean Views, Pool, Minutes to Honolulu
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...
Kaanapali Alii 354
Welcome to Kaanapali Alii 354, your luxury vacation rental in the heart of Lahaina, HI. This stunning two-bedroom plus den condo offers breathtaking ocean views and a perfect blend of comfort and elegance. Ideal for families and groups, this short-term rental promises...
𝐅𝐢𝐧𝐝𝐢𝐧𝐠𝐌𝐞𝐢𝐥𝐢 Luxe Beachfront Kaanapali Residence Club+Amenities. 2BR
𝐇𝐘𝐀𝐓𝐓 𝐕𝐀𝐂𝐀𝐓𝐈𝐎𝐍 𝐂𝐋𝐔𝐁 𝐀𝐓 𝐊𝐀𝐀𝐍𝐀𝐏𝐀𝐋𝐈 𝐁𝐄𝐀𝐂𝐇 – 𝟐-𝐁𝐄𝐃𝐑𝐎𝐎𝐌 𝐎𝐂𝐄𝐀𝐍 𝐕𝐈𝐄𝐖 𝐕𝐈𝐋𝐋𝐀Welcome to...
Westin Kaanapali Ocean Resort North - Christmas & New Year's - Studio
Note, this listing is for a studio unit with a Saturday - Saturday stay. It is available for either one week, Dec. 21 - 28 or Dec. 28 - Jan. 4, or the entire 2-week stay. You are welcome to check in or check out on a different day, but will be charged for the entire...
Marriott Maui Ocean Club Napali Villas Beachfront Resort/Spa!
Marriottu2019s Maui Ocean Club - Napili Villas is one of the most popular timeshare resorts - and for good reason! Kids and kids-at-heart will get a kick out of the resort's 3.5-acre super pool complete with a water slide, waterfalls, and children's area. The poolside...
4-bedroom house in tranquil Keaau ~ HPP with pool ~ Authentic Hawaiian Oasis
About this spaceAolani Hale is a high quality local property and is a self-contained vacation destination! From the moment the remotely controlled gate swings open, it’s obvious that this is a place where once in a lifetime memories of paradise are bound to happen. As...
Large studio/bedroom unit in Haleiwa with beach access and next to the park.
Haleiwa is waiting for you at this studio unit. Inside, guests find a nice space featuring a cozy twin bed and a clean bathroom with a refreshing shower, all new renovated. The layout is simple and inviting, perfect for a relaxing getaway. Whether you’re unwinding...
Honua Kai Ocean View 1 Bedroom
Experience island living with panoramic ocean views from this comfortable one-bedroom condo on Maui’s Kaanapali North Beach. Perfect for relaxing after a day of exploration.Ocean View 1 Bedroom 1 Bathroom• Exclusive on-site provider with the only homes that meet the...
Kapalua Golf Villa 23T1 Gold Ocean View 1 Bedroom
- 1st floor villa with 3 stairs between parking in front of condo and front door- Carpet in living room, dining room, bedroom and tile floors in kitchen and bathrooms- Kitchen with black stainless steel appliances includes – fridge with ice maker, stove/oven,...
Pili Mai 6M by Gather: Garden-View Condo w/ Lanai & Beach Access
Tucked along the Kiahuna Golf Course in sunny Poipu, Pili Mai 6M blends resort comfort with Kauai’s signature indoor-outdoor ease. This single-level, three-bedroom, three-bath condo offers 1,478 square feet of bright, air-conditioned living space framed by golf-course...
Maui Resort Rentals: Honua Kai Hokulani 138 – Upgraded Large Ground Floor 1BR, Spacious Lawn Area + Easy Pools/Beach Access!
Maui Resort Rentals is proud to bring you this extraordinary 1BR Ground Floor Garden View Suite at the Honua Kai Resort, newly launched on 2/5/2025 to start taking reservations for check-ins starting 3/14/2025!Hokulani 138 is a luxurious ground floor suite with one of...
Kaanapali Alii | 122
Welcome to Kaanapali Alii 122, your perfect luxury vacation rental nestled in the heart of Lahaina, Maui. This inviting one-bedroom residence offers partial views of the sparkling Pacific and is located within the prestigious Kaanapali Alii resort. Whether you're...
NEW | KBM Resorts | FREE CAR | Hale Nalu At Montage Kapalua Bay, Sleeps 10! Oceanfront 3-Bedroom Condo with Daily Housekeeping, Spa! MON-6302
** 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 | 4 FREE Rental Cars | KBM Resorts | Well Appointed, Magnificent views | 4 Units, 5 Bedrooms | HK ML-1733
** 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...
Mauna Lani Point G202
Welcome to your dream vacation getaway at Mauna Lani Point on the beautiful Big Island of Hawaii! Nestled in a serene and luxurious setting, this one-bedroom ocean view condo offers an unforgettable experience.Mauna Lani Point G202 - This is the perfect place for golf...
Kaanapali Alii 4112
Welcome to Kaanapali Alii 4112, a luxury vacation rental nestled in the heart of Maui's exclusive Kaanapali Alii Resort. This stunning condominium offers a breathtaking view of the Pacific Ocean and the pristine white sand beaches of Kaanapali Beach. Immerse yourself in...
Whaler | 3 Free Rental Cars | KBM Resorts | Ocean View 2-bedroom Unit At The Whaler Resort | 3 Units, 4 Bedrooms | WH ML-1592
** 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...
*Honu Hale: Penthouse 2 BDR Ocean View Waikiki*
Experience breathtaking panoramic views from our spacious penthouse 2BDR/ 2 Bath condo. With floor-to-ceiling windows and two lanais, soak in the vibrant cityscape and sparkling ocean. Enjoy privacy with ensuite bathrooms and modern kitchen amenities. Access a plethora...
Kapalua Bay Villas | 2 Free Rental Cars | KBM Resorts | Large Master Suite | 2 Units, 3 Bedrooms | KBV ML-2014
** 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...
Ocean View Retreat Sauna • Yoga • Sound Bath 5 Bedroom Villa with Amenities
Oceanview Wellness Retreat — Sauna • Sound Healing • Movie Room • Yoga Dome - 30 day minimumWelcome to your breathtaking ocean-view sanctuary, where luxury meets wellness. Nestled in a serene coastal neighborhood with panoramic ocean and city views, this...
Palms at Wailea Villa 1103 Ocean View 1 BD 2 BA
- Ground floor unit- Kitchen includes stovetop, oven, microwave, refrigerator, dishwasher, coffeemaker, toaster, cookware and tableware- Spacious private 473 square feet deck- Bedroom with 1 king- Queen sofa bed in living area- 1022 square feet / 95 square meters-...
Waipouli Beach Resort Garden View 1 BD 2 BA
Surrounded by lush tropical greenery, this inviting one-bedroom condo offers a quiet island escape. Perfect for two, it features a private lanai and all the comforts of home Garden View 1 Bedroom 2 Bathroom• Kitchen features granite countertops, Wolf cooktop and...
Stunning Remodel I Kamaole Sands 5-207
Welcome to your perfect getaway in South Kihei! This beautifully designed and recently remodeled condo blends modern comforts with a warm, inviting atmosphere. Perfectly situated in the vibrant heart of the neighborhood, it’s just steps away from one of Maui's most...
New Listing: Waikoloa Hills 1203 – Sleeps 6, Newly Remodeled for Your Stay
Escape to the Big Island in style at Waikoloa Hills 1203, a beautifully updated 2-bedroom, 2-bathroom condo nestled in the peaceful Waikoloa Village community. This freshly renovated space features a brand-new kitchen and bathrooms, stylish new furniture, and crisp,...
VI 507 Maui Studio Retreat – Enjoy Panoramic Lanai Views Near Beaches, Shopping & Restaurants
FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch (seasonal), Dinner Sunset Sail, Snorkel Sail, Alpaca Farm Tour, Pineapple Farm Tour, and All Day Electric Bike Rental. (W1)*One ticket per...
A piece of paradise located in the heart of South Kihei.
This 1 bed, 1 bath condo located in Kihei Alii Kai is a meticulously designed living space that offers both comfort and convenience. Located in the beautiful area of Kihei, this condo provides a peaceful and relaxing environment.As you step inside, you'll be greeted by...
Hyatt Residence Club Maui, Ka'anapali, Top Floors and "BEST" Ocean Views
Available Jun 1-8 2024 and Jun 8-15 2024. Look no further for your Maui escape - the unrivaled beauty of Ka anapali Beach is just a few steps away at this highly acclaimed Hyatt Vacation Club property. The resorts sprawling grounds are home to everything needed to...
Kona Hawaiian Resort 2 Bedroom w/ POOL
At Kona Hawaiian Resort in Kailua-Kona on the Big Island's west coast, you'll feel transported to a simpler, unspoiled era. Designed to evoke the charming traditional Hawaiian island ambiance of the 1930s, the resort blends nostalgic details with modern amenities and...
Ka’anapali Royal C102 - Lovely 2BR Golf Course Condo, Easy Walk to Beach
Enjoy your dream getaway in the best of paradise in Maui, Hawaii, with this exquisite 1534 sqft ground-floor condo offering the ultimate in comfort and luxury. Designed to accommodate up to 6 guests comfortably, this home boasts two well-appointed bedrooms, each with...
Royal Sea Cliff Kona Ocean View 2 Bedroom
Surrounded by greenery, this two-bedroom condo offers a peaceful island retreat. Perfect for families or couples traveling together, and it’s just a short drive from beaches, dining, and town. Ocean View 2 Bedroom 2 Bath• Condos located on 6th and 7th floors •...
Awesome Kihei Beach Suites
Aloha!Wonderful location right across from the beach, with a wall to sit and enjoy the sunset. Shopping and many fabulous dining spots right at the end of the property driveway. Don't miss Fred's Mexican Restaurant for the ever popular Taco Tuesday!! Yummy tacos and...
Tower 2 Suite 1207 (1-Bedroom Condo) with Pool and Golf Course view
Mountain View Waikiki Condo With 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. This condo has the perfect sleeping...
Kona Wave Rider Studio Apt: Where Every Day’s a Swell Day
Tropical breeze or cool A/C? Your island base has it all.Your tropical hideaway (in a family-friendly neighborhood) is near it all. Walk to restaurants, shops, and the farmers' market. Chill with cool A/C or let the island air flow through the wide-open windows. You'll...
3 Bedroom Princeville Kauai Sleeps 6
Please Send An Inquiry Before Requesting To Book By Clicking The Contact Host Tab.This townhouse is situated in Princeville, less than 1 km from Princeville Golf Club Prince Course and 2.6 km from Makai Golf Course and 1.8 km from Sea Lodge Beach. The air-conditioned...
Kaanapali Alii 451
Welcome to Kaanapali Alii 451, a luxury vacation rental nestled in the heart of Maui's exclusive Kaanapali Alii Resort. This stunning condominium offers breathtaking views of the sparkling Pacific Ocean and the lush greenery surrounding the resort. Immerse yourself in...
Kaanapali Alii 1114
Welcome to Kaanapali Alii 1114, a luxury vacation rental nestled in the heart of Lahaina, Maui. This stunning 2-bedroom, 2-bathroom condominium is perfect for a family-friendly getaway, offering breathtaking ocean views and a prime location on Kaanapali Beach.Step...
2 Bedroom Lockoff Villa at Westin Princeville Ocean Resort Villas
Spread out with the whole family in this spacious two-bedroom suite.Set on pristine waterfront with the towering, verdant backdrop of Kauai’s Hanalei National Wildlife Refuge as a backdrop, Princeville puts wild shores and staggering mountains at your fingertips....
3-bedroom house close to beach
Make yourself at home in this 3-bedroom retreat. This adorable house features 2 twin beds and 1 king bed, perfect for a serene getaway. Enjoy the convenience of a washing machine, WiFi, and AC during your stay. With 2 bathrooms equipped with a shower, bathtub, and hair...
Kapalua Bay Villas | 2 Free Rental Cars | KBM Resorts | 180 Degree Views | 2 Units, 2 Bedrooms | KBV ML-1531
** 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...
Cozy Happy hill inn
This cozy, renovated Ohana (guest house) has 2 bedrooms and 1 bathroom in a comfortable space of about 46 ㎡ (500 square feet) and can accommodate up to 6 people.The private backyard has a BBQ grill, perfect for relaxing and outdoor dining under the stars.Magic Sands...
Spacious 1BR Mountain View Suite – Hyatt Kaʻanapali Beach Resort
Experience the beauty of Maui from this 1-Bedroom Mountain View Suite (Lower Floor Band: Floors 1–4) at Hyatt Vacation Club at Kaʻanapali Beach, located on one of the island’s most iconic shorelines. Perfect for couples or small families, this villa offers a serene...
Maui Lahaina 1 Bedroom Condo Sleeps 4
Please Send An Inquiry Before Requesting To Book By Clicking The Contact Host Tab.This newly updated (in February 2023) 1-bedroom, 1-bath ground floor condo is the perfect place for you and a loved one to spend your dream Maui vacation! The condo sleeps 4 people...
Serene Island Condo w/ Mountain View and pkng
This 1-bedroom condo in the heart of Waikiki offers a spacious open layout that can sleep up to 4 people. The unit is fully equipped with a kitchen that has all the appliances you need to cook up a meal, as well as a lounge area with comfortable seating. The Waikiki...
Royal Kahana Maui 814 Ocean View 1 Bedroom
- 8th floor condo with patio- 1 king bed and 1 queen sofa bed- Vinyl plank flooring in living room, dining room and bedroom. Tile flooring in bathroom and kitchen- TV with cable channels and DVD player in living room, TV with cable channels in bedroom- Complimentary...
Shaka Shack Maui-Ideal Paia location!! Clean Bright 1 bdrm 1 bath ohana with AC
DEAL LOCATION! This clean, bright, air-conditioned "Shaka Shack" cottage offers the best of Maui’s North Shore lifestyle — private, stylish comfort and ideally located in Ku‘au, less than one mile from Paia Town, Baldwin Beach and walking distance to Ku‘au...