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.
Summer sale! Fairways at Mauna Lani: Deluxe Island Getaway
10% discount for bookings 7 nights or more.The deluxe 2 bedroom town home will delight you and the island of Hawaii will not disappoint. Golf course view, private patio, 2 coaster bikes, resort pool and on-site gym. Enjoy the beautiful walking/running trails and the...
Relaxing Hawaiian Suite for a Exiting Getaway in the Upcountry of Maui!
The Makani suite is named after the wonderful trade winds we receive here on Maui! Enjoy the breeze in the front lanai rocking chairs while sipping your cup of coffee. Though this is our economy suite it is spacious and has all the comforts and amenities. Designed in a...
"The Happy Seal" Oceanfront House, watch seals sunbath from our deck while BBQ
[A legal rental of minimum 30 days]This is the story of a little beach house doing its part in preserving a sanctuary on this stretch of sand for the endangered Hawaiian monk seals. For many years the beach in front of the house was known as the home of a famously...
Pure comfort in Paradise!
Location is everything with this property. Not only is the beach right across the street, you are also a short walking distance from restaurants and shops of every kind. This unit is away from the street completely remodeled from top to bottom in 2020 and on the second...
MODERN HAWAII ⛳️ Luxe Remodel, Closest 3BR Kapalua Golf Villa to Beach & 4th Tee!
Modern Luxury at Kapalua Golf Villas – Your Ultimate Maui RetreatWelcome to Modern Hawaii at Kapalua Golf Villas, a rare three-bedroom, three-bathroom retreat offering over 2,000 sq. ft. of beautifully remodeled living space. Nestled in the front row of the...
Pili Mai Family Condo 5C, 3 Bedroom 3 Bath, Mountain View, Cool Lanai,
Pili Mai is the south shore's newest development and adjacent to Poipu's ocean view Kiahuna Champion Golf Course. Your dream vacation is waiting at this second story, 3 bedroom, 3 bath spacious condo. The lanai gives plenty of outdoor space to enjoy outdoor living for...
Aloha Waikiki Condo 2Beds, 2Baths, Free Parking.
Aloha, thanks for checking in our listing. A Newly remodeled penthouse 2 bedrooms and 2 full baths. There are 4 queen beds and 1 single beds, full kitchen with kitchenette. It's spacious 1,000 sq. ft. with 2 patio and 3 Air-Con. It’s on 17 top floor with beautiful...
Hale Nana Kohola – Puako Oceanfront Vacation Home
Hale Nana Kohola (Whale Watch House) Located in the heart of Puako, offers a tropical retreat that showcases the best of Hawaii and is perfect for a romantic getaway or a family vacation. Escape to the sunny Kohala Coast on the Island of Hawaii. Hawaii's perfect...
Maui's BEST AC Beachfront – Panoramic Ocean Views! No Cleaning/ Parking Fees
Free Parking | Free WiFi | No Resort FeesWelcome to your dream Maui getaway! Our stunning beachfront corner unit condo on Kahana Beach offers breathtaking panoramic ocean views with floor-to-ceiling windows and doors, filling your space with endless blue horizons. Relax...
ICC 41 Remodeled 3BD Kaanapali Cottage w Heated Pool
International Colony Club 41 NEW LISTING Spacious and Beautifully Remodeled Kaanapali Cottage, Rare 3Bedroom, 2Bathroom, Walk to the Beach! FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch...
Hale Leimomi: Luxurious Comfort + Pool + Views!
In this sparkling new villa, laid-back comfort harmonizes—beautifully—with the ultimate in luxurious appointments & upscale amenities. Extraordinarily spacious, with 3,902 square feet under roof, Hale Leimomi combines the elegance of a 4-star resort hotel with the...
Spacious 2bedroom/2bath Beach Front Condo
Royal Kahana end unit condo 620 offers what need to make lasting memories in comfort and private. The master bedroom includes King size bed, with private master bath and its own private access to the lanai. The second bedroom has 2 Full size beds. The condo is central...
Halehikiola: 3 BR, 2 BA House in Volcano, Sleeps 10
Aloha, we invite you to stay at our “house of new dawns.”Halehikiola was named for the refreshing way it evokes the Hawaiian value of Ka la hiki ola each morning as the house fills with light. As “the dawning of a new day,” Ka la hiki ola is the value of...
One Bedroom Oceanview Deluxe Luana Kai A202
Aloha!Welcome to Luana Kai Resort Unit A202. As you walk into the unit you are drawn to the direct unobstructed panoramic views of the ocean where the beach is just a very short walk away, across from the greenbelt of the Waipuilani Park without having to cross any...
Beautiful Pili Mai Condo-2 Bdrm + sleeping den, sleeps 6, with A/C
Relax and enjoy modern living at Kauai’s newest townhome community, Pili Mai! This condo, also known as Nani Ka Hale, is located on the second and third floor of the building. It overlooks the lush greens of Kiahuna Golf Course and offers stunning distant ocean views...
Waikiki Sunset Hotel remodeled unit with a magnificent view of the Koʻolau Range
**Looking for other accommodations, please view my other unit located in the same building #2773517**This unit is located on a high floor of the Aston Waikiki Sunset Hotel, this condo offers one bedroom (one king size bed), one bath, expansive living area (queen sofa...
This modern Princeville gem shines in comfort, luxury, and design
This modern Princeville gem shines in comfort, luxury, and design. Artfully remodeled and curated by published designer, special features include a stylish sunken living room and open concept living area with twenty-foot beamed ceilings. Relax inside with AC and ceiling...
Kihei Akahi D614 -Top Floor/Panoramic view-Hotel zone- Full A/C Owner managed
Kihei Akahi D 614 is a top floor condo across from Kamaole II Beach Park with views of the ocean and outer islands of Molokini, Kahoolawe, and Lanai, renovated and fully stocked with everything you could need for a complete tropical vacation. ELECTRONIC KEYLESS ENTRY...
Relax in this OceanView Estate w/ Lava stone-lined Infinity Pool & Private Spa
September 15 – Mid-November, 2025The Hualalai Resort Spa will be undergoing enhancements to the outdoor aqua-thermal areas of both the men’s and women’s locker rooms. During this time, massage, body, and facial treatments will be temporarily relocated to the...
Hale Kai - Large Enclosed Lanai - Sleeps 2
Hale Kai - Spacious Enclosed Lanai - Sleeps 2Welcome to Hale Kai, your “Home by the Sea” in the charming Kuilima Estates East community. This beautifully designed island-style retreat offers 875 square feet of living space, including a large enclosed lanai, perfect...
Pineapple Cottage B&B Vacation Rental Haiku Maui, Lic#BBPH2015/0011
Pineapple Cottage enjoys a 5-star rating. Enjoy peace and quiet overlooking a private gulch and stream with a bit of with ocean view. Pineapple Cottage offers hardwood floors, shaker cabinets, granite countertops, newly purchased leather sofa, and a covered lanai with a...
Mahina Cottage, Mahina Cottage
Mahina Cottage is a charming and romantic Thai-inspired guest house. It is perfectly set up for a truly rejuvenating stay or intimate retreat.This marvelous accommodation is for the nature-lover who enjoys luxury. It boasts a large bamboo-rail deck which looks out onto...
Spacious 2BR Best Ocean Views -Kapalua Golf Villas 11P 5-6
This is a legally permitted vacation rental according to the County of Maui ordinances.Oceanfront Bliss & Golf Course Serenity – Kapalua's Premier Escape AwaitsE komo mai (welcome) to the Hawaiian escape of your dreams, where every sunrise whispers serenity and every...
Breathtaking 1 Bed True Oceanfront Retreat Maui
Aloha, E komo mai (welcome) to Napili Point Resort Unit A13 in West Maui, Hawaii"You will absolutely LOVE this privately owned, Spectacular, 1 Bedroom Oceanfront Condo (A Unit) at the exclusive Napili Point Resort in Maui". - Actual quote from a guest. Bring your...
Tropical style Luxury Townhome, newly renovated - Paradise!
Located in Princeville on the island of Kauai, this beautifully fully redone property will have everything you will need for your vacation in one of the most beautiful places.The master bedroom features a king bed, television and an en suite bathroom. The second bedroom...
☼ Stylish & Bright 2bd Oceanfront Condo｜5★ Views
Step into the comfort of this stylish 2BR, 1Bath condo in the heart of Maui, Hawaii. Located right on the oceanfront, just steps from the beach, this is your perfect retreat close to top restaurants, attractions, and stunning beaches!Enjoy modern design, breathtaking...
Waikīkī Beach Loft Near Restaurants
Stay close to Waikīkī Beach, minutes to Fort DeRussy Beach Park. Our 2-bedroom designer loft is in a secure building with a free offsite parking pass. Highlights include a full kitchen, unique wet room, beach gear, kids accessories and onsite laundry room. Find an ABC...
Largest Ocean Villa at Turtle Bay! Fully Renovated 4BR w/ beach, pool & hot tub
Ocean Villa G218 is the largest and most luxurious 4BR/3BA unit at the gated Ocean Villas at Turtle Bay. With ocean-facing views, spacious interiors, and elegant design, it offers privacy and comfort just steps from the beach, pool, dining, golf, and hiking trails....
Waikiki Ocean View with AC, Full Kitchen, Washer/Dryer, FREE Parking & Wi-Fi!
Waikiki Skytower #2604 – 2410 Cleghorn St.(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)Enjoy magnificent Pacific Ocean views from this contemporary, updated high-floor, one-bedroom condo (585sf plus 90sf lanai with table & chairs)! With only 4...
Kailani #315, Top Floor, Walk to Kapaa Town and Beach, AC
Kauai Kailani #315, Kapaa, Hawaii. Kauai vacation rental conveniently located in Kapaa Town on Kauai’s Royal Coconut Coast. This cute boutique condo is walking distance to the ocean, shops, restaurants, coffee shops and more! No Resort Fees.Newly remodeled Unit! Two...
Ground floor just steps away from sandy beaches
Hono Kai A4 is a ground-floor, 1-bedroom, 1-bathroom condo that offers a portable A/C in the bedroom and ceiling fans throughout, which helps to keep you cool. Unit A4 can accommodate up to 4 guests. The bedroom presents a queen-size bed, while a queen-size sofa sleeper...
Maui Resort Rentals: Honua Kai Hokulani 112 – Super Quiet and Private Ground Floor 2BR, Easy Access to Pools, Beach, and BBQs, Large Lawn Area!
Boasting a convenient ground-floor location, Hokulani 112 features numerous upgrades throughout and offers partial ocean views from the large adjacent lawn area. Enjoy easy and convenient resort access with the pools, beach, gourmet market, and BBQs just steps away.The...
Outstanding modern condo with ocean view in Kihei
Hale Kamaole 241 is a 1-bedroom,1-bathroom second-floor condo featuring amenities such as a covered private lanai, air-conditioning, and a washer/dryer. This condo accommodates up to 2 guests with a King-size bed in the bedroom. The main living room has a lovely...
Laule'a 'Ohana Hale - Luxurious 'Ohana home with A/C
Laule'a 'Ohana HaleWelcome to Laule'a 'Ohana Hale, Princeville, a luxurious and luxe vacation rental home on Kaua'i! This home boasts impressive panoramic mountain views from the main living areas, lanais and primary bedroom suite. Wake to glimpses of Hanalei waterfalls...
Hale Ka Nani stunning ocean and mountain views, 1 bdrm/1 bath kitchen & laundry
Minimum 31 day stay required. Hale Ka Nani, which means “beautiful house” in Hawaiian, is situated on 3.3 acres in the private, gated community of Kohala Ranch on the beautiful Kohala "Gold" coast. Kohala Ranch is a large 4,000 acre secure/gated “working” ranch,...
Waikīkī Shore 404 - Studio Waikīkī Beach View
Castle Waikīkī Shore Unit 404 offers all the comforts of home on your Hawaii vacation: a fully equipped kitchen, air conditioning, WiFi, mounted flat screen television, washer/dryer, and private lanai. The unit is tastefully furnished with beautiful koa wood furniture...
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...
First-floor condo across from Magic Sands with balcony, pool & sauna
White Sands Resort #108Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'The soft, white sand of Magic Sands Beach Park is right across the road from this completely remodeled...
Enjoy Grand 2BR, 2 Baths, Executive Condo Near Beach and Everything Else
Discover Luxury Living in Honolulu Near the Beach and Everything ElseWelcome to a stunning 2-bedroom, 2-bathroom, fully furnished rental perched on the 15th floor of Yacht Harbor Towers in picturesque Ala Moana, nestled between Waikiki and Kakaako. This spacious 1500...
OPEN! REDUCED RATES FOR MAY!! nHonua Kai Ground Floor LUXURY
BOOK NOW ! REDUCED RATES10/7-10/31-$950 PER NIGHT!!!9/1-9/14 & 9/20-9/26-$650. PER NIGHT!!!8/5-8/31 $750. PER NIGHT!!!This is ground floor unit Konea 102 at Honua Kai. Currently, new bookings in my units through VRBO come with my book in confidence COVID guarantee. My...
Hawaiian Charm..Just Steps From The Ocean..On Kauai's Sunny W Side * TVNC4216
PROPERTY OVERVIEW: House, 2 Bedrooms, 1.25 Baths, (Sleeps 4)The Nene Nest, Kauai is a classic, sugar plantation- style cottage located on the always sunny West Side of Kauai. Just 152 steps from the ocean, it offers a true Hawaii feel. Designed with a 'slow' pace in...
Maui Eldorado ~ J-106 ~ Walk-Out Ocean Views
This is a legally permitted vacation rental and hotel zone according to the County of Maui ordinances. Breathtaking Ocean Views, Spacious Lanai, and Exclusive Beach Cabana at Maui EldoradoE Kō Mo Mai (Welcome) to your perfect Hawaiian retreat at Maui Eldorado, where...
Wailea Ekahi 40A - 5-Star South Maui Oasis
Welcome to your piece of paradise in a completely remodeled, fully furnished, ground floor unit! Our home is located in Wailea Ekahi, one of the few Kihei and Wailea properties located directly on the beach; no need to cross a road or even sidewalk!Our private corner...
The Wave at Kapalua, Ocean10th Hole Golf Course Views NEW Full Remodel late 2022
3 years in the making completely remodeled top to bottom, new everything as of Aug 2022, "The Wave At Kapalua" is your perfect Maui vacation condo with an ocean view! Designed with an elegant tropical whimsey, bright, and colorful, with accents and attention to detail...
Maui Resort Rentals: Hilton Maui Bay Villas - Brand New 2BR Penthouse Oceanview Suite!
Nestled among 27 acres of lush tropical gardens, the Hilton Maui Bay Villas is a luxurious, secluded resort located on South Maui's sun-drenched coast. Situated minutes from several upscale resorts, pristine beaches, and championship golf courses, guests will enjoy...
Pili Mai 11K: Luxury Condo w/ Community Pool, Hot Tub, AC & Ocean/Golf Views
Set on the lush Kiahuna Golf Course with panoramic mountain views and the Pacific just beyond, Pili Mai 11K is a spacious three-bedroom retreat on Kauai’s sunny south shore. Recently upgraded with new furnishings, central air conditioning, and high-speed Wi-Fi, this...
1 Mile to Magic Sands Beach: Kailua-Kona Cottage
Beach Equipment | Natural Lighting | Quiet Neighborhood | 5 Mi to Downtown KonaClear the calendar and say 'Aloha' to your next tropical getaway at this 1-bedroom, 1-bath vacation rental cottage in Kailua-Kona. Perched on the west coast of the Big Island, this quaint...
Hidden Jewel Beach front
Your Private Beachfront Retreat in Haleiwa – 30-Day Minimum StayEscape to your own slice of paradise at Haleiwa Beach on Oahu’s legendary North Shore. This charming one-bedroom, two-bath condo offers the perfect blend of comfort and island charm, with breathtaking...
Oceanfront at Sugar Beach Resort - #226
Our ocean front condo has unobstructed views of the ocean with the islands of Kahoolawe and Molokini in the distance. SBR#226 is in the middle of the second floor of Plantation Building at Sugar Beach. The Resort has large, free, off-street parking areas with easy...