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.
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 RATES10/22-10/31-$650 PER NIGHT!!!NOV & DEC -$950 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 book in confidence COVID guarantee is...
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 Resort Rentals: Honua Kai Konea 338 – Luxurious 1BR Suite w/ Upgraded Interior and Tranquil, Private Location
Konea 338 is a luxurious one-bedroom suite that offers glimpses of the Pacific Ocean and Honua Kai's lush grounds. Enjoy relaxing in the suite's upgraded interior or on the spacious lanai because this suite has one of the most tranquil, private locations in the entire...
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...
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 30 Day rental
Your Private Beachfront Retreat in Haleiwa – 30-Day Minimum Stay Escape 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...
Valley Isle Resort #105 - Oceanfront Condominium
Free Wi-fi, Free Parking, No Resort Fees**Brand New Split AC System installed**Valley Isle Resort #105 is a charming ground floor 1-bedroom unit situated along Maui's picturesque western coastline. This cozy retreat features a queen bed in the bedroom and a convenient...
❤️PiH❤️ SEA GLASS★ Best Views ★ Private Heated Pool★
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to Sea Glass House, a part of our Hawaiian Luxury Collection.Sea Glass House at KaMilo is the pinnacle of luxury at KaMilo and was built on the best lot in KaMilo for privacy and views.It is surrounded by...
Hale Kipa Ohana
Experience our Beautiful town of Waimea in this 3-bedroom 2 bath home on a one acre parcel. This home gives you the Country tranquil setting of the Kohala mountains surrounded by the lush green outdoors. A great yard to play volleyball and any outdoor sports. A play...
Kauai Beach Resort~Beautiful Mountain View
**Please read 'Other Things to Note' in listing** Capture the tranquility and beauty of the Garden Isle from this charming, centrally located condotel unit at the Kauai Beach Resort. From your private lanai, take in Kauai's lush landscape and majestic mountain views,...
Exceptionally Pristine Haleiwa North Shore Beachside Retreat
FIND PEACE & ESCAPE FROM STRESS HERE. -This is considered one of the best North Shore neighborhoods! Avoid most of the North Shore's traffic mess by not having to drive past popular "Turtle Beach". The large Winter surf is still down right now and diving, paddling &...
Poipu Pili Mai 9B, Flexible Cancellation, 4 bdrm, AC, Sunset/ Golf Course View
This is a 3 story building with our 2 story unit located on second and third floors with entry to condo up a flight of stairs. We have four bedrooms, 2 on the second story (the condo's main floor) which are Master suites. While upstairs on the third floor there are two...
Gorgeous Fairway View Home w/Shared Pool, AC & Relaxing Lanai: Kamilo #123
Mauna Lani KaMilo #123 – A brand-new designer home in the heart of Mauna Lani Resort, Kamuela, offering over 2,400 SF of luxury living space. Whether you’re here to relax or entertain, this 4-bedroom, 3.5-bathroom home accommodates up to 10 guests, with ample room...
Exceptional Kona Reef Condo: Full AC, Oceanfront, Easy Walking Distance to Town
*New Listing* Oceanfront, fully updated one-bedroom condo in the Kona Reef Resort. AC throughout the entire unit.Perfectly located just a 5-minute walk from dozens of shops, restaurants, and beaches.As you walk through the door and see the deep blue ocean waves out the...
Alii Cove G3 Beautiful Ground Floor Spacious 2 Bedroom with AC
Alii Cove#G-3 is an excellent beautifully furnished option for your Vacation. This spacious 2 bedroom, 2 bath unit has fantastic features that many guests enjoy. A perfect option for up to 6 people. ~No stairs! Walk right into the unit, there are 2 assigned parking...
Beautiful, renovated Home. Discover the North Shore of Oahu. Great location.
Aloha!My name is Lindsey and I was born and raised right here in beautiful Laie, HI located on the world famous North Shore of Oahu. This is our personal family home and we will go going on vacation. I love this town so much, that once I got married and started a...
Kona Reef: B-15: Direct Beachfront, Pool/Hot Tub, Air Conditioning, Elevators
Located on the second floor, Kona Reef#B-15 offers stunning year-round views of golden sunsets and easy access to Honl's beach. Hear the crashing of the waves day and night! If what you're searching for is a private seaside apartment that's close, short walking distance...
Spacious 2Bedroom/2Bathroom Oceanfront Condo with Central-AC
This spacious end-unit ground floor condo at Royal Kahana Resort is the perfect place to relax and unwind on your Maui vacation. With two bedrooms and two bathrooms, it can comfortably sleep up to six guests. The condo features a fully equipped kitchen, a washer and...
Beauty, comfort, and value describe this one bedroom condo in sunny Poipu!
Beauty, comfort, quality, and value are what best describes this spacious renovated one bedroom condominium in sunny Poipu! This is a real gem with stunning ocean and mountain views from the lanai that backs up onto Prince Kuhio Park, a lush, quiet open space that meets...