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.
Wailea Beach Villas | E202
Warm breezes and lush tropical gardens greet guests of Wailea Beach Villas E202 as the spacious and comfortably appointed interior blends seamlessly onto the private outdoor lanai. Contemporary neutral and earth-toned furnishings are complimented by splashes of color...
NEW! Oceanfront Condo at Lawai Beach Resort
Welcome to our beautifully updated one-bedroom condo at the Lawai Beach Resort with AC! This is a wonderful opportunity to stay at one of the most sought after locations in the heart of sunny Poi'pu!The spacious living and dining area opens to your own private lanai...
Have it ALL! Spacious 2Bdrm 2Bath w/ awesome view, location & exceptional value
One of the best properties in West Maui with amazing grounds and fantastic views. New owners maintaining the tradition set by the previous owners of excellent quality throughout and spectacular service! We would love to host you in our paradise home!The highly...
Completely remodeled 2 bedroom King bed AC Kauhale Makai on the top flood
• Oceanfront• Central A/C • King bed and queen bed• Remolded March 2023• Beach access from condo complexWelcome to our home at Kauhale Makai 612. Our home was fully and immaculately remodeled in March of 2023. Our beautiful and pristine two-bedroom condo sits...
Rivendell Oasis-Peaceful garden setting with private hot tub close to waterfalls
This location is ideal for a visit to Hawaii Island's lush tropical east side. Close to all the amenities of town, yet secluded enough to only hear the sounds of nature. Located in a quiet secluded neighborhood at a cool elevation minutes from beautiful waterfalls and...
🏖️Ocean Front | Fantastic Ocean Views | Completely Upgraded | vrKCV🏖️
vrKCV - Alii Villas 131, Professionally Managed by Kona Coast VacationsWelcome to Oceanfront Bliss! Step into breathtaking, panoramic ocean views of the Kona coastline, including an unobstructed view of Kailua-Kona from this beautifully updated 2-bedroom, 2-bathroom...
3-Min Walk to Beach! Ground Floor - No Resort Fee
Just a 3-minute walk from the beach-cross the street and you're there from this first floor condo! Minutes drive to coveted Wailea beach and the area's best sunset views, shopping, and restaurants.★ No resort fee★ Private bedroom and bathroom★ Three beds★ Two...
3-Bedroom Available for MAY! 250 Steps to the Beach! MONTHLY DISCOUNT!
E komo mai to Hale Makai, our piece of island paradise in Kailua. Beachside and just three houses from Kailua Beach - you are going to love it here.Lying alongside a fabulous three-mile stretch of protected beach, Kailua is a small town on the windward side of Oahu....
Wai'ula'ula C102 - Magnificent Ground-Level Residence
This magnificent, corner, ground-level, oceanview residence offers a great room with sliding glass pocket doors for indoor/outdoor island living, a chefs' kitchen outfitted with stainless steel appliances and granite countertops, plus a dining area for six. Additional...
NEW! Experience oceanfront bliss at Napili Point A26
* NEW PROMO: Stay 5 or more nights from August 1st - October 25, get 1 FREE! Welcome to your home away from home! Napili Point A26 has an amazing location at the resort with oceanfront, and unobstructed views! This 1-bedroom, 1-bath features 2 split A/C systems that can...
The Emerald Turtle Room. Direct Oceanfront Studio, Maui.
"You will not find better views anywhere in Maui, for any price."Proud to be a "Superhost" for 12 years straight, we would love to share our Maui direct oceanfront studio with you. Our condo is situated about 10 feet from the water's edge with incredible ocean views. It...
Streaming with Sunlight 2+2 Hawaiian Villa
2 bedroom, 2 bath Villa with ocean views nestled in picturesque Kona Coffee Villas. Higher elevations, and mountainside complex presents an ideal setting for your Hawaiian Life Style. After a day at the beach, sink into one of two comfortable sofas in the living room...
Turtle Bay Villa G318
Welcome to Villa 318, one of the most spacious and luxurious properties at Ocean Villas and Turtle Bay. Nestled on Oahu's stunning North Shore, this tropical retreat is the ideal escape for families looking to relax and enjoy a slice of paradise. We look forward to...
Ukulele Oasis @ Kiahuna l AC l Family-Friendly l Beach Amenities l Ground Floor
Welcome to Ukulele Oasis at Kiahuna Plantation! New A/C Unit New King Bed Ground Floor/End UnitFamily-Friendly New Sofa Sleeper Beach AmenitiesAt Ukulele Oasis you’ll enjoy an unforgettable family-friendly vacation immersed in the island spirit in your private...
Ilikai 1 Bedroom City Views, minutes to the Beach!
This spacious 7th floor unit at the Ilikai Hotel offers comforts of home while on vacation. Relax on the cooler side of the building and enjoy the tropical breezes from the mountain. KITCHEN- Refrigerator- Cooktop/Oven- Microwave- Dinnerware, Glassware, Silverware,...
Discount ending soon! Ocean View - Deluxe Studio - Marriott's Ko’Olina
Discover paradise in our stunning Deluxe Studio at Marriott's Ko Olina Beach Club! Enjoy breathtaking ocean views from your private balcony while relishing the luxurious amenities and exclusive activities we offer.Our facilities include a relaxing adult pool, a kids...
Paradise found 2 bed, 2 bath renovated condo @ White Sands Village-Magic Sands
Paradise has been found in this beautiful two bedroom, two baths upgraded renovated condo in White Sands Village! Ocean view from this third floor condo with absolutely no steps to access the unit. Completely handicap accessible and no need to carry suitcases and...
Laid back cozy bungalow two bed air conditioning
Welcome to Hale Kai Hideaways, Bungalow D. This gently restored stand-alone vacation rental built in 1955, has two cozy bedrooms, a living room, kitchen and outdoor space and parking. Smack in the middle of Alii Drive, you can bike to town or walk across the street to...
Waipouli Beach Resort H201 - Presidential Suite Oceanfront Penthouse Luxury
Waipouli Beach Resort H201 - Presidential Suite Most Luxurious Penthouse Oceanfront on Kauai, Hawaii!The one-of-a-kind Waipouli Beach Resort H201 Presidential Suite is the Most Luxurious Penthouse Oceanfront Condo on Kauai, Hawaii! The Two-Bedroom Presidential Suite was...
Mauna Lani Point | A107
Welcome to your dream Big Island getaway at Mauna Lani Point A-107! This stunning one-bedroom residence offers breathtaking ocean views that will captivate you from the moment you step inside. Immerse yourself in a tranquil ambiance as you relax in the spacious living...
Spacious affordable 2br/2ba/3lanai remodeled condo, perfect location in Poipu!
If you are looking for a beautiful, spacious, incredibly clean, affordable condo with fantastic amenities located right in the heart of Poipu….you've come to the right place!! Pakele Kahakai or "Beach Escape" is what our family calls our dream Kauai home. This...
Walk to Golf 250' from your door. Swim, Play, Feel the Warmth of Caring Owner
Turn the corner, and head straight to paradise. This welcoming 2 Bedroom / 2.5 Bath airy and bright condo is yours to enjoy with your family and friends. On a quiet side of the active stay-and-play Waikoloa Resort area, Waikoloa Colony Villas is the perfect place to...
Gorgeous Beach Front Home with Amazing Sunsets
30 Day minimum @ $7800.00 monthly. Wake up each morning to the soothing sounds of the waves and go to sleep after watching a memorable sunset , relax and enjoy the breathtaking sunsets on the beautiful beaches of Makaha. Step right outside to the beach from the home,...
Honoiki Hale Hou ~ Princeville Resort Residence ~nOn Makai Golf Course
Princeville, above Hanalei Bay... Rated "Best In Resort" Location and Condition!Stay Luxuriously on the Makai Golf Club Course 2nd fairway. Book now, new dates have opened!Our action packed community surrounds itself as a Bluff above the Bay and Ocean with views...
B209: Ocean Views from every room of this Ko Olina Beach Villa!
Beach Tower villa 209 has a spectacular view of the sunset! Its location is superior to all other units in the complex because it is truly beachfront. Beautifully decorated with high end furnishings, two very comfortable sofas and a beautiful dining area. The master...
KBM Resorts | FREE CAR | Honua Kai Hokulani | 1-Bedroom Condo at Beachfront Resort, Pools, Hot Tub & Spa! HKH-424
Updated 1-bedroom, 1-bath villa at Honua Kai with scenic mountain views, spacious lanai, gourmet kitchen, luxury king suite, and resort amenities including pools, fitness center, and beach access.** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii...
KR405-Beautifully Remodeled Beachfront Condo with Park and White Sand Beach!
Beachfront Kealia #405 is a remarkable vacation rental that has recently undergone an impressive renovation. Upon entering, you are welcomed by a beautifully designed space featuring travertine tile flooring in the living area and bamboo in the bedroom. The kitchen is a...
🌴Immaculate, ocean view townhome offers quiet island living, located in Na Hale O Keauhou🌴
Immaculate ocean view townhome! Ocean views, epic sunsets and poolside afternoons: That's what a true Hawaii vacation is all about. This immaculate, three-bedroom townhome is set in the quiet, gated community of Na Hale O Keauhou just a mile from Kahaluu Beach, Kona...
Beautifully remodeled 2 Bd, 2 Bath Condo, short walk to the Beach
This spacious two bedroom, two full bath condo is located in the perfectly manicured, lush landscape of Kihei Garden Estates. The fully remodeled, 850 sq ft top floor unit, has an open floor plan and a lanai with a table and four chairs that overlooks the pool and...
❤️PiH❤️ Hale Moana★ Private Pool & Spa ★ Detached Ohana Suite ★ eBikes ★ water slide
Brought to you by Paradise in Hawaii Luxury HomesWelcome to Hale Moana!Hale Moana is a brand new exquisite 4 bedroom, 4 1/2 bath home located in Hapuna Estates within the Mauna Kea Resort. Prepare to embark on a truly remarkable escape where luxury, comfort, and natural...
New! Kailani #213, Oceanfront, Sunrise and Moon Rise Views!
Welcome to Kauai Kailani #213, Kapaa, Kauai Vacation Rental.Escape to paradise in this charming oceanfront condo located on Kauai’s stunning Royal Coconut Coast. Perfectly positioned within walking distance to delightful shops, restaurants, and coffee houses, this...
Poipu Crater 23 - Vacation in the Crater/Air Conditioning in Bedrooms
POIPU CRATER 23 AT KOLOA KAI VACATION RENTALSA Tropical Retreat in an Extinct Volcano CraterDiscover the unique charm of Poipu Crater 23, nestled amidst acres of lush tropical foliage in the heart of Poipu. This two-bedroom duplex condo offers the perfect blend of...
Maui Stunning Beachfront Luxury Ground Floor with A/C. *Nani Kai Hale 101*
Stunning luxury, ground floor condo directly on Sugar Beach, one of Maui's best beaches. The unit was completely remodeled floor to ceiling in 2017 and includes 2 bedrooms (1 king, 1 queen) each with en-suite bathrooms, a full luxury kitchen, living area with large...
FROG POND Cozy, streamside family cabin for 3 - 4
Family friendly. Be immersed in nature at our peaceful, cozy stream side retreat. Located next to the Waipio Lookout, our Hamakua Coast rain forest property is the perfect place for two adults with two children. Hear the rush of our waterfall and adventure in our...
Relaxing oceanfront home overlooking Kaneohe Bay
Take in the expansive ocean views and relax in this 3 bedroom, 1 bathroom downstairs unit just steps from the ocean! The unit is fully furnished, includes a full kitchenette with a 2 burner induction cooktop, a countertop convection oven (can cook up to a 20 lb...
Luxury 5 BR Estate over Beach w/ Huge Views, Pool, Hot Tub - TVNC#4201
Welcome to Hale Mana, one of Kauai's most beautiful island treasures. This stunning three-acre private estate will bathe you in every luxury with its beautifully appointed amenities, secluded beach, and tremendous ocean views.If you are looking for Hawaii's best...
A Piece of Paradise at The Beach Villas in Ko Olina 2 Bedroom 2 Bath
Aloha and welcome to the Beach Villas at Ko Olina!The Beach Villas at Ko Olina are in the World-Famous Ko Olina Resort and Marina on the second of the four spectacular lagoons. You’ll enjoy the mile-and-a-half walkway along the lagoons, passing the Four Seasons...
Three Bedroom Villa at The Beach Villas at Ko' Olina
* Book with confidence! This vacation rental is a LEGAL Oahu vacation Rental Operating in a Resort Zoned District and is not affected by passage of Bill 89. This Luxury Condo is a spacious and beautiful 3 bedroom, 3 bath, professionally decorated Villa with a beautiful...
Beautiful home in Kailua-Kona with easy access to all the Island.
Our 3 bedroom 2 bath vacation house is conveniently located just 5 minutes from Kailua-Kona town and its many shops, restaurants and grocery stores. You are just 10-15 minutes from many of Kona's most popular beaches, snorkel spots and activities. Only 15 minutes from...
Stunning KoOlina Kai 2BR/2BA Condo sleeps 4
This vacation rental is a LEGAL Oahu vacation rental operating in a Resort Zoned District and is not affected by the passage of Bill 89. This property has a mandatory 30 day minimum. This property may not be rented for less than 30 consecutive days. Rental prices will...
Oceanfront condo with resort amenities, stunning views, and top-notch comfort
Ali'i Cove Y1Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Experience luxury living in this stunning condo located in the exclusive Ali'i Cove Condominium complex in Kailua-Kona,...
Puna Rainforest Retreat Hotspring - Blue Ginger Cottage
Puna Rainforest Retreat Blue Ginger Cottage has a complete kitchen with all the amenities, a full bathroom and cozy queen size bed. Perfect for couples. This colorful cottage is clean, comfortable and affordable! Enjoy the rainforest trail, steam vents, plunge pool,...
Oceanfront, Split A/C, incredible sunsets, king bed, remodeled October 2023
• Oceanfront• Split A/C units• King bed• Remolded Oct 2023• Beach access from condo complexFully remodeled in October 2023, this custom built, detailed, upscale condo 209 welcomes you. You will find this bright, beautiful one bedroom, one bathroom oceanfront...
Wailea Elua 1308 - Direct Beachfront Luxury Condo in the Heart of Wailea, Maui
Introducing: Wailea Elua 1308. Offering a front row beachfront location, this immaculately maintained unit features unobstructed ocean view corridors, privacy, convenient access to the Wailea Beach Path, and one of the world’s best beaches as the front yard....
Ka Hale Kealoha A215
Welcome to Molokai Shores luxury condo Ka Hale Kealoha A215! This beautifully updated (and freshly painted Sept 2021!!) 526 sq ft condo boasts high end appliances as well as a fully equipped kitchen with everything you would ever need. Sleeps 4 in a brand new (9-2021)...
Prince Kuhio 110 - Ground Floor Portable AC
PRINCE KUHIO 110 AT KOLOA KAI VACATION RENTALSA Romantic Escape on Kauai’s Sunny South ShoreDiscover the charm of Prince Kuhio 110, a recently remodeled one-bedroom condo offering a cozy and modern retreat for couples. Located on the ground floor with easy access to...
Fully Remodeled Hanalei Bay Villa #34 w/ Amazing Views!
Hanalei Bay Villas are located on a bluff with incredible mountain and ocean views and just a short walk away from the new 1 Hanalei Bay Hotel. Villa #34 has been completely remodeled and designed in cool neutral tones with a clean modern vibe. All new, high end...
Aolani House+ Cottage | #1 AirBnb on Big Island | Condé Nast
Aolani House & Coffee Cottage – Your Private Hawaiian SanctuaryNestled in the serene coffee farms of Holualoa, Aolani House & Coffee Cottage offers an exclusive retreat for relaxation and rejuvenation. Perched on 5 private acres of Kona Coffee and Macadamia Nut farms,...
Open-concept and modern decor with ocean views
Nestled within the breathtaking Kapalua Bay this exquisite 1-bedroom, 1.5-bathroom villa that can accommodate up to 4 guests, effortlessly combines modern comfort, breathtaking ocean views, and practical amenities for a truly unforgettable vacation experience. Kapalua...
Mar- May special rates. Eco friendly modern home, gorgeous Ocean & Mt views
Welcome to Island Sunset Villa, where modern luxury meets nature’s finest. This tranquil eco-friendly home is nestled on 2 acres of lush, organic orchard, offering the perfect blend of seclusion and convenience. Step inside this architectural gem, where walls of...