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.
Breathtaking Ocean View 1 BR Condo with Free Parking!
Aloha from Midway Vacations! Our team of local hospitality experts is dedicated to turning your Hawaiian getaway into a reality. When you stay at one of our properties, you can count on a professionally cleaned and meticulously maintained experience. We're even...
Breathtaking ocean views from beautifully renovated condo on secluded beach in Kahana
This fully renovated, two-story condo with spectacular ocean views can be the perfect base for your West Maui getaway! Located in Kahana Outrigger, unit 4B1 lives like a home. Enjoy sunsets from your lanai, living room, and kitchen. The small complex has a shared pool...
Sugar Beach Resort - Ocean View, (Off Season Special Rates)
Beach Front Sugar Beach Resort, Ground Floor, Ocean View Unit. We recently remodeled this unit and it now represents outstanding quality. Enjoy all of the amenities in a clean, well kept property. The entire complex sits ocean front, there are no roads to cross, you are...
404 - Gorgeous remodeled oceanfront 1 bed/1.5 bath unit spectacular view!
This fourth floor oceanfront condo at the Kihei Surfside Resort is located on the sought after proximate ocean side of the building, and has a spectacular ocean view from the living room, dining area, lanai and kitchen areas. It is one of the larger one bedroom units...
Stylish Studio w/ Great Ocean Views & Near Beach!
Aloha from Midway Vacations! Our team of local hospitality experts is dedicated to turning your Hawaiian getaway into a reality. When you stay at one of our properties, you can count on a professionally cleaned and meticulously maintained experience. We're even...
Kona Alii#401 Beautiful 4th Flr corner condo w/ Elevators,INCREDIBLE LOCATION
Welcome to the listing page of our gorgeous Kona Alii, Unit#401! You are as close to the heart of Kona as it gets. Enjoy Hawaiian Living just above the excitement of Alii Drive. This complex is directly across from the ocean & the unit is recently renovated. A beautiful...
Kapili 52 Oceanfront Condo
Welcome to Koolkondo.com where you will experience luxury vacation rentals at its finest. Our stylish boutique hotel style condos and homes have it all. You will absolutely enjoy your home away from home with VIP concierge style services in modern island luxury! Our...
2-Bedroom Garden & Ocean Views!
Welcome to your slice of paradise! After your long journey, we know you will be ready to unwind. To make your arrival extra special, we have prepared an Aloha Basket filled with snacks and coffee, so you can relax right away.This spacious single level 2-bedroom,...
Kahana Village #19 Beach Front Luxury
Enchanting, elegant and romantic, Unit 19 is one of the most highly requested 3 bedroom beach houses at Kahana Village. We just remodeled our entire Unit with a brand new kitchen, new bathrooms and remodeled wet bar. Enjoy our new high-end Teak furniture out on the...
Reduced Rate at Private Tropical End Unit Townhouse w AC & Outdoor Lanai!
Absolutely the best location in Kauai with rare AC! Nestled next to the famous Princeville Makai Golf Course on the picturesque north side of the island, this beautiful end unit townhouse is close to all the natural beauty Kauai has to offer. Minutes from Hanalei Bay,...
Breathtaking Ocean View! 20% off Feb - Apr
Keep your eye open for last minute discounts!Relax with the whole family at this peaceful place to stay! Maui Sands is a low density property, a great location for a family vacation or a couples retreat. This upgraded condo sits directly over the ocean in the heart of...
Kuhio Shores #211 - Best Value Oceanfront Condo in Poipu!
This air conditioned two bedroom two bath oceanfront unit is on the second floor of Kuhio Shores condominium located in sunny Poipu, Kauai. Fronting a sandy bay this complex has as an elevator and offers some of the best surfing, body-boarding, swimming and snorkeling...
Waikiki Banyan Cozy Condo Suite - Ocean View + Free Parking!
Aloha from Midway Vacations! Our team of local hospitality experts is dedicated to turning your Hawaiian getaway into a reality. When you stay at one of our properties, you can count on a professionally cleaned and meticulously maintained experience. We're even...
Upscale escape with pool, hot tub & grill - near beaches & water sports
Maui Kamaole H110Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Luxury and privacy meet at this Kihei Condo, located in the condo resort known as Maui Kamaole®, and just minutes...
🏖️Top Floor | Nice Ocean View | Close to Town | vrKCV🏖️
vrKCV - Sea Village 3311, Professionally Managed by Kona Coast VacationsSpectacular Top-Floor Condo with Unbeatable Ocean and Coastline Views!Welcome to your perfect getaway at Sea Village! This top-floor condo, perched directly above the pool, offers unparalleled ocean...
🏖️Spacious | Lagoon View | AC | WIFI | vrKCV
vrKCV - The Shores at Waikoloa 115, Professionally Managed by Kona Coast VacationsWelcome to Tranquil Shores at Waikoloa #115Discover ultimate relaxation in this spacious 2-bedroom, 2-bath condo with picturesque lagoon views, nestled in The Shores at Waikoloa Beach...
Paradise is Here! Big Ocean Views in newly remodeled luxury condo
Condo 1504. This 2 bedroom 2 bath is perfect for your stay on Maui. Enjoy the sweeping ocean views from the lanai with some of the worlds best sunsets! This is one of the ONLY condos on property with panoramic ocean views. This unit has approx. 1100 square feet of...
New open concept Garden Delux Kiahuna, Partial Ocean View Retreat!
Celebrate Aloha and the tradition of Hawaii with a stay at our slice of paradise. You'll take a step back in time to a simple more relaxing period when you arrive at Kiahuna Plantation on the sunny south shore of the beautiful island of Kauai, 'The Garden Island'....
Pili Mai 2-Bedroom, 2 bath, A/C Condo unit 11G, Sleeps 6
Two bedrooms plus loft, 1 king bed, 1 queen, plus 2 twins in the loft, 2 full bathrooms, nice upgrades, washer and dryer in unit, lanai space, incredible views, great complex amenities.This brand new 2 Bedroom plus loft, 2 Baths condo is ready for your next vacation...
New Furnishings! Panoramic Ocean and Mount Makana Views with A/C
Pali Ke Kua 103 boasts unparalleled panoramic Hanalei Bay, Pacific Ocean, and Bali Hai Mountain sunset views from its oceanfront perch. The world-class views are said to be the most spectacular on the extraordinarily beautiful North Shore of Kauai and, many say, the...
Sandy Beachfront Cottage
This beautiful, beachfront cottage was remodeled and converted from a 1-bedroom unit into a spacious, loft studio that can accommodate 4 guests. The kitchen and bath feature upgraded fixtures, appliances, and marble counters that add extra charm and functionality to the...
Corner penthouse, oceanfront prime views! Great kitchen+bath.
Alii Kai 5301 occupies a prime top floor corner because you enter the building at the second floor level, you've got just 13 steps to climb to reach your door! Inside this updated Princeville condo you'll find elegant appointments and comfortable tropical furniture. The...
Luxurious Seaside Retreat ~ Heated Pool & Jacuzzi
Wow... this condo is truly AMAZING. This Top-Floor End Unit is Quiet & Private. Geared specifically towards Travelers who enjoy the FINEST ACCOMMODATIONS while Vacationing in PARADISE. Picture Perfect & once inside, it's the Lap of LUXURY. Enjoy the Trade Winds from...
Laniakea Beach House – Oceanfront Bliss on Oahu’s Turtle Beach
- Laniakea Beach House - NUC 90-TVU/0373 or 1990/NUC-2113- NUC Registered. Recently remodeled to reflect a stylish Hawaiian beach videUltra High Speed Internet Spacious and sunny family home on stunning “Turtle Beach” – Amenities include large deck, hot tub, outdoor...
Westin Ka'anapali 1 bedroom guaranteed Ocean View as low as 350 per night
Book a whole week for 2900 or nightly for as low as 350 per night. (Check calendar for availability)The luxury vacation villas at this resort feature large lanais, stone flooring, granite counter tops, roomy bathrooms, fully equipped kitchens, washer/dryer, and the...
Kepuhi Beach Resort #2202--Paradise Found
Located on Molokai’s West End in Kepuhi Beach Resort, our beautifully remodeled ocean-view condo has everything you need to experience your aloha paradise. The king size bed in the bedroom loft and accommodates up to 2 guests comfortably. Enjoy the sunset over the ocean...
A Premier Tropical Retreat at Kamaole Sands
Our condo is a distinctive one-bedroom, two-bath end unit vacation condominium rental (5-301) at beautiful Kamaole Sands, across from popular Kamaole III Beach Park in South Maui.........Smoke free condo and lanai. Top 'Superior' rating from our property management...
2 Bedrooms / 2 Bath Oceanfront Cliff House On Hamakua Coast
The unique and extraordinary Cliff House of Laupahohoe is a perfect retreat for someone who wants the 'real Hawaii' experience and to get away from it all. The Pacific Ocean is your constant companion from almost every room in the house. The property excels in location...
REMODELED-LARGE LANAI-GROUND FLOOR-AC-OCEAN VIEWS-METICULOUS CLEANING
Book with confidence, Wailea Ekahi 46 B is a brand new luxurious 1100 sq. ft. condo. This condo is managed by PMI Maui, a local Real Estate Brokerage that specializes in vacation rentals. We are located within a mile of the resort and available 24/7. We are committed to...
KBM Resorts | FREE CAR | The Whaler | Renovated 1-Bedroom Villa with A/C, Beachfront views! WH1-211
** 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...
Simply the Best: Oceanview 3rd Floor Kaha Lani Condo – 1 Bedroom, 1.5 Bath with Private Lanai!
Welcome to Simply the Best, a third-floor oceanview retreat at Kaha Lani on Kauai's stunning Royal Coconut Coast. Tastefully updated with subtle coastal touches and Hawaiian-style furnishings, this bright and breezy condo invites you to relax, recharge, and soak in the...
Resort-style home with pool & hot tub access - near beach & golf
Waikoloa Colony Villas 1104Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Enjoy peace, quiet, and all the pampering you need with this upscale Waikoloa home. You'll be only a short...
Wailea Ekahi 33A 1bd/2bth, luxury, remodel, 3 min walk to beach, many amenities
Wailea Ekahi 33A is a beautiful, romantic, family friendly, 1,100 square-foot 1 bedroom, 2 bath condo in a magnificent, lush tropical paradise resort on spectacular Keawakapu beach. Views are of a tropical garden with partial ocean and mountain views. The condo has...
LOVELY GROUND FLOOR UNIT. n
We love our beautiful ground floor unit at Kona Isle. Step out from the lanai onto the lovely grounds and you are but a few steps from the heated pool and the lovely beach with its BBQ area and gorgeous view. There are lounge chairs and tables on the beach where you can...
Ocean front location perfect for whale watching
Hololani A203 is a stunning 2-bedroom, 2-bath condo that offers breathtaking views stretching to Molokai and Lanai and ceiling fans throughout. This property has elevators. Unit A203 can accommodate up to 4 guests and does not have A/C. The master bedroom presents a...
Premier Ocean Front with Incredible Views! Polo Beach 604
Relax on the lanai and enjoy sweeping views of Molokini and Kahoolawe Island at sunrise or sunset. Stroll along the world famous Wailea Beach Path, enjoy fantastic snorkeling at uncrowded Polo Beach or unwind and sunbathe at the oceanfront pool and jacuzzi.Spend a dream...
Tropical Paradise Awaits: Steps to Sugar Beach, Pool, Hot Tub & Free WiFi!
Welcome to your perfect Hawaiian getaway! Nestled in the lush tropical gardens of Kihei Resort, this beautifully renovated one-bedroom condo offers the ideal blend of comfort, convenience, and island charm. Whether you’re seeking adventure or relaxation, our condo is...
Makaha Beach Front Luxury Bamboo Compound Resort
Take the country road out to West Makaha's Crystal Blue Waters. Feel the ocean breezes where Bethany Hamilton's soul surfer movie was filmed in the waves in front of our very unique new beachfront luxury bamboo compound resort with over 150 feet of sandy beach!! - all...
@ Marbella Lane - Stylish House + Impressive Views
Summary:Welcome to your tropical paradise in the heart of the Makaha Valley. This stylish vacation home offers the perfect retreat for you and your family to unwind and create lasting memories after exciting days of snorkeling, hiking, and sightseeing. Nestled within...
A Cozy and Romantic Studio at Heart of Waikiki
A private cozy and comfortable studio at the heart of Waikiki. Welcome morning with rejuvenating breeze throughout the unit with a wonderful view of the beautiful Ala Wai Canal. New kitchen cabinets and laminate granite counter top, new stylish Livingroom light and...
Updated 1 bedroom in paradise!
Newly listed on VRBO, see our great reviews on alternate platforms! Escape to paradise with this charming 1-bedroom vacation condo in Waikoloa Village on the Big Island of Hawaii. Nestled in a central location, it's your gateway to island adventure. Unwind in style amid...
Poipu Makai Villas C1 - Amazing Views, Ocean Front, AC
Summary:Oceanfront ground-floor condo with breathtaking views, air conditioning throughout, and complimentary access to the Poipu Beach Athletic Club. Enjoy a spacious lanai, direct ocean views, and an unbeatable walk-to-beach location near Brennecke’s and Poipu...
Hale Hui Kai 104 on Keawakapu Beach
This private garden condo is on the first floor of the south side of the building ...about 50 steps along the pathway leads to the gem of south Maui, Keawakapu Beach!Keawakapu Beach, located on the south shore of Maui, Hawaii, is known for its stunning natural beauty...
Your adobe among the trees
The Jungle Canopy is your private oasis at GingerHill Farm Retreat Center. Tucked inside our Teak Forest awaits your "glamping"-style getaway with a luxurious queen-size bed, hot water shower, and flushing toilet. Enjoy the best indoor-outdoor living in your private...
Tropical Comfort - Two Story Ocean View Kihei Condo - Central Air
What a treat it is to dine on either one of your two oceanview lanais and watch the sun slip below the horizon! Did you see the green flash? Over a cool evening cocktail, plan to lazily walk across the street in the morning for a dip in the warm, crystal clear water of...
Tropical Garden 1 Bedroom Condo--Private, Quiet, and Romantic, Wi/Fi, A/C
This 1 BR Condo is a lovely, private, even romantic, GARDEN VIEW CORNER UNIT, with a good partial OCEAN VIEW. Two walls of glass look out from the living room to private, tropical gardens and to the West a partial ocean view. Lanai's are on the West and North sides...
Ground Floor Ease w/Lanai, Gourmet Kitchen, Laundry, AC+WiFi–Halii Kai Waikoloa 3H
Say aloha to this island-style home away from home with tropical-inspired bedrooms, luxe master bath, gourmet kitchen, open living area and lanai. You’ll love the convenient dishwasher, air conditioning, ceiling fans, laundry room and high-speed Internet. Amid 29-acres...
@ Marbella Lane - Serene & Lovely MT + Ocean Views
Summary:Indulge in relaxation and rejuvenation as you take in the breathtaking ocean and mountain views from the living area windows of this peaceful and comfortable house. With convenient access to tropical beaches, surf spots, and hiking trails, your Hawaiian...
KB201-2 bedroom 2 bath Ocean Front Charming Condo with Central Air Conditiong
Experience the ultimate beachfront getaway at the Kihei Beach Resort unit 201, located on the stunning Sugar Beach of North Kihei. This beautifully appointed second-floor unit offers breathtaking panoramic views and convenient access to the beach and pool. The spacious...
Stunning Modern Beachfront Resort Vistas
Summary:Upscale remodel with high-end furnishings 2br oasis situated directly across from Kameole Beach. Fantastic lanai with direct ocean views. Experience the resorts many amenities such as tennis courts, pool and jacuzzi and grills. We provide everything from beach...