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.
Quiet Condo on the Kona Country Club Golf Course
This spacious 1,200 SF 2-BR 2-Bath condo is in a quiet and relaxing spot at the south end of Ali'i Drive. Adjacent to the 8th teebox of the Kona Country Club, it's a beautiful setting whether you're a golfer or not. It sleeps 4 Adults max, and up to 6 total including...
Hidden gem awaits your arrival. Newly renovated condo just minutes from one of Oahu’s many beautiful beaches, Makaha Beach. A welcoming family retreat 2 bedroom, 2 full bath, AC and full kitchen facility. Spacious living and dining providing ample space to plan your...
Turtle Bay East 1 Bedroom with Loft SLEEPS 4-6
Turtle Bay Retreat with Loft | Sleeps 4–6 | Golf Course ViewsNewly refreshed and now under new management! Enjoy laid-back island living in this spacious and clean 1-bedroom + loft unit, ideally located on the stunning North Shore of Oʻahu. Nestled beside the Arnold...
KKSR#197 Direct Oceanfront Air Conditioned Townhome, Extended Lanai & Yard
Welcome to this spectacular very popular oceanfront townhome in the heart of historic Keauhou! This 2-bed, 2-bath townhome offers the perfect blend of privacy and convenience sleeping a maximum of 4 guests.Townhome#197 is very unique, you'll notice an extended lanai,...
Spacious Townhome at Mauna Lani Resort - Close to Beach!
This newly renovated 2-bedroom condo at the Mauna Lani Resort is now available for your next vacation. This condominium/townhome is bright and airy and spans two floors with large windows to allow in the natural light. This popular floor plan features a second floor...
Lovely, spacious private estate, 300 ft to Sunset Beach TA#083767910401
30 DAY RENTAL*****A beautiful, peaceful, private north shore estate, 300 ft from sunset beach. The main house has 4 bedrooms and 4 bathrooms and sleeps 8 in beds. You may rent the cottage for an additional 2 people-check availability-it's called the plantation cottage;...
Kihei Kai Nani - 1BR Unit, Just Steps Away From Kamaole Beach!
This 1BR/1BR, 2nd floor corner/end unit features a beautiful garden view and a remodeled tropical interior. The extra windows in the living room and bedroom create openness, ventilation and light. The trade winds and the peaceful garden setting make it one of the best...
MV 1410 2BD Condo w Pool AC Ocean Views Across from Beach
Maui Vista 1410 NEW LISTING Ocean View 2 Bedroom Condo. Perfect Backdrop for Your Hawaiian Vacation Aloha From Maui Vista 1410 in Kihei, Maui. Our 2-bedroom, 2-bathroom condo offers ocean views, beach views, and pool views, from the outdoor lanai. Enjoy your morning...
Luxury condo next to Disney Aulani Resort and Marriott's KoOlina Beach Club
Beach front condo on lagoon #2 at Ko Olina shoreline. Only steps away to the white sandy beach where you can explore Hawaii vacation. Very convenient for eat-out, golfing, luau show and shopping. The unit is large enough for 3 couple's and even with kids. The oversized...
⛱ Ocean Escape🌴 Your Perfect Spot! Ocean View, Upscale, Clean, Cozy, Prkg, WiFi
Welcome, 'E Komo Mai'CALENDAR IS ALWAYS CURRENT... Please check the availability and if it is full check out our other unit 'Mountain Retreat' VRBO listing https://www.vrbo.com/382565haAloha Hideaway offers a high quality unit at a reasonable price. The Views are...
Kihei Surfside #508: Gorgeous Oceanfront Escape with Mesmerizing Views
Kihei Surfside #508 – Oceanfront Escape with Split-Duct AC and Breathtaking ViewsWelcome to Kihei Surfside #508, a beautifully situated 1-bedroom, 1-bathroom oceanfront condo offering unobstructed views of Maui’s stunning coastline. Perfect for two guests, this...
Maui Family Owned/Managed - Keawakapu Beauty
A mere four minute walk from the lavish Keawakapu beaches will find you in the serenity of our peaceful condominium. Our quiet first floor unit has a partial ocean view where guests can enjoy the vibrant colors of a Maui sunset at the closing of the day on the patio....
OCEANFRONT RESORT- Great Views - Kihei Sands Beachfront Condos- B6
Trade cold snowstorms for warm shorelines this winter. With sunny skies, golden sands, and spectacular whale sightings, Maui's inviting landscape and our NEW SEASONAL PRICING brings you a step closer to your island escape!This condo is priced for 4 persons - we'll add...
Oceanview #202 at Hana Kai Maui - Lofted Studio Upper Floor, Panoramic View!
"Alau” – Unit 202 – is an upper-floor, lofted, ocean-view studio located in Hana Kai’s Mauka Building. The unit accommodates up to 4 guests with 1 queen bed on the main floor and another queen bed in the loft. *Note* SLEEPING IN THE LOFT JUNE THROUGH OCTOBER OS NOT...
Napili Shores E-243 - Upgraded, steps to ocean and pools. Napili Bay - ideal location for vacation
E Komo Mai - Welcome to Napili! Attention to detail in this One Bedroom / One Bath Fully Renovated Condominium with air conditioning. Napili Shores Resort is adjacent to the gorgeous sandy beach of Napili Bay. Not only are the accommodations ideal, you are just steps...
Kihei Beach #404- Serenity by the Shore
Kihei Beach #404 – One-Bedroom Beachfront Condo with Two BathroomsWelcome to Kihei Beach #404, a one-bedroom, two-bathroom beachfront condo offering panoramic views of the Pacific Ocean and Maui’s neighboring islands. Located in a six-story beachfront property with...
Beautiful Oceanfront Views! Enjoy Hotub, Grill & 3 Lanais!
Located in South Maui along the shores of beautiful Makena Bay, the Makena Bay House is a private, two-story residence located in an island paradise. The Makena Bay house's size and location make it an ideal choice for couples looking for a tropical getaway!Built in...
Top Floor! Direct Ocean View! Vaulted Ceilings! Winter Spec! #218
ALOHA AND WELCOME TO HALE KAI # 218 Located right on the ocean on the beautiful island of Maui, our condo can be your _home by the sea_. Comfortably decorated with tropical Hawaiian furniture and artwork, our unit will provide you with all the comforts of home,...
Poipu Kai 1BR Retreat w/ Ocean View & Pools, Walk to the Beach
E Komo Mai — Welcome to Kahala 621 at Poipu Kai ResortExperience island living at its finest in this spacious 1-bedroom, 1-bath condo at the premier Poipu Kai Resort on Kaua'i's sunny South Shore. Relax on your private lanai with ocean views and enjoy lush tropical...
Hilton Pool Pass for 2025 and Golf Discounts. Waikoloa Beach Villas C4
This vacation rental is professionally managed by ResorticaHawaiiWaikoloa Beach Villas C4Please scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom Upstairs: One Queen BedGuest Bedroom Downstairs: One Queen BedAdditional...
Kahana Village #28 Beach Front Deluxe
Located out on the point at the Kahana Village Resort, our 2 Bedroom 2 Bath condo is 1200 sq feet, completely remodeled and very well appointed. We are just steps from the waters edge and enjoy sunset views in between the island of Lanai & Molokai. Our fully equipped...
Aloha Spirit in Downtown Kona - Right by the Ocean
Welcome to Aloha Spirit at Kona Alii, your peaceful retreat in the heart of downtown Kailua-Kona. This beautiful 1-bedroom, 2-bath condo offers the perfect balance of privacy, comfort, and location — just steps from the best shops, restaurants, and beaches along Alii...
Ocean View Escape: Steps to Beach & 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...
Pali Ke Kua 12, Upgraded Hawaiiana Princeville Condo with A/C
Welcome to Pali Ke Kua #12, PrincevillePali Ke Kua #12 is a 2 bedroom/2 bath condo, located in a park-like setting on the tropical grounds of the Pali Ke Kua complex in the residential and prestigious resort community of Princeville.Open the sliding glass doors in the...
Absolute Amazing View, One level, 2 Lanai’s,New bed types King,Queen,Twin Qsofa
Guests are sure to enjoy a memorable vacation in this fully furnished, 2 bedroom/2 bath condo. The master bedroom has a King size bed. The 2nd bedroom is furnished with a Queen size bed and a Twin size bed. There is a Queen pull out sofa sleeper bed in the living room....
Hale Makai at Diamond Head – Oceanfront Estate
Ideally positioned along Honolulu’s prestigious Gold Coast with Diamond Head Crater as its backdrop, Hale Makai at Diamond Head is a licensed nightly oceanfront rental (NUC 90/TVU-0390) offering luxury, privacy, and the rhythm of true island life—just three miles from...
Peaceful & Elegant Treetop Hideaway in Volcano Village
Set on a quiet street in historic Volcano Village, Hiʻiaka Guesthouse is a private, romantic pied-à-terre on the second floor of a beautiful 2-story custom home. Surrounded by old-growth ʻōhiʻa forest, and overlooking a lush and peaceful garden, the guesthouse offers a...
Beautiful Mountain View in Waikiki Sunset + 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...
Kona Ocean View: Beautifully Furnished, Amazing View, White Sands Beach
Great location within the White Sands complex--front building, top floor. Partial ocean view. Steps away from Magic Sands Beach, close to the best snorkeling in the area, and convenient to downtown Kona and area attractions. White Sands complex has all you need with...
Palms 306 Ocean Views, 5 Star Reviews: Remodeled
AMAZING 2 BEDROOM 2 BATH CONDO IN POPULAR PALMS AT WAILEA. SLEEPS UP TO 6 PERSONS. Largest 2 bedroom in area.This two-bedroom villa boasts stunning ocean vistas and a tranquil setting within Wailea’s resort community. With a full kitchen, comfortable living space, and...
Beachy Boho Retreat in the Heart of Kihei – Steps to Beach!
Ready to get away from it all? Say aloha to this beautiful beach side retreat in easygoing Kihei, ready for you and your guests to enjoy the fun, sun and experience why ‘Maui no ka ?oi’! Just across the street from the beach, this 2 bedroom, 2 bath condo sleeps up to 6...
*Ocean and Mountain Views!* | Lush Hawaiian Oasis
Summary:🌴 Wake up in paradise at Hanalei Bay Resort! Nestled on 20 lush acres in Princeville, this luxury condo offers ocean & mountain views, private beach access, pools, tennis courts, yoga, spa, BBQs & more. Golf lovers enjoy exclusive discounts too! Your dream...
Lymans Bay Hale: Ocean View Surfer's Paradise with Hot Tub & Game Room
Right off Ali’i Drive in Kailua-Kona, Lymans Bay Hale is a spacious three-story, 5-bedroom, 3.5-bath home designed for ocean lovers and family gatherings. With sweeping ocean, beach, and mountain views, a game room, and a hot tub framed by tropical gardens, this private...
Ko Olina Beach Villas O822: Elegant Retreat, Lagoon Views, Spacious Lanai
Ko Olina Beach Villas O822 invites you to experience refined island living from its perch on the eighth floor of the Ocean Tower. Just steps from Ko Olina’s tranquil lagoon, this three bedroom retreat blends indoor comfort with open-air living, where panoramic views,...
Maui Resort Rentals: Honua Kai Konea 149 – Deluxe 3BR Ground Floor Interior, Huge Lawn Area!
Konea 149 is an expansive three-bedroom deluxe ground floor residence offering the perfect opportunity to gather, reconnect, and celebrate. This exquisite three-bedroom suite offers an incredible location, the first unit back from the very front of the building. The...
BEAUTIFUL BREATH-TAKING Ocean and Sunset Views w/ AC, Upscale Furnishing, & Art.
Enjoy Breath-Taking Beautiful Ocean views w/ AC, Upscale Furnishing, & Art.Our spacious split level condo offers incredible and unobstructed ocean views. The private lanai is the perfect spot for true relaxation, listening to the sounds of the waves crashing against...
OCEANFRONT Condo. Steps from the water! KULEANA 622
Perfectly located between Kaanapali and Kapalua, this beautiful 1-bedroom, 1-bath oceanfront condo at the highly sought-after Kuleana Resort offers guests the ultimate Maui getaway. Situated on the 3rd floor, this unit delivers breathtaking panoramic ocean views,...
Luxury 2bd villa with stunning views
Kapalua Bay Villa 28B 1&2 is a stunning 2-bedroom, 3-bathroom retreat that offers breathtaking ocean views, newly remodeled interiors, and access to top-notch amenities. This condo features a lanai that's ideal for relaxing, feeling the ocean breeze, and listening to...
Haleiwa Beachfront Condo. Perfect Peaceful Paradise!
E komo mai!Hawaiian for "Welcome" to the North Shore of O‘ahu. Make this one bedroom/two bath beachfront front condo your home away from home. In June 2019 the interior was completely remodeled: A beautiful kitchen; waterproof flooring throughout; smoothed ceilings,...
Stunning, Oceanfront Deluxe Penthouse with Island Views - Sands of Kahana 282
🌺 Oceanfront Penthouse Paradise – Sands of Kahana Resort 🌊2 Bedroom • 2 Bathroom • 8th Floor • Sleeps 8 • AC • 1645 Sq FtWelcome to your dream Maui escape at the Sands of Kahana Penthouse, where breathtaking oceanfront views, stylish upgrades, and resort-style amenities...
🏖️Beautiful Ocean Views | Top Floor | Concierge Included | vrKCV
vrKCV - Alii Villas 309, Professionally Managed by Kona Coast VacationsWelcome to Alii Villas 309, a top-floor, one-bedroom, one-bath unit offering stunning ocean views from both the lanai and living room. Whether you're sipping your morning coffee or relaxing after a...
Kona-Keauhou Sunsets+Style! Full Kitchen, Washer/Dryer, WiFi, Lanai, DVD, TV Kanaloa 2106
Castle Kanaloa at Kona Resort #2106 - Relaxing is easy when listening to the sound of the waves from this cozy two-bedroom, two-bathroom ocean view suite. You’ll love how spacious this corner unit feels, with lots of room to sprawl out with family and friends.Enjoy warm...
The HALE, perfect Family Base Camp, centrally located, short walk to the beach
This property is located on a quiet street across from the Morman Temple. The property consists of a Front Cottage, The Hale (where this unit is located) and a parking lot for the Hale Renter and the Owners (who live 0n site). We are close to town (5-7min walk) the...
Beautifully Remodeled 3bedrooms/2bathrooms
Aloha and Welcome to our newly remodeled stand-alone Cottage!Nestled hillside across from the Maui's Kahekili Beach, which was voted one of the world's Top 10 Beaches, and is also the winter playground of the humpback whales. Enjoy the spectacular views from your...
Welcome to Hokulani 622, 2 bedroom 2bath Rainbow & Mountain Views great rates
Make wonderful memories in paradise with this beautiful 2 bedroom/2 bathroom suite located on the 6th floor of the Hokulani tower at Honua Kai, boasting gorgeous rainbow and west Maui Mountain views. Honua Kai remains one of the top 10 luxury resorts on Maui. The...
Kona MAKAI#2-201 Corner Remodeled Unit with ALL Tile. Breathtaking Ocean View
Kona Makai#2-201 is a fantastic option for your Hawaiian Vacation. The owners extensively updated the property with beautiful new furnishings, installed tile throughout the entire condo & have upgraded the property with everything any guest may need.This beautiful 2nd...
North Shore Oahu Beachfront Condo, 2BR / 2BA
This fully equipped, ocean front, condo unit is located in Waialua on the beautiful north shore of Oahu. The minimum stay is 30 days at a rate of $185 per day or $5,550.The mountain side master bedroom features a queen size, comfort foam pillow top bed, full on-suite...
Quiet privacy with sensational ocean and coastal vistas!
Property Highlights • Five minute walk from three world-class beaches, including Kapalua® Bay, rated the #1 beach in the world by Dr. Beach, and #1 beach in the US by Conde Nast • The very best in affordable luxury living • Sensational ocean and coastal views, including...
Remodeled, ground-floor home w/ beach access, shared pool & hot tub, & A/C
Kolea Kai 16DOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This incredible ground-floor condo is the perfect place to call home for your Waikoloa vacation. You'll love grilling...
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...