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 Island Getaway
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...
Waterfront Home near Beach. Peaceful Community w/ Swimming Pool and Boat Dock
Experience Oahu like a Kama'aina (local) in this 3 bedroom, 2 1/2 bath waterfront home. Safe community. Views from every room. Private lanai, BBQ grill, community pool, and boat dock. Walk to dining, shopping, bars, farmers market, hiking, beaches. 5 minutes drive to...
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...
Beautiful Luxury Peek Ocean and Mountain View
Beautiful Luxury Peek Ocean and Mountain View 1 Bedroom, 2 Bathroom Condo at #1 Rated 1st Class Waipouli Oceanfront and Beachfront Resort & Spa on the beautiful island of Kauai. This well decorated second floor 1 Bedroom, 2 Bath Condo offers easy access to the pool and...
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;...
Tropical condo in a central location with pool and grill access - W/D and AC
Casa De Emdeko A110Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Say aloha to paradise when you call this Kailua-Kona condo your next vacation destination! Nestled in a prime...
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
FREE daily activities included with your stay value up to $554! Complimentary admission, every day of your stay*: Whale Watching (seasonal), Sunset Dinner Cruise, Molokini Snorkel Trip, Alpaca Farm Tour, Pineapple Farm Tour, and Tea Farm Tour. (S1)*One ticket per...
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 white sandy beach where you are looking for and enjoy tropical trade winds. Very convenient to almost everything like eat-out, golfing, luau show and even shopping. The unit is large enough for 3...
Maui Sunset Vacation Rentals B209
Watch the life of Maui unfold from the morning till evening from your private 114 sq foot private view deck. New flooring throughout 2023Second floor means easy access to tropical gardens and the ocean beyond. Quiet location features large private view deck and...
⛱ 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...
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....
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...
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,...
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...
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
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 living area...
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
We want to inform our valued guests that there is ongoing construction next door to Hale Makai at Diamond Head. This construction is expected to last into 2026. We apologize for any inconvenience and appreciate your understanding in this matter.This Diamond Head...
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 areaThis is the largest (1299 sq ft ) two-bedroom ‘C’ plan, built in The famous Palms at Wailea. with vaulted ceilings with huge picture window looking out over...
White Sands Village #207 Lanai Ocean/MT Views Beach Access Pool Hot Tub
Almost oceanfront, well equipped condo conveniently located in White Sands Village on Alii Dr - just 4 miles from Kona Village Center- 2nd floor w/elevator access right outside the unit -sleeps up to 4 people with a king bed in the master bedroom and two twin beds or 1...
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...
Ko Olina Beach Villas O822: Elegant Retreat, Lagoon Views, Spacious Lanai
Welcome to Ko Olina Beach Villas O822 by Gather where luxury meets the serene beauty of Hawaii. Situated in the Ocean Tower at Ko Olina Resort, this villa is a stone's throw away from a well-groomed lagoon, offering guests an intimate connection with nature's wonders,...
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
Kuleana is perfectly located between Kaanapali and Kapalua. Ocean Front, 1 bedroom, 1 bath condo.Private lanaiSwimming PoolTennisBBQ AreaAir conditioningFree parking and NO Resort Fees!Take a breath of fresh air at our beautiful, remodeled 1 bedroom, 1 bathroom...
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...
Family Friendly, Fully Furnished Villa In Ko Olina Resort near the Golf Course
Welcome to paradise! This beautiful Villa is nestled in the quiet neighborhood of Hillside Villa. You will love having breakfast ein your private lanai surrounded by palm trees and blue skies. This Villa has 3 bedrooms and can sleep up to six guests. This villa has 3...
Stunning, Oceanfront Deluxe Penthouse with Island Views - Sands of Kahana 282
Oceanfront Sands of Kahana Resort- beautiful, remodeled ocean front view, 2 bedroom, 2 bathroom PenthouseOceanfront Pool and second poolRestaurant and BBQ areasFitness CenterTennisACWalking distance to restaurants and storesEnjoy STUNNING oceanfront views from this...
🏖️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...
Includes Mauna Lani Beach Club Pass. Fairways at Mauna Lani 2001
This vacation rental is professionally managed by ResorticaHawaiiPLEASE NOTE: The swimming pool will be closed for Maintenance Mon-Fri from 8:30am-4:30pm Oct 6-27, 2025. Dates may be subject to change due to unforeseen delays.Fairways at Mauna Lani 2001. Includes Mauna...
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...
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...
Amazing Oceanfront Penthouse 🌊 with Stunning Views From The Lanai! 🏝️ Kona Bali Kai 419
Absolute oceanfront top floor condo with a big lanai (balcony) boasting an even bigger view. Located on the top floor of a four-story building, this oceanfront condo boasts first class views as well as excellent proximity to Kona Town and all activities. Whales, surfers...
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 new owners have 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...
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!
Enjoy the 5th Night Free for stays between now and December 15, 2025. Reservations must be made by August 31, 2025. *Applies to new reservations only. Property Highlights • Five minute walk from three world-class beaches, including Kapalua® Bay, rated the #1 beach...
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...
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...
Wailea Beach Villas | D301
Discover for yourself why D301 is one of the most requested Villas in our vacation rental collection. Impressive artwork by internationally known Maui artist Elan Vital provides a fabulous backdrop to the welcoming great room in rich jewel colors of amethyst and jade...
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...
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...
koolkondo 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...