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.
Beachfront Home + Cottage at Center of Hanalei Bay!
Welcome to our stunning, historic Hawaiian plantation home and cottage—nestled beachfront on over 1/3 acre at Hanalei Bay’s famous Pine Trees Park. A surfer’s dream in winter and a calm, swimmable bay in summer, this family-friendly, single-level compound includes...
Relaxing oceanfront studio on the beach
Enjoy panoramic, unobstructed views of the neighboring islands of Lanai and Molokai, while watching whales (seasonal) breach out of the water, sea turtles and fish swimming by and enjoy breath taking beautiful sunsets!Experience the time of your life in this spacious,...
Surfers Paradise!
AMAZING COUNTRY RETREAT ON THE COVETED NORTH SHORE!! Enjoy creating memories with your family and friends at our favorite place in the world. Surf, hike, swim, snorkel, take in the rays!!! This private estate offers ocean views just up the hill from world renowned...
Waipio Valley and Ocean View
Enjoy this breathtaking fully equipped home over looking Waipio Valley up close in this 4 bedroom, 2 bath and outside shower home with incredible views. There are plenty of rooms and views for a family or group of friends to experience the lush and tropical...
Shells At Poipu, lovely home, short walk to beach
Just a short walk to the beach, this lovely home is also a short walk to the resort community's swimming pool and tennis courts. Your beautiful home-away-from-home welcomes you to relax and enjoy a wonderful visit to the "Garden Island" of Kauai. Perfect for families...
3 minute walk to the beach! Close to restaurants/shops. Updated, clean with A/C
Our beautiful updated condo in the Maui Vista complex is conveniently located on the ground floor of Building 1, which gives direct access to the beautiful garden, heated pool and walkway to Charley Young Beach. It is well furnished and includes a well stocked kitchen,...
Hale Kai Lily - Waterfront Hawaiian Getaway
This single-level waterfront, home is thoughtfully curated & designed. New AC in every room. Featuring a full kitchen, living room, and lanai as well as 4 bedrooms and 3 bathrooms. The property is fully furnished and boasts captivating marina views from all common areas...
Diamond Head Luxury Home w/Pool, AC, Lanai and close to Waikiki, Hale Le'ahi
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Let your dream tropical vacation begin when...
Hilton Waikoloa Pool Pass Included for 2025. Waikoloa Beach Villas C1
This vacation rental is professionally managed by ResorticaHawaiiWaikoloa Beach Villas C1Please scroll down for detailed informationPLEASE NOTE: Waikoloa Beach Villas C1 is listed for sale. Guests may be asked to accommodate showings/inspections with 48 hours notice....
Ekahi Ocean View Escape and close to beach (21F)
Hawaii Tax ID: TA-200-429-5680-01TMK: 210080600026We invite you to stay in one of Ekahi's premier ocean view units; with a 3 minute walk to the top rated Keawakapu Beach. Your home away from home is also close to private amenities including 4 pools (2 very close to the...
Hale Hanai - near Kealakekua Bay - Proximity to ocean without oceanfront price
PLEASE NOTE: DURING THE HOLIDAYS, FROM DECEMBER 15 TO JANUARY 1, WE REQUIRE AT LEAST A TWO-WEEK BOOKING. "Pathway of the Gods" is the meaning of the name given by ancient Hawaiians to Kealakekua Bay. Five hundred feet from the bay, nestled among the palm trees and...
Gorgeous Remodel, BEST location! KAKC206
This is a brand new unit; light, bright with beautiful breezes! Fantastic location in the complex. Close to everything you want/need in Kihei! Gorgeous sunset views. Come be our guest and enjoy the comforts of being in Paradise!!Aloha and welcome to PARADISE!!! This...
Ocean View Studio at Islander on Beach with AC
Island Escape – Ocean View Corner Studio at Islander on the Beach 309Welcome to Island Escape, a rare top-floor corner studio at Islander on the Beach. Nestled along Kauai's stunning Royal Coconut Coast, this bright and breezy retreat offers panoramic ocean, garden,...
1D Aloha Manor is Elegant Gated Oceanfront Luxury Living with A/C!
Welcome to Serenity. Large Ocean Front Home with Vast Views of Sea and Sky. Watch the Whales, Dolphins and Giant Sea Turtles. Soak in the View of Turquoise water in this Hawaiian Paradise from your Living Room. This home is absolutely Elegant. Open, Light, and...
Relax and Regenerate on Kauai's North Shore
DISCLOSURE 8/29/25: The Nihilani spa is currently inoperable and we do not have an estimated date for repairs to be complete. More information will be provided as it becomes available.Located at the tropical complex of Nihilani at Princeville, this spacious, two...
Waikiki Banyan OCEAN VIEW Plumeria Suite - lots of amenities, free parking, Waikiki Beach
Enjoy breathtaking ocean views on the 30th floor!Want to be steps away from the beach, indulge in a fully-equipped kitchen to cook any meal, and relish in the astonishing ocean views from a wonderfully remodeled 1 bedroom unit at the Waikiki Banyan?Welcome to the age of...
Kona Oceanview Penthouse in Kailua Village - Best Kona Location/View!
This is the BEST location on the Kona Coast, right in Kailua Village. This spacious (~1300 ft²) condominium includes two Master Bedroom Suites with King beds and a 3rd Bedroom with trundle bed. Sleeps five adults comfortably, six people with children sharing 3rd...
Keauhou Palena 1102, 11th Fairway Of Golf Course, Quiet & Beautiful Surroundings
Close to dining and shopping in nearby Kailua-Kona Village the Keauhou Palena is a great vacation get-away.The Keauhou Shopping Center is with-in a short walk. It offers interesting shops, restaurants, a large super market, a great farmers market every Saturday, cinema,...
Puakenikeni Hilo Hale
Private unit in a lovely open oasis of a yard with fruiting trees and flowering shrubs. Has its own dedicated serene yard space with a picnic table bench and grill for outside enjoyment. It also has its own dedicated parking next to the unit. Property is conveniently...
Garden view. Free WiFi & phone (US only) Many extras. Great Kihei location
This is a beautiful condo decorated with a tropical theme. Sleeps 2-4. It has a new A/C unit in the living room, quiet ceiling fans in the living room and bedroom, and sunscreen and drapes to prevent overheating in the afternoon. On many days the cool ocean breezes...
119 night April discount Ali'i Dr location, Clean, salt water pool by Poke shack
Inviting Vacation Rental in Kona, HawaiiHolualoa Gardens, nestled along the scenic Great Ali'i Drive, offers a perfect haven for your Hawaiian getaway. This charming one-bedroom condo is ideally situated near the iconic Banyan surf spot, tranquil Lyman's Bay and up the...
Poolside, Ground Floor and Beach Gear Included! Waikoloa Beach Villas B3
This vacation rental is professionally managed by ResorticaHawaiiWaikoloa Beach Villas B3Please scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom: One Queen BedBeach Equipment: All of our vacation rentals include beach...
Island Surf 506 | Incredible Views + Amenities!
Within steps of sunny Kalama Beach’s warm turquoise waters, you’ll discover the perfect Maui, Hawaii getaway for a romantic retreat or small family vacation or friends’ trip at Island Surf 506.Light, bright, and beautiful, Island Surf 506 has everything you need...
Includes Beach Gear! F1 Na Hale o Keauhou
Na Hale O Keauhou #F1 on the Big IslandThis vacation rental is professionally managed by ResorticaHawaiiPlease scroll down for detailed informationBedroom Configuration:Master Bedroom: King BedGuest Bedroom: Queen BedGuest Bedroom: Two Twin BedsAmenities:Beach...
❤️PiH❤️ Hapuna Beachfront Bliss ★ Steps to the beach ★ Amazing Sunsets ★ B29
Welcome to Hapuna Beachfront Bliss at Hapuna Beach Residences brought to you by Paradise in Hawaii Luxury HomesThe shimmery Pacific Ocean beckons you from the moment you wake. Enjoy vibrant sunsets over the ocean each evening. Steps away from your condo is the stunning...
Romantic Oceanfront Studio with Gorgeous Ocean Views Overlooking Napili Bay w/AC
Newly remodeled oceanfront studio at Napili Shores Building A 204 with sweeping views of beautiful Napili Bay. A few steps to the white sand beach of Napili which has been named the most beautiful beach in the world by Travel and Leisure 2017. No need to leave the...
Turtles and Whales with 25% Sale into 2025 , Ocean Views, Great Sunsets with A/C
Unit C-15 at Napili Point is under new ownership and new to VRBO starting September 2022. Currently we have entered into a lease with FEMA to house a Lahaina Fire family from February 1, 2024 to July 31, 2025. Therefore this unit is unavailable to rent during this time....
206 - Gorgeous Remodeled Oceanfront One Bedroom Unit! Fantastic!
* This is one of the premier one bedroom one bath units at the Kihei Surfside! * This ocean front condo has been significantly upgraded * 70 feet from the ocean - Watch the whales (in season) from your private Lanai * 100 feet from one of the finest beaches in Maui -...
Poipu Beach Townhouse, 5 Minute Walk to Brenneke's Beach and Pool
Spacious 1600sq ft,2 king beds,2+ baths ,beautifully furnished. ALSO THE PROPERTY WILL BE FULLY AIR CONDITIONED STARTING NOVEMBER 23, 2024.Located among the lush acreage of the Poipu Kai Resort and within a 5 minute walk of Brenneke's Beach and another few minutes along...
Modern Coastal Remodel I Koa Resort 1G
Fully equipped with flat screen smart TV & cable, high speed internet, IPad, printer and office desk; you will have all of the comforts of home or a hotel business center. The kitchen is fully stocked with all of your cooking and entertaining needs, including new top of...
Last min May opening! Love watching sunsets and dolphins from this large lanai!
A perfect place to relax watching whales, dolphins not to mention beautiful sunsets!! This newly remodeled 2 bedroom 2 bathroom ocean front condo on the top floor with large lanai has new furniture, beds, bedding and more! The building has an evaporative cooling system...
$149 a night Book Now B -208 Ocean View, Pool
Welcome to Waiohuli Beach Hale B -208, your peaceful Maui escape in an oceanfront paradise!Located upstairs in this charming low-key complex, B-208 is beautifully remodeled with granite countertops, tiled floors, modern cabinetry, and a fully equipped kitchen with...
Maui Sunset B201: Beautiful 2 Bedroom, 2 Bath, Kihei Condo. Sleeps up to Six
Beautiful, spacious, Kihei Maui ocean side of road, two bedroom, two bath condo. Maui Sunset, unit B201. Top quality remodel in 2015 with granite counter, custom kitchen and bathroom vanities. Enjoy the garden view and all the amenities of the highly acclaimed Maui...
Beautiful 3 Bedroom Oceanfront
New Kitchen, bathrooms, carpeting, bunk beds and couch! Our three bedroom, two bathroom oceanfront condominium offers luxurious accommodations for up to eight people. Situated within the Kahana Outrigger Resort - a low-rise, low-density complex of only 16 units, located...
Resort-Style Rental - Ocean View, Pool/Hot tub/Gym
This luxurious resort condominium with spectacular views is located along the 12th fairway of the Waikoloa Beach Golf Course and is exclusive only to residents and guests. From the shimmering blue ocean and breathtaking fiery sunsets, to the volcanic mountain top of...
Ocean View! Golf Course Princeville Townhouse! Walk to Beach! High speed WiFi
Brand new remodel!Experience the beauty of Kauai's North Shore through this luxuriously appointed townhouse situated right on Makai Golf Course with mesmerizing ocean and mountain views. This brand new remodeled 2 bedrooms, 2 bathrooms Townhouse is in the heart of the...
Casa Tropical Kona in Kailua-Kona with an ocean view & pool - walk to the beach
Casa Tropical Kona -Kailua Bay Resort 2-201Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Perfectly located in the heart of Kailua-Kona, this one-bedroom condo is affectionately...
Kauai Adventure Base Camp. Let this be your Gathering Place! A Spectacular Pool to Enjoy!
This Resort is a Dream and right on the Beach. Just Steps to the Warm Turquoise Ocean. Kids and Adults alike will love the Lazy River to the Huge Pool. Hot Tubs are Incredible. This Large Home is a Great Room Concept, full of Light. Elegance and Quality Abound. 2 Full...
Prestigious oceanfront condo, perfect location
Experience the complete Maui vacation when entering the top floor luxurious Mana Kai 810, a prestigious 2-bedroom two-bathroom ocean front condo. This unit offers everything you need for the perfect vacation. From location to amenities Mana Kai has it all. Mana Kai is...
Newly Renovated Sweeping Ocean and Diamond Head View Waikiki Condo
Sweeping view of Ocean and Diamond Head from beautiful 1 bedroom sparkling just renovated condo unit in the Waikiki Sunset Hotel! The location is perfectly located just 2 short blocks to the main area of Waikiki beach, International Marketplace, the best shopping and...
Hale Mano - TVNC 5047 - A mod beach cottage on the sunny, south side.
Hale Mano (The House of Sharks) is a 3-bedroom, 2-bath home built in 1963 from solid California redwood. Located on a cute residential street, it's the perfect getaway from the typical resorts. You will love this well curated, retro, beach house that's just a 6 minute...
Mauna Lani Terrace E201
Mauna Lani Terrace E201 offers a nice ocean view out over the ponds. This one bedroom villa has been nicely upgraded to include granite counters and stone floors. The living area has a sleeper sofa with two chairs that faces a LCD television and looks out over the ocean...
Aloha Condos, Na Hale O Keauhou, Townhome D-6, Ocean View, AC
Best location at Na Hale O Keauhou and added to the website on December 18, 2014. • Beautiful Ocean-View Gated Complex• Large & Luxurious 2 & 3-Bedroom Townhomes• Resort Pool, Spa, Clubhouse & Fitness Facilty• Pavilion with Kitchen• Golfing, Swimming,...
Kona Reef#A-7: Direct Oceanfront Corner Unit,Newly Remodeled, AC,Walk to Town
Completely Remodeled First Floor Corner End Unit, One of the Best. Direct Oceanfront. THIS IS ONE OF ONLY 2 UNITS THAT HAVE LARGE LIVING SPACE 2 FULL BATHROOMS AND WINDOWS GALORE!Enjoy Split system AC that's Quiet AC & cools the bedroom or the living room or both!...
Kaanapali Villas, Oceanfront Luxury Maui Condo #180
We welcome you to stay and relax in our well appointed oceanfront luxury, villa. Our villa offers breathtaking ocean views and is decorated with the finest touches. This one bedroom villa accommodates only two adults. The gourmet kitchen features custom cabinets, GE...
Villa Kai Lani - Oceanfront Poipu Home with Pool, Spa & AC
Located on the dramatic Poipu Beach coastline, this distinctive estate among our Kauai oceanfront rentals offers its guests breathtaking views, unique architecture and a spacious layout. The five bedroom residence opens up to the ocean and is designed to fully take...
Ocean Front, Kuhio Shores, 30 ft = 9 m from water! A/C
ON THE OCEAN condominium "Turtle Haven" steps from the sea near Poipu with spectacular views. Swim, surf, snorkel, sunbath or just relax in a peaceful corner of Kauai Island. Dazzling views of the tropical Pacific Ocean welcome you as you step in the door. Your unit...
Luxurious, Remodeled 2-bed/2-bath, Wrap-around Lanai, Short Walk To Beach!
Bright, Airy, Spacious 2-bed/2-bath, Ground Floor - Aloha & welcome to Makanui @ Poipu Kai Resort. This wonderfully appointed 2-bedroom, 2-bathroom ground floor condo features an upgraded kitchen and bathrooms with granite countertops, stainless steel appliances and...
Sugar Beach Resort Condo w/ Shared Grill, A/C-Surf, Bike, Golf, More
Sugar Beach Resort 225Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Join the many guests who return each year to Maui's Sugar Beach Resort to enjoy the spectacular views from this...
OCEANFRONT CONDO - $359-May 15! Kihei Sands Beachfront Condos-B8
We can't wait to welcome your party of 4 to Kihei Sands Beachfront Condominiums B8 in sunny South Maui! Condo B8 is a 2-bedroom, OCEANFRONT townhouse-style condo on the 2nd level (no elevator) with stunning views of Haleakala, West Maui Mountains & Pacific...