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.
Mesmerizing Ocean & Coastline Views 🌅 Sandy Private Beach 🏖 Kona By The Sea #422
Mesmerizing Ocean & Coastline Views with Sandy Private Beach! Romantic Sunset Views & Ocean Views depending on the time of year– Updated throughout! Direct ocean front! Spacious with two Bedrooms & two bathrooms, central air conditioning, top of the line kitchen and...
🏖❤️Gorgeous🌴 2BD/2BA LUXURY CONDO, 180 REVIEWS, Updated & Painted🏝❤️
Newly painted interior, New coffee table, two new chairs, new kitchen lights, tile floors.🌺 You are renting directly from the owners Bob & Family. We would love to have you stay in our condo. As our guest, you have full access to all resort Amenities at Honua...
⛵️Mahana 1217 OCEANFRONT PENTHOUSE 1 BDRM/1 BATH Condo/12th floor/Legal Rental⛵️
The Mahana at Kaanapali is an OCEANFRONT resort located on the NORTH BEACH section of the famous Kaanapali Beach on West Maui. We are located just north of Duke's restaurant and several miles from the recent Lahaina fire. Our resort had no damage as a result of the...
Executive Luxury Luxury Home in the Safe Gated Community
Effective October 23, 2022 we will not accept rental for less than 91 days because we have to comply with the new law of city and county of Honolulu. In an exclusive Gated Community, this home is safe, quiet and situated in just on top of the hill for peaceful enjoyment...
Luxe Maunalani Resort Condo w/ Pool + Beach Access
Just minutes from the stunning beaches of South Kohala, this 3-bedroom, 2-bathroom vacation rental condo offers the perfect retreat for your island getaway. With a spacious lanai, community pool, and sauna, you'll have everything you need to relax and unwind. Spend your...
Large 3 Bedroom Ocean Front Villa on 7th floor, Lahaina Tower
Come to the gorgeous Maui Ocean Club and vacation in beachfront style! Marriott Vacation Clubs offer a luxurious and relaxing way to vacation while enjoying all the conveniences of home. Located in the Lahaina tower, this very large 3 bedroom/3 bath corner villa has...
399+ 13 years same ownership: Accountable
We're Accountable 24/7. This condo, however, is not a hotel. We will service immediately whatever needs attention. Our Cancellation Policy Protects both the guest and us. If a guest cancels their reservation outside 60 days, we'll refund their money immediately less...
Beautiful 2 Bedroom Oceanfront Condo Makena Surf F307 - Luxury Awaits!
Surround yourself in luxury while enjoying privacy and seclusion all while being close to world class dining and shopping. Enjoy unparalleled views and seamless indoor/outdoor living with a top notch beach steps away and some of the best snorkeling on island directly in...
Modern, Romantic Vibes in the Tropics
The SpaceCome enjoy this newly updated, spacious end-unit condo in beautiful Turtle Bay. It is as comfortable as it is beautiful. Whether it's breakfast in bed or a drink on the lanai swing, you may not want to leave. Everything has been updated, including hand-picked...
Breathtaking Pool & Ocean Views! - Updated Corner Unit -Sugar Beach #412
Welcome to Sugar Beach Resort #412 – Updated Corner UnitExperience the serene beauty of North Kihei at Sugar Beach Resort, a picturesque beachfront condominium resort offering breathtaking Pacific Ocean views. Two six-story buildings, equipped with elevators, provide...
Relax by the sea! Two bedroom retreat near Kailua Pier - 11 min
Discover your tropical retreat at our enchanting two-bedroom holiday house in Kailua-Kona. Paradise is ready for you. Nestled just a short 11-minute drive from the vibrant Kailua Pier, you'll be perfectly positioned to explore the island's top attractions, including the...
Hale Ho'ouluulu – Luxury Poipu Villa with Infinity Pool & Ocean View
Wherever you look, this stunning Kukui'ula villa inspires admiration, and sparks delight. First, there’s the expansive view: an enchanting parfait of rolling hills and verdant orchards in the foreground, the glittering sea beyond, and impossibly blue skies overhead....
Beautiful Villa just steps from Pool. Long Term and Senior Discounts Available.
The Waikoloa Colony Villas is part of private gated community of luxury townhomes. It is on the South Kohala Coast within the world renown Waikoloa Beach Resort.It is centrally located with the best beaches and weather on Hawaii's Big Island. BEAUTIFULLY DECORATED UNIT...
Kaanapali Alii | 263
Experience luxury oceanfront living in this stunning sixth-floor Maui condo at Kaanapali Alii. Spanning 1,843 square feet, this two-bedroom, two and a half bath vacation rental comfortably accommodates up to four guests, offering the perfect blend of togetherness and...
Four Seasons Hualalai 5BR Ocean Estate
Escape to your own private paradise at this stunning newly renovated expansive 5 bedroom, 5 bathroom 6500 square foot ocean adjacent estate, a beautiful custom home on 3/4 of an acre, nestled within the exclusive Four Seasons Resort Hualalai. Experience the height of...
LUXURIOUS, REMODELED MAUNA LANI VILLAGES TOWNHOME! VIP BEACH PASS INCLUDED!
BEST KEPT SECRET IN MAUNA LANI - Mauna Lani Villages 329 is a modern, highly renovated three bedroom townhome located right in the middle of the exclusive Mauna Lani Resort, where guests are able to access private beach clubs, secluded oceanfront trails and restaurants...
Luxury Alii Cove Ocean View Townhome In Kailua Kona
This 3 bedroom, 3 Bath luxury townhome is located in the gated Alii Cove Condominium complex. This location provides a short walking distance to the of town of Kailua Kona where you will find fine ocean front dining, shopping, St. Michael’s Church, and coffee shops...
Whispering Palms - Tranquility and Elegance
WHISPERING PALMS AT KOLOA KAI VACATION RENTALSTranquility and Elegance in Poipu’s Kiahuna Golf VillageWelcome to Whispering Palms, your luxurious Hawaiian retreat in the heart of sunny Poipu! Perfect for families, multi-generational groups, or friends traveling...
Beautiful Ocean View High-Rise in Ka’anapali 🌴😎⛵️
Experience breathtaking ocean and resort views from one of the best vantage points in the entire Kaanapali Shores Resort. This unit is unique in that it is one of only eight studio units that are placed in the inner courtyard (the other face neighboring properties and...
Lei Ohana - Private Pool, Separate Guest House
LEI OHANA AT KOLOA KAI VACATION RENTALSA Private Island Retreat in PoipuEscape to Lei Ohana, a luxurious ranch-style home offering over 3,000 square feet of spacious living on Kauai’s sunny south shore. Nestled in a tranquil residential neighborhood in Poipu, this...
Top floor condo & loft with partial AC, W/D, outdoor pool, hot tub & grills
Hanalei Bay Resort 8233 fourOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Hanalei Bay Resort 8233/4 is located in the Plumeria Building with air-conditioning in the bedrooms....
West Oahu vacation rental with stunning views
Oahu's best kept secret! Affordable, updated Hawaii condo is perfect for your stay in paradise. Off the beaten track and away from the crowds-live like a local with uncrowded, nearby beaches and a pristine, serene pool. Ko Olina lagoons, shopping and restaurants are a...
❤️ PiH❤️ISLANDS DELIGHT ★ Dual Master ★Newly Renovated ★ Privacy
Brought to you by Paradise in Hawaii Luxury Homes.Welcome Islands Delight, a part of our Hawaiian Luxury Collection. Island Delight at Islands is a wonderfully large, 2,189 square foot two-bedroom home that can sleep 6. Located in the Islands at Mauna Lani, a low...
❤️EPIC PANORAMIC OCEAN VIEW⭐️RENOVATED-DUAL AC❤️OWNER MGMT🐳
Aloha! 🌺 Welcome (e komo mai) to Epic View Suite, your gateway to paradise across from the Maui famous Kamaole Beaches! This stunning condo offers an unforgettable experience, combining the comforts of home with the allure of a tropical getaway. We are in South Kihei...
Beach Theme Home, with 2021 Mercedes SUV, West Oahu, Wai Kai Lagoon resort.
Aloha! Beach themed home in west Oahu! Located next to many golf courses (7 courses within 4 mile radius), including the prestigious, Ernie Els designed, Hoakalei Country Club. This 3Br, 2.5Bath 2-story townhome features 1400sq ft of living space, full amenities as you...
New home in quiet neighborhood, amazing views, minutes from top resorts.
This beautiful, custom built home was completed last year and has never been rented before. Outdoor living is a premium with a 700 square foot deck and a 700 square foot lanai facing west that capture the entire Kohala coast line. Enjoy views of the ocean, sunsets,...
Incredible Views!!!
Sun Tracks Across the Water ---Sun Tracks Cross the WaterBeautiful panoramic sunset views across the curvature of the earth. Close enough to watch whales, away from crowds and the beaten tourist path, your vacation starts here. This brand new custom vacation house is...
Oceanview Condo w/Athletic Club Access, Shared Pool, Hot Tub, Free WiFi, & A/C
Pili Mai 13COur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Ready to experience Hawaii as a family? Feel right at home in 13C, even when miles away in the middle of the blue Pacific....
OCEANFRONT Bliss! FIXED UNIT 1414 Building 1 3BR, 2BA, sleeps 8
This luxurious Fixed unit 1414 in building 1 is a 3 bedroom oceanfront villa that features nearly 1500 sq. ft. of living space and comfortably sleeps up to 8 adults. The master bedroom is outfitted with Westin’s signature king size Heavenly Bed and the master bath...
Mahalo Hale - Private Luxury Resort Property
Welcome to your private luxury resort on the stunning north shore of Kauai.Four king bedrooms, one with additional media center + queen bed, three full baths, grand gathering room with pool/ping pong table, additional media room with 72” TV. Whole house AC -...
Kumulani Residence A2
This ground-level, oceanview residence, finished in classic Hawaiian decor, offers a great room with sliding glass doors for indoor/outdoor island living, a full kitchen with premium stainless steel appliances (including a wine refrigerator) and granite countertops,...
🏖️Upgraded 2BD Plus Loft | Amazing Golf & Ocean Views | AC | vrKCV
vrKCV - Country Club Villas 341, Professionally Managed by Kona Coast VacationsWelcome to Country Club Villas #341 – Your Dream Vacation Awaits!Aloha! Step into paradise and experience breathtaking views from Country Club Villas Unit #341. Perched on the third floor,...
Brand New to the rental Pool Take Advantage of our Introductory Rates
This home has been beautifully upgraded with Solid hardwood Maple flooring throughout. The kitchen has Monkey Pod solid wood cabinets and granite counter tops throughout. The bathroom has a beautiful walk in shower, Koa wood countertop and large soaking tub. TV stand is...
Maui Resort Rentals: Hyatt Residence Club – 3BR Oceanfront Lower Floor VIlla
3 Bedroom Oceanfront Luxury at The Hyatt Residence Club – Ka'anapali's Newest, Most Exclusive Resort.Perched upon Ka'anapali, one of the world's most beautiful beaches is the Hyatt Residence Club Ka'anapali. Within the lush borders of this sprawling tropical paradise,...
Honu Hale on Turtle bay golf course - Kuilima Estates West
2 bed 2 bath condo with a loft. Sleeps 4 people. Explore Oahu and enjoy North Shore's beautiful ocean. Just a 8 minute walk to the relaxing beaches of Turtle Bay Resort. A short 5-15 min drive to many legendary beaches with soft sand, turquoise water, & amazing waves!...
Enjoy ocean views and a private lanai at Akahi #408, 2-bed, 2-bath condo!
Come enjoy paradise at Keauhou Akahi unit #408, at this two-bedroom, two-bathroom property. Enjoy your private lanai, with ocean views, and BBQ!Keauhou Akahi is conveniently located in the Keauhou area of Kona. You are a close drive or walk to the stunning and iconic...
WBH D116 Aloha Wai2 – Serene Garden view by the Sea
Summary:Ground floor 1-bedroom/ 1-bath air-conditioned Condo Suite comes with a comfortable king-size bed and living room couch that pulls out to a queen size sofa-sleeper (8.5" mattress) allowing the unit to sleep up to 4 people. Complete Full Kitchen, Cable TV, Air...
🏖️Secluded yet Close to Everything | Ocean View | vrKCV
vrKCV, Orchid Hale, Professionally Managed by Kona Coast VacationsAccess to the Orchid Hale property is via a rustic farm driveway, flanked by coffee trees. At the stone pillars, the property opens up to a secluded, park like sanctuary. The house is perched on an 1 &...
Prime Location for Oceanfront Lovers
*This is a NEW listing and it's gorgeous!Situated in Maalaea, just a short drive from the airport, Island Sands 110 is the perfect base to enjoy all that Maui has to offer. The condo is steps away from the daily bustle of Maalaea Harbor, where you can indulge in a...
Hale Nalani O-202 a hidden Gem, comfort and fun
A Wonderful 3-Bedroom Villa to Enjoy the Beauty of Ko OlinaWelcome to your ocean-view beach villa, where privacy and beauty come together in a breathtaking setting. The property features serene koi ponds with waterfalls, a lagoon pool with a sandy beach for children, an...
Ko Olina Beach Villa Ocean View Condo 2BR/2BA
Penthouse Beach Tower 10th Fl (1003) - Steps from the Ocean. Escape to a Hawaiian Paradise at the Beach Villas Palekaiko on Oahu! Sleeps up to 6.The Palekiko welcomes you to paradise from the moment you walk in the door with all you need to relax and rejuvenate during...
Two Bedroom Ocean View Deluxe Luana Kai Resort A203
Luana Kai A203 is a two bedroom/ 2 bath oceanview. Enjoy the spectacular view while dining on the lanai. This condo has a King in the master with two twin beds in the guest bedroom, and a sofa bed in the living room. A203 does NOT have AC. Includes Wifi, cable Tv,...
Peaceful Petfriendly Paradise Home | with A/C
Welcome to Hale Kāhili! Enjoy a relaxing retreat at our peaceful, pet-friendly home in Hawaiian Paradise Park. Our spacious 4 bed 2 bath home accommodates up to 9 guests and is perfect for families or groups looking for a comfy and convenient stay close to Hilo. With a...
Oceanview Beautifully Renovated Kihei Condo D206
Escape to paradise with a stay in our stunning, recently renovated Oceanview condo in Maui. Perfect for a romantic retreat, this second-floor gem features brand new engineered hardwood floors and a stylish kitchen with a large center island, quartz countertops, a chic...
Pili Aloha: 3BR Condo w/ Lanai, Pool & Mountain Views
Welcome to Pili Aloha by GatherPili Aloha is a beautifully designed 3-bedroom, 3-bathroom luxury condominium offering 1,318 square feet of elegant living space in the heart of Princeville, Hawaii. Situated on the upper level, this home provides stunning panoramic views...
Newly renovated Waikiki Sunset unit with STUNNING Diamond Head and ocean views
**Looking for other accommodations, please view my other unit located in the same building #2824127**This unit is located on a high floor of the Waikiki Sunset with sweeping Diamondhead, ocean, coastline, and park views, this condo offers 2 bedroom (one queen bed and...
Large End Unit - Special Pricing - Luxurious 3 Bedroom/3 Bath Town Home
This beautiful 1850 square foot 3 bedroom / 3 bath town home is a very private end unit which has a wall of windows that fill the living area with natural light. On the main floor, you will find a gourmet kitchen with granite counter tops and brand new stainless steel...
Stunning Remodeled 2BD/2BA Oceanview Condo
Kauhale Makai (Village by the Sea) truly embodies paradise. This newly remodeled 2-bedroom, 2-bathroom condo has been beautifully updated, boasting a brand-new kitchen complete with granite countertops and high-end appliances.The elegantly designed bedrooms and...
Hawaiian Elegance – 5BR Retreat Steps from Mauna Kea & Hapuna Beaches
Welcome to Hawaiian Elegance! From sunrise to sunset, beautiful views surround this exquisite five en-suite bedroom estate in the prestigious Kauna'oa gated community in the heart of the Mauna Kea resort. Hawaiian Elegance is a brand new home just completed in March...
Perfectly located budget friendly condo, across the street from the beachnn
Welcome to Kihei Akahi C308. This updated 3rd floor condo has partial ocean view and tropical foliage from the private lanai. Fully equipped and ready to host your Maui memories. The condo can accommodate 4 people and has in unit washer/dryer. Kihei Akahi is located in...