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.
2 Bedroom Vacation Condo - West Maui - Great Location!
Nice Two Bedroom, one bath condo furnished 'Island Style'. Great location across from beach park! Next door to farmers market, coffee house, historic church, and walking distance to many great beach spots! Great beaches for swimming, sunning, snorkeling, and whale...
Ocean & Garden Views Await at Wailea Ekahi 34B: Spacious 1BR/2BA Ground Floor
Welcome to Wailea Ekahi 34B where lush tropical foliage surrounds you and views of the majestic Pacific await! This updated 1 bedroom / 2 bathroom unit is the perfect setting for your Maui vacation. This ground floor unit boasts incredible ocean and garden views! Enjoy...
Beachfront Penthouse w/ 3 Lanais on O’ahu!
Pats at Punalu'u | Spectacular Ocean & Mountain Views | Community Pool | 4 Mi to Polynesian Cultural CenterLive like a local at this 3-bedroom, 2-bath Hauula vacation rental condo where sand and surf are just outside your door! Fall asleep to the sound of waves and wake...
Sugar Beach Resort Condo w/ Shared Pool/Hot tub, Private W/D-Near Everything
Sugar Beach Resort 229Our 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...
Spectacular Unobstructed FULL Oceanfront Unit
Nestled within the picturesque Kihei Beach Resort, this enchanting 1-bedroom, 1-bathroom unit invites you to experience the allure of an authentic Hawaiian aesthetic, effortlessly blending modern comfort with the timeless charm of the Aloha spirit.As you step inside, be...
Winter Specials! Family Friendly, Close to Beaches!
This is a lovely, spacious 3 bed & 3 bath condo located in the desirable Waikoloa Village within the Paniolo Greens complex, C-206. It's only minutes aways from wonderful beaches, a grocery store and plenty of hiking and sight-seeing! The kitchen has been renovated...
Kihei Beach #307- Your Oceanfront Oasis
Kihei Beach #307 – One-Bedroom Beachfront Condo with Two BathroomsWelcome to Kihei Beach #307, a remodeled one-bedroom, two-bathroom beachfront condo offering panoramic views of the Pacific Ocean and neighboring islands. With modern upgrades and a prime location on...
Seclusion & luxury in west Maui! Condo #212
Unit 212 has a spectacular view of Honokeana Cove and Molokai Island across the Pailolo Channel. The Cove is home to dozens of turtles and offers sheltered snorkeling and paddle boarding above coral formations and tropical fish. This attractive two-bath unit sleeps five...
KBV 32B4 New Listing Oceanfront Kapalua w Spectacular Ocean Views
Kapalua Bay Villas 32B4 NEW LISTING Oceanfront 1Bedroom, 1Bathroom, Kapalua Villa with Spectacular Ocean Views! FREE daily activities included with your stay value up to $1035! Complimentary admission, every day of your stay*: Lu'au, Golf, Whale Watch (seasonal), Dinner...
Kihei Akahi D510, Your perfect Maui Getaway!
This property is hotel zoned, and not being affected by the recent proposed legislation.Welcome to your slice of heaven in the heart of Kihei, Maui! This beautifully updated 1-bedroom, 1-bathroom condo offers the perfect blend of comfort, convenience, and breathtaking...
Poolside Gem- Kealia Resort #102 -Ground-Floor - Walk Right Out to the Beach!
KEALIA RESORT, #102Welcome to Kealia Resort #102, a charming ground-floor oceanfront condo designed for the perfect tropical retreat. Step from your private lanai directly onto Maui’s longest stretch of sandy shoreline, where you can enjoy morning walks, days filled...
Ocean Views/Mountain Views!! HUGE LANAI Directly across the road from the BEACH!
LARGE LANAI condo directly located across from beautiful Magic Sands Beach!!! (sands appear and reappear at this beach depending on swell and current). Come stay at this perfect beach condo that sleeps 6! This condo is very spacious with 2 bedrooms, 2 bathrooms, also a...
Royal Mauian 601: Stroll to Shops, Dining, & Witness Haleakalā's Majesty!
Royal Mauian #601 – Upgraded Top-Floor Retreat with Mountain ViewsRoyal Mauian #601 offers a unique Maui experience with its top-floor privacy, completely upgraded interior, and sweeping views of Haleakala and the lush island landscape. This two-bedroom, two-bathroom...
Sugar Beach PH21 - Direct Oceanfront 1 bedroom
Book with us and come to Maui to explore everything we have to offer!Just Renovated!Beautiful views from a great unit. You will love the well maintained, upgraded corian kitchen and white cabinetry. Enjoy your coffee on the top floor balcony while looking at whales and...
Save up to 30% Instantly on stays thru 5/31/25! Whaler 456-Oceanview,1B/1B,AC!
Experience unparalleled oceanfront living at Whaler 456, where breathtaking views of the Pacific Ocean surround you from the spacious lanai to the master bedroom and throughout the entire residence. This exceptional condo offers sweeping vistas of the crystal-clear...
Hale Kai O Kihei condo with pool & free WiFi - swim, surf, & more
Hale Kai O Kihei 212Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This Hale Kai O’ Kihei condo offers a breathtaking ocean view from every room and includes a private lanai that...
Walk to Beach! HUGE 5 bedroom, 5 bath with Pool!!
This wonderful beach house with private pool is perfect for all your vacation needs! Centrally located one short block from beach and walking distance to Magic Sands and Kahaluu Beach Park.Permitted 5 private bedrooms all with their own bathroom . The upper level has...
Breathtaking Ocean Views Beach Cottage
This cozy cottage sits on a private white sand, reef-protected beach. Great for snorkeling and safe for kids! You'll enjoy swimming with turtles an a variate of colorful fish! Just sit on the serene sandy beach, enjoy the lush mountains, and captivating sunrises. You...
KAS 1101 Spacious 2BD Condo w Pool Across Beach
Kamaole Sands 1101 Family Vacation Destination at Spacious 2Bedroom, 2Bath Condo in Central Kihei. On-site Pool, Across Street from Beach, Steps to Shops and Dining FREE daily activities included with your stay value up to $554! Complimentary admission, every day of...
Beachfront, Ocean View, Polo Beach Wailea/Makena #306
Unit 306 is a 2 bedroom and 2 bath condo located on the third floor at the Polo Beach Club. The Polo Beach condo's sleep 6. Please call for very latest openings as there may be a new booking in progress. Polo Beach Club has both ocean front and Prime (on sand) ocean...
Classic Hawaiian Charmer - Spacious and Cheerful w/ Wraparound Lanai
Alii Kai 1201 is a light-filled, classic Hawaiian getaway in the heart of Princeville! Your home-away-from-home has two comfortably furnished bedrooms (king sized in the master suite, queen sized in the guest bedroom), a well appointed living and dining area, and a...
Luxurious Kapalua Golf Villa: Stunning 2BR/2BA Retreat with Ocean & Golf Views
Escape to Paradise at our Luxurious Kapalua Golf Villa!Welcome to your dream Hawaiian vacation at this exquisite 2-bedroom, 2-bathroom retreat, nestled in the highly sought-after Kapalua Golf Villas. From the moment you step foot into this tranquil haven, you'll be...
Maui Resort Rentals: Luana Garden Villas 5D – Modern 3BR Villa at Kaanapali’s Newest Luxury Residences!
This luxurious 3Bedroom/3Bath residence is conveniently set within Enclave One of the Luana Garden Villas. This premiere offering's southern orientation offers a bright inviting setting for you and your ohana (family) and its designation within our "Elevated" collection...
Gorgeous renovated corner unit just 1 block to Waikiki Beach!
Niihau #805 – 247 Beach WalkLocation, location, location! Ni'ihau is a hidden gem found within the hustle and bustle of Waikiki just a block away from world-famous Waikiki Beach where surfers and paddlers spend their days! Recently renovated (2024) from floor to...
OCEAN FRONT! Paradise in Kona! Best Location!
GET LOST IN PARADISE!! Absolute BEST location with direct ocean front view at historic Alii Drive. This unit is upgraded with tropical island theme. We are 15 mins from the Kona airport and ocean fronting!!!FAST INTERNET!! for those of you decided to escape to paradise...
Million Dollar Views...Affordable Rates...Traveling on a Budget?
The view will take your breath away from the second you walk in until you leave. On the slopes of Haleakala, this second floor unit is high enough to have breath taking views but just over a mile from award winning beaches. Dinner on the lanai (balcony) while watching...
Direct OCEANFRONT, Rare Enclosed Lanai, AC - Maui Kai 804
Experience elevated island living at this beautifully updated 1-bedroom, 1-bathroom oceanfront condo at Maui Kai Resort on North Kaanapali Beach. With unobstructed views of Lanai and Molokai, a fully enclosed lanai for extended living space, and central air...
Sunny condo with pools, hot tub & washer/dryer - near swimming & surfing
Maui Kamaole I105Our 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...
KBM Resorts | FREE CAR | Honua Kai Konea | Mountain view | 1-Bedroom Condo with Easy Access to Beach! HKK-424
** 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...
Stunning Oceanfront Retreat, Kahana Reef 218
Direct oceanfront unit in a highly desirable location right in between the popular areas of Kaanapali and Kapalua. When you sit on the balcony, you have panoramic views looking out to the islands of Lanai and Molokai. You will also see whales and sea turtles and have...
In Town Ocean View Condo-Walk to the Beach, Shops, Restaurants and Bars!
This top floor condo is spacious with open beam ceilings and an ocean view. It is located in the center of Kailua Kona. You can walk to the pier, to restaurants, shopping, even the bank and the grocery store are nearby. The condo has two bedrooms with California King...
Akala Pua Cottage By Parrish Kauai - great location in Poipu!
Akala Pua is a lovingly cared for three bedroom home within walking distance to two popular South Shore beaches in Poipu. Lawai Beach is to your left and Baby Beach is to your right, so choose your direction and in 200 plus yards you will enjoy the sun and sand. Distant...
Ocean front Quiet Top Floor Maalaea Kai
Welcome to your top-floor oceanfront getaway in peaceful and centrally located Maalaea Bay, Maui. This bright and breezy condo offers the perfect mix of comfort, convenience, and unforgettable views — ideal for couples, families, or small groups looking to unwind and...
Villa Sky@Poipu Kai, Resort Amenities, Sunset Walk To Beaches & Restaurants W/AC
VILLA SKY @ POIPU KAI, NO ADDED FEES! This Bright, newly renovated, Island Chic condominium is in the heart of Poipu Kai Resort. A short stroll along a beautiful Green Pathway to Poipu Beach & 3 more Beaches. Great top floor location is unbeatable with the high vaulted...
Rain Forest Paradise Ideally located betwn Hilo & Volcano National Pk 2BD/2BAnn
Paradise awaits you at this cozy, Big Island getaway. Boasting lush, tropical grounds, a wraparound lanai, private gas grill, and a large outdoor dining table, you'll have everything you need to relax over your favorite tropical meal.Welcome to your slice of paradise at...
Gorgeous Diamond Head Views from 34FL 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...
Ilikai Hotel - Waikiki City Lights! Full renovations to be completed 12/2023!
The condo has been fully gutted and will be modernized and styled for your comfort. New appliances, open kitchen, brand new furniture!Enjoy the Hawaiian breeze from the mountains and watch the city from the condo. Added bonus, this unit comes with a washer +...
Spacious home w/ AC, lanais, shared pool, hot tub, & views of Makai Golf Course
Nihilani 21COur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'There's something simply magical about the Garden Island of Kauai that speaks to people throughout the world. It's all...
Romantic Tropical Retreat, 150 yds from the Ocean!
Please note, effective Jan 1st. 2026, Hawaii`s Transient Accommodations Tax will increase from 10.25% to 11% for all stays with an arrival in 2026 forward. We may need to collect the tax difference to secure and finalize your booking. We will contact you to confirm the...
Waikiki Banyan 1909 Amazing Views and Just Steps to the Beach
Beautiful Views of Ocean and Diamond Head, Relax on the Lanai with a tropical drink and enjoy this Beautiful view's 1 Block to Waikiki Beach. Full Kitchen equipped just like home Bedroom has a Queen and Twin Bed, Queen Sofa sleeper in the living room and a pack & play...
Unit 123, Two Bed,Two Bath, Ocean View Condo
This condo is a beautiful ground floor condo with a direct view of the ocean; Maalea harbor; west Maui mountains; and whales, during whale season, from your private lanai. You can head up to the roof top to enjoy the full kitchen, gas BBQ grills, picnic tables plus a...
Top-floor corner unit - amazing ocean views - steps to beachside pool & hot tub
Islander on the Beach 333Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Discover the perfect ocean getaway at Islander on the Beach, a 6.5-acre oceanfront resort with stunning...
CORNER Unit with 11th Floor Waikiki Ocean, Lagoon & Marina Views! Washlet!
Ilikai Marina #1180 – 1765 Ala Moana Blvd.CORNER UNIT! Incredible panoramic views of the Pacific Ocean, Duke Kahanamoku Lagoon/Beach, and marina; and stunning sunsets! Bring your binoculars!CONSTRUCTION NOTICE: Due to emergency building exterior spalling repairs, unit...
Steps from the beach and elevated views
Welcome to Kaleialoha 310, a spacious 1-bedroom, 1-bathroom condo that offers an open concept design and ocean views from the 3rd floor. This property has elevators for easy access. Unit 310 can accommodate up to 4 guests. Rest peacefully in the spacious bedroom, which...
AIR CONDITIONING ON NORTH SHORE! 10 Minutes From Hanalei Bay!
*** Additional Fees Payable to the Resort Directly:Hawaii Transient Accommodation Tax: 1B Condo - $10.84/dayResort fee of $17.70/day for the 1B CondoThis incredibly quiet, family-friendly resort is perfectly situated alongside the Makai Golf Course. The resort is a...
❤️PiH❤️ ENDLESS SUMMER ★Big Golf Discounts★Heated Pool&Spa★
Brought to you by Paradise in Hawaii Luxury HomesWelcome to Endless Summer Villa, a part of our Hawaiian Luxury Collection. Endless Summer Villa at KaMilo is a wonderful large single-level 4 bedroom, 4 1/2 bathroom home that includes three bedrooms in the main house,...
Spacious Kauai townhome w/ pool & hot tub - close to world-class beaches
Nihilani 25COur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This two-story townhome with three bedrooms and a den feels open and spacious thanks to its many windows, floor-to-ceiling...
Kauai Birdsong at Poipu Crater! Spacious and private 2/2 minutes from the beach.
Your home away from home in Poipu with 2 bedrooms. This fantastic townhome features a cozy queen bed and a luxurious king bed, perfect for a good night's sleep. With amenities like a hair dryer, washer & dryer, WiFi, and AC, you'll have everything you need for a superb...
Oceanfront 2 bedroom suite in Sunny Kihei
Third floor ocean view easy access to tropical gardens and the ocean beyond. Large private view deck and renovated interior. Large private condominium apartment at the resort condominium complex on the beach in sunny Kihei, Maui, Hawaii. 2 bedrooms with private attached...
Maui Kamaole 2 Bedroom Corner Unit J101
Welcome to one of the rare ground floor 2 bed/2bath den units, offering extra side windows and even an extra lanai off the master bedroom. Indoor/outdoor living is what we love about our tropical home, with 3 lanais you can always find a quiet piece of paradise here....