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.
This three-bedroom bungalow at The Lodge at Kukui'ula on Kaua'i offers luxurious accommodations and exclusive access to the award-winning private club facilities and amenities of The Club at Kukui'ula, including the 18-hole Tom Weiskopf designed golf course, sprawling...
Kaanapali Alii 11121 Bedroom | 2 Bathrooms | Sleeps 6 | Ocean View_________________________________________________Welcome to Kaanapali Alii 1112, a beautiful 1-bedroom, ocean view residence overlooking the turquoise waters of Maui’s Kaanapali coastline. This spacious...
** 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...
The Famous Peacock House – Spacious & Whimsical Big Island RetreatWelcome to The Famous Peacock House, a vibrant and whimsical Hawaiian getaway designed for families and friends to create unforgettable memories together. With space for large groups, thoughtful...
2BR Ocean View Condo at The Windsor Waikiki Near the Beach
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company. Welcome to your elevated island escape at The Windsor Waikiki, where iconic views of Diamond Head meet...
Chic Hawaiian Remodel• Rooftop Pool & Spa • 5 Min Walk to Waikiki Beach
Welcome to your Hawaiian-style retreat in the heart of Waikīkī!Freshly remodeled, this beautifully designed 1-bedroom condo blends modern comfort with island charm — just a short walk to Waikīkī Beach, Duke’s Statue, shopping, and dining.Located in the Pacific Monarch,...
Boutique Hotel Waikiki FREE parking
Excellent Location, free parkingEnjoy a comfortable stay in this independently owned hotel room featuring a king-size bed, along with a twin-size pull-out for a third guest if needed, full bathroom, central AC, and a flat screen TV. The room includes a mini fridge,...
Incredible REMODELED condo-bonus-peak ocean view, AC available!!
Beautiful condo-oceanfront complex! Simply paradise!Aloha and welcome to paradise! We are located on Kauai's beautiful south shore known for it's sunshine and pristine beaches. The Kiahuna plantation sits on 35 tropical acres landscaped with rolling lawns, koi ponds,...
Modern Princeville Retreat – Hanalei Bay Rental with Private Pool
This beautiful brand new home is overlooking Hanalei Bay & the beautiful tree canopy of Princeville. With a 10 min walk to the 1 Hotel beach, a short walk to Princeville Center and a quick drive to Hanalei Town, it is the ideal central north shore location. Featuring...
Waikiki Gem-Mins to Beach, Lanai w/City View, King Bed&Surf Lessons in Building!
Wake up steps from Waikiki Beach in this bright city-view studio at Kuhio Village Tower 2 — perfectly located just 2 minutes from the Duke Kahanamoku Statue and Kuhio Beach.Sip your morning coffee on the lanai and watch Waikiki come alive, then head downstairs for surf...
Step Out into Waikiki | Family Hotel w/ Outdoor Pool & Breakfast
Unwind in a spacious suite with private lanai, deep soaking tub, free WiFi, and plush bedding. Enjoy continental breakfast with Kona coffee, then stroll to Waikiki Beach or nearby shops. After exploring, relax by koi ponds or dip in the pool. Perfect for couples,...
Hale Malu: Gorgeous 5 BR Kauna'oa Home, 10-Minute Walk to Beaches!
Brand new and gorgeous private estate at the only community that is walking distance to the two best beaches on the Big Island, Mauna Kea and Hapuna! This home has a prime location atop a bluff in the luxurious Kauna'oa community. Built with open space and privacy in...
Wyndham Mauna Loa Village | 1BR King Bed Suite
Summary:If sunset cocktails, pools, and plenty of tennis sound like your style, you’ve found your spot. Located in Kailua-Kona next to a country club, this tranquil oasis sits away from town traffic and crowds while offering convenient access to the island’s many...
This Stylized Captain's House is located minutes away from family friendly scenic Kealakekua Bay beaches, the national park Pu'uhonua O Honaunau, & the island's best snorkeling spot "Two Step".An ideal setting for tropical adventures of all kind, offering spacious...
Ground Floor Ease - Golf & Ocean Views
Welcome to your luxurious retreat at Mauna Lani Point G101, a stunning short-term rental nestled in the heart of Kamuela, Hawaii. This elegant 1-bedroom, 1-half-bathroom condo offers a perfect blend of comfort and style, ideal for your next getaway. Step inside to...
Kaanapali Alii 11133 Bedrooms | 2 Bathrooms | Sleeps 8 | Ocean View_____________________________________________Welcome to Kaanapali Alii 1113! This is a gorgeous 2-Bedroom Ocean View condo, with a fully enclosed den that comfortably serves as a third bedroom. This...
Experience Oceanfront Bliss at Sugar Beach Resort 530
One of the best features to this tropical getaway is waking up to the sound of waves. Enjoy stunning views of Molokini, Kaho‘olawe, and the West Maui Mountains from your private lanai at Sugar Beach Resort 530. Just 60 feet from the ocean, this one-bedroom condo offers...
Scenic Kauai Stay Near Allerton Garden + Free Pool Access + Kitchen
Experience oceanfront serenity with stunning views, spacious rooms, a full kitchen, a private balcony, and in-room laundry—ideal for couples and families. Snorkel nearby, hike the Mahaulepu Trail, or spot turtles at Poipu Beach. Relax in our large outdoor pool. Whether...
Hale Makana: Portlock Luxury Home with Pool & Ocean Views
Set along Oahu’s exclusive Portlock coastline, Hale Makana is a refined single-level oceanfront estate that celebrates effortless island living. With postcard-worthy views of Diamond Head and the deep blue Pacific, this five-bedroom, seven-bath retreat blends...
Unique Treehouse at Magic Sands beach, ocean view
Under a huge, landmark Royal Poinciana tree, sits our Treehouse. Treetop views of the ocean across the street. Large, standalone cottage. Tall bamboo ceilings, lots of air through large windows, screened. Ceiling fans and cool shade make this place uniquely cool for...
Kapalua Golf Villas | Large Bedrooms | KBM Resorts | 3 Units, 4 Bedrooms | ML-2291
** 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...
The Heart of Kapaa walking distance to the beach, groceries, and fine dining.
A condo with beach access, and 2 pools! Grocery store, health food store, shopping and many fine restaurants all within 5 minute walking distance. The condo sits at the very beginning of the 8 mile costal bike path and we supply 2 bikes. Ground floor unit, easy access...
Modern Beach Apartment North Shore Home
Your Waialua adventure begins at this fantastic 1-bedroom apartment. The space features a queen bed, AC, a washing machine, and WiFi. The bathroom includes a shower and a hair dryer for your convenience. Nestled in a serene setting, this tremendous property is the...
Oceanfront 3BR Prime Location in Kahana
Discover the perfect island getaway at Kahana Outrigger #2B2, a spacious oceanfront 3-bedroom, 2-bath retreat nestled on Maui’s stunning west coast. This 1,448 sq ft condo offers breathtaking panoramic views of the Pacific from a large lanai, where you can whale watch...
Ke Alaula Hale 7 – Private & Secluded | Onsite Staff & Daily Housekeeping
This centrally-located 3-bedroom, 3.5 bathroom private home is a short 6-minute golf cart ride from the heart of the Four Seasons Resort. Designed for convenience and uncomplicated family living for up to 6 guests, this property offers a vaulted, wood-beamed great room...
Maui Kaanapali Villas 292 Ocean view 1-bedroom Pool AC
Maui Kaanapali Villas 292 Remodeled Oceanview Getaway on North Kaanapali Beach Steps to the Beach, Pool and Hot TubWelcome to your Maui Retreat: Spend your next Maui vacation at this beautifully remodeled ocean-view condo located just steps from North Kaanapali Beach....
Honua Kai | 2 Free Rental Cars | KBM Resorts | Family Friendly | 2 Units, 3 Bedrooms | HK ML-1436
** 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...
Kiahuna Plantation Resort 162 Ocean View 1 Bedroom
Soak in beautiful ocean views from this 2nd floor private one-bedroom retreat on Kauai’s most famous beach. Cozy, charming, and well-located, it’s everything you need for a relaxing island stay. Unit 162 Ocean View 1 Bedroom 1 Bath• Fully equipped kitchen includes full...
Napili Bay Beach-Spacious 3Br Condo
Spacious 3BR Townhome – Steps to Napili Bay, Pool, Hot Tub & More!Welcome to your home away from home on Maui! Just steps from three stunning beaches—Napili Bay, Honokeana Cove, and Kapalua Bay—our spacious 3-bedroom, 2-bath townhome is perfect for families and groups...
Sunlit Island Escape in Kailua
Welcome to your island getaway! Nestled in the heart of Kailua, this bright and inviting home is perfectly located just minutes from Kailua Beach, where you can soak up the sun, enjoy crystal-clear waters, or try your hand at paddleboarding.This property combines modern...
KHV 36 Beautifully Remodeled Direct Oceanfront 3BD Kahana Condo, Steps to the Beach and Pool!
Kahana Village 36 NEW LISTING Spectacular 3Bedroom Beachfront Condo in Kahana with Amazing Ocean Views, and Privacy! Welcome to your dream getaway at Kahana Village—an oceanfront oasis nestled on the scenic shores of West Maui. This ground-floor condo boasts 1,566...
Charming studio for 3 at Waikiki Grand Hotel® in Waikiki with AC & Pool
Legally permitted vacation rental—〽Waikiki Grand Hotel® 900〽Quiet 9th-floor studio above street noise. ☮WG 900 is just a short walk toWaikiki Beach, Kapiolani park, & Diamond Head CraterThis studio-suite includes:✺(1) Queen bed✺AC✺Sofa-Bed ✺Tub/shower ComboSimple...
Spacious Ground Floor Maui Retreat, Grand Champion
Summary:🌴 Prime Location – 5-min stroll to Charley Young Beach🏊 Resort-Style Living – Pool, hot tub, BBQ & tennis courts🛏️ Ultimate Comfort – King bed + memory foam sofa bed🍹 Private Lanai – Sip cocktails with lush garden views🍽️ Chef’s Kitchen – Fully equipped for...
Kaanapali Alii 31012 Bedrooms | 2 Bathrooms | Sleeps 4 | Ocean View________________________________________Welcome to Kaanapali Alii 3101, an elegant one-bedroom ocean-view condo, with a fully enclosed den that comfortably serves as a second bedroom. From the private...
Fabulous Poipu 7 bedrooms for 16! Amazing pool! New Listing
New Listing!! The Listing is made up of two separate townhomes just steps apart!This fabulous property located in wonderful proximity to Brenneckes, Poipu, and Kiahuna Beach!Surrounded by a championship golf course, the property enjoys a prime spot on Kauai’s sunny...
Soothing studio with AC that is a five minute walk to the best beach on Maui.
Consider this adorable studio your home away from home while you visit Lahaina. Guests enjoy a superbly cozy space with one bathroom, perfect for relaxing after a day of exploring. This studio is five minutes away from the best beach on Maui. You can rent snorkeling...
2 Bed 2 Bath 2 Parking at Cove Waikiki
Spacious 2 bed 2 bath 2 parking, end unit. A perfect home away from home that you will instantly fall in love with, and never want to leave! It sleeps 4, with one queen bed in the primary and two twin beds in the second bedroom. There is an AC unit in each room, free...
Kauna'oa 22 Five Bedroom Residence
Step into the Hawaiian serenity of Kauna’oa 22, a luxurious five-bedroom, six-bathroom villa offering sweeping views of the Kauna’oa golf course and the ultimate in indoor-outdoor living. This elegant retreat features a grand vaulted ceiling and a spacious open-plan...
Aqua Aloha Surf Waikiki 1211 Deluxe Studio with Lanai and Partial City Views
Aqua Aloha Surf Waikiki 1211 Deluxe Studio with Lanai and Partial City Views located just 2 Blocks to Waikiki Beach, (1) Queen bed+ (1) Queen Sofa sleeper, Sleeps 4, 374 St FtAqua Aloha Surf Waikiki brimming with island personality offers a range of accommodations that...
Hidden gem in Heart of Waikiki! AC, Wi-Fi, full kitchen, free nearby parking!
Ni'ihau Apartments #704 – 247 Beach WalkThis hidden gem in the heart of Waikiki, just a quick 1-block stroll to the white sands of Waikiki Beach, is the perfect launching point for your dream Hawaiian getaway! FREE Wi-Fi and parking at nearby lot. Secured...
IA21 Ocean Breeze Retreat: Luxe High-Rise 21F
Experience the Ultimate Waikiki Friday Night Delight!Welcome to your front-row seat to one of Honolulu’s most beloved traditions—the dazzling weekly fireworks lighting up the tropical sky. From your private lanai, sip a handcrafted cocktail, feel the gentle trade winds,...
Relax by the Sea – Napili Point A27, Maui Sunsets
Napili Point A27 is a one-bedroom, one-bath oceanfront condo with air conditioning that can accommodate up to four guests. It is in the highly desirable neighborhood of West Maui. This condo features a unique entryway that doubles as a second patio. The location of this...
Experience luxury in Wailea Ekolu 1106, a spacious 2BR Stunning Ocean views
Wailea Ekolu 1106 Breathtaking Panoramic Ocean and Neighboring Island Views from High Above Wailea MauiWelcome to your Maui Retreat: Wailea Ekolu 1106 is a newly remodeled 2-bedroom, 2-bath upper-level townhome tucked into the serene Wailea Ekolu Village on South Maui's...
@ Marbella Lane - Lux Condo n Waikiki w/ Pool View
Summary:Stay in the heart of Waikiki at this stylish retreat by Marbella Lane. Enjoy serene pool views from your private space while being just steps from world-famous beaches, shopping, dining, and nightlife. Relax with resort-style amenities including pool and hot tub...
Charming Ilikai Marina Studio, Great Location In Waikiki!
Construction Notice 10/20/25: Exterior spall working is currently scheduled for 11/3 - 12/17/25 and painting work is currently scheduled from 8/10 - 9/4/26. During this time, the lanai will be locked and not accessible to guests. For your safety, please do not attempt...
** 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...
Maui Resort Rentals: Honua Kai - 6 Total Bedrooms, Stunning 3rd Floor Ocean Views!
This premier six-bedroom offering combines three neighboring 3rd-floor two-bedroom suites to create the perfect place for your group to gather, reconnect, and celebrate. Konea 303 and 305 occupy a fantastic interior courtyard location directly next door to one another...
Just What You Were Looking For! Short Drive to Honolulu Zoo and Kuhio Beach!
In the heart of Waikiki near amazing beaches and attractions!This listing is for a room within a hotel.✦ Your room is 226 sq. ft, equipped with complimentary toiletries, TV.✦ Cleaning services included in the nightly price.There are a few additional details to know...
Enjoy the ranch with large groups by booking our 12-bedroom property: The Lodge. The Lodge features a majestic room (about 1,350 sq ft) with rough-cut wood beams, a lava-rock display fireplace, a library, and sitting areas. Attached to the lodge are a certified...
Private Oceanfront Ohana Retreat Near Hanalei!
Enjoy the very best of Kauai’s north shore from this beautifully remodeled cliffside getaway in the heart of Princeville! Perfectly situated just minutes from Hanalei Bay & some of the world's most iconic surf spots. Step outside to enjoy warm trade wind breezes, relax...