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.
Maui Resort Rentals: Honua Kai – Incredible 5 Bedroom Oceanfront Gem, Over 3400 combined Sq. Ft. w/ Built-in Viking B.B.Q.
This five-bedroom gem combines one of our very finest 3BR oceanfront residences with a spacious partial ocean view 2BR suite located directly next door and is perfectly suited to larger groups or families.The generous 3400+ sq ft of the combined interior living area...
Spacious & Breezy 3 Bedroom Home with Ko'Olau Views and a Pool
Nestled in a quiet neighborhood, this charming home is located just one mile from the heart of Kailua town's shopping and resturants. It is also just a bike ride away from the world famous Kailua and Lanikai Beaches. With stunning views of the Ko'olau Mountains and the...
Kapalua Golf Villas Gold Fairway View 2 Bedroom
Golf Villas Gold Fairway View 2 Bedroom 2 Bath- Situated along Kapalua’s Bay Course fairway- Fully equipped kitchen includes stovetop/oven, microwave, refrigerator, coffeemaker, cookware, tableware- Master bedroom with 1 king bed and bathroom- Guest bedroom with 2 twin...
Honua Kai | 3 Free Rental Cars | KBM Resorts | Extra Large Lanai | 3 Units, 5 Bedrooms | HK ML-1463
** 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...
Napili Point | 2 Free Rental Cars | KBM Resorts | Ocean View 1-bedroom Villa At Napili Point Maui | 2 Units, 2 Bedrooms | ML-1559
** 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...
Kaanapali Alii | 124
Kaanapali Alii 1242 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean View________________________________________Kaanapali Alii 124 is an exquisite two-bedroom ocean-view rental that is perfect for families or groups seeking a luxurious getaway in Maui. Well maintained and...
Tropical Comfort – 1BR Villa with Lanai at Sheraton Kaua‘i Resort
Set along Kaua‘i’s famous sunny South Shore, this 1-Bedroom Villa at Sheraton Kaua‘i Resort offers the perfect mix of island charm and modern comfort. With approximately 550–600 square feet of space, this villa is ideal for couples or small families looking to enjoy...
New Listing! Ocean and Pool Front Remodeled Condo
Newly Renovated Oceanview Paradise at Kaha Lani Resort - Steps from Pool and BeachWelcome to your own slice of Hawaiian paradise in this beautifully updated ground-floor one-bedroom unit at the prestigious Kaha Lani Resort. Brand-new furnishings throughout, this...
Royal Kahana Resort Unit 218 - Oceanview Studio near Beach, Pool. A/C
Discover the perfect Maui getaway in our affordable Condo, ideally located in West Maui between Ka'anapali and Kapalua. This studio features a California king bed, a twin sleeper sofa, and a compact kitchen with full-size appliances—perfect for preparing anything from...
New Listing! Save up to 25% Instantly on stays thru 5/31/25! 2B/2B, AC, Pool
Experience tranquil island living at Kaanapali Plantation 12, nestled on 10 acres of lush tropical gardens. This serene and spacious retreat is just minutes from the renowned Kaanapali Beach. This charming 2-bedroom, 2-bath condo is a haven for golf enthusiasts,...
Charming 2-bedroom apartment on beautiful farm in Honaunau with WiFi
Honaunau Farm Wellness Retreat is a 7-acre organic, regenerative farm with sweeping views of Kealakekua Bay & lush tropical surroundings.The Ohana house has a full kitchen, living room, & covered patio with access to our retreat area with infrared sauna, outdoor shower,...
Kaanapali Alii Unit 221
Kaanapali Alii 2212 Bedroom | 2 Bathrooms | Sleeps 4 | Partial Ocean View________________________________________Step into 221, a beautifully appointed one-bedroom condo with a fully enclosed den that comfortably serves as a second bedroom. Overlooking lush tropical...
Hale Hibiscus
Welcome to Hale Hibiscus, the perfect home base for an unforgettable stay in the heart of beautiful Hilo Town. This rare gem offers comfort, convenience, and true island charm—now featuring air conditioning in every room and a private laundry room for the ultimate in...
Cozy 2-bedroom apartment in charming Kailua with AC steps from the beach.
Kick back and relax in this calm, stylish beach getaway. This recently updated apartment features a living space with an ocean view from the balcony. Bright and airy, you’ll enjoy ocean breezes and fall asleep to the sound of waves. Have your pick from the gorgeous...
15th Fl Ilikai | Ocean & Harbor View | Pool | AC | King
Wake up to stunning blue-water views in this 15th-floor Ilikai Hotel suite, perfectly located at the entrance of Waikīkī.The Space• King bed in the bedroom• Queen sofa bed in the living room• Accordion partition for privacy• Full kitchen with granite countertops, custom...
Kona Makai 3-204 2nd Flr, Ocean View, Remodeled Throughout!
Kona Makai 3-204 – Elegant Coastal Retreat in Kailua-KonaWelcome to Kona Makai 3-204, a beautifully upgraded condo that combines modern luxury with the relaxed charm of Hawaiʻi living. Nestled in one of Kailua-Kona’s most desirable oceanfront communities, this...
New Listing – Quam Properties: Lahaina Shores 610 • Ocean Breezes & Island Charm
Lahaina Shores 610 – West Maui Mountain ViewsLahaina Shores is a charming boutique resort located directly on the oceanfront in the heart of historic Lahaina Town. Unit 610 is a 6th-floor West Maui Mountain view studio offering privacy, comfort, and can accommodate 2...
Charming 4-bedroom cottage with WiFi and AC in serene Laie
Consider this cottage your home away from home while you visit Laie. This delightful property boasts 4 bedrooms including a king bed, 2 bunk beds, a queen bed, and a futon. With 4 bathrooms equipped with showers, your group will have plenty of space to freshen up. The...
Maui Resort Rentals: Honua Kai - 5 Total Bedrooms, 8th Floor "Penthouse" Ocean AND West Maui Mountain Views, Deluxe Corner Floor Plan!
This premier eighth-floor offering pairs one of our most sought after two-bedroom "penthouse" suites with three neighboring one-bedroom suites to create the perfect place for your group to gather, reconnect, and celebrate. Enjoy unparalleled views of the blue Pacific...
LS 215 Direct Beachfront Views Remodeled Studio
Lahaina Shores 215 NEW LISTING Amazing West Maui Sunsets Every Night from your Private Lanai! Steps to the Beach and Pool FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch (seasonal), Dinner...
Kona By the Sea #302 Oceanfront 2-Bedroom Retreat with Central A/C
35-Night Minimum • Central A/C • Heated Salt-Water Pool & SpaSavor jaw-dropping, third-floor ocean vistas and nightly Kona sunsets from the private lanai, living room, and even the kitchen of this spacious 2-bedroom, 2-bath suite at coveted Kona By the Sea.Inside the...
Pineapple Paradise - Natural rock tidal pool
**30-day rental. Please inquire.Welcome to Pineapple Paradise! This 2 bedroom, 2 bath oceanfront home has breathtaking ocean views along with a natural rock tidal pool, a unique feature for enjoying the water as the tide comes in. This is a perfect getaway paradise for...
1 Bedroom Oceanfront W/Lanai-Kahana Reef #216
Kahana Reef #216: Grab your phone for selfies on your private lanai that has a backdrop of spectacular ocean views! Enjoy captivating sunsets nightly and during the winter, watch whales play in the distance. Lounge at palm-tree-top levels on the lanai. Here you can...
Stunning Beachfront Condo, Sans Souci, Kitchen, WiFi, Smart TV & Free Parking
Unwind in Honolulu at this cool condo. This excellent property is on the beach & features a cozy living space with a Queen murphy bed plus sofa bed, perfect for relaxing after a day of exploring. The well lit bathroom includes a bathtub / Shower combo, hair dryer &...
4 Units Perfect for Groups! Outdoor Pool, Close to the Beach!
Our spacious suites with private lanais offer breathtaking views of the pristine shoreline, courtyard, or garden, providing the perfect backdrop for relaxation and adventure. Stay connected with high-speed internet, unwind in our unique whale-shaped outdoor swimming...
Wailea Point Contemporary 2 Bedroom+Loft/3 Bath Oceanview Condominium
Yes, you can treat yourself and stay in a vacation home at Wailea Point! A premier hospitality destination nestled between the Four Seasons Wailea Resort and the Fairmont Kealani Wailea, featuring an optimal location near beaches, golf, restaurants and entertainment....
Tropical Garden Tranquility HNL
From kid-friendly splash pads and playgrounds to calming koi ponds, a private pool, meandering paths and shaded bbq and dining areas, this outdoor oasis offers endless outdoor spaces. This serene home-away-from-home offers two private bedrooms, full bath, full kitchen,...
🏖️Ocean Front | Amazing Views | Walk to Beach
vrKCV - Surf and Racquet 1205, Professionally Managed by Kona Coast VacationsExperience oceanfront living in this comfortable second-floor condo at Keauhou Kona Surf & Racquet Club #1205. Enjoy direct ocean views, beautiful sunsets from the lanai, and a relaxed island...
Island Escape: 2BR Villa at Wyndham Kona Hawaiian Resort
Get ready for the ultimate family escape to paradise at Wyndham Kona Hawaiian Resort on the breathtaking Big Island of Hawaii! Nestled along the stunning Kona coastline, this family-friendly resort offers the perfect combination of relaxation, adventure, and Hawaiian...
1 Bedroom Resort View - Silver
Kaanapali Alii 2522 Bedroom | 2 Bathrooms | Sleeps 4 | Partial Ocean View________________________________________Welcome to Kaanapali Alii 252, a gorgeous one-bedroom partial ocean view condo with a fully enclosed den that comfortably serves as a second bedroom. This...
Kapalua Bay Villas | 3 Free Rental Cars | KBM Resorts | 180 Degree Views | 3 Units, 4 Bedrooms | ML-2065
** 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...
Kapalua Ridge Villas | 2 Free Rental Cars | KBM Resorts | 180 Degree Views! | 2 Units, 2 Bedrooms | ML-2162
** 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...
Ohana Kai – Premier Luxury Retreat in Princeville
Welcom to Ohana Kai, Princeviile.Escape to your own private island retreat in the heart of Princeville, Kauai. This stunning 4-bedroom, 3.5-bath vacation home offers the perfect blend of tropical luxury, comfort, and space—ideal for families, groups, or anyone seeking a...
Escape to Paradise! Townhome in Coconut Plantation, just minutes from lagoons!
Welcome to the wonderful resort area of Ko Olina! Located within the gated community of Coconut Plantation, this gorgeous townhome offers guests the perfect blend of comfort and convenience, the ideal island getaway. Features of the townhome include: Prime Location:...
Tropical Oceanfront Paradise
Experience the ultimate Hawaiian getaway in the oceanfront home of your dreams! “Tropical Oceanfront Paradise” is a newly custom-built estate located on prime oceanfront property along Oahu’s scenic and peaceful west coast. Designed for relaxation, the luxury home...
HGVC Hokulani Waikiki Luxury, 1 BR Suites, Rooftop Pool/Spa, Close to Ft Derussy
Anchoring the northernmost stretch of the celebrated Waikiki Beach Walk® entertainment district, Hokulani Waikiki, a Hilton Grand Vacations Club offers ideal access to Waikiki’s most vibrant showcase for dining, shopping and entertainment. Just a brief walk from the...
Maui Resort Rentals: Honua Kai Hokulani 1029 - 2BR Deluxe Oceanview Grand Penthouse, BBQ on Balcony + Jaw-Dropping Ocean Views!
We are proud to present this jaw-dropping 10th-floor deluxe oceanview grand penthouse at the Honua Kai Resort—newly launched on 3/4/25 to start taking bookings beginning May 7, 2025!Unquestionably one of the finest residences on offer at Honua Kai, this stunning 2BR/3BA...
Ko Olina Kai 1081C: 3BR Tropical Retreat, Steps from Golf and Dining
Tucked within the Ko Olina Resort, Ko Olina Kai 1081C by Gather is a cheerful two-story villa where bamboo floors, high ceilings, and breezy indoor-outdoor flow set the tone for easy island days. With three bedrooms, three full bathrooms, and 1,625 sq. ft. of interior...
Honua Kai Konea | 2 Free Rental Cars | KBM Resorts | Extra Large Lanai | 2 Units, 4 Bedrooms | ML-1466
** 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...
1 BR Suite City View, w/ AC, WiFi and Kitchen - Bamboo Waikīkī Hotel #504
Castle Bamboo Waikīkī Hotel #504 - The living area is furnished with a and a desk/workspace for all those business travelers. Enjoy watching the Flat screen TV while sitting on the new couch, which doubles as a fold-out sofa bed to accommodate additional travelers. Fall...
Waipouli - An Ocean Front Beach Resort
Waipouli Beach Resort – Private Corner Unit Steps to Beach and PoolAbout the PropertyWelcome to your Kaua‘i escape at Waipouli Beach Resort F101 — where comfort, convenience, and coastal beauty come together. This one-bedroom, two-bath condo offers ground-floor access...
Whaler | 3 Free Rental Cars | KBM Resorts | 3 Units, 4 Bedrooms | ML-1589
** 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...
@ Marbella Lane - Vibrant and Refreshing Studio
Summary:Welcome to this vibrant and refreshing studio located in a secured apartment building in the heart of Waikiki This unit features large windows making it bright and airy with 2Queen beds a full kitchen and access to the shared BBQ area Just blocks away from the...
"BEAUTIFUL LUXURY CONDO WITH GORGEOUS VIEWS 1BR/1BA/1PKG AT SKY ALA MOANA"
"MODERN LUXURY CONDO WITH BEAUTIFUL VIEWS 1BR/1BA/1PKG AT SKY ALA MOANA""WELCOME TO SKY ALA MOANA" Luxury condominium built in 2023 conveniently located in Ala Moana. Enjoy beautiful views of city, mountain and sparking ocean. 1br/1ba /1assigned parking with Full...
Kihei 2 Bedroom Condo Sleeps 6
Please Send An Inquiry Before Requesting To Book By Clicking The Contact Host Tab.Located in South Maui, nestled within five acres of lush tropical landscaping. This low-density complex features amenities such as a large swimming pool, hot tub, tennis and pickleball...
NEW! Spacious 3BR Home in Old Wailuku Town | Central to All of Maui
Modern Comfort in Old Wailuku Town – 3BR Ground Floor of DuplexStay where Maui locals live, in the historic Wailuku Town—an authentic small town with coffee shops, galleries, family diners, and historic charm. This fully rebuilt ground floor duplex (completed in 2025)...
Wailea Grand Champions 102 - 2 Bedroom Golf Course View Condo
Welcome to Wailea Grand Champions 102, a luxurious 2-bedroom, 2-bathroom residence nestled between the fairways of one of Maui\'s most popular championship golf courses. This spacious second-floor unit, spanning over 1,400 square feet, offers a perfect blend of privacy...
Marriott Maui Ocean Club | Three 3BR/3BA Villas
Summary:Located on the shores of Ka'anapali Beach, Marriott Ocean Club is surrounded by Hawaii's beautiful scenery! The resort is the perfect family getaway with something for everyone to enjoy - beautiful pools, golf, on-site dining, spa services, and sports courts....
Ocean-MT Views From the Luxury Sky Ala Moana Condo with Amazing Amenities
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.The Sky Ala Moana is the newest addition to the luxurious building scene in Honolulu. Consisting of two...
Kapalua Golf Villas | Large Bedrooms | KBM Resorts | 3 Units, 4 Bedrooms | ML-2294
** 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...