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.
Tranquil Oceanfront Retreat | Lahaina Shores 421, Pure Aloha!
Lahaina Shores 421 - Many upgrades!Welcome to Lahaina Shores 421—a beautifully appointed oceanfront studio on the 4th floor, designed for comfort and relaxation. Perfect for two guests, this retreat features central air conditioning, a brand-new platform bed with a firm...
Beautifully designed quiet townhome with a fenced backyard!
Unique and inviting 2 story townhome with a yard ! Upper level features a master suite with separate bathroom and trundle bed under California King, second bed has a Queen bed and a single bed folded in closet and it’s own full bathroom. Main level has a sectional couch...
The Westin Kāanapali Ocean Resort/ 2-Bedroom
Summary:Explore the summit of a dormant volcano. Or hike through a rainforest to a 400-foot waterfall. There’s no better place than Maui for a once-in-a-lifetime experience. The Westin Kā‘anapali Ocean Resort Villas maintains relationships with the top tour operators on...
Wyndham Royal Sea Cliff | 2BR/2BA King Balc Suite
Summary:Nearby Pu‘uhonua o Hōnaunau, an ancient sanctuary whose name means "the place of refuge," could easily describe this resort. Oceanfront, modern, and conveniently tucked outside Kailua-Kona, tranquility reigns. It’s the ideal home-base for all of your island...
Westin Princeville Ocean Resort Villas Studio Unit - Many Dates Available!
Located on the north shore of the Princeville Resort, along a cliff two hundred feet above the ocean, you might just have found your paradise. The beautiful Westin Princeville Ocean Resort Villas is set on eighteen oceanfront acres and absolutely packed with the...
Diamond Head Grandeur: Kahala Luxury Villa with Ocean View
Welcome to Diamond Head Grandeur, a breathtaking 5 bedroom, 5.5 bathroom luxury villa located in the prestigious Kahala neighborhood on Oahu’s south shore. Just minutes from the iconic Diamond Head State Monument, Kaalawai Beach, and the vibrant energy of Waikiki and...
Kapalua Bay Villas | 2 Free Rental Cars | KBM Resorts | Whale Watching | 2 Units, 3 Bedrooms | KBV ML-1987
** 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...
Pool House with 2Queen Beds – Poolside Comfort
Enjoy a relaxing poolside retreat in this 484 sq. ft. studio featuring two queen beds and a wet bar. With air conditioning, free Wi-Fi, and modern comforts, this studio provides a perfect blend of convenience and luxury for your stay.Key Features: • Design-Centric Hotel...
Luxury condo w/ ocean views, private lanai, full kitchen, shared pool & hot tub
Hali’i Kai 11A on the Big IslandOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Luxury Living at Hali’i Kai: Waikoloa’s Only Oceanfront Condo Community!Aloha and welcome to your Big...
Royal Sea Cliff Kona Garden View 2 Bedroom
This garden-view two-bedroom retreat tucked away near Kailua-Kona, offering privacy, comfort and local charm. Enjoy quiet mornings on the lanai and easy access to beaches, shops and dining. Garden View 2 Bedroom 2 Bath• Condos located on 1st, 4th, and 5th floors •...
The Heights Hideaway
About this spaceCute & cozy two-bedroom apartment on the ground level of a single-family home. Private entrance. Includes a full kitchen with appliances and a private bathroom with a shower.The spaceYour space is located on the ground level with a private entrance.You...
Kailua Beachside: Lux Beachfront Villa w/ Heated Pool, Ocean Views & Modern Amen
Welcome to Kailua Beachside, a five-bedroom, five-bath beachfront villa where modern design meets the relaxed rhythm of island life. Located on the peaceful north end of world-famous Kailua Beach, this two-story residence offers a seamless connection between indoor and...
Relax in Maui: Ocean View Studio Premium at Westin Kaʻanapali North
Unwind in paradise with this Studio Premium – Ocean View Villa at The Westin Kāʻanapali Ocean Resort Villas North, where comfort meets sweeping views of Maui’s coast. Designed for up to four guests, the villa offers around 500 square feet of thoughtfully appointed...
The Lodge at Kukui‘ula - Cottage 7
Escape to an extraordinary Hawaiian sanctuary nestled in the breathtaking South Shore of Kaua'i within a private 1000-acre resort community. Cottage 7 at the prestigious Lodge at Kukui'ula offers a perfect blend of luxury, comfort, and authentic island living.This...
Spacious 2br Waikiki
Conveniently located in the middle of Waikiki, just a block away from the famous International Market Place. This spacious 2 bedroom 1 bath boasts a full kitchen and private lanai to enjoy the Ala Wai views. Secured assigned parking. Washer / Dryer available on every...
Kaua‘i 2BR Ocean-View Escape – Lanai Living, Full Kitchen & Poipu Beach Nearby
Discover the perfect blend of island comfort and spacious living in this two-bedroom, two-bath villa at The Point at Poipu on Kauaʻi’s sunny south shore. Ideal for families or friends traveling together, the residence includes a master bedroom with a king bed and...
Puunoa Beach Estates 105
Puunoa Beach Estates 105 2 Bedrooms | 2 Bathrooms | Sleeps 4 | Oceanfront ________________________________________ Welcome to Puunoa Beach Estates 105, your idyllic two-bedroom oceanfront retreat overlooking Lahaina’s family-friendly Baby Beach. This ground-floor slice...
Aqua Aloha Surf Waikiki 1002 Superior Studio w/Lanai & Partial City Views
Aqua Aloha Surf Waikiki #1002 Superior Studio with Lanai and Partial City Views located just 2 Blocks to Waikiki Beach, (1) King bed, Sleeps 2, 335 Sq Ft.Aqua Aloha Surf Waikiki offers a range of accommodations that are perfect for couples and solo travelers. On-site...
Island Surf 510 | Water Views, Across from the Beach + In the Heart of Kihei!
Escape to the serene paradise of Island Surf 510C, a cozy tropical condo nestled in the heart of Kihei, Hawaii. This charming vacation rental offers a tranquil retreat for up to 4 guests, boasting 2 spacious bedrooms and 2 bathrooms all conveniently situated on one...
Fantastic Location - Beautiful Beach Front Condo -Makena Surf # B-208
Makena Surf B-208Welcome to Makena Surf B-208, a luxurious oceanfront condo that combines the serenity of beachfront living with upscale finishes and exceptional comfort. Located in the prestigious Makena Surf Resort, this second-floor unit boasts panoramic views of the...
Konishiki Beachhouse: Luxury 4BR Oceanfront Home w/ Private Pool, Beach Access
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.Welcome to Konishiki Beachhouse 4BD by Gather,...
Kapalua Golf Villas Ocean View 2 Bedroom
Golf Villas Ocean 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 beds;...
Butterfly House: Beautiful Ali'i Drive Home with Ocean Views!
Incredible Modern Alii Drive Home with Ocean Views! A beautifully renovated home right across Kahalu'u Beach on the historic Ali’i Drive.Modern finishes throughout. 2 Master bedrooms with 2 full baths. Modern fixtures in all areas of the home.Stay cool with ceiling fans...
2/2 Modern & Elegant Penthouse Oceanfront Vistas
Summary:Spacious and elegant. Completely remodeled in December 2022, no expense was spared to create our gorgeous oceanfront oasis. This two-bedroom, two-bathroom condo features luxurious touches paired with oceanfront serenity. Located in sunny Kihei, all of Maui is...
Waterfront Bliss at Tropical Townhouse
Step into your own slice of paradise with this beautifully updated waterfront 3-bedroom, 2-bath ground-floor townhome in the exclusive, gated enclave of Mawaena Kai. Nestled along the marina’s edge, this breezy retreat offers the perfect blend of coastal charm and...
Princeville Kauai 2 bedroom 2 Bath Sleeps 5
Please Send An Inquiry Before Requesting To Book By Clicking The Contact Host Tab.This premier complex, perched on a verdant bluff, provides a paved path to Hideaways Beach, where you can snorkel, swim and soak up the sun. On-site amenities include a restaurant,...
Hilton's Point at Poipu - Luxury 2 Bedroom Villa
Weeks are offered on a Friday, Saturday, and Sunday check-in & out in SEVEN NIGHT INCREMENTS.The REQUEST TO BOOK feature is a request for a reservation, not a confirmed stay. Please do not reserve your airfare until you have communicated with us and we have accepted the...
New Listing: 1BD Oceanfront Views at Lahaina Shores
Lahaina Shores 601 – Oceanfront Elegance with Panoramic ViewsDiscover the magic of Maui from Lahaina Shores, a charming boutique resort set directly on the ocean in the heart of Lahaina. Unit 601 is a rare, highly coveted 1-bedroom, 1-bathroom corner retreat on the 6th...
Oceanfront Paradise Awaits at Kahana Reef 215
Your Oceanfront Escape Begins at Kahana Reef 215Step into paradise the moment you arrive. Kahana Reef 215 sits directly on the water’s edge—so close you’ll fall asleep to the lull of the waves and wake to stunning, unobstructed ocean views. Enjoy your morning coffee or...
Dlx 1 br Waikiki Condo Rental...Sleeps 5/Lovely views. Waikiki Beach!
Enjoy your own 1-BR Oahu condo rental getaway - just a short stroll to Famous Waikiki Beach & and ideally located near world-famous Diamond Head. We're On the 'quieter side' of Waikiki, near Kapiolani Park. Your 1-bedoom Waikiki Beach Condo vacation getaway is appointed...
Maui Resort Rentals: Honua Kai Konea 504 – Luxurious 2BR w/ Beautiful Partial Ocean & Mountain Views!
Konea 504 is a luxurious two-bedroom suite, offering guests the best of both worlds, beautiful partial ocean and mountain views right from the comfort of your spacious private lanai. Located in the very first two-bedroom stack from the oceanfront column, your group will...
Hawaiian Oasis w/ Private Pool, 2 King Suites & Sunset Views!
Discover true Aloha at this stunning 3-bedroom oasis, where island charm meets luxury. Behind a gated front entry, this beautifully designed home features soaring vaulted ceilings, dramatic lava rock wall & 2 king suites and a chefs kitchen, offering a serene and...
Maui Resort Rentals: Honua Kai - 3 Total Bedrooms, Premier 5th Floor Interior Courtyard Offering w/ Stunning Ocean Views!
This tandem 3BR/3BA pairing is comprised of two fantastic 5th-floor oceanview suites located directly next door to each other. Both suites overlook the lush resort grounds and pools of the Hokulani Tower interior courtyard and provide stunning full ocean views.Gather,...
Marriott Maui ocean club full kitchen, 2/22/26-3/1 on beautiful Kaanapali Beach
February 22/26 thru 3/1/26 only Escape to this fabulous condo in picturesque Lahaina. This wonderful property features 2 gorgeous bedrooms with king beds, 2 bathrooms with luxurious amenities like a full kitchen, jetted bathtub, and a cozy living room with a sofa bed...
Waikiki Shore Park View 1 Bedroom
Park views and beachfront living come together in this cozy one-bedroom condo, located in the only condo building on Waikiki Beach. Featuring a private bedroom, full bath, and all the essentials, it's the perfect island escape for couples or small families.Park View 1...
Fairways North 22 Four Bedroom
Located within the desirable North Fairways at the prestigious Mauna Kea Beach, this charming 4-bedroom residence will meet all of your Hawaii resort vacation wants. This beautiful vacation rental not only offers breathtaking panoramic ocean views it also provides views...
Honua Kai | 3 Free Rental Cars | KBM Resorts | Large Floorplan | 3 Units, 6 Bedrooms | HK ML-1227
** 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...
*Hono Kai A14* New Listing! Maui condo steps to the sand!
Beautiful ground floor and newly remodeled! Hono Kai A14 is a garden-view unit, immersed in rich tropical foliage with a spacious private lanai only steps from the complex beach access! Decorated with a modern beachy decor, this unit features a master suite with a comfy...
1 Bedroom Partial Ocean View Condo - Kaanapali Shores 830
Settle into your Hawaiian vacation in this Oceanfront and ground-floor condo with beach and pool access in Kaanapali. Wake up to the ocean breeze and just steps away from one of the most popular beaches in Maui. Recent upgrades include: The kitchen has all-new stainless...
Allure Very Nice 2-bedroom condo 30 Day Rental Minimum
This beautiful 2 bedroom condominium at Allure Waikiki #2609, offers state of the art kitchen appliances, great for people that love to cook. It also has a washer and dryer in the unit. The Allure is located in a prominent Waikiki location, walking distance to lots of...
"Windjammer" Studio w/FREE parking & Full Kitchen
Our Premium WINDJAMMER STUDIO is spacious, recently renovated, fully furnished and centrally located just steps away from famous Waikiki Beach where you can enjoy the sand and surf. We include FREE PARKING, full kitchen, free Wi-Fi and a private lanai. We provide 100%...
Ocean View Studio at Marriott’s Maui Ocean Club – Beachfront Paradise
Discover island comfort and breathtaking views in this Studio Ocean View Villa at Marriott’s Maui Ocean Club – Molokai, Maui & Lanai Towers, located along Kaʻanapali Beach. This well-appointed studio accommodates up to four guests and is ideal for couples or small...
The Lodge at Kukui‘ula - Cottage 10
Cottage 10 at The Lodge at Kukui'ula is a private sanctuary nestled on Kauai’s sun-drenched south shore. This charming three-bedroom cottage blends classic Hawaiian style with modern luxury, creating a warm and inviting retreat perfect for couples, families, or small...
Airy Coastal Dream Vistas
Summary:Completely remodeled 1 br, 1 bath modern condo with upscale Hawaiian style. Located directly across from the beach in warm & sunny Kihei. Nestled in the lovely and desirable Kihei BayResort, you will be embraced in the tranquil grounds and ocean views. We...
RELAX w/ Direct Beach Access High Flr. Sans Souci 2BD/2BA🌴Stunning Ocean Views
Nestled along the southeastern coast of Oahu, Hawaii, welcome to Sans Souci condominium 901/902, on the only beach in the heart of Diamond Head along the Gold Coast adjacent to Waikiki. The first thing you will notice is the incredible ocean view from this luxurious...
Tropical Comfort & Poolside Peace—2 Room Island Haven Awaits
Endless adventure awaits in Kailua-Kona! Whether you're staying for a day or a week, our hotel puts you close to top attractions, local dining, and must-see spots like the Amy B.H. Greenwell Ethnobotanical Garden and Pu'uhonua o Hōnaunau National Historical Park....
4BR Kona Home with Ocean Views and AC!
Walua Hale – Oceanview Escape in Kailua-KonaWake to dazzling Pacific views and end your days dining al fresco on the lanai at this stylish 4-bedroom retreat. With space for up to 10 guests, Walua Hale blends coastal charm with comfort—think breezy open spaces, a hammock...
A11y Room with 2 Double Beds, Lanai and City Views
Designed with accessibility in mind, this 242 sq. ft. room features two double beds and a private lanai with city views. With accessible features, air conditioning, free Wi-Fi, and modern amenities, this room ensures a comfortable and convenient stay for all guests.Key...
Luxe Ke Iki Beach Villa by Gather: North Shore Getaway w/AC Near Waimea Bay
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.On Oahu’s North Shore, Ke Iki Beach Villa is a...
Kai Lani 3D Oceanfront ground floor with direct access to the beach
Don't miss this newly listed vacation home. Please send us an inquiry to accommodate your travel dates and requests, or book instantly—one of the more desirable ground-floor units with direct access to the grassy area and the beach. This oceanfront two-bedroom, two-bath...