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.
7 nights from Jan 11-18 at The Ritz Carlton Club, St. Thomas
Indulge in a week of pure Hawaiian luxury at The Westin Princeville Ocean Resort Villas.Your stay in a 1-Bedroom Premium Villa from January 11–18 offers the perfect blend of elevated comfort, privacy, and island serenity on Kauaʻi’s breathtaking North Shore.Perched high...
One Bedroom Suite with Kitchen, King bed & sofabed
Discover a serene oasis just steps from the iconic Waikiki Beach, where tranquility meets excitement. Explore nearby treasures such as the Royal Hawaiian Center and Diamond Head State Monument. Only a short drive from Daniel K. Inouye International Airport, this vibrant...
Paradise resort home in Ko Olina Coconut Plantation
Welcome to your dream vacation home at Coconut Plantation - the most amazing destination in Ko Olina! Whether you're looking for a breathtaking sunset, a romantic getaway, a fun beach stroll, an exciting round of golf or a relaxing spa retreat, this resort has got you...
New Listing Lahaina Shores 533 Oceanfront Retreat
Lahaina Shores 533 – Oceanfront Romance & Unforgettable ViewsPerched on the 5th floor of the beloved Lahaina Shores Beach Resort, this beautifully renovated studio offers an unbeatable combination of modern luxury and timeless island charm. With first-class décor,...
Hale Ohana Ho’omaka by Gather: 3BR Condo w/ Lanai, Pool & Loft
Welcome to Hale Ohana Ho'omaka, a newly furnished three-bedroom, 2.5-bath retreat in the heart of Princeville that sleeps up to 8 guests. With vaulted ceilings, breezy lanais, and distant ocean views, this 1,173-square-foot home offers island living that feels both open...
Breathtaking Views -Remodeled Ocean Front Condo - Makena Surf Resort F-111
Makena Surf #F-111 – Oceanfront Comfort with Ground-Floor ConvenienceEnjoy luxurious oceanfront living at Makena Surf #F-111, a spacious ground-floor, 2-bedroom, 2-bathroom condo featuring beautiful ocean views and a peaceful island ambiance. With a prime location just...
Serene Makaha Retreat
Discover serenity at our home. 3 beds, 2 baths, steps from world class Makaha beaches. Enjoy a spacious retreat with a fully equipped kitchen, outdoor BBQ, and scenic views. Nearby hiking, golf, and local attractions. Safe and convenient. Your Hawaiian escape awaits!
Marriott's Waikoloa Village Condo 1 Bedroom, 2 Bathroom
Marriott's Waikoloa Ocean Club is a paradise in paradise, where the ancient love story between the goddess Pele and Kamapuaʻa comes to life and inspires every detail. From the island's lush green flora and pristine waterfalls to its fiery red volcanos and black lava...
Princeville's Best-Kept Secret! 2 Spacious Units, Swimming Pool, Full Kitchen!
Set on the scenic shores of Princeville, this resort offers direct access to Hanalei Bay and nearby beaches, perfect for water activities and nature exploration. Enjoy well-appointed accommodations with convenient proximity to local dining and shopping options, ideal...
Puunoa Beach Estates 104
Puunoa Beach Estates 104 3 Bedrooms | 3 Bathrooms | Sleeps 6 | Oceanfront ________________________________________ Welcome to Puunoa Beach Estates 104, a beautifully renovated three-bedroom oceanfront villa that blends refined island design with the comforts of a...
Cozy studio condo with AC and WiFi in charming Koloa/ Poipu
Nestled in Koloa, this delightful condo is a tranquil oasis for guests seeking a serene getaway. With a cozy bedroom and a well-equipped bathroom featuring a shower and hair dryer, this gorgeous property provides all the comforts of home. Enjoy modern amenities like...
Aqua Aloha Surf Waikiki 218 Moderate Studio with Partial City Views, Sleeps 2
Aqua Aloha Surf Waikiki #218 Moderate Studio with Partial City Views located just 2 Blocks to Waikiki Beach, (1) Queen bed, Sleeps 2, 253 Sq FtAqua Aloha Surf Waikiki brimming with island personality offers a range of accommodations that are perfect for couples and solo...
Makani A Kai A4 - Oceanfront Walkout - 15 feet from beach
Oceanfront Escape at Makani A Kai A4 – Maalaea, Maui. Welcome to your own slice of paradise on Maui's southern shore! This 1B/1B walkout sits on the beach in Maalaea, offering breathtaking ocean views, and private access to 3 miles of the secluded sandy Sugar beach....
Royal Kahana Maui 605 Ocean View Studio
This charming ocean-view studio offers a cozy spot to unwind after a day of island adventures. Ideal for small groups or families. Unit 605 Ocean View Studio• 6th floor studio with balcony overlooking the ocean and view of the island of Molokai • Studio kitchen includes...
Comfortable Studio for 2 | Full Kitchenette
Spend your next vacation discovering the beautiful beaches and stunning hikes in Oahu! Our comfortable Studio for 2 is conveniently located close to numerous shops and restaurants! Soak up the sun on Waikiki Beach, only 7 minutes away. We think you'll love:• Studio with...
Kanaloa at Kona Partial Ocean View 2 Bedroom
- Condos located on 1st or 3rd floors- Private balcony with wet bar- Kitchen features stovetop, oven, refrigerator, microwave, dishwasher, coffeemaker, blender, disposal, cookware and tableware- Master bedroom with 1 king bed or 1 queen bed and private bathroom with...
Oceanfront Suite with Private Balcony at OUTRIGGER Waikiki Beach Resort!
Looking for a beachfront getaway in Waikiki? Look no further than this convenient property! Just minutes from the most popular attractions, the excitement of Waikiki is all around you! With comfortable amenities and authentic Hawaiian hospitality, you'll have everything...
Tropical Tranquility and Sunset Views! Maui Vista 2223
Tropical Tranquility and Sunset ViewsWelcome to your perfect Maui getaway! Nestled in the heart of South Kihei in the desirable Maui Vista Resort, this beautifully renovated condo offers the ideal blend of comfort, convenience, and island charm. Whether you’re seeking a...
1 Bedroom Condo-Princeville, Kauai-Family Friendly!
Perched above the sparkling waters of Hanalei Bay, this resort offers families a front-row seat to some of Princeville’s most awe-inspiring natural beauty—from the dramatic Na Pali Cliffs and iconic Bali Hai Mountain to cascading waterfalls, golden beaches, and palm...
Kaanapali Alii Residence 365
Welcome to 365, a gorgeous condominium in Maui’s exclusive Kaanapali Alii Resort. This luxury residence offers dazzling unobstructed views of the sparkling Pacific Ocean disappearing into the horizon and neighboring islands Lanai and Molokai. Vast windows and a private...
Moani Heights 13 Four Bedroom
Rest and recharge in this luxurious four-bedroom, four-bath island retreat, where indoor comfort meets stunning outdoor living. The open-concept kitchen and living area flow seamlessly onto a spacious, furnished lanai, perfect for enjoying the coastal breeze. Step...
Wailea Beach Villas PH106 - 2 Bedroom Garden View Penthouse
Welcome to Wailea Beach Villas Penthouse 106, a luxurious ground-floor retreat in one of Maui’s most prestigious beachfront communities. This stunning 1,899-square-foot villa offers the perfect blend of island elegance and modern comfort, making it an exceptional...
Christmas Week Dec 19-26th at The Westin Nanea ocean resort on Kaanapali beach
Special week December 19th - 26th!!!!!Experience Nanea - a state of relaxation and repose - firsthand. Resort blends a top-notch vacation experience with the authentic history and culture of Hawaii. Amenities include a 10,000 square foot lagoon style pool with a upper...
Honua Kai K204 Elegant 2BD Maui Condo w/ Lanai, Pools, Beach Access & Mountain View
Honua Kai K204 Experience the Maui Beach Resort Life from this West Maui Condo, Steps to the Pool and SandWelcome to your Maui Retreat: Welcome to Honua Kai Konea 204, an expansive two-bedroom, two-bath retreat that blends island luxury with a warm sense of home. Set on...
Honua Kai Hokulani | 3 Free Rental Cars | KBM Resorts | Spacious Lanai | 3 Units, 4 Bedrooms | ML-2531
** 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...
Escape to Paradise! 2 Serene Units, Pool, 3 Restaurants, Right on Beach!
Looking for a beachfront getaway in Waikiki? Look no further than this convenient property! Just minutes from the most popular attractions, the excitement of Waikiki is all around you! And with comfortable amenities and authentic Hawaiian hospitality, you'll have...
New Listing Lahaina Shores 421 Tranquil Oceanfront Retreat
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 by Gather: Luxury Villa w/ Ocean View & Private Pool
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 | 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 by Gather: Beachfront Villa w/ Heated Pool & Ocean Views
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...
Lodge at Kukuiula 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...
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-207
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 3-Bedroom 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...