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.
New Listing! Ocean Views from your bed and Lanai
Kaanapali Plantation 6 is a stunning, fully renovated 2-bedroom, 2-bathroom condo located in the highly desirable West Maui area. Blending comfort, convenience, and island charm, this ground-floor retreat has been thoughtfully updated with modern finishes, brand-new...
LS 428 Dream Vacation Studio by the Beach and Pool
Lahaina Shores 428 NEW LISTING Relax in this Charming Studio with Majestic West Maui Mountain Views FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch (seasonal), Dinner Sunset Sail, Snorkel...
Luxury Poipu Kai 3 Bedroom for 8 Villa with Pool and Tennis!
Listing provided by "The Vacation Rental Experts". Contact directly for more options!Enjoy tropical foliage and pool views with an exceptional level of luxury at this 1800 square foot villa. This stunning 3 bedroom, 3 bathroom condo offers all of the comforts of home...
Kaanapali Alii Residence 393
Kaanapali Alii 3932 Bedrooms | 2 Bathrooms | Sleeps 4 | Ocean View________________________________________Welcome to Kaanapali Alii 393, a stunning platinum-rated two-bedroom condo in Maui’s exclusive Kaanapali Alii Resort. This beautifully appointed residence offers...
3 HGVC Hawaiian Village Beachfront Resort and Spa!
Enjoy the glamour of this stylish, upscale place. Set among 22 acres of pristine Waikiki beachspace, Hilton Grand Vacations at Hilton Hawaiian Village provides visitors with spectacular amenities and an unrivaled position in the heart of paradise. Guests are treated to...
Marriott Ko Olina Beach Club 2BR Villa - July 4th or Thanksgiving on the Beach!
A beautiful Hawaiian Resort awaits your family and friends to celebrate Thanksgiving Week. Your charming 2 bedroom villa invites relaxation and restoration with two lanais offering island, mountain, and/or partial ocean views replete with the occasional rainbow or...
Island-style living with upgrades and nearby beach proximity- Kihei Akahi D115
Welcome to Kihei Akahi D115, a hotel-zoned 2-bedroom, 2-bathroom corner unit located directly across the street from the beautiful Kamaole II Beach Park. This ground-level retreat offers the perfect blend of comfort, convenience, and island style living. Building D is...
Palms at Wailea Villa 805 Garden View 2 BD 2 BA
- Ground floor unit- Kitchen includes stovetop, oven, microwave, refrigerator, dishwasher, coffeemaker, toaster, cookware and tableware- Spacious private 219 square feet deck- Master bedroom with 1 king bed- 2nd bedroom with 1 queen bed- Queen sofa bed in living area-...
Honua Kai Konea | 2 Free Rental Cars | KBM Resorts | Grand Suite | 2 Units, 6 Bedrooms | ML-1415
** 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...
Prestigious and luxurious Allure Waikiki with 3 bedroom and 2.5 bathrooms!
This beautiful 3 bedroom and 2.5 bathroom condominium at Allure Waikiki #2608, offers state of the art kitchen appliances, great for people that love to cook. It also has a full-sized washer and dryer in the unit. The Allure is located in a prominent Waikiki location,...
Direct Ocean Front 1 BDRM 2Ba Whaler #601
Whaler 601 is a privately owned, beautiful, 1 bedroom, 2 bath, DIRECT ocean front, corner unit, with a wraparound lanai on the North tower on the 6th floor of the Whaler resort. Many listings say 'ocean front' but in reality, are common ocean views. The attached photos...
Kaanapali Alii Residence 183
Kaanapali Alii 1833 Bedrooms | 2 Bathrooms | Sleeps 8 | Ocean View________________________________________Welcome to Kaanapali Alii 183, a nicely remodeled 2-bedroom ocean-view residence, with a fully enclosed den that comfortably serves as a third bedroom. This...
Maui Ka’anapali Villas #C258: One bedroom, one and a half bath loft with a garde
Maui Ka’anapali Villas #C258: One bedroom, one and a half bath loft with a garden view on N. Kaanapali Beach with Pool and Beach AccessThe space:Relax in the lush garden and pool views at this Hawaiian oasis in the serene Coconut building. This condo has been upgraded...
Tropical Fruit Farm Sanctuary
Characterful and bohemian, this fully furnished studio has a large screened lanai and outdoor kitchen. The 550 square foot space sits on a private half acre of beautiful land with abundant fruit trees including starfruit, coconut, breadfruit, citrus, and lychees. The...
Enjoy the island breeze & afternoon sunsets in your island condo, Ground Floor
Located in Lihue, this charming condo offers a peaceful retreat for guests. With two comfortable bedrooms featuring queen beds and a cozy living room that includes a twin bed, there’s plenty of space to relax. The two bathrooms make getting ready easy and convenient....
Lani One’ā: A Handcrafted Island Sanctuary with Seaside Community & Aloha Spirit
This charming, elevated home in Pahoa, Hawaii, blends modern comfort with island charm. Painted in soft green hues that complement the lush tropical surroundings, this rental is perfect for a relaxing escape.
Kanaloa at Kona Ocean View 2 Bedroom
- Condos located on 1st or 3rd floors- Kitchen features stovetop, oven, refrigerator, microwave, dishwasher, coffeemaker, blender, disposal, cookware and tableware- Private balcony with wet bar- Master bedroom with 1 king bed or 1 queen bed and private bathroom with...
New Listing! Private Maui escape with Island charm
Welcome to Alaeloa 35 – Your Private Maui Getaway! Tucked within the peaceful, oceanfront enclave of Alaeloa in Napili, Alaeloa 35 is a charming 3-bedroom, 2-bath freestanding cottage that effortlessly blends island comfort with timeless Hawaiian charm. Surrounded by...
Gorgeous, Newly Built, Cabin- Off the Grid & 10 Minutes from Black Sand Beaches!
Unwind in Pahoa at this tranquil cabin. Nestled in trees and nature, but only 10 minutes from the warm black sand beaches, the turtles love too, make this the perfect spot! The Best of both worlds only 10 minutes apart and down a convenient paved road, on the upper side...
Waikiki Getaway! Pool, Near Honolulu Museum of Art, Parking!
Sandy beaches or exciting adventures--look no further than this Oahu property!This listing is for a room within a hotel.✦ Your room is 300 sq. ft, equipped with complimentary toiletries, high definition 40-inch TV, available with Premium cable.✦ Cleaning services...
Christmas Week 2026 Westin Kaanapali Ocean Resort Villa - Full Resort Access!!
Christmas week: 12/20/2026- 12/27/2026Westin Kaanapali Ocean Resort Villas - stunning property.Garden/Island View 2 Bedroom Lock-off UnitWith views of the West Maui Mountains and the beautiful resort grounds, guests can enjoy Westin's unrivaled luxurious Two Bedroom...
Westin Ka'anapali Ocean Resort Villas 1 Bedroom Villa Ocean View
The Westin Ka'anapali Ocean Resort Villas - whale watching, snorkeling, sailing, windsurfing and scuba diving just steps away, there are plenty of activities at our Maui beachfront resort near Lahaina - comes with Westin touches keeping in harmony with the Hawaiian...
30 Day Rental in Waikiki with Parking!
Welcome to Fairway Villa, your ideal retreat in the heart of Waikiki! This studio, available for a minimum 30-day stay, is perfect for remote workers, traveling nurses, or anyone needing a longer-term stay in Waikiki. The studio features a comfortable Queen-sized bed, a...
Peaceful Peacock Palace in Makaha
Nestled in the lush landscapes of Makaha Valley, backed by the beautiful Mountains with a 24 hour Oceanview, our enchanting retreat offers guests a unique blend of serene natural beauty and luxurious comfort. As you enter the gates, you are welcomed by the sweet...
Hilton Hawaiian Village Lagoon Tower 2BR 2BA sleeps 6--Ocean View
Consider this condo your home away from home while you visit Honolulu. Lagoon Tower offers 2 bedrooms and 2 bathrooms, ensuring a comfortable stay for guests. With amenities like a hair dryer, heating, WiFi, a washing machine, an iron, a fitness room, and AC, your needs...
Lahaina Condo Studio • 2 Beds • 1 Bathroom
Begin your Maui journey at The Westin KÄÊ»anapali Ocean Resort Villas. Our dedicated guest services team helps plan amazing island trips, such as volcano visits or waterfall treks. Your pre-arranged activity passes await you upon check-in. Unwind in your private villa or...
Brand New_Tropical Modern Style
Looking for a quiet, peaceful, and relaxing place to stay while visiting the Big Island? Well, Look no further. We offer you a beautiful & Newly built ohana unit that eludes a modern-tropical aesthetic feel; just minutes away from the Ellison Onizuka Kona International...
Entire House, Ocean front, White Sand Beach across the street.
Located directly across from a stunning white sandy beach, this home offers the perfect Hawaiian country retreat. Start your day with breathtaking oceanfront sunrises and end it with serene mountain-view sunsets—all from one property. Enjoy snorkeling, fishing,...
Aqua Aloha Surf Waikiki 1405 Studio w/Lanai & Partial City Views
Aqua Aloha Surf Waikiki 1405 Studio with Lanai and Partial City Views located just 2 Blocks to Waikiki Beach. A surfer’s lifestyle is all about being inspired by the ocean, hitting the beach for sun therapy, and laid-back living with aloha,(1) Full/double bed, (1) Twin...
New Listing! Waikoloa Colony Villas, Sleeps 6, AC by Coldwell Banker
Colony Villas 2004 – Spacious Luxury Townhome in Waikoloa Beach ResortWelcome to Colony Villas 2004, your perfect tropical escape on the stunning Kohala Coast of the Big Island. Nestled within the private, gated community of Waikoloa Colony Villas, this beautifully...
Kaimana Beach Hotel | Classic Queen | Beachfront Getaway
Tucked at the serene end of Waikiki, Kaimana Beach Hotel offers direct beachfront access, steps from Kapiolani Park and beneath Diamond Head. The Classic Queen is a cozy retreat with a plush bed and breezy island-inspired design. It's perfect for solo travelers or...
Waikiki Beach Walk Resort 2BR/2BA
Located on nearly eight acres of new Waikiki pleasures. If you're looking for a resort that packs a ton of nearby fun, be among the first to reserve your spot at the new Club Wyndham at Waikiki Beach Walk®, part of Outrigger's huge Waikiki Beach Walk project. This...
Kapalua Golf Villas | 2 Free Rental Cars | KBM Resorts | Beautiful Remodel | 2 Units, 4 Bedrooms | ML-1129
** 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...
Chic Coastal Living in the Heart of Wailea
A brand-new split air-conditioning system has been installed throughout the property, ensuring year-round comfort with contemporary efficiency and quiet operation.This is a NEW listing and it's gorgeous! We are confident you will have a great experience. Welcome to...
Kai Lani 21C: Spectacular Ocean Views, Upgraded 2BR Condo
Welcome to Kai Lani 21C by Gather, an elegantly upgraded upstairs condo located in the pristine Ko Olina Resort. Offered as a monthly rental, this home provides a luxurious escape framed by unobstructed Pacific Ocean views, sophisticated interiors, and direct access to...
Honua Kai Konea | 2 Free Rental Cars | KBM Resorts | Partial Ocean Views | 2 Units, 5 Bedrooms | ML-1315
** 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...
Snowbird-friendly home near the beach with patio, grill, outdoor dining area
Hale Olena Ohana - 31-Day MinimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Conveniently located just 26 blocks from the ocean, this snowbird-friendly home offers the perfect...
Royal Kahana Maui 415 Ocean View 1 Bedroom
Enjoy the perfect blend of comfort and stunning ocean scenery in this charming one-bedroom near white sand beaches. Great for couples, honeymooners, or nature lovers. Unit 415 Ocean View 1 Bedroom 1 Bath• 4th floor condo with nice views of ocean and the island of Lanai...
Kihei Kai Nani 134 - 100 Yards From Beach
About this spaceBEST PRICE for the best vacation across street from Kamaole 2 beach on Maui. The condo is on the ground floor and the third one from the right end of building 12 across the driveway from the pool. The condo complex is not pet-friendly and smoking is...
Oceanview Suite and Cottage
We are a 3 Acre Luxury Vacation Rental Property with an Award Winning Coffee Farm comfortably nestled on the slopes of Hualalai overlooking Kailua-Kona.This rental is composed of 1 Suite and 1 Cottage.We have a brand new split system AC and heating in every room and...
Stunning Oceanfront 1BR/2BA Retreat with Spectacular Views - Wailea Elua 1802n
Wailea Elua #1802 – Luxurious Oceanfront Retreat with Panoramic ViewsExperience upscale coastal living at Wailea Elua #1802, a beautifully renovated second-floor, 1-bedroom, 2-bathroom oceanfront condo located in one of Wailea’s most desirable beachfront communities....
3 Westin Nanea Ocean Villas Resort & Spa, Hot Tub!
A state of relaxation and repose - firsthand at The Westin Nanea Ocean Villas! Set on twenty-six acres of lush, tropical land and infused with a variety of Hawaiian design elements, The Westin Nanea Ocean Villas blends a top-notch vacation experience with the authentic...
Alii Park Place#N-202: Gorgeous Remodeled Top Floor 3 Bedroom unit with AC
Alii Park Place is one of the premier developments on Alii Drive. Tinguely Development group created this complex wanting to offer true quality living. It's clearly apparent this reigns supreme as you walk into the space. Unit#N-202 is beautifully furnished, and offers...
Oahu Dream! 3 Amazing Units, Pool, Minutes to Waikiki Aquarium, Waikiki 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...
Private Napili Nest Near Beach
Tucked away, yet within minutes of Napili Bay, Kapalua resorts, golf, hiking and restaurants, Napili Nest is a private, remodeled and well-appointed end-unit studio with an A/C, a balcony, peek-a-boo ocean/garden view and thoughtful guest amenities. Located in a quiet,...
*Free Parking!* Palms at Waikīkī Hotel
This elegantly remodeled unit is located in the heart of Waikiki. Just steps away from world-famous Waikiki Beach, this condotel is across from the Hilton Hawaiian Village, Fort DeRussy Parkl and short walk to the Ala Moana Shopping Center. Restaurants, grocery stores,...
Newly remodeled 2bd condo with ocean breeze
Mahina Surf 205 is sure to impress! Stunning tropical hues greet you the moment you walk in. New and modern furnishings, Maui-inspired designs, and artwork throughout the condo transport you to the perfect beachy abode where you can instantly unwind and enjoy the beauty...
Cozy 2-bedroom condo in charming Kailua-Kona with fitness room
Discover this brilliant 2-bedroom gem in Kailua-Kona. This pleasant condo features 2 king beds, a cozy living room with a sofa bed, and 2 bathrooms. Guests can enjoy amenities like an iron, fitness room, and hair dryer during their stay. Our tremendous place will help...
Honua Kai Hokulani | 2 Free Rental Cars | KBM Resorts | Close To Beach | 2 Units, 5 Bedrooms | ML-1643
** 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...
Wailea Ekahi Village 52D - 1 Bedroom Garden View Condo
Wailea Ekahi 52 is a luxurious vacation rental property located in the heart of the idyllic Wailea resort community on the southern shores of Maui. This spacious, one-bedroom, one-bathroom condominium offers guests a serene and indulgent island getaway, with all the...