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.
Honua Kai | 2 Free Rental Cars | KBM Resorts | Custom Hardwood Floors | 2 Units, 5 Bedrooms | HK ML-1412
** 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...
Easy Access to Maui’s Top Sights, with Outdoor Pool, Pets Allowed | 3 Units
This listing is for 3 separate rooms within a hotel. The price shown in the listing covers all 3 rooms.✦ Each room is 300 sq. ft, equipped with complimentary toiletries, TV.✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival...
Mauna Lani Point J101
Welcome to the serene and luxurious Mauna Lani Point J101, a perfect retreat nestled in the heart of Kamuela, Hawaii. This stunning 1-bedroom, 1-full and 1-half bathroom condo offers a cozy yet elegant space for up to two guests. The master bedroom features a plush...
Relaxing Beachside getaway.
Relax and unwind in this oceanfront 2BR/2BA condo in Honokowai with breathtaking views from the lanai. Perfect for families or couples — it sleeps 6 with a King, Queen, and Full pull-out sofa bed. Enjoy free parking, free Wi-Fi, a fully equipped kitchen, beach gear, and...
Wailea Beach Villas PH403 - 3 Bedroom Ocean View Penthouse
Wailea Beach Villas Penthouse 403 offers a luxurious escape with stunning ocean views and ample space for the whole family. Spanning 2,000 square feet, this penthouse features three bedrooms and three full bathrooms, making it an ideal holiday retreat. Guests can enjoy...
North Shore Sweet Spot w/ King Bed Overlooking Lush Valley
Welcome to Hale Moi, your tropical escape on Kauai's stunning North Shore! Our charming Princeville condo offers comfort, authentic island experience, and lush greenery. Enjoy breathtaking views from your private lanai, modern amenities, easy access to Hideaways Beach...
FREE Parking1BR Penthouse Condo @Palms +near Beach
【Basic Info】This is a private 1 Bedroom 1 bathroom condominium unit in Waikiki!!You can enjoy your stay by only yourself, friend or partner. The condominium is located in Waikiki.It's closed to many famous shopping centers like Royal Hawaiian Center, T Galleria!You can...
50% Off! 3 BR Bed & Breakfast Steps from the Beach with AC
The Space:Welcome to our newly refreshed Maui Beach House Bed & Breakfast, where you can enjoy All 3 ensuite guest rooms each with private access through the shared lobby-lounge, located at a private estate directly across from the beach! ✔ Beach access across small...
Kaanapali Maui Eldorado A106 Partial Ocean 1 BD
This airy one-bedroom condo overlooks Kaanapali golf course with a glimpse of the ocean beyond. Located near the beach, it features a relaxed living area, kitchen, and lanai for enjoying morning coffee or evening sunsets. Unit A106 Partial Ocean View 1 Bedroom 1 Bath•...
🏖️Beautiful Mountain View | Concierge Included | Spacious | vrKCV
vrKCV - Vista Waikoloa D204, Professionally Managed by Kona Coast VacationsWelcome to Waikoloa Vista D204, a comfortably appointed condo ideal for couples or families. This 2-bedroom, 2.5-bathroom second-floor unit is nestled in the heart of Waikoloa Beach Resort and...
Beachfront Condo, Hale KAI O' Kihei, View Amazing Sunsets on Your Private Lanai
IMAGINE YOUR PERFECT DAY AT HALE KAI O KIHEI - OCEANFRONT MAUI LIVING!Unlike most condos in Kihei, this one is not on the main road (South Kihei Road) but is instead on a small quiet side street between the main street and the ocean. And unlike many Kihei condos, this...
Discovery Bay Waikiki, 2BR 2BA, close to beach, free parking, washer/dryer, cable & streaming TV!
Enjoy comfort and convenience in this updated, fully furnished 2-bedroom, 2-bathroom condo with city views from the 9th floor of Discovery Bay. The full kitchen and spacious layout make it perfect for families, friends, business travelers, or anyone needing extra room...
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...
Lahaina Shores 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 Escape to the charm of Lahaina Shores Resort with this updated mountain-view studio in West Maui. While the condo offers peaceful views of the West Maui Mountains from...
Luxury Poipu Kai 3 Bedroom 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 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...
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 | 2 Free Rental Cars | KBM Resorts | Grand Suite | 2 Units, 6 Bedrooms | HK 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...
Wyndham Kona Coast Resort| Two 2BR/2BA Suites!
Summary:Nestled along the scenic Kona coastline of Hawaii’s Big Island, this resort is just a few miles away from pristine Keauhou Bay, the Hulihee Palace, and two historic national parks. Get ready for panoramic views of sapphire blue waters and endless activities like...
Kaanapali Alii | 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...
Waikiki Shore 1016 Ocean View 1 Bedroom
Take in breathtaking ocean views from this one bedroom, one bath condo — located in the only condominium building directly on Waikiki Beach. Ideal for couples or small families, this relaxing retreat offers all the comforts of home just steps from the sand.Unit 1016...
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
Beautiful condominium situated on 16 acres of a secluded oceanfront lava flow overlooking beautiful Keauhou Bay. Relax in tropical gardens and lush flower-filled landscapes. Golfers, families and outdoor enthusiasts will enjoy snorkeling, golf and deep-sea fishing...
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...
Puna Rainforest Retreat Hot Spring-Ocean views on 20 acre Estate
Enjoy the solitude of Hawaii's rainforest on a lovely 20 acre estate. This ocean view home is super clean and spacious, on gated private property and very comfortable for up to 10 guests. Appreciate the rainforest sounds, rainbows, starry skies and sunshine, far from...
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 2024 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...
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...
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...
Kapalua Golf Villas | 2 Free Rental Cars | KBM Resorts | Beautiful Remodel | 2 Units, 4 Bedrooms | KGV 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 | 2 Free Rental Cars | KBM Resorts | Partial Ocean Views | 2 Units, 5 Bedrooms | HK 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 1802
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....