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 | 3 Free Rental Cars | KBM Resorts | Exceptional Value | 3 Units, 6 Bedrooms | HK ML-1628
** 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...
Peek-a-Boo Ocean View Studio in Waikiki w/ AC - Bamboo Waikīkī Hotel #803
Castle Bamboo Waikīkī Hotel #803 - Expansive sliding glass doors allow for natural sunlight and open to the private outdoor lanai where you can relax in comfort while taking in the views and enjoying your morning cup of coffee. The sleeping/living area is furnished...
Worldmark Wyndham, Luxurious 1 Bedroon sleeps 4, across from Kama'ole Beach Park
Escape to this delightful resort in picturesque Kihei. This cozy retreat features one bedroom with a king bed, plus there is a murphy bed in the living area, perfect for a small group of guests. Enjoy the convenience of a fully equipped bathroom with a bathtub and hair...
Vehicle to rent, Hilton Pass, Family Friendly, Grill, Beach Gear, 3bedroom, N1
This pristine 3 bedroom, 3 bathroom home has 1,725 square feet in 2 stories with expansive outdoor spaces and backs up to Hole 3 of the prestigious Waikoloa Beach Resort Golf Course.Primary Bedroom: enjoy serenity in your primary suite. King bed, large walk-in closet,...
Ohana Villa Princeville • Pool & AC • Sleeps 20+
Aloha & Welcome to Ohana Villa — Your North Shore Retreat!Escape to paradise at Ohana Villa, a spacious and newly upgraded 6-bedroom, 2.5 bathroom, AC & private pool/jacuzzi home perfectly situated in the heart of Princeville, Kauai. Designed for comfort, connection,...
Kahana Villas Resort & Spa, Lahaina, Hot Tub, Pool
Enjoy returning each day to your luxurious suite with views of the ocean worthy of a postcard! Kahana Villa offers one-bedroom and 2-bedroom suites featuring a fully equipped kitchen, in-room washer/dryer and private lanai. All two-bedroom units at this resort are two...
Sunny Hilo Home w/ Game Room: Walk to Golf Course!
Aloha, and welcome to Hilo! This spacious 3-bedroom, 2-bath vacation rental, on a quarter-acre of lush Hawaiian land, offers all the comforts necessary for an ideal extended stay. Boasting a game room, in-unit laundry, and a central location near many attractions, this...
1 bedroom condo with great Waikiki view
Perfect 1 bedroom in 38th floor. You may view 180 degree panoramic ocean view from the living room!!As you enter, you will find the fully equipped kitchen just remolded. In the bedroom, there is queen size bed for your full recharge. Through the bedroom, you can go to...
Hawaiian Getaway: 2BR at Hilton Grand Islander in Waikiki
Discover the perfect blend of space, comfort, and resort living in this two-bedroom, two-bathroom suite at The Grand Islander, a Hilton Grand Vacations Club in Waikiki. With accommodations for up to six guests and all the comforts of home, this suite is ideal for...
Lahaina Shores 527 – Relax, Unwind, Repeat
Wake up to the sound of waves and endless blue horizons — this 5th-floor oceanfront studio puts Maui's beauty right outside your door.Set directly on the shoreline in historic Lahaina Town, Lahaina Shores is a charming boutique resort where the ocean is just steps...
New Listing Kalanikai 213, close to Ironman start! by Coldwell Banker
New Listing Kalnikai Unit 213, Walk to Ironman Start, Pier and Ali'i Drive!Welcome to Kalnikai Unit 213, your perfect Big Island getaway nestled in the heart of Kailua-Kona! This beautifully maintained unit offers a serene retreat just steps from the action. Ideal for...
Dreamy Ocean Views, Private Lanai, Updated Kitchen
Experience the best that Maui has to offer at our updated coastal retreat with dreamy ocean views and a large private lanai. Stroll to the beautiful, world-renowned beaches, dine at delicious local restaurants, and shop at charming boutiques. South Maui's main surf...
Kapalua Golf Villas | 2 Free Rental Cars | KBM Resorts | Large Bedrooms | 2 Units, 2 Bedrooms | KGV ML-1333
** 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...
Stunning remodeled oceanview in the heart of Kihein
Welcome to Kihei Akahi C610. This beautifully remodeled 6th floor ocean view condo is the perfect place to make your Maui memories. This condo has been completely remodeled with high end finishing, and split AC throughout. Admire sunsets & ocean views from your private...
4 Suites with Balcony and Living Area | Outdoor Pool & Free Breakfast
Unwind in a spacious suite with private lanai, deep soaking tub, free WiFi, and plush bedding. Enjoy continental breakfast with Kona coffee, then stroll to Waikiki Beach or nearby shops. After exploring, relax by koi ponds or dip in the pool. Perfect for couples,...
Oasis Kona: Luxury Ocean View peaceful Home with Pool, Spa & Outdoor Shower
Welcome to Oasis Kona, a beautifully curated ocean-view home for your perfect Hawaiian vacation. Relax by the pool, enjoy the spa & heated outdoor shower, and take in unforgettable sunsets. With an open floor plan, lush gardens, and a private setting, you’ll feel at...
Hillside Villas 1498-3 by Gather w/ Garden Views, Close to Golf & Beach
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 Hillside Villas 1498-3 by Gather, a...
Brand new! Cozy and safe lockout unit in Kihei condo. Close to everything!
Escape to this charming studio in picturesque Kihei. This fabulous rental features 1 cozy bedroom with a queen bed, perfect for a single or couple's getaway. Enjoy the convenience of amenities like WiFi and AC during your stay. Experience the magic of Kihei at this...
Kailua Hale Kahakai by Gather: Lux Oceanview Villa w/ Beach, Walk to Attractions
Welcome to Kailua Hale Kahakai, a serene beachfront estate set along one of the most breathtaking stretches of Kailua Beach. With six bedrooms, five bathrooms, and over 4,300 sq. ft. of breezy living space, this expansive retreat blends open-air island design, panoramic...
Westin Princeville Ocean Resort Villas | 2BR Villa
Summary:With its cascading waterfalls, tropical rainforests, and mountainous landscapes, Kauaʻi is a magnificent vacation destination. The Westin Princeville Ocean Resort Villas offers a collection of amenities to keep you entertained without ever having to leave the...
NEW Waipo'o Hale: Luxury 4 Bedroom Estate w/private Pool & AC
Named after one of Kauai’s most majestic places Waipo’o Falls, this brand-new home is the perfect place to enjoy all the best that Kaua’i has to offer. With luxury and elegance from the moment you pull into the driveway, Hale Waipo’o is sure to be your luxury...
Comfort and Convenience! 4 Serene Units, Pool, Near Honokowai Beach Park
Your oceanfront tropical oasis awaits on beautiful Maui!This listing is for 4 separate rooms within a hotel. The price shown in the listing covers all 4 rooms.✦ Each room is 1050 sq. ft, equipped with complimentary toiletries, TV.✦ Rooms are not adjoining and...
Royal Mauian 205 - Splendid Oceanview Retreat, Stroll to Dining and Shopping!
Royal Mauian #205 – Upgraded Oceanfront Two-Bedroom CondoRoyal Mauian #205 is a two-bedroom, two-bathroom condo with an upgraded interior and breathtaking oceanfront setting. Perfect for families or small groups, this stylish retreat offers split-duct air...
Breathtaking Ocean Views + Luxury Amenities + Gorgeous Beachfront Retreat
The Space:Welcome to our 1 BR Oceanfront home in Kahana, conveniently located at the prime location in the heart of West Maui within walking distance to some of the island’s most popular spots, including local favorites. We are offering a free Hawaiian Inspired Brunch...
KBM Resorts | FREE CAR | Honua Kai Konea | Ocean view | 3-Bedroom Condo with Easy Beach Access! HKK-349
** 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...
Ko Olina Kai 1105E: Upscale 3BR, BBQ Lanai, Near Golf & Disney Resort
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.Nestled in the heart of the exclusive Ko Olina...
Tropical Paradise Awaits: Marriott's Maui Ocean Club for Family Fun
Immerse yourself in Hawaiian luxury at Marriott’s Maui Ocean Club - Molokai, Maui, & Lanai Towers, a breathtaking resort on the golden shores of Ka’anapali Beach, where every moment feels like paradise.Spacious accommodations designed for families include one-,...
Marriott's Kaua‘i Beach Club | Two Parlor Suites
Summary:Experience the beauty of Kauai from the cozy parlor suite, the resort offers ocean views and easy access to Kalapaki Beach, consistently ranked among Hawaii's best swimming beaches. Enjoy resort amenities including a communal pool and hot tub, and relax on your...
Hale Namakeha! Brand New Construction with Exquisite Design! Mins to Beach with Air Conditioning!
Enjoy brand new construction & professional design with air conditioning! Located in the lush landscapes of Princeville, Kauai, Hale Namakeha offers the perfect blend of comfort and sophistication. Boasting three spacious bedrooms and three immaculate bathrooms, each...
Cozy 1-bedroom condo with AC, fitness room in welcoming Kihei
This brilliant 1-bedroom condo in Kihei is perfect for your escape to relaxation. With a cozy king bed and a charming living room featuring a comfy murphy bed, guests can unwind in style. Enjoy the convenience of a fitness room, washing/drying machine, full kitchen,...
Kona Bali Kai 213 – Oceanfront Condo–Private Lanai
Wake up to the sound of the waves on the shore. This 2-bedroom condo looks directly over the Pacific Ocean, offering a waterfront retreat unlike any other. The spacious lanai gives you a private place to relax and enjoy the views. Inside you’ll find a relaxing space...
Kaanapali Maui Eldorado H204 Garden 1BD + Bonus BD
Tucked away on Kaanapali golf course, this garden-view retreat includes one bedroom and a bonus room for extra flexibility. Just a short walk to the beach, it features a fully equipped kitchen, comfortable living space, and plenty of room to relax. Unit H204 Garden View...
Spacious Waikiki Beach Condo with 2 bedrooms 2 baths
Just a few minutes walk from the famous beaches of Waikiki, this spacious, ocean facing unit with 2 bedrooms 2 full bathrooms in Discovery Bay gives you the perfect opportunity to live the Hawaii city life with tree top and ocean views. Just two floors away from the...
Spacious 1BR Premier Suite at Grand Waikikian – Aloha Comfort in Waikiki
Experience a blend of tropical luxury and home-like comfort in this 1 Bedroom Premier suite at Grand Waikikian. With about 836 square feet, this suite accommodates up to 4 guests, offering plenty of space for families or couples wanting both relaxation and adventure in...
High Floor 1 BD Condo - Steps away from the beach!
Wake up to gorgeous mountain views in this 30th Floor, corner-end unit at Waikiki Banyan!Perfect for hosting guests while you visit, this unit features a large, leather couch, a work station, a dining table with seating for 4, as well as 2 adjustable bar-stool chairs...
Lahaina Shores 529 — Luxury Meets Aloha — Oceanfront Paradise
Lahaina Shores 529 is a perfect studio getaway!Outstanding, endless Pacific Ocean and neighboring island views from your private lanai. Set directly on the shoreline in historic Lahaina Town, Lahaina Shores is a charming boutique resort where the ocean is just steps...
Freshly Remodeled w/ Vaulted Ceilings ,Lanai view 3.5 mi from Airport Live Local
Freshly (July 2025) remodeled Kona retreat with vaulted ceilings and a partial ocean view from the lanai. Enjoy year-round comfort at 1,070 ft elevation in a bright, spacious home just 3.5 miles from the airport. You're minutes from beautiful beaches, golf courses,...
Kiahuna Plantation Resort Ocean View 2 Bedroom
Enjoy sweeping ocean views from this spacious split-level two-bedroom condo on Kauai’s most iconic beach. Perfect for families or couples traveling together, it offers comfort, space, and stunning scenery. Ocean View 2 Bedroom 2 Bath• Fully equipped kitchen includes...
15th Fl Luana Waikiki Studio | City & Mountain Views | Pool | Balcony
Enjoy a stylish 15th-floor studio at the Luana Waikiki, featuring city and mountain views just steps from Waikīkī Beach. Perfect for couples or small families, this boutique stay sleeps up to 4 guests and includes a kitchenette, pool, fitness center, and BBQ area —...
Kapalua Bay Villa 36B3 Oceanfront 1 Bedroom
- Split level Condo- Villa closest to Kapalua Beach- No stairs between parking lot and front door- Tile flooring throughout and carpet in bedroom- Kitchen with stainless steel appliances – fridge with ice maker, stove/oven, microwave, dishwasher, cookware, tableware-...
Ilikai Hotel One-bedroom Unit with am AMAZING view of the Duke Kahanamoku Lagoon and Waikiki Beach
This condo is located on the floor of the 12th Ilikai Hotel.This AMAZING condo has beautiful views of the ocean overlooking the lagoon at the Ilikai Hotel. Relax in this cozy, Hawaiian styled condo. You'll love waking up to the beautiful and calming view of the ocean...
Hapuna Beach Residence B11 at Mauna Kea Resort
This oceanfront, newly-constructed, ground-level masterpiece offers floor-to-ceiling sliding window walls that create indoor/outdoor living space, a magnificent chefs' kitchen with Wolf, Sub-Zero and Miele appliances, including double ovens and a wine refrigerator, as...
Cozy studio in charming Laie, Ocean view, AC, 30 day
This studio in Laie is a hidden gem for guests seeking a tranquil retreat right across from beautiful Hukilau Beach. With a cozy atmosphere and a spacious bathroom, this space is perfect for unwinding after a day at the beach or exploring. And the AC ensures a...
Maui Resort Rentals: Kaanapali Alii 313 - Ground Floor 1BR Steps from the Beach with Expansive Lawn!
Maui Resort Rentals is proud to present this luxurious 1BR residence at the acclaimed Kaanapali Alii in the heart of Kaanapali Beach—newly launched on October 21, 2025 to start taking bookings for check-ins starting December 19th, 2025!Nestled just one column back...
Private North Shore Studionn
Our newly renovated attached studio is located between Sunset Beach & V-land one block to the beach. Well suited for a single guest or couple (queen loft bed) who want to enjoy the comforts of home while experiencing the North Shore culture. Walk distance to beautiful,...
Kaanapali Alii Unit 1111
Welcome to your dream vacation in Maui! Kaanapali Alii Unit 1111 is a luxurious vacation rental that offers a perfect blend of comfort, style, and convenience. This deluxe condominium is nestled in the exclusive Kaanapali Alii Resort, providing a stunning partial ocean...
Hanalei Bay Resort 4302: Oceanview w/ Lanais & Resort Perks, Pools & Tennis
Overlooking the legendary Hanalei Bay on Kauai’s lush North Shore, Hanalei Bay Resort 4302 offers an inspiring island retreat with sweeping ocean, mountain, and Na Pali Coast views. Designed for couples or solo travelers who crave both tranquility and connection, this...
Oceanfront condo with pool, hot tub, sauna, tennis, BBQ, putting green, & lanai
Pono Kai Resort A308Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Escape to your dream vacation and make yourself at home in this magnificent top-floor oceanfront condo, offering...
The Cliffs at Princeville Resort, Tennis Courts
You’ll love the stylish decor of this charming place to stay. Located on the north shore of Kauai, The Cliffs at Princeville lies within the Princeville Resort on over twenty acres of lush tropical land. This dream of a resort overlooks the Pacific Ocean from atop a...
Oceanfront Poipu Pool Home - Fabulous 7 BR Estate
This beautiful 7 bedroom for 14 oceanfront pool home is only 75 yards to famous Brenneckes Beach! Enjoy uninterrupted sunrise and sunset views from your oceanfront pool and jacuzzi. Enjoy the playfulness of breaching whales and spinner dolphins by day and the quiet calm...