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.
KBM Resorts | FREE CAR | Papakea | Ocean view | Renovated Studio! PKE-304
** 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...
Luxury Lanikai Oceanfront Home – Secluded Beachside Elegance
LUXURY Lanikai oceanfront home built in 2006, charming board and batten home, concrete floors throughout with the charm of old Hawaii. Beautiful gardens, outside dining and entertainment areas, large pool, big yard spaces, and awesome private outdoor showers that you...
Wyndham Ka Eo Kai | Four 2BR Suites - Sleeps 24!
Summary:Escape to a serene South Pacific paradise overlooking the breathtaking Anini Bay on the mesmerizing north shore of Kauai. Our resort offers a tranquil retreat where you can immerse yourself in the natural beauty and tranquility of the island. With stunning...
Oceanview Ground Floor Studio | Islander on the Beach 111
Islander on the Beach 111 – Garden View Ground-Floor Studio | Private balcony | Pool, Hot Tub, A/CRelax in this charming ground-floor studio at a 6.5-acre oceanfront resort on Kauai’s East Side. Enjoy partial ocean views from your raised lanai, a king bed, A/C,...
2-bedroom apartment with WiFi, AC in Kihei
Condo A307 is a 2 bedroom, 2 bath with AC. A307 has a kitchen, upstairs and downstairs bathrooms, laundry equipment. There is a king bed in the upstairs loft bedroom and two twin beds in the guest bedroom. There is a sofa bed in the living room. A307 has a spectacular...
Kaanapali Alii | 441
Welcome to Kaanapali Alii 441, a luxury vacation rental nestled in the heart of Kaanapali on Maui's stunning western coastline. This spacious 1,544 square feet garden view condo offers a perfect blend of comfort and elegance, making it an ideal short-term rental for...
Jungle Tiki Ohana with Spa
Escape to a hidden paradise where the sounds of the jungle become your lullaby and the lush greenery paints a backdrop for unforgettable moments.Unwind in a private hot tub under the stars, enveloped by the beauty and tranquility of the jungle in one of Big Island’s...
CW Shearwater Resort | 2BR/2BA King Balcony Suite
Summary:CW Shearwater Resort | 2BR/2BA King Balcony Suite• Size: 1316 - 1368• Kitchen: Full• Baths: 2• Accommodates: 6 Guests• Beds: King Bed - 1 Queen Sleeper Sofa - 1 VariesRoom Amenities• Ceiling Fan• Hairdryer• In Room Safe• Washer/Dryer In Unit•...
Marriott’s Kauai Beach Club- 1BR
Summary:Welcome to Hawaii's Garden Isle of Kauai. Explore lush valleys and timeless canyons, majestic waterfalls and rainforests that merge into the blue-and-green sea. Marriott's Kauai Beach Club is located on beautiful Kalapaki Beach, rated one of the best swimming...
Luxury Ko Olina 2 story resort villa - 5 minutes walk to the beach!
True resort living in a tropical paradise.We offer Acura MDX SUV for rent to our guests.ResortThis spacious luxury 2-story premier resort villa is located in the most desirable area of the Ko Olina Resort - Coconut Plantation community, the closest to the beach - mere 5...
KPL 20 Experience ocean views, Cozy 2-bedroom retreat in West Maui.
Kaanapali Plantation 20 NEW LISTING! Sweeping Ocean Views and Sunsets from the North Kaanapali Hillside West Maui, 1 Minute from the Beach!Welcome to your Maui Retreat: Perched above the Kaanapali coastline on West Maui, this vacation home offers sweeping ocean views...
Honua Kai | 2 Free Rental Cars | KBM Resorts | Large Floorplan | 2 Units, 4 Bedrooms | HK ML-1325
** 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...
Orchid Isle Pool Paradise- Private Hawaiian Estate w/Pool and Air Conditioning!
Paradise found! This beautiful, new home is situated off a paved road behind a solar powered entry gate, on 3 gorgeous acres. You will feel relaxed the moment you arrive, from our comfortable and welcoming fully furnished lanai to the spacious and well appointed...
KBM Resorts | FREE CAR | Islands at Mauna Lani | 2-Bedroom Condo with Multiple Lanais! IML-D3
** 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...
Sheraton Kaua'i Resort Villas - Studio Villa
*** Sanitation/Cleaning Update ***Building on a Legacy of CleanFor 92 years, Vistana has been recognized as a hospitality leader for its commitment to quality, exacting standards, and rigorous training. These expanded protocols reflect elevated cleanliness standards and...
3-bedroom townhome in delightful Aiea with AC, WiFi
Your home away from home in Aiea with 3 bedrooms. This amazing townhome features 1 king bed, 1 queen bed, and 1 full bed, perfect for a soothing night's sleep. Enjoy the convenience of AC, a washing machine, WiFi, iron, and a hair dryer. With 2 bathrooms equipped with...
Wonderful 6 Bedroom for 10 Hanalei Home. Beachfront!
Listing provided by "The Vacation Rental Experts". Contact directly for more options!This beautiful 6 bedroom for 10 Hanalei Beachfront home, offers an amazing location right in the central area of Hanalei Bay! Huge beachfront lawn onsite, as well as a spacious...
Terrific three bedroom Villa at Sands of Kahana. Stunning Beach!
Concierge Realty is proud to present luxury villas at Sands of Kahana.We are able to offer reservations in weekly increments with arrival and departures on Wednesdays, Fridays, Saturdays, and Sundays.Please note: Please be aware that air conditioning is not available in...
Waikiki Condo Beach+Mall!
Stunning views with an amazing sunset awaits you! Perfectly situated steps away from Waikiki beaches, delicious restaurants, great shops and walking distance to the Ala Moana Mall. All the conveniences with a GREAT location and SPECTACULAR views right from your own...
Fully Decked Lifted 4WD Tan FJ Cruiser!
Your Adventure AwaitsExperience Big Island like never before with our unique 2-in-1 adventure! Explore in the island’s only outfitted Matte Tan FJ Cruiser, complete with 4WD, lift kit, and 33-inch wheels. After booking, you’ll receive our handcrafted guidebook...
Cozy Ocean-view studio in the heart of Waikiki
Wake up to beautiful ocean views in this cozy Waikiki studio, just steps from the beach, shops, and restaurants. Located in a hotel building, it offers 2 queen beds, air conditioning, fast Wi-Fi, and a kitchenette for light meals. Enjoy your morning coffee with a view...
Oceanfront Elegance With Stunning Views - Double-Sized Lanai & Full AC
Aloha and e komo mai to Poipu Shores 304A - the perfect setting for an unforgettable oceanfront experience on Kauai's south shore. From the double-sized lanai to the deluxe floor plan, from theAs you walk through the front door, you'll be immediately struck by the rich...
Charming 1-bedroom condo in brilliant Lahaina with AC
Indulge in the ultimate Maui getaway at our full oceanfront condo.The cozy balcony beckons you to unwind and marvel at the mesmerizing sea life. Sip on your morning coffee, or relish a sunset cocktail while you watch the ocean's playful inhabitants.For those warm...
Ocean Front Beautiful Remodeled Unit 418! - Maalaea Bay
**Special Introductory Rate September - November 23rd - 2025!! New Unit to Vacation Rental!! Book Now!!**Looking for the perfect tropical escape? Book now and let the island vibes take over! Kanai A Nalu 418 at Ma'alaea Resort is calling your name! This oceanfront,...
Kaanapali Alii Unit 3113
Welcome to Kaanapali Alii Unit 3113, a luxury vacation rental nestled in the heart of Maui's exclusive Kaanapali Alii Resort. This stunning 1,723 sq. ft. condominium, offering breathtaking ocean views, is the perfect family-friendly retreat for your next getaway. Step...
Style and Comfort Over the Ocean
Relax with the family at this peaceful place to stay. Enjoy your long awaited retreat in this newly renovated 2 bedroom 2 bathroom condo in this desirable Princeville location. Rustic on the outside but brand new on the inside, you will be able to chill and enjoy the...
Sugar Beach 417 Direct Row Beach Views in Beautifully Upgraded Ocean front Condo Home
Book with us and come to Maui to explore everything we have to offer!Incredible views in a well maintained oceanfront unit right over the beach. You will love the remodeled kitchen and bath. Upgraded granite kitchen and cabinetry. Take time to relax with your morning...
Kona 2-bedroom condo with oceanfront pool
Welcome to our Slice of Paradise! As of June 2023, our unit has been remodeled/updated - see new photos in listing. Kona Shores is an oceanfront complex on Ali'i Dr south of Kona Town. An excellent location for affordable lodging. A great choice for exploring the Big...
Royal Kahana Maui 408 Oceanfront 1 Bedroom
- 4th floor condo with balcony on north side of the building- Updated open kitchen with granite counters includes stove, oven, refrigerator, microwave, coffeemaker, toaster, coffee starter kit, blender, tea kettle and complimentary tea- Tiled entry into the kitchen and...
Royal Sea Cliff Kona Ocean View 1 Bedroom
Set above rugged lava rock cliffs just outside Kailua-Kona, this one-bedroom feature sweeping ocean views and island charm. With a private lanai and all the comforts of home, it’s a peaceful hideaway. Ocean View 1 Bedroom 1 Bath• Condos located on 2nd through 6th...
Oceanview Top Floor Studio | Islander on the Beach 361
Islander on the Beach 361 – Oceanview Top-Floor (3rd) Studio | Pool, Hot Tub | Mini-Split A/CWake up to stunning ocean and sunrise views from this top-floor studio at Islander on the Beach. Located in the Molokai Building, this breezy unit features a king bed, private...
Romantic view walk to beach, malls &Restaurants. Fireworks view Avery Friday..
Free coffee/TeaFree wifi Free parkingFree washer/DryerFree AC/HeatRelax in this stylish 1-bed, 1-bath condo in Honolulu with breathtaking beach views. Perfect for couples or solo travelers, it’s just steps away from the beach, dining, and shopping. Enjoy a fully...
Montage Kapalua Bay | 2 Free Rental Cars | KBM Resorts | Gorgeous Ocean Front | 2 Units, 6 Bedrooms | MON ML-1577
** 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...
Discovery Bay deluxe ocean view, near Ala Moana Shopping Center & the beach!
Soak in stunning views of the Pacific Ocean from this spacious 1-bedroom, 1-bath condo located on the 35th floor of Discovery Bay! With 769 sq ft of comfortable living space, this fully furnished unit features a full kitchen, two twin beds (pushed together in photos) in...
Perfect Getaway, Steps to the Ocean, Puamana 145-4
Summary:Aloha and E Komo Mai (Welcome) to your Maui retreat at Puamana 145-4! Nestled in the heart of the beloved Puamana community, this well-appointed 2-bedroom, 2.5-bath townhouse offers the perfect balance of comfort, convenience, and tropical charm. With direct...
Kalia Suites, a Hilton Grand Vacations Club - 1 Bedroom Plus
*** Sanitation/Cleaning Update ***We understand that our guests’ expectations for hotel cleaning and disinfecting have changed. That’s why we’ve taken additional measures beyond our industry-leading cleaning standards by partnering with RB, maker of Lysol &...
Paradise Green, golf course front near beach
Experience a prime location on the North Shore! This single-level, ground-floor condo at Kuilima Estates West is situated along the golf course, offering serene views and direct garden access from the lanai.Conveniently located within walking distance to Turtle Bay...
Beautiful Private Garden Apartment w/ AC
Beautifully appointed super clean executive suite! The perfect air-conditioned private garden apartment minutes from the best beaches on the Big Island. This is the perfect executive suite for working visitors who want to get out of the heat and do a little work,...
Kaanapali Alii 276
Welcome to your dream vacation at Kaanapali Alii 276, a stunning 2-bedroom luxury vacation rental nestled along the world-famous Kaanapali Beach. This meticulously designed property offers a luxurious escape for up to 6 guests, making it an ideal short-term rental for...
Elevated Island Elegance in Kukui'ula - A Refined Retreat in Poipu
Graciously set within the exclusive enclave of Kukui'ula, this thoughtfully designed 3-bedroom, 3.5-bath residence offers an elevated South Shore experience—both in setting and sensibility. Wrapped in the soft embrace of trade winds and tropical foliage, the home...
Stylish 23rd floor condo near Ritz Carlton Spacious Ocean and Mountain views
Relax in a newly renovated 670 sq ft 23rd floor condo in residential Waikiki across from the iconic Ritz Carlton hotel with stunning views of the ocean and mountainsWalk to Waikiki Beach, restaurants and shopping at Luxury Row and International Market PlaceKing...
MA 311 Ocean-view in West Maui, a spacious 2-bedroom condo for 6.
Mahana 311 Enjoy Unbelievable Oceanfront Views and Watch Breathtaking Sunsets from as Close to the Ocean on Maui as it Gets Welcome to your Maui Retreat: This stunning 2-bedroom, 2-bathroom corner condo at The Mahana in Kaanapali offers an unforgettable oceanfront...
Honua Kai | 2 Free Rental Cars | KBM Resorts | Huge Lanai | 2 Units, 4 Bedrooms | HK ML-1394
** 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...
Kanaloa at Kona Unit 1403 Partial Ocean Vw 2BD 2BA
- Kanaloa at Kona is located at 78-261 Manukai Street, Kailua-Kona, HI 96740- Beautiful condominium situated on 16 acres of a secluded oceanfront lava flow overlooking beautiful Keauhou Bay. Relax in tropical gardens and lush flower-filled landscape. - Condo located on...
Cozy Volcano Room 🌋
The Volcano Room is nestled in the Hawaiian Volcanic Rainforest followed down a paved road then a 2 min gravel road that is close to the National Reserve. You will have your en-suite private bathroom in your bedroom! In the house there is a shared kitchen. Plus, we...
Maui Kā’anapali Villas 291: 1-bedroom condo located ocean side
Maui Kā’anapali Villas 291: 1-bedroom condo located ocean side in the Emerald building, overlooking the Pool, with partial Ocean views.The space:This one-bedroom condominium is located in the popular Emerald building, renowned for stunning views of the pool, grounds,...
Witness mesmerizing Sunsets!! nOcean View 2BR @ MVC Ko Olina Beach Club 2/1-2/8
Escape to Marriott's Ko Olina Beach Club, a serene oceanfront retreat nestled within the lush, gated Ko Olina Resort & Marina on Oʻahu's west coast. Just 30 minutes from Honolulu, this tropical haven offers the perfect blend of relaxation and adventure, making it an...
Oceanfront 2BR Villa at Westin Nanea – Maui Luxury by the Sea
Step into tropical elegance with this two-bedroom, two-bathroom oceanfront villa at Westin Nanea Ocean Villas, perched on 16 acres along Ka‘anapali’s North Beach. With approximately 1,260 sq ft of interior space, this villa comfortably accommodates up to six adults,...
Maui Resort Rentals: Honua Kai - 3 Total Bedrooms, 6th Floor Deluxe Ocean Views
This fantastic three-bedroom offering delivers stunning 6th-floor ocean views in addition to views of the majestic West Maui Mountains. This tandem pairing combines one of our best two-bedroom deluxe ocean view corner suites with a neighboring one-bedroom suite to offer...
Downtown Kailua | Steps to shops | W/D | Parking
New Listing Special!Welcome to this charming 2-bed, 1.5-bath condo in a prime downtown Kailua location, just a short stroll from world-famous Kailua Beach. This updated home features a fully equipped and stocked kitchen, 2 comfortable queen beds, and modern amenities...