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.
Mahana 1215 Penthouse
This one bedroom two bath condo is located at the Mahana on Kaanapali Beach, once inside you will enjoy million dollar views of the Pacific Ocean which face West for sunsets you will never forget. Don't miss whale season as you will have the best location on Maui to sit...
Paradise at The Shores at Waikoloa Beach - Includes Golf Package!
Approximately 18 miles from the Keahole Kona Airport on the Kohala Coast, surrounded by impressive lava fields and drenched in sunshine sits the Waikoloa Beach Resort. Rich in Hawaiian history and culture, come to experience the beauty of Ana’eho’o male Bay, the...
Top Floor OceanFront Remodel I Menehune Shores 612
Enjoy expansive ocean views from the lanai at this bright and beautifully remodeled oceanfront one bedroom in the heart of Kihei town.Take a dip in the heated pool, or enjoy long walks and a swim at the protected beach just steps from the condo. The lanai is perfect for...
Beautiful Private Cottage
Spectacular private entire home 2 bedroom cottage, brand new construction in 2017, located on the "sunny side" of Kamuela/Waimea town. 12 minutes from world renown white sand beaches and resorts of Kohala's Gold coast. Also closely located within minutes from...
Fully Remodeled Elegance in Wailea 2Bed 2Bath
Welcome to The Palms at Wailea, where we offer you exceptional experiences in a variety of realms that exceed your expectations. Nestled within the prestigious Wailea town, our villa complex exudes charm, luxury, and allure.Nestled within the exclusive town of Wailea,...
Kamaole Sands 5307 condo with ocean view. Updated in November 2024. Split AC.
Welcome to our one-bedroom condo in Kamaole Sands located in desirable Building 5, unit 307. As new owners we strive to provide an excellent service and environment for our guests, so did multiple upgrades for our condo:July 2023:-New Split AC system in both living room...
Have it ALL! Spacious 2Bdrm 2Bath w/ awesome view, location & exceptional value
The highly sought-after Papakea Resort is a gem on the West side of Maui which keeps guests returning year after year. The grounds are meticulously manicured for a classic Hawaii vibe and the pools, putting greens and coy ponds are absolutely beautiful. Check-in is easy...
Air Conditioned 2 Bedrooms 1 Bath Apartment, fine decorated, Free Laundry in HPP
Built in 2022!This is a 2-bed, 1-bath apartment with a separate kitchen and dining area, has air conditioners in both bedrooms, located on a one-acre land harboring the most unique feature of Hawaii Paradise Park in Keaau, offering a real retreat from the busy world....
Central tropical streamside retreat $0 CLEANING FEE. Ask about shorter stays.
Our clean, tropical streamside home is perfectly situated to explore the entire island. Wake up listening to birds chirp and the stream flow. Explore for the day on the North Shore, West Side, Waikiki, East Side or just relax and use it as your paradise home. Our 3 bed...
PERFECT 2 bdrm near beach, eateries, shopping, activities Very nice & so clean!
A nicely appointed space in a quiet complex. Very clean and spacious, suitable for one or two. Property is in a Non Smoking complex that accommodates both residents and visitors. Located steps from the beach and a few minutes from eateries, coffee shops, food trucks,...
Tropical Wailea Retreat
We invite you to come and stay at our spacious suite where you can enjoy the exclusive Wailea lifestyle. Relax & restore in this serene space surrounded by tropical palms!This bright and airy 1 bed/2 bath, corner end unit is a modern Hawaiian retreat. The suite features...
Watch for albatross and nene from ocean view beauty
Located on the North Shore of Kauai in Princeville, Ka Mea Nui is surrounded by lush tropical landscapes overlooking the Pacific Ocean and the 15th hole of the Makai golf course. The verdant golf course is a favorite playground for endangered nene (Hawaiian geese) and a...
*Remodeled Oceanfront in Waikiki - Ilikai Marina
Welcome to our oceanfront home offering stunning ocean views and Hawaiian sunsets, all within walking distance to the beach. Whether you're seeking adventure, family fun, or relaxation, this is the perfect destination while visiting Oahu. On Friday nights, enjoy...
Beachfront Molokai Sanctuary Romantic Getaway Writers retreat Solo Rejuvenations
3 Minute walk to the Beach! Hawaii as you imagined it 50 years ago! Breathtaking beaches only steps away in a serene, uncomplicated paradise of days gone by. Sparkling ocean views from the airy screened in lanai with only the sounds of waves at night and tropical birds...
Koa Lagoon- Beachfront - Spectacular Location with Incredible Views
The top floor ( 6th floor) Corner unit makes this a prime location! A beachfront location with a panoramic views of the gorgeous Pacific Ocean. This property is upgraded and updated with an open floor plan and two bedrooms and two bathrooms. The decor is tasteful and...
Charming 1 Bedroom w/Lanai - Kamaole Sands 10213
Kamaole Sands unit #10-213 located on the second floor: This charming one-bedroom/one-bathroom partial ocean view features modern Hawaiian décor throughout the space. The open-concept layout and design were curated with style and comfort in mind so that guests will find...
Le'ale'a by AvantStay | Ocean + Mountain Views!
Le'ale'a — that sunny, blissful feeling of wonder and joy you only feel when immersed in the beauty of a place like the Hawaiian islands. And there’s plenty of it here! In the heart of Mākaha Valley and surrounded by stunning tropical mountains, this bright...
Kalo Homes ~ Tropical Makaha Sanctuary
Imagine waking up to breathtaking views of the ocean, mountains, and valley, while surrounded by lush tropical landscaping. You can unwind in the Jacuzzi or fire up the Traeger grill for a tasty BBQ. We`ve got you covered with all the beach amenities you`ll need to...
Charming Hale Mokolea in Lanikai –2BR, 2BA, Full Kitchen
Nestled in the beachside community of Lanikai, Kailua, this fully furnished home is over 1400 square feet of island style living. Beautifully yet simply decorated, this unit is the whole upper half of the main house. The entrance is at mid-floor level with a Brazilian...
Spectacular golf course front, steps from the beach
Enjoy the amazing experience of staying at Turtle Bay without resort pricing! Our Kuilima West condo is ideally situated just steps from the Turtle Bay Ritz Carlton Resort, and has all the amenities you need, parking, AC, free wifi, washer and dryer.More than 5 miles of...
Romantic Getaway, on the East side. Perfect location, with access to everything!
OCEAN FRONT, one bedroom unit which has been redecorated top to bottom. We chose the total traditional island style with rattan and bamboo...from the furniture to the bamboo drapes, which give the whole place a warm, fresh feeling. We used sand style tile to hide the...
Experience Paradise At Our Modern Hawaiian Cottage With Ocean Across The Street
Experience paradise living at "Surf Temple," a stunning Hawaiian Cottage with a perfect blend of modern decor and traditional charm. With lava rock walls gracing both the house and property, every corner of this place embodies the essence of Hawaiian culture and spirit....
Gem near Keawakapu Beach - Privacy, Ocean Views, Split A/C - Palms at Wailea
The Palms at Wailea #2204 has been totally remodeled. This large condo of 1022 sq feet has soaring ceilings and stunning garden and ocean views from every room. Two covered lanais are ideal for outdoor living and dining. It's only a 7-minute walk to the famous Keawakapu...
Alii Villas #230 Direct view into Kailua Bay
Fabulous 2nd story condo with an oceanfront view! Located on the desirable Kailua Bay side of Alii Villas Condominiums. Beautifully decorated and well appointed for your comfort while on the Big Island. Fully furnished with everything you need for an relaxing vacation....
2 bed/2 bath luxury condo in sunny Poipu with AC
*** Welcome to our Regency Villa in Poipu *** NEW LISTING!We recently bought this luxurious 2 bedroom condo and fell in love with the garden views, chic decor and the prime location. The boutique resort is one of the newest in Poipu. You will love staying here with your...
🏖️Discounted Golf Rates - Big Savings! | Great Location! | vrKCV
vrKCV - Hali'i Kai 24G, Professional Managed by Kona Coast VacationsWelcome to Hali'i Kai 24G – A Serene Retreat in Waikoloa Beach ResortNestled within the prestigious, oceanfront gated community of Hali'i Kai, Hali'i Kai 24G offers an inviting Hawaiian experience in...
New Luxury Kanoala, Upscale, Oceanfront. Total remodel. 3 bed, 3 ba, AC Sleeps 8
Wake up to ocean waves and panoramic views at this stunning Kona retreat. Steps from turquoise water in a resort with 3 pools and jacuzzi's, shaded lounge, and tropical gardens. (next to golf course) and the bay that does Manta Ray and boat tours. Perfect for families,...
Charming Oceanview Oasis: Wailea Elua 802 Surrounded by Lush Tropical Grounds
Wailea Elua #802 – Panoramic Oceanfront Luxury, Fully Remodeled in November 2024Welcome to Wailea Elua #802, a stunning second-floor oceanfront condo that redefines luxury in Maui’s premier resort community. Completely remodeled in November 2024, this 2-bedroom,...
Luxury 30th floor 2 bedroom condo in Waikiki
Luxury living with 24hr state of the art gym and resort like pool and bbq area. Smart TV. Washer and dryer. Great location with walking distance to Waikiki shopping. Beautiful view from 30th floor balcony. 24hr security. Japanese bidet. The list goes on.
Right on the water in West Maui.
Looking for a getaway that is right on the water with a full ocean view on the west side of Maui? This condominium has a full kitchen with stainless steel appliances including a dishwasher to create your own meals and save money on your vacation. Features a king size...
Hilton Waikoloa Pool Pass thru 2025. Waikoloa Golf Discounts! J2 Waikoloa Beach
This vacation rental is professionally managed by ResorticaHawaiiWaikoloa Beach Villas J2Please scroll down for detailed informationHilton Pool Pass: Valid for stays now through December 31, 2026. Maximum 6 persons per pass (children under the age of 5 are not counted...
Kamaole Sands 1-307 - Prime Location, Stunning Renovation, Large Lanai, New AC
Experience elevated comfort and modern luxury at Kamaole Sands 1-307. This fully remodeled, one-bedroom, two-bathroom condo blends thoughtful design with premium amenities to deliver the ultimate Maui retreat.Enjoy cooking in the spacious, chef-inspired kitchen,...
NEW Full Reno 4BD/3B PRINCEVILLE HOME, STEPS FROM QUEEN'S BATH w/ AC & Jacuzzi!
LUXURY PRIVATE 4 bed 3 bath 1760 sf home on a >10K lot w/mtn views in Princeville, a luxury high end community. AC/Jacuzzi/Bikes/Beach Gear included. ***MAJOR RENO NOW DONE!*** ***New photos now up! 5 min. walk to Queen's Bath trailhead (follow safety signs!), ≈15 min....
Mountain & Waterfall Views - Pool & BBQ
Hawaiian jungle paradise awaits you at Villas of Kamali'i. Welcome to this fabulous split-level townhouse with wonderful mountain and waterfall views. The spacious design is beautifully furnished and is loaded with amenities to make your stay an extraordinary and...
Rainbow Retreat - Ocean Front - Molokai - Peaceful
*MOLOKAI - NOT MAUI*Here at Rainbow Retreat, we take your comfort extremely seriously. From the Cozy Earth bamboo bedding (Oprah's favorite, 5 years running) to the quality furniture and design you will sink into and enjoy the quiet.Comfortable, minimalistic...
Beautifully Remodeled studio Makaha Valley Towers
Beautifully remodeled studio apartment with breathtaking views of the mountains and ocean. The Makaha Valley Towers is located in the scenic Makaha Valley and is minutes away from Makaha Surfing Beach. The area is known for its quiet, relaxed atmosphere. There are...
🌴Immaculate, ocean view townhome offers quiet island living, located in Na Hale O Keauhou🌴
Immaculate ocean view townhome!Enjoy free late checkouts on bookings made by December 15th 2025! Ocean views, epic sunsets and poolside afternoons: That's what a true Hawaii vacation is all about. This immaculate, three-bedroom townhome is set in the quiet, gated...
Breathtaking Sunset Views and Perfect Backyard Pool and BBQ
House sits a right up the hill from downtown which makes for an amazing sunset. The property has a saltwater pool, patio and BBQ. Inside is fully furnished for a comfortable stay. The garage is remodeled and includes a ping pong table, corn hole, darts and full of beach...
Renovated 03/23! Direct Oceanfront Condo with 2 Master Suites!
*Available for booking! Thankfully, our condo is not located in the wildfire affected area*Enjoy stunning views in this newly renovated oceanfront condo located on Kahana Beach! This spacious 1,040 sqft condo located at Valley Isle Resort has been completely renovated...
Sapphire Oasis- Heavenly Ocean View and Resort
Summary:As soon as you walk into this 2 bedroom 2 bath condo, you'll feel it. The sounds of the waves will lull you immediately. The striking panoramic view will have you feeling like you're in the endless blue ocean. And as you rest on the lanai, the fresh island...
Kehena Moana Kai - Amazing OCEANFRONT Private Retreat
Perched in the sunbelt at the edge of a dramatic oceanfront sea cliff, this honeymooner’s paradise sits in the heart of the lush Puna District rainforest on the Big Island of Hawaii. With two air-conditioned bedrooms, this private cliff house retreat accommodates up to...
Ocean view 2 bed/2bath Kaanapali Shores gem
Welcome to Kaanapali Shores 423. This beautifully positioned 4th floor ocean view 2 bed/2 bath condo features newly upgraded central AC, fully equipped kitchen with granite counter tops, in unit washer/dryer, & more. This condo can accommodate 6 people. Admire the...
1 bedroom at Honua Kai Mountain view remodeled April 2023 King Bed, Central AC
Fully remodeled in April 2023, this upscale and spacious one-bedroom retreat awaits you. Unit # is 626 on the 6th floor of the Hokulani tower. Enjoy all the amenities the Honua Kai resort has to offer, freshly prepared meals in your fully stocked kitchen and a cool,...
Turtle Bay Fairway Condo - Kuilima Estates East
Welcome to your North Shore paradise! Step into our fully remodeled Turtle bay condo, boasting breathtaking views of the 18th hole through wall-to-wall windows. Outside, Indulge in luxury with 2 private pools, tennis and pickleball courts, and 5+ miles of pristine...
Marriott Waiohai Beach Resort - On The Beach- Family Friendly
Escape to the beauty of Kauai and indulge in luxury at this premium Marriott property in Hawaii. With direct access to Poipu Beach and a wealth of amenities, the resort promises an unforgettable Hawaiian experience. Conveniently situated within walking distance of Poipu...
Sugar Beach Resort. Beautiful Front And Center Beachfront Condo! A/C Wifi
Aloha and Welcome to Sugar Beach 517This is a terrific BEACHFRONT vacation condo. Sugar Beach Resort is a centrally located complex with a beautiful oceanfront pool and spa. The ocean views are amazing and, due to the fact that it is on the 5th floor..... privacy and...
Kamaole Sands 3104-BRIGHT, Clean, and Fresh!
Kamaole Sands 3-104 has some features that separate it from other condos and make it a great choice for your vacation:1) The lanai is not only oversized and covered, but it also faces SW. This means you ALWAYS have the choice between full sun or full shade. It is on the...
Pili Mai 10 I: Luxury Resort-Style Condo, Pool+Spa
Elegant design meets luxurious comfort in this beautifully bright, airy 3BR/2.5 BA townhome in the acclaimed Pili Mai at Poipu vacation-resort complex. Inside and out, the artistically color-coordinated furnishings are a rhapsody in oceanic blues—indigo, cobalt,...
BEST LOCATION with Incredible Direct Ocean Views, A/C Papakea L207
L207 rests in the most HIGHLY DESIREABLE locaton at the Papakea Resort. Enjoy a front row seat to direct oceanviews and spectacular nighly sunsets. This condo and location is everything you dreamed about when coming to Maui. This one bedroom one bath has been remodeled...
Mauna Lani Fairways #204: Tropical Home w/spa, lanai, lagoon pool & activities
Welcome to Mauna Lani Fairways #204, a refined two-bedroom, two-and-a-half-bath townhome set within the gated Mauna Lani Resort along Hawai‘i Island’s celebrated South Kohala Coast. With serene garden and fairway views, thoughtful design, and complimentary access to the...