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.
Stay in our Private Recently Updated Home in The Villages-Closest to The Shops!
OUR HOME IS CLOSEST TO THE SHOPS YET GUESTS LOVE THE SPACIOUS GROUNDS AND PRIVACY OF OUR UNIT.We continue to update and refresh our home to ensure it's the optimal space for your stay in paradise including:*All new comfortable beds *Brand new quartzite kitchen...
Ali'i Kai 1-202 · Beautiful Mountain View Condo in Princeville
Recently remodeled 2-bedroom, 2 bath condo close to many amazing beaches. This unit features great mountain views and you can even peek at the ocean from the dining area to check out the swell. Close to restaurants, spas, shops, golf, and tennis this is the perfect...
KBM Resorts | FREE CAR | Mahana | Oceanfront | Gorgeous 2-Bedroom Condo! MAH-301
Stunning Oceanfront, 2-Bedroom Villa, Direct Ocean Views, Includes Rental Car!*Special Offer - Book any KBM rental Home in Hawaii for 6 nights or more with an arrival date between Jan 1 - Dec 31, 2025 & receive a complimentary 4-door rental car from Hertz, Alamo, Avis,...
Wailea Beach Villas | PH502
Wailea Beach Villas Penthouse 502 boasts a panoramic ocean vista, ideal for whale watching in the winter, and with spectacular sunset views all year long. This top floor penthouse has been exquisitely redecorated with an elegant, casual décor.Your private elevator...
Professional Design: Ocean View: Private Apartment
Designed by Twin Islands Interior Design Group - Escape to Big Island and indulge in the tropical paradise of Hawaii with this charming 1 bedroom, 1 bathroom Airbnb property. Enjoy an ocean view from your breezy porch and sleep peacefully in a comfortable queen-size...
❤️PiH❤️SPARKLING WATERS ★ Hilton Passes ★ Large Pool & Waterfall Spa ★
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to the newest elegant home, Sparkling Waters, in our Hawaiian Luxury Collection.Sparkling Waters is a wonderful new large single level 4 bedroom, 3 bathroom home. This home has one of our largest private heated...
Napili 1st-level serene and peaceful retreat
Welcome to Napili Shores E135, a stunning ground-level 1 bedroom 1 bathroom condo nestled in the heart of Napili featuring a garden view and split AC system. This condo sleeps up to 4 guests. This resort does not have elevators. The living room is enhanced by an...
Puu Poa Ocean Bluff Condo, Incredible Views, Walk to Beaches
Are you looking for the absolute perfect condo for your once in a lifetime vacation to Kauai? Do you want breath taking views from almost every room? Do you want to be within walking distance to multiple beaches? How about be close to shops and dining? Do you want...
Coconut Villa Entire home in KoolinanWalking distance to the shops and beaches
Enjoy your morning coffee or evening cocktails out on our lush tropical lanai with the tranquil backdrop of the Ko Olina golf course. Take in the stunning sunsets from this perfect vantage point.Our villa is located in an ideal location; everything is within walking...
Kuhio Shores 217 Superior Air Conditioned Condo at Kuhio Shores
New mini split Air Conditioning system just installed to make your Kuhio Shores 217 cooling experience perfect. Open windows, trade winds, fans to hear the soothing sounds of the ocean. And now if none of the above works you have use of a quiet, efficient air...
Private and Quiet Luxury Beach House 5 minute walk to beach TVNV#5151
Live like a local in this professionally designed two bedroom, two bath retreat, offering the perfect blend of luxury and laid back Hawaiian charm. The area is known for its slowed down pace and ocean-centric lifestyle to escape the hustle and bustle of city life.The...
Big 3BR / 4BA (3056sq ft) Kona Home with Pool/Jacuzzi, OceanView (Sleeps 16 max)
BEFORE BOOKING, PLEASE THOROUGHLY READ ALL ITEMS LISTED BELOW ...Three bedroom HOSTED property (Main House; 3056 sq ft / 284 sq m) sitting on a single level with a panoramic view of the ocean. We are fully Hawaii County bill HB 108 COMPLIANT; our General Excise Tax...
KBV 35G2 Best Rate LUXE OceanFront Villa w Oceanview | Lanai | AC
Welcome to our spacious one-bedroom, one-bathroom condo nestled along the coast in the luxurious Kapalua Bay Villas. This oceanfront location offers breathtaking views of the Pacific, inviting you to immerse yourself in the beauty of West Maui. Situated on the ground...
Kaanapali Alii -11th Floor - Ocean & Mountain View
Spectacular Ocean and West Maui Mountain views can be enjoyed from this luxurious 11th floor newly remodeled condominium. This family owned 2-bedroom vacation home offers vacation privacy in one of the most desired upscale resort locations in Hawaii. Kaanapali Alii is...
Ko Olina Beach Villas B301: Serene Beachfront Luxury w/ Pool Views
Welcome to the captivating Ko Olina Beach Villas B301 by Gather, a luxurious three-bedroom, three-bathroom beachfront vacation rental with unbeatable views and space for up to eight guests. This third floor unit, adorned with direct ocean and poolside views, provides a...
2Bd/2Ba Condo at Lagoon Tower Hilton Hawaiian Village Sleeps 6
Nestled within the renowned Hilton Hawaiian Village, this spacious 1,025 square foot, two-bedroom, two bath condo offers the ideal retreat for families seeking relaxation and adventure.Step into the expansive living room, where ample seating invites you to unwind after...
Waiulu Villa 119A – Bright & Updated | Includes Onsite Staff & Daily Housekeeping
Recently Updated! Located in the popular Waiulu Villa neighborhood, this luxurious 2 bedroom, 2 bath single-level lower floor corner villa was just updated with new furnishings and decor in the living room, dining room and lanai. Accommodating up to 4 guests, this light...
Kaanapali Alii | 255
This two-bedroom, two-bath residence with an open floorplan offers sweeping ocean views and features a warm and inviting contemporary design. This spacious vacation rental can comfortably accommodate up to six guests.The primary bedroom has a king bed, a flat-screen...
COMPLETE REMODEL | Central AC | WIFI | vrKCV
vrKCV - White Sands Village 220, Professionally Managed by Kona Coast VacationsExperience Island Living at Its BestWelcome to your perfect Hawaiian retreat! This beautifully appointed 2-bedroom, 2-bathroom condo is located directly across from White Sands Beach—also...
Trendy Hawaiian Monarch Studio | Ocean View | Pool
Relax in this beautifully renovated, modern studio at the Hawaiian Monarch building. Located at the beginning of Waikiki, this unit offers ac, smart tv, wifi and cable. It is a short walk from Fort DeRussy Beach Park, Hilton Hawaiian Village, Ala Wai Canal and more. The...
MRR Presents Kaanapali Ali'i 465 - Renovated 2BR Corner Suite w/ Gorgeous West Maui Mountain Views!
Luxuriously renovated and meticulously maintained, suite 465 boasts epic views of the majestic West Maui Mountains and the Kaanapali Royal Golf Course from its 6th-floor vantage point. Its stunning interior has been beautifully updated with modern tile flooring, custom...
North Shore Condo Rental at Kuilima
Relax to swaying palms, stunning seas and a tropical breeze! You deserve it! Step right out the lanai onto fairway one of the Fazio golf course. Swaying Palms is an end unit, situated within the complex to provide lots of natural light, privacy, and a more spacious...
Stunning Luxury Estate 🌺 Superb Private Lanai & Breathtaking Sunsets! 🌅 Keauhou Luxury Estate
Experience island lifestyle in one of Kona's most desirable gated communities: Keauhou Estates.Amazing home with 3 bedroom with 3 and 1/2 baths. Beautiful great room, dinning room and gourmet kitchen overlook the pool to the ocean beyond. Imagine a beverage and sunset...
Hawaiian Luxury at Mauna Lani Point J105n1-bedroom 1.5 Bath @ Mauna Lani Resort
Get ready to relax in this fabulous 1-bedroom condo in Mauna Lani. This terrific property features a king bed, and a day/child bed, along with 1.5 bathrooms. The primary bathroom has a large walk in shower and a Japanese soaking tub. The living room offers an additional...
Spacious 3 Bed 2.5 Bath House in Kahakai Estates
Please note, effective Jan 1st. 2026, Hawaii's Transient Accommodations Tax will increase from 10.25% to 11% for all stays with an arrival in 2026 forward. We may need to collect the tax difference to secure and finalize your booking. We will contact you to confirm the...
2 Bed 2 Bath Surfing & Snorkeling in Kahaluu Bay
Aloha! Come and stay at the Hale Hamoa created for everyone with everything we love about Hawaii. Only 1 minute walk to one of the best snorkel beaches on Kona Side and the Surf school next door. The condo comes with all the essentials you need for an awesome vacation...
Beachfront Spectacular Ocean views , steps to white sand Beach & walk bike Path
Listen to the sound of the waves from this beautifully furnished corner unit and admire the views up and down the coast from the spacious lanai. Upgraded with granite countertops and travertine floors in kitchen and bathrooms. Unit 219 is very private with unobstructed...
Mahana 1117 - Direct Oceanfront - Special Rates!
Mahana 1117 - DIRECT oceanfront in Kaanapali. Located on the 11th floor of the The Mahana at Kaanapali, the full panorama from your lanai captures breathtaking views of neighbor islands - and is a perfect spot for those famed Maui sunsets. Mahana 1117 features:• Fully...
Great Location - Snorkel, Surf & Sunsets!
Beach Villas at Kahalu’u is right across the street from the best snorkeling beach on the Big Island! See green turtles and reef fish! The ground floor condo has 2 bedrooms, one with a king bed, the other with twin beds, and 2 bathrooms, each connecting. There is a...
Oceanview Retreat in Puamana – Steps from the Beach & Surf
Nestled just a 30-second walk from the beach and three popular surf breaks, this beautifully remodeled 3-bedroom, 3-bathroom townhome in Puamana offers the perfect blend of modern comfort and laid-back island living. Located on the safe side of Puamana, untouched by the...
Paia Family Cottage - Walk to everything in Paia Town
Walk to everything in Paia Town. Paia Family Cottage is well equipped, with comfortable indoor, and sweet outdoor living spaces for everyone. There is AC in all bedrooms and living room. And a yard where kids can play, with views out over the green sugar cane fields....
Fantastic Hana Bay Oceanfront Location! 5-Minute Walk to Hana town & beaches!
AUTHENTIC HAWAIIAN BEACH HOUSE ON HANA BAYManini Cottage captures the relaxed comfort and charm of a true Hawaiian beach house in a rare and secluded oceanfront setting. Perched at the edge of Hana Bay, this one-bedroom, one-bath cottage features open-concept living, a...
Luxury Ko Olina Oceanfront Villa O1105 w/ Stunning Ocean Views near Golf Course
Welcome to Ko Olina Beach Villa O1105 by Gather, a luxurious 3-bedroom, 2.5-bathroom retreat nestled in the heart of the stunning Ko Olina Resort in Kapolei, HI. This villa is designed for up to 6 guests and offers an exceptional blend of modern comfort and breathtaking...
Ocean Front Dream Suite- Spectacular Views! 2Bedrooms/2Bath Steps to Amenities!
Wake up to unforgettable views and the soothing sounds of the ocean waves a few steps away! Build your book of Maui memories and support the economic recovery of Maui, owners and their teams! This is where you will find relaxation and inspiration for adventure! This...
Liko Lehua Cottage in Volcano - Hot Tub & Fireplace - Mauna Loa Estates
Liko Lehua Cottage - Your Hawaiian Forest Retreat!Escape to the enchanting Liko Lehua Cottage, a hidden gem just six minutes from the awe-inspiring Hawaii Volcanoes National Park. Nestled in the lush, serene Hapu'u forest of Mauna Loa Estates, this newly reimagined...
🌴Alii Villas 109 Newly remodeled. Easy access to pool and parking 🌴
Monthly rates available until October 1st This newly remodeled ground floor one bedroom condo is perfect for your island getaway. Comfortably furnished and well equipped, just bring your suitcase Short walk to your parking space and pool area.Perfect for visitors with...
Kaanapali Stunner - Spectacular Ocean Views
Updated 2025 - New Furniture and flooring. New pictures soon.As owners, we are committed to providing a high quality safe and clean vacation experience for both first time and loyal guests of Whaler 559. This unit is highly upgraded with loads of extra amenities and...
Rare Beauty and Luxury at Kealakekua Bay
Your hosts Tammy and Joe are committed to providing a 5-star experience. The home is maintained in immaculate condition with the highest levels of spotless cleaning before you check in. The property is very private with secure gated access. Parking at the guest house...
Villa By The Sea - Stunning Sunset & Ocean Views, Gated Community, A/C
Nestled in a sought after gated community you will find our Villa By The Sea with a stunning ocean view of Kailua Bay. 24 hour check in is available.The view from the living room, kitchen and lanai is simply mesmerizing, with front row seats to watch seaside activities...
Oceanfront Beachfront Escape Hale Kai 1Bed
Discover charm and comfort in our ground floor vacation rental, nestled by the pool and oceanfront. Immerse yourself in stunning sunsets just steps from the water. This cozy unit boasts a fully equipped kitchen, a luxurious king-size Tempur-Pedic bed, and a sofa sleeper...
Three bed three bath luxurious townhome in gated Princeville community
3 Bedrooms, 3 Baths, Sleeps 6VILLAS ON THE PRINCE #2 is a luxurious 3 bedroom, 3 full bath townhome in one of only 3 gated communities in Princeville on Kauai’s beautiful north shore. Newly renovated, it is one of the only units offering A/C upstairs as well as in...
Maui Kamaole B101 - Gorgeous designer condo! Modern luxury and great rates!
Condo was fully renovated, new cabinets, tile floor, granite countertops, stainless appliances and new A/Cs. The Master Bedroom boasts a California King bed, ensuite bathroom, and private courtyard. The modern kitchen is very well stocked and you will enjoy the Weber...
LUXURY VILLA, 3 Private Suites, Pool/Spa, Gym, Central A/C, Beach
This exquisite Villa has it all! Located in The Villas at Poipu Kai boutique development. With 1900 s.f. living area, this three bedroom three bath view unit features an expansive covered lanai, private elevator access, central air, central vacuum, washer/dryer, and...
5-Star Reviews! All Remodeled! Split Air! Quiet Building 5! Ocean/Garden View!
We are a 2-3 minute walk to beautiful Kamaole Beach III. Our building is located in quiet building 5 on the 2nd floor. Our unit is close to the elevator but far enough away to not hear it. Additionally, there is a beautiful ocean view from our lanai!The remodel of our...
Gorgeous Oceanfront! - Sweeping Views & Steps to the Beach
Welcome to our oceanfront home away from home! You'll find views straight out to the ocean and the wild coastlines of Kapalua. The villa is perched above the sweeping white sands of Oneloa Beach and is steps away from three other world-renowned beaches. Our...
Luxurious, 2 bedroom / 2 bath, FULL Ocean View Wailea Condo
Situated on 18 acres of perfectly manicured tropical foliage, bordering the award winning Wailea Blue Golf Course, Ekolu Village is an exclusive and desirable complex that is exceptionally quiet and free of any traffic noise. This property is located in less than a 5...
Edge of Cliff Luxury Penthouse over Largest Coral Reef in Hawaii - Beach Access & AC
Very large penthouse with 2, 000+ square feet of living space under roof, vaulted ceilings and the most incredible views over the largest coral reef in the State of Hawaii. Ocean views available throughout the condo's living area and into the huge master bedroom suite....
Hale Hihimanu - newly renovated house and guest cottage with AC
Hale Hihimanu - a newly renovated house and guest cottage with AC throughout. Located on a private driveway with just two neighbors, this property offers unprecedented privacy for a home in the resort community of Princeville. The beauty and elegance of this property...
Luxury Villa: Hilton Pool Passes, Renovated, Private Beach Club, Sunset Views
Enjoy staying at the best location at Golf Villas, featuring ultimate privacy with breathtaking sunset views and unlimited access to a private beach club and unlimited access to the Hilton Pool for 6 people. Our well-appointed and recently renovated villa is located in...
Kaanapali Alii | 265
Welcome to your dream vacation rental at Kaanapali Alii! This luxurious two-bedroom paradise is the perfect destination for your Hawaiian getaway. Nestled in the heart of Maui's renowned Kaanapali Beach, this spacious rental offers a blend of comfort, convenience, and...