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.
Wai'ula'ula J202 - Fairway-Adjacent Home
This designer-inspired, upper-level, oceanview residence offers a great room with sliding glass pocket doors for indoor/outdoor island living, a chefs' kitchen outfitted with Sub-Zero, Wolf and Fisher & Paykel, dual master suites each with a king bed, a third bedroom...
Mauna Kea Villa 3022 - Ultra-Luxe Hawaiian Villa for Rent
This single-level, sophisticated, oceanfront estate offers a sunken living room with sliding glass pocket doors for indoor/outdoor island living, a chef’s kitchen with Wolf and Sub-Zero appliances, a dining area for 10 with adjoining wet bar as well as bar seating in...
Pili Mai 6K: Beautiful Oceanview Condo w/Shared Pool, Spa & AC
Experience the beauty of Kauai’s South Shore at Pili Mai 6K by Gather, a single-story second-floor condo overlooking the scenic Kiahuna Golf Course with ocean views beyond. This modern, air-conditioned retreat offers the perfect blend of island luxury and resort...
Magnificent....Marvelous....Open Dates...Wonderful Waves!
Magnificent.....Marvelous...that's what you will say upon entering this 2 bedroom/2 bath oceanfront air conditioned home away from home. You will be greeted by comfort and impeccable decor and comfortable furnishings....a walk-in shower in the master bathroom! If you...
Beautiful Ocean/Resort View Villa- in Ka'anapali: Westin Nanea-2 bd 2 ba
Hi! Please "CONTACT HOST" about a you are interested in BEFORE booking. Inventory is always in flux. I can reserve most dates 8-12 months out, but not always. Anything less than 8 months is hit and miss depending on the month you are interested in going. But I am always...
Orchid House - Pool and Endless Ocean views!
ORCHID HOUSETA # 087-311-0016-01With magical views of the Mokuluas from most rooms, this 3 bedroom, 4 bath custom home was just renovated using exotic hardwoods and stone from around the world. Features include solid hardwood floors, granite countertops, slate stone...
Private Renovated Manoa Cottage
Go back in time to this renovated 1950's Hawaiian Cottage located in luscious Manoa Valley on the Island of Oahu. Lounge indoors on mid century Hawaiian koa furniture or outdoor on either the dining patio or the sitting patio. A short drive to shops, restaurants,...
Ground floor 1 bedroom, Ocean Front Condo with 150 ft access to beach
Please come to Maui! The tragic losses in Lahaina left the community devastated and forever changed. Despite the tragic loss, the locals on Maui still need your support. Local restaurants and business are open. Please come support the local community on Maui. Your...
Honolulu Condo for Rent Steps to Kahala Beach
Ask owner about available dates/rates. The perfect studio for a couple on their Hawaiian get-away who want to live like locals during their stay. Please inquire about your specific dates and we can try to accommodate your stay. This beautiful and spacious studio with 1...
Hanalei Bay House - Large, luxurious beach home! TVNC-5099
“Even more beautiful than I imagined!” will be your first thoughts upon checking into the Hanalei Bay House. There is no better way to experience Hanalei than from this exquisitely detailed home located steps from the world famous Hanalei Bay and a short stroll to the...
Sunset Hale: Spectacular Oceanview Home w/Private Pool & Spa, AC & Lanai
Sunset Hale by Gather | Private Kona Retreat w/ Ocean Views, Pool & Lanai – 30-Night MinimumSunset Hale welcomes you to elevated island living on the sunny slopes above Kailua-Kona, where distant Pacific blues, fragrant palms, and a private stone lap pool create an...
Alihi Lani 4: Full A/C - top floor Ocean Views! Upgraded throughout
ALIHI LANI. This small, six unit complex called a 'Real Gem' by the Ultimate Kauai Guidebook. Enjoy endless views from our oceanfront pool. The front landscaped area also has two gas grills and comfy lawn furniture. We are named 'Premier Hosts' by VRBO and won the Trip...
***SPRING SPECIAL*** Fairway Villas: Golf View-AC- 2br - Golf Discount
Aloha and welcome to our Hale Okakopa, Fairway Villas A22 in the Waikoloa Beach Resort. Each room features its own treasures: from intuitive Sapele built-ins like the kitchen desk and entry bench, to the tropical elegance of the primary suite—complete with a handsome...
❤️ PiH❤️ISLANDS DELIGHT ★ Dual Master ★Newly Renovated ★ Privacy
Brought to you by Paradise in Hawaii Luxury Homes.Welcome Islands Delight, a part of our Hawaiian Luxury Collection. Island Delight at Islands is a wonderfully large, 2,189 square foot two-bedroom home that can sleep 6. Located in the Islands at Mauna Lani, a low...
🏖️Renovated Penthouse | Lake & Golf Course Views | AC | vrKCV
vrKCV - Fairway Villas Waikoloa J34, Professionally Managed by Kona Coast VacationsRelax. Rewind. Renew. Welcome to "Nani 'ola ola" at Fairway Villas Waikoloa Beach Resort, a stunning mid-century modern penthouse retreat designed for relaxation and unforgettable views....
Tropical Garden Family Home & Penthouse - Sleeps 8 Walk to Beach, BBQ, Hot Tub
• 2 fully stocked kitchens • Outdoor hot tub and private jacuzzi tub in the penthouse• Fully fenced yard and lush tropical garden• Top-of-the-line amenities.• Have fun with the whole family at this stylish place.• Feel free to message us with questions or check out our...
Makanui 711 - Garden/Mountain View
Summary:Ground-floor 1-bedroom retreat with garden and mountain views, just a short walk to Poipu Beach, Brennecke’s, and Shipwreck Beach. Features a king bedroom with portable A/C, queen sleeper sofa, full kitchen, in-unit laundry, beach gear, and access to both the...
🐬Georgeous 5-STAR Wailea Retreat!🏝Tranquil Corner unit, Top tier Upgrades🌈
Wailea Grand Champions Villas -- Condo #188Aloha!You are coming to Maui for your Dream vacation---Why not stay in a Tranquil, spacious condo full of High-end amenities while enjoying the island? We welcome you to share our well-loved Maui paradise in stunning Wailea!...
Spectacular Maui Beachfront 3 Bdr. Home - Great Location - Family Friendly
The fabulous Sunset Beach House is located on a sandy beach in the sunniest part of Maui. This 3 bedroom home will be the perfect location for your group of friends or family. Enjoy your own gated luxury home right on the beach for about the same price as accommodating...
Beachside 🏖 Family, vacation home with pool 🌺 NO CLEANING FEE!
This Kailua, beachside, pool (heated) home was completely remodeled in 2019 with all new kitchen, bathrooms, pool house, pool surround, landscaping, TV's, furnishings, etc. And NO CLEANING FEE on 30 day bookings!Each room has an individually controlled AC system. The...
Modern + Serene Oceanfront Napili Getaway W/AC - No parking or resort fees
Welcome to the Napili Point! This oceanfront 1 bedroom directly on the stunning Honokeana bay in Napili is a relaxed, contemporary space designed to create special memories in a stylish, comfortable environment. Freshly remodeled, this air conditioned property is...
Kona Townhome w/ Lanai & Resort Amenities!
Experience paradise from this 3-bedroom, 2.5-bathroom vacation rental townhome in Kailua Kona where you have the chance to create life-long memories with your loved ones. Sip coffee from the balcony each morning while taking in ocean views, spend your days using the...
Marriott Kauai Beach Club
This listing is for a studio suite. A studio comes with a Murphy wall bed with a real mattress and a kitchenette. Marriotts owners calendar does not sync with VRBO. Please click on ask owner a question button before pressing book it now. Marriott timeshare's are only...
Hale Minoaka Main by Destination Kauai - Poipu Beach Estates, A/C
🌺 E Komo Mai — Welcome to Hale Minoaka Main House | Private Poipu Retreat with Hot Tub & A/CDiscover island comfort and relaxation at Hale Minoaka Main House, a beautifully appointed 1-bedroom private home located in the prestigious Poipu Beach Estates neighborhood on...
Contemporary upgraded villa with ocean views
Kapalua Bay Villa 11G1 sits at the front of the resort, offering stunning views of Oneloa Bay and the island of Molokai. This one-bedroom, one-and-a-half-bathroom villa is the perfect getaway for a small family or couple, with a maximum occupancy of 3 guests—2 adults...
Garden Retreat w/Ground Floor Ease - Kiahuna #2115
Kiahuna Plantation #2115: Tropical décor delights in this 690sf rare deluxe ground-floor suite. You and your friends or family can easily access the grounds from your ground-floor balcony and walk to world-famous Poipu Beach which according to "Travel Channel" was once...
Waipio's Enchanted and Private Hideaway Pool, Slide, Hot tub & Spectacular Views
Waipio Heaven – Cliffside Luxury Estate with Ocean Views, Pool, & OrchardLocation: Hamakua Coast, Big Island, Hawaii Bedrooms: 4 | Bathrooms: 4.5 | Sleeps:** 10 Minimum Stay: 5 nightsProperty Overview:Discover Waipio Heaven, a private, luxury 4-bedroom estate nestled...
🏖 ❤️ LARGE LUXURY GROUND FLOOR LUANA VILLA,POOL VIEWS, GRT LOCATION & Reviews❤️
🌺 You are renting directly from the owners. We would love to have you stay in our villa. Enjoy all the amenities that Honua Kai has to offer. 🌺 One of the closest Luana Villas to the ocean. 🌺 Over 40 great reviews! Please read what others are saying about our villa.🌺...
❤️🏖beautiful Largest 1BD, Ocean View ONE of the Closest to Ocean 120 Reviews❤️
🏖 LARGEST ONE BEDROOM WITH OUTSTANDING REVIEWS. UPDATED! Newly Painted interior and lanai. COMPARE OUR FLOOR PLATE TO SEE OUR LOCATION COMPARED TO OTHERS ON VRBO.🌺 You are renting directly from the owners. We would love to have you stay with us. As our guest, you have...
🏖❤️Gorgeous🌴 2BD/2BA LUXURY CONDO, 180 REVIEWS, Updated & Painted🏝❤️
Newly painted interior, New coffee table, two new chairs, new kitchen lights, tile floors.🌺 You are renting directly from the owners Bob & Family. We would love to have you stay in our condo. As our guest, you have full access to all resort Amenities at Honua Kai.🌺 Need...
Sunny Side Waves-Beachfront Property-Ground Floor, Corner Unit-Sleeps 5-Remodel
Remodeled ground floor, corner unit in exclusive Bld 11. Steps from Poipu Beach! Only oceanfront condos in Poipu! One of only few air conditioned units (located in bedroom)! New cal-king bed in primary bedroom, queen sleeper sofa & twin in the living room. Expansive...
LUXURY Condo!! One Ala Moana Large 1 bedroom 1 bath, 877 Sf
Location: Come experience the very best of island living at One Ala Moana, steps away from Ala Moana Shopping Center. Minutes to Waikiki, downtown.Interior: Features Philpotts designed deep-smoked walnut wide plank flooring. Magnificent floor-to-ceiling windows capture...
Coastal Elegance Across from the Beach
Ekahi 20b is a 1 bedroom / 2 bath, tastefully decorated condo in the LOWER VILLAGE of the Ekahi complex, at the bottom of the hill and closest to the beach. In fact, it's only a 2 minute walk to the world renowned Keawakapu Beach so you can maximize your time there for...
Stunning Beachfront Retreat 45 steps from Sugar Beach-Hotel Zoning District
Welcome to your tropical paradise! Step into our inviting ground floor condo, just a stone's throw from the golden sands of Sugar Beach. Featuring modern furnishings and cozy beds, you'll feel perfectly at home here. Unwind on your private lanai, where you can soak up...
Dream Vintage Surf Cottage TVNC 4301
Step back in time in this charming cottage by the beach. Built in the 1920's, this plantation style home will give you a true Hanalei experience. Just steps to the beach and a short stroll or bike ride to many restaurants and shopping. This is a dream location in the...
Hallor House: Breezy Hideaway Near Tunnels & Na Pali Trail
Discover the serene charm of Hallor House TVNC #5147, nestled in the tropical beauty of Hanalei, HI. This inviting vacation home offers 1,158 square feet of thoughtfully designed space, perfect for families and friends seeking an authentic island experience.**What...
Kona Alii Condo with Ocean, Sunset, Mountain and Town Views
Located in the heart of Kailua Kona, this special retreat makes it easy to enjoy the day and night life of Kona town. With restaurants and shops within a few steps of the front door, it is also an ideal launching point for day trips to state and national parks, and the...
Stunning Maui oceanfront resort. 2 bedroom, 2 baths
2 bedroom 2 bath ocean front condo in Kihei.Aloha! Our condo is in Kauhale Makai - or Village by the Sea which is a great resort complex on a large grassy ocean front property. There is a saltwater pool and a hot tub. It is a 2 minute walk across the grass to a sandy...
SUMMER SPECIAL! AMAZING VIEW! Book Between May 25th - Aug 31 375/night!
Breathtaking views from our Unit 507 at The Whaler on Kaanapali Beach. 1 back from oceanfront! 1 bedroom unit has a king sized bed and a full size Murphy bed. 2 full baths. Sleeps 4 comfortably. Also a well equipped full kitchen.Relax on the spacious lanai while...
World Famous Kailua Beach Charming Cottage
Studio Cottage near Kailua Beach and Beach Park! Large, 200 square foot lanai, fully furnished. Nice neighborhood setting. You won't believe how close this is to the beach! Also close to Kalapawai Market and other Beach Shops & Food. All utilities - A/C, Cable,...
Ocean Views, Walk to beach and town. AC, Huge lanai
Aloha!Great for longer stays! We supply reliable internet/wi-fi, a desk and comfortable office chair, and large monitor that makes our condo an ideal remote working location. Our spacious 2 bed 3 bath condo has ocean views, not only from our huge wrap around lanai, but...
A perfect suite for temporary short term visitors
To our dear and faithful previous visitors and new vacationers Please always remember we NEVER charge an owner host fee - everything you see is yours to use, eat - candy, snacks, coffee, all beach and snorkel equipment etc etc etc. enjoy and of course no cleaning fee....
Westin Ka’anapali Ocean Villas North, OCEAN FRONT 2 bedroom lock off - 2025!
Welcome to the beautiful, family friendly, Westin Ka’anapali Ocean Resort Villas, North. We have both Nanea and an OCEAN FRONT 2 bedroom lock off available. Best availability occurs when inquiry is at least 8 months in advance as the resort and type of unit is very...
Just Across The Street From The Ocean And Beach. 2 Bed 2 Bath Great Location
This condo has 2 bedrooms 2 Full Bath with a open floor plan in the Living room, Dinning room and Kitchen. You are looking at a lovely and functionally designed 2bd/2ba condominium situated on the third floor of a building. An elevator is provided.The SpaceAre you sick...
Large 3 Bedroom Ocean Front Villa on 7th floor, Lahaina Tower
Come to the gorgeous Maui Ocean Club and vacation in beachfront style! Marriott Vacation Clubs offer a luxurious and relaxing way to vacation while enjoying all the conveniences of home. Located in the Lahaina tower, this very large 3 bedroom/3 bath corner villa has...
Private One Bedroom Condo in the heart of Waikiki
Perched near the top of Foster Tower, this high-floor one-bedroom retreat offers an unrivaled vantage point over Waikiki. From the moment you step inside, the sweeping ocean and Diamond Head views create a breathtaking backdrop for your island stay. Sunlight streams...
Napili Point A10 - A Piece of Paradise - Swim With Turtles Just Steps Away
Do you want to enjoy paradise? Make memories as beautiful as the sunsets? Enjoy beautiful sunsets, walking on the beach, smelling tropical flowers, looking at breathtaking scenery, being one with nature? If so, you will want to book this fully equipped one bedroom Point...
Christmas 2023 Maui! 2 Bedrooms-Sleeps 8-Dec 22 thru Dec 29 Friday-Friday
This year make it a very MAUI CHRISTMAS!!For years MAUI HAS BEEN VOTED #1 ISLAND IN THE WORLD. Come see for yourself...All of the amenities of a resort, with the comforts of home! The Westin Ka'anapali Ocean Resort Villas is all about the details, which makes it such a...
Monthly Discovery Bay 2810 Studio Ocean / Sunset / Marina Views King Bed, Sofa Bed
PANORAMIC Ocean VIEWS, 5 Minute Walk to Beach, High Floor, Remodeled, Furnished and Fully Appointed. No smoking room. Parking, Pool, Utilities, WIFI, BBQ, Gym, Security, Washer/Dryer Included. 1 Month Minimum / contact Agent.Sweeping Ocean Views from High Rise, Tasteful...
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...