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.
Experience Island Paradise at The Grand Islander by Hilton - 2 Bd. Ocean View
Discover the perfect blend of fun, relaxation, and tropical beauty at The Grand Islander by Hilton Grand Vacations in Waikiki, an unforgettable family-friendly destination in the heart of Honolulu. Set against the lush, verdant backdrop of Oahu, this two-bedroom suite...
𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢’𝐬 Gorgeous Waiohai Club Beachfront Resort + Amenities
𝐕𝐢𝐬𝐢𝐭 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 to enjoy 𝐄𝐱𝐜𝐥𝐮𝐬𝐢𝐯𝐞 𝐒𝐚𝐯𝐢𝐧𝐠𝐬 on this elegant, 𝐬𝐩𝐚𝐜𝐢𝐨𝐮𝐬 𝟐-𝐁𝐞𝐝𝐫𝐨𝐨𝐦 𝐕𝐢𝐥𝐥𝐚 at one of Poʻipū Beach, Koloa’s most sought-after 𝐁𝐞𝐚𝐜𝐡𝐟𝐫𝐨𝐧𝐭 𝐑𝐞𝐬𝐨𝐫𝐭𝐬 — 𝐌𝐚𝐫𝐫𝐢𝐨𝐭𝐭’𝐬 𝐖𝐚𝐢𝐨𝐡𝐚𝐢 𝐁𝐞𝐚𝐜𝐡 𝐂𝐥𝐮𝐛 𝐑𝐞𝐬𝐨𝐫𝐭.Unlock 𝐌𝐞𝐢𝐥𝐢 𝐌𝐞𝐦𝐛𝐞𝐫-𝐎𝐧𝐥𝐲 𝐑𝐚𝐭𝐞𝐬 & 𝐔𝐩𝐠𝐫𝐚𝐝𝐞𝐬:𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 𝐄𝐱𝐜𝐥𝐮𝐬𝐢𝐯𝐞 𝐒𝐚𝐯𝐢𝐧𝐠𝐬...
Kapalua Bay Villas | 2 Free Rental Cars | KBM Resorts | Premium Bay Villa | 2 Units, 2 Bedrooms | ML-1960
** 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...
Wailea Beach Villas | Penthouse Panoramic Ocean Views | KBM Resorts | 2 Units, 6 Bedrooms | ML-3485
** 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...
🏖️Oceanfront Island Living — Beautiful Kona Condo for Extended Stays
vrKCV - Kona by the Sea 115, Professionally Managed by Kona Coast Vacations Relaxed Oceanfront Living at Kona by the SeaEscape to your own slice of island life at Kona by the Sea, a popular oceanfront community along Kona's scenic Alii Drive. This updated, spacious...
Napili Point | 2 Free Rental Cars | KBM Resorts | Ocean View 1-bedroom Villa At Napili Point Maui | 2 Units, 3 Bedrooms | ML-1544
** 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...
Kapalua Golf Villa 16P7 Fairway View 2 Bedroom
Golf Villa Unit 16P7 Fairway View 2 Bedroom 2 Bath- 1st floor villa overlooking Kapalua Bay Golf Course’s 6th fairway- 19 stairs between parking and front door- Two interior stairs between front door and living room/kitchen/second bedroom- Tile entry, kitchen and...
Maui Banyan H-308 1 Br Ocean View Condo, Walk to Kamaole Beach Park II
Bright and open Ocean View Condo. This unit has one bedroom with a queen bed and a pull-out sofa bed in the living room, allowing this unit to sleep up to four people. The Kitchen opens up to the dining and living areas, creating a wide-open living space. The bedroom...
Kaanapali Alii 476
Kaanapali Alii 4762 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean View________________________________________Welcome to Kaanapali Alii 476, a stunning condominium in Maui’s exclusive Kaanapali Alii Resort. This deluxe residence offers a beautiful view of the Pacific Ocean...
Aqua Aloha Surf Waikiki 1210 Superior Studio with Lanai and Partial City View
Aqua Aloha Surf Waikiki #1210 Superior Studio with Lanai and Partial City Views located just 2 Blocks to Waikiki Beach, (1) Queen bed, Sleeps 2, 335 Sq Ft.Aqua Aloha Surf Waikiki brimming with island personality offers a range of accommodations that are perfect for...
Stunning 2 Bedroom Deluxe at Wyndham Bali Hai
This delightful two-bedroom provides the perfect respite for the whole family. Nestled high in the cliffs of Princeville, this Kauai resort blends natural and man-made pleasures into magnificent harmony. Take the opportunity to enjoy a meditative retreat at the on-site...
Lahaina Shores Luxury Oceanfront Ocean View & Mountain View w/ 2 Lanais
Lahaina Shores Beachfront Luxury with Stunning Dual Pacific Ocean Views and Majestic Maui Mountain Views & Two Expansive Lanais Studio CondoWake Up to Paradise Every Day!Experience the ultimate Hawaiian getaway at our spectacular luxury oceanfront retreat, where endless...
3-bedroom Diamond Head Floor-Through Apartment On Ocean - Minimum 3 months
3 month Min: The ultimate diamond head apartment. 2000 square feet on ocean. Newly renovated. Surf in front @ Tonggs. Walk/Run around Diamond Head. Right off Kapiolani Park. The ultimate super chill; elegant; breezy and easy place to hang/enjoy/live.
Ocean View King | Kaimana Beach Hotel | Scenic Stay by the Beach
Kaimana Beach Hotel is a beachfront haven just minutes from Waikiki’s shopping, dining, and surf. The Ocean View King offers a spacious layout and sweeping Pacific vistas. Enjoy the best of beach life from the comfort of your room.This listing is for a room within a...
Stylish w/Waikīkī Vibe! WiFi, AC, and Kitchenette – Waikīkī Grand #822
Castle at Waikīkī Grand #822 - Soak in gorgeous Diamond Head views from this 253-square-foot air-conditioned studio designed to maximize space! It’s all about casual comfort with queen and sofabed sleeping, dining table, flat screen and WiFi. You’ll also appreciate the...
Honua Kai Konea | 2 Free Rental Cars | KBM Resorts | Easy Pool Access | 2 Units, 4 Bedrooms | ML-1376
** 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...
Kapalua Ridge Villa 2522 Fairway View 1 Bedroom
- The Ridge Villas are perched high above with views of The Kapalua Bay Course’s Fairway.- Very spacious lanai with views toward mountain, golf course, and ocean. - Second floor unit, two-level townhome, with multiple stairs from parking to the villa. - Tile in kitchen,...
Wai'ula'ula Villa 348 Three Bedroom
Perched in the uplands of the prestigious Mauna Kea Resort, this stunning villa offers sweeping panoramic views of the Kohala Coast, where breathtaking sunsets paint the sky. Designed for seamless indoor-outdoor living, it features an expansive covered lanai with plush...
Ilikai Hotel Oceanfront, Top Grade Upgrades Throughout! 30-day Rental Only!
If you're seeking a place with stunning views, this condo is perfect for you! Don't miss out on this once-in-a-lifetime experience—book now!Experience the ultimate Waikiki luxury in this one-of-a-kind 3-bedroom, 3-bathroom condo at the iconic oceanfront Ilikai...
Oceanfront 2BR/2BA, 20ft from Shore, 180° Ocean View, Pool
OCEANFRONT, RIGHT ON THE WATER, spacious 2-bed, 2-bath condo on the 2nd floor just south of Kailua-Kona town. With breathtaking 180-degree Kona coastline and ocean views, watch humpback whales, spinner dolphins, yellow tangs and boats from the waterfront lanai as you...
Oceanfront Napili Shores ~AC~Ocean View
Escape to this fantastic condo in picturesque Lahaina. This cozy retreat features 1 bedroom with a comfortable king bed and an additional living space with a queen bed and a twin bed. Guests can enjoy amenities like WiFi, AC, and a hair dryer. With a convenient location...
Romanna’s Golden Ray Oceanfront Condo, Maui Resort
Welcome to your slice of paradise at Maui Sunset, where you can enjoy partial ocean and stunning garden views from the living room and lanai! Experience the convenience of direct access to the pool, BBQs, and sandy beach, all just steps from your lanai. The beautifully...
3BR Paradise with Direct Ocean Views – Westin Nanea Villas
Indulge in sweeping ocean views with this exceptional three-bedroom, three-bathroom oceanfront villa at Westin Nanea Ocean Villas, perched upon the pristine North Beach of Ka‘anapali. Boasting approximately 1,760 sq ft of indoor living space, this villa is designed to...
Large 3/2 House in Kailua-Kona with ALL New Furnishings and Yard Above Airport
Kona Coastview SubdivisionAs you step inside, you'll discover a spacious layout boasting three cozy bedrooms, each brand new furnishing master bedroom with a comfortable queen-sized bed set and ample closet space for all your belongings. Master bathroom with tub/shower....
Waikiki King Bed· 65”Screen@ No resort fee
Your cozy getaway awaits in Honolulu at this adorable condo. Guests enjoy a tranquil space featuring one bathroom and thoughtful touches like air conditioning, a hair dryer, and an iron to keep things comfortable and convenient. Whether you’re relaxing indoors or...
Lodge at Kukui'ula Bungalow 3 - 3 Bedroom Bungalow - Platinum
This three-bedroom bungalow at The Lodge at Kukui'ula on Kaua'i offers luxurious accommodations and exclusive access to the award-winning private club facilities and amenities of The Club at Kukui'ula, including the 18-hole Tom Weiskopf designed golf course, sprawling...
Kaanapali Alii Unit 1112
Kaanapali Alii 11121 Bedroom | 2 Bathrooms | Sleeps 6 | Ocean View_________________________________________________Welcome to Kaanapali Alii 1112, a beautiful 1-bedroom, ocean view residence overlooking the turquoise waters of Maui’s Kaanapali coastline. This spacious...
Kapalua Bay Villas | 3 Free Rental Cars | KBM Resorts | Panoramic Ocean Views | 3 Units, 4 Bedrooms | KBV ML-2083
** 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...
The Famous Peacock House
The Famous Peacock House – Spacious & Whimsical Big Island RetreatWelcome to The Famous Peacock House, a vibrant and whimsical Hawaiian getaway designed for families and friends to create unforgettable memories together. With space for large groups, thoughtful...
700ft to Waikiki Beach • 1BR Condo • King Bed • Rooftop Pool
Stay just 700 ft from Waikīkī Beach in this newly remodeled 1BR condo with a king bed, balcony, and access to a rooftop pool, hot tub, sauna, and BBQ area. Perfectly located in the heart of Waikīkī, you’re only steps from the Duke’s Statue, top restaurants, cafés,...
Boutique Hotel Waikiki FREE parking
Excellent Location, free parkingEnjoy a comfortable stay in this independently owned hotel room featuring a king-size bed, along with a twin-size pull-out for a third guest if needed, full bathroom, central AC, and a flat screen TV. The room includes a mini fridge,...
Incredible REMODELED condo-bonus-peak ocean view, AC available!!
Beautiful condo-oceanfront complex! Simply paradise!Aloha and welcome to paradise! We are located on Kauai's beautiful south shore known for it's sunshine and pristine beaches. The Kiahuna plantation sits on 35 tropical acres landscaped with rolling lawns, koi ponds,...
Modern Princeville Retreat – Hanalei Bay Rental with Private Pool
This beautiful brand new home is overlooking Hanalei Bay & the beautiful tree canopy of Princeville. With a 10 min walk to the 1 Hotel beach, a short walk to Princeville Center and a quick drive to Hanalei Town, it is the ideal central north shore location. Featuring...
Waikiki Gem-Mins to Beach, Lanai w/City View, King Bed&Surf Lessons in Building!
Wake up steps from Waikiki Beach in this bright city-view studio at Kuhio Village Tower 2 — perfectly located just 2 minutes from the Duke Kahanamoku Statue and Kuhio Beach.Sip your morning coffee on the lanai and watch Waikiki come alive, then head downstairs for surf...
Step Out into Waikiki: Homely Hotel Perfect for Family Retreat | Outdoor Pool
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,...
Hale Malu: Gorgeous 5 BR Kauna'oa Home, 10-Minute Walk to Beaches!
Brand new and gorgeous private estate at the only community that is walking distance to the two best beaches on the Big Island, Mauna Kea and Hapuna! This home has a prime location atop a bluff in the luxurious Kauna'oa community. Built with open space and privacy in...
Peaceful 3 Bedroom Home with Fabulous Views
This is a minimum 31 day rental listingPerfect for extended vacation or traveling worker; traveling nurses or doctorsWell appointed, well maintained, privateBeautiful home in desirable, safe neighborhoodClose to beaches, shopping, town, golf, tennis and pickleball, as...
Wyndham Mauna Loa Village | 1BR King Bed Suite
Summary:If sunset cocktails, pools, and plenty of tennis sound like your style, you’ve found your spot. Located in Kailua-Kona next to a country club, this tranquil oasis sits away from town traffic and crowds while offering convenient access to the island’s many...
Stylized Captain's House
This Stylized Captain's House is located minutes away from family friendly scenic Kealakekua Bay beaches, the national park Pu'uhonua O Honaunau, & the island's best snorkeling spot "Two Step".An ideal setting for tropical adventures of all kind, offering spacious...
Mauna Lani Point G101
Welcome to your luxurious retreat at Mauna Lani Point G101, a stunning short-term rental nestled in the heart of Kamuela, Hawaii. This elegant 1-bedroom, 1-half-bathroom condo offers a perfect blend of comfort and style, ideal for your next getaway. Step inside to...
Kaanapali Alii Unit 1113
Kaanapali Alii 11133 Bedrooms | 2 Bathrooms | Sleeps 8 | Ocean View_____________________________________________Welcome to Kaanapali Alii 1113! This is a gorgeous 2-Bedroom Ocean View condo, with a fully enclosed den that comfortably serves as a third bedroom. This...
Experience Oceanfront Bliss at Sugar Beach Resort 530
One of the best features to this tropical getaway is waking up to the sound of waves. Enjoy stunning views of Molokini, Kaho‘olawe, and the West Maui Mountains from your private lanai at Sugar Beach Resort 530. Just 60 feet from the ocean, this one-bedroom condo offers...
Scenic Kauai Stay Near Allerton Garden + Free Pool Access + Kitchen
Experience oceanfront serenity with stunning views, spacious rooms, a full kitchen, a private balcony, and in-room laundry—ideal for couples and families. Snorkel nearby, hike the Mahaulepu Trail, or spot turtles at Poipu Beach. Relax in our large outdoor pool. Whether...
Hale Makana: Portlock Luxury Home with Pool & Ocean Views
Set along Oahu’s exclusive Portlock coastline, Hale Makana is a refined single-level oceanfront estate that celebrates effortless island living. With postcard-worthy views of Diamond Head and the deep blue Pacific, this five-bedroom, seven-bath retreat blends...
Unique Treehouse at Magic Sands beach, ocean view
Under a huge, landmark Royal Poinciana tree, sits our Treehouse. Treetop views of the ocean across the street. Large, standalone cottage. Tall bamboo ceilings, lots of air through large windows, screened. Ceiling fans and cool shade make this place uniquely cool for...
Kapalua Golf Villas | Large Bedrooms | KBM Resorts | 3 Units, 4 Bedrooms | ML-2291
** 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...
The Heart of Kapaa walking distance to the beach, groceries, and fine dining.
A condo with beach access, and 2 pools! Grocery store, health food store, shopping and many fine restaurants all within 5 minute walking distance. The condo sits at the very beginning of the 8 mile costal bike path and we supply 2 bikes. Ground floor unit, easy access...
Modern Beach Apartment North Shore Home
Your Waialua adventure begins at this fantastic 1-bedroom apartment. The space features a queen bed, AC, a washing machine, and WiFi. The bathroom includes a shower and a hair dryer for your convenience. Nestled in a serene setting, this tremendous property is the...
Oceanfront 3BR Retreat with Stunning Views in Kahana
Discover the perfect island getaway at Kahana Outrigger #2B2, a spacious oceanfront 3-bedroom, 2-bath retreat nestled on Maui’s stunning west coast. This 1,448 sq ft condo offers breathtaking panoramic views of the Pacific from a large lanai, where you can whale watch...
Ke Alaula Hale 7 – Private & Secluded | Onsite Staff & Daily Housekeeping
This centrally-located 3-bedroom, 3.5 bathroom private home is a short 6-minute golf cart ride from the heart of the Four Seasons Resort. Designed for convenience and uncomplicated family living for up to 6 guests, this property offers a vaulted, wood-beamed great room...