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.
Ka'anapali Livin' the Dream Home - Private, luxury, resort-style property!
Come stay at our newly renovated, beautifully appointed, 3000+ sq ft., 3 bedroom, 2.5 bath beach home located on the Kaanapali Kai Golf Course. A short 3-minute drive or 10-minute walk to world famous Kaanapali beach, award-winning restaurants and Whaler's Village...
HEAVENLY OCEANFRONT CONDO!!! PH22 STEPS TO THE BEACH!!!
The perfect place for a romantic honeymoon, a restful getaway, or a fun-filled family vacation. Welcome to Penthouse 22. Our top floor, ocean front condo is just steps from the sand and surf. We are a consistently A+ rated unit and have just re-decorated with new...
Tropical cottage with fresh rain water hot tub close to Volcanoes National Park
Enjoy the fresh rainwater hot tub after a long day's hike. The hot tub is drained, sanitized, and refilled with fresh triple-filtered, chemical-free rainwater between each booking. This cozy cottage is in the heart of Volcano Village with luxury features such as a...
Moani Heights Mauna Kea Resort - Free Resort Access May-September! Great House!
When Laurance S.Rockefeller opened the Mauna Kea Resort in 1965, it was a new level of luxury for its hotel guests and now the guests of residential homeowners. Times have changed! At that time, Trent Jones Sr. was challenged to build a course on lava bluffs, but met...
Now Booking! Enjoy your next vacation in our newly remodeled condo! Pool, A/C!
New listing and availability just opened for this brand newly remodeled, stunning studio condo! Our condo is perfect for a honeymoon stay or romantic getaway with a gorgeous garden view and air conditioning! The condo features a king bed, small dining table and chairs...
Oceanfront tropical oasis in West Maui
Hale Mahina A 102 is a ground floor one-bedroom, one-bathroom unit making it convenient to unload groceries and beach equipment and does not have A/C. The master bedroom features a comfortable King size bed with bamboo sliding doors for privacy. The bathroom features a...
Beautiful Hali’i Kai 15-C, oceanfront, watch whales from your lanai
Welcome to the beautiful Kohala coast on the Big Island of Hawaii! Unit 15-C at luxurious Hali’i Kai gives you a rare front row seat with ground floor access to lush green grass over looking the beautiful Pacific. During the season, watch whales up close from your...
HONUA KAI- HK 314-1 BEDRM-1 BATH-⭐️⭐️⭐️⭐️⭐️ 67 FIVE STAR REVIEWS-OCEAN & MNT VIEWS
Aloha, Our condo (Hokulani 314) has just been newly upgraded and remodeled with new furnishings and wall art. Our beautiful one bedroom unit has a king bed and living room with a Queen sofa bed. The condo comfortably sleeps up to 4 guests and is located in the beautiful...
Spectacular Oceanfront Penthouse, AC, Sleeps 6
Luxury oceanfront penthouse in paradise!From endless deep blue of Kalapaki Bay to emerald greens of the Hokuala golf course this penthouse is the kind of paradise you’ve been dreaming of. Perched upon the Kalapaki Cliffs, this location provides the ultimate...
Oceanfront, Stunning Designer Masterpiece now Includes A/C
If you like Kauai Haven (VRBO Listing #683110), you're going to love this condo too. It is nestled within a classic Hawaiian style backdrop, resting on a bluff overlooking the spectacular Pacific Ocean. An award-winning designer, who is part of the Coastal Living...
Hawaii Oceanview Oasis: Come to Work, Play, Relax.nOn Ironman Path!
Welcome to your dream Hawaiian escape! This spacious 3-bedroom, 3-bathroom ocean-view condo offers the perfect blend of comfort and convenience, making it an ideal retreat for couples, families, remote workers, or anyone seeking a rejuvenating getaway. Enjoy the unique...
SPECTACULAR OCEANFRONT A/C Near everything! at the Kahana Beach. Studio, Lanai
Welcome to our relaxing Kahana Beach Condo, 20 ft from ocean, fantastic location, cozy comfort meets paradise! Our air-conditioned haven provides a refreshing retreat from the tropical heat, ensuring you stay cool and relaxed throughout your stay.Step into our spacious...
Hokulani 306 at Honua Kai ~ Upgraded Floors & Furniture with Stunning Ocean View
You'll love the ocean & mountain views from this 1240 square foot, updated third floor, two bedroom two bathroom condo. This is one of only six condos in Honua Kai that have this exact configuration and the only one with these beautiful upgrades. Hokulani 306 is so...
WHALE Watching & OCEAN Views! Honua Kai Penthouse- Top Floor- Remodeled June'24
🌴 West Maui is Open – and Honua Kai is Resort-Zoned. 🌴Book with confidence knowing you’re safe from the recent legislation impacting other short-term rentals.🌊 Welcome to Hokulani 749 at the award-winning Honua Kai Resort – a stunning penthouse offering...
Beachfront ocean View Condo With Unobstructed Ocean Views. 5 star reviews *****
Beachfront condominium! Watch the sunrise and sunset from the deck, whale watching from the balcony and snorkeling right in front of this recently updated property. Access to the longest sand beach on Maui. Centrally located 20 minutes from the airport, Lahaina and...
Oceanfront Luxury Villa Near Town- Easy Access to Kalapaki Beach & Hiking Trails
Experience the refined charm of the Pali Kai Suite, a private 2-bedroom retreat nestled within the exclusive Pali Kai Palace estate on Kauai’s East Shore. Surrounded by lush tropical beauty, the suite features central A/C, a private balcony, stylish interiors, and...
Ke Ola Kai "Sea Life"
Brand new beachfront renovation in beautiful Puako. Enjoy year-round sunsets from the private lanai and step directly onto the beach for easy access to swim, snorkel, boat or dive... Daily sightings of sea turtles (Honu) and with luck some playful whales or a monk seal....
Island Adventure: Minivan Rental, Contact Us
Mahalo is the Hawaiian word for thanks, and a feeling of profound gratitude is what inspired this beautiful home. From the moment you arrive at Hale Mahalo, you’ll understand why. This lovely 3-bedroom, 3-bathroom home is a tribute to the stunning beauty of its...
Oceanfront Holiday <br>
Aloha!Welcome to Hale Mahina Beach Resort , your Maui home away from home.Located between Lahaina and Kapalua, it is a short drive to many wonderful Hawaiian experiences. Beachside dining, sunset cruises, snorkeling excursions, hula shows, and championship golf courses,...
MAUI BEAUTY ~ Tropical Napili Bay Lahaina CONDO ~1BR King ~ Kitchen ~ AC!!!
All New Interior - New Listing! Hidden gem of the West Side of Maui, Completely remodeled condo w/ all New Furniture, full kitchen with dishwasher, beautiful bathroom w/ walk-in tile shower, brand-new AC in Living Room AND Bedroom.***Napili Ridge is just north of...
Jungle Bee: 23 Acre Estate on Kauai's North Shore with Private Beach Access
GE/TA 125-285-3760-01TA#W90869281-01Permits: TVNC 4272 SP2012-10Welcome to Jungle Bee!Note: Pricing includes both homes on the property and exclusive use of the estate.Jungle Bee Farms is a stunning 23 acre estate overlooking the northern most point in the Hawaiian...
Breathtaking Ocean View Condo w/ new furnishings - Poipu Kapili #30
Amidst the luxurious oceanfront Poipu Kapili Resort, is an exquisite 1 bedroom, 2 bath remodeled single level, second floor holiday home endeared as Poipu Kapili 30. Perfectly manicured lawns, immense palm trees along with fragrant and vibrant blossoms promise a...
Beach House: Oversized Lanai with Indoor/Outdoor Flow. EZ Stroll to Magic Sands!
Check out this drone video showing the home, neighborhood and proximity to the ocean: https://youtu.be/4d2V5HbQ1cYUpgrade your Vacation at our Magic Sands Beach House! Best Location, Lifestyle & Amenities! Maximizing Kona's beaches & weather, this open & airy retreat...
Maikalani at Poipu Kai By Parrish Kauai - quaint cottage for 4 with AC & private
Tucked into the Lanai Villas section of the tropical Poipu Kai Resort, Maikalani is a Kauai vacation rental home exquisitely decorated and outfitted with all the necessities of home, including zoned air conditioning. Located on the lush green belt with easy access to...
Olivine Surf Lodge - Corner Unit w/ Ocean Views & Amazing Sunsets
Newly updated, light-filled condo on the North Shore of Kauai! This modern, tranquil retreat has a wide-open floor plan and a lanai with stunning ocean and golf course views. Superb location, close to walking paths and the Princeville town center, with great cafes,...
15% off March & April 2025! Luxury Penthouse - Ocean, Beach & Pool View!
Welcome to our luxurious paradise retreat at Ko Olina Beach Villas, where relaxation meets first-class amenities. This impeccably maintained penthouse in the Beach Tower offers breathtaking views of the ocean, beach, and lagoon pools—a true tropical haven designed for...
New Listing: Stunning Studio at Maui Banyan
Welcome to Maui Banyan P409A, your serene escape in sunny Kihei, Maui! This beautifully updated studio condo offers the perfect blend of comfort, convenience, and island charm—ideal for couples, small families, or solo travelers seeking a relaxing Hawaiian...
Bright and airy 1-bedroom cottage in charming Kailua, 1 block to beach. WiFi, AC
This sunny cottage in Kailua is a perfect choice for guests seeking a quiet retreat in a fantastic location, so conveniently close to all that Kailua has to offer, including sandy beaches, popular restaurants and eateries, all kinds of great boutique shops, Whole Foods,...
Luxe Coastal View 2907C Villa at Hualalai w/ Resort Pool & AC
Important Resort Notices* Hualalai Spa Enhancements (Sept 15 – Mid-Nov 2025): During this period, the resort’s outdoor aqua-thermal areas will be under renovation. Massage, body, and facial treatments will be temporarily relocated to the Makaloa Villa. The infrared...
Oceanfront Condo in Kaanapali! Fully Renovated & Air Conditioned! Best Views!!
Kaanapali beach welcomes you with this spacious home with Stunning Views! This is the perfect apartment if you are looking to get away from it all and re connect with your significant other. There is nothing better than sitting on the Lanai and listening to the waves!...
Luxuriously updated condo with easy access to the beach, restaurants and shops
*Recently remodeled in May 2024*Set apart from similar units with luxuriously updated bathrooms, bright modern decor & updated furniture, Sunrise Hale is sure to impress. Begin your day with an awe-inspiring sunrise above majestic Mauna Kea and golf course from the...
Gorgeous sunsets, quiet property
Views! Golf! Listen to the Birds! Situated on the third (lagoon) hole of the renowned Robert Trent Jones Jr. golf course, unobstructed views extend all the way to the Pacific Ocean. To the right, impressive cloud formations settle over the green hills of Waimea as the...
Kailua-Kona Condo w/ Resort Amenities Access!
Pack your bags for a trip to paradise at this Kailua-Kona vacation rental! This 1-bedroom, 2-bathroom penthouse unit boasts vaulted ceilings and proximity to local attractions, making it an ideal island home base. Begin your adventures by sampling Kona coffee and fresh...
Stunning Oceanfront Property! Spectacular Ocean Views!
This exceptional oceanfront Penthouse is located on the sunny, south shore of Hawaii's Garden Island in Poipu. This beautifully remodeled, luxurious condo is just 30 feet from the ocean's edge. It offers 180-degree ocean, coastline and mountain views from the lanai,...
NICELY UPDATED-SLEEPS 8-WELL EQUIPPED-AC-METICULOUS CLEANING
Book with confidence, this stunning, 3 bedroom, 2 bathroom spacious condo that has been nicely updated. This condo is managed by PMI Maui, a local Real Estate Brokerage that specializes in vacation rentals. We are located within a mile of the resort and available 24/7...
Oceanview-Pool-AC-Gourmet Kitchen-W/D -Golf-14D
A full bedroom and bathroom on the first floor provide convenience for guests' privacy and ease of access. Located in the heart of Princeville, this condo is ideally positioned within walking distance of Anini Beach, scenic parks, farmers’ markets, and picturesque...
Charming 2-bedroom house in peaceful Keaau with WiFi, AC
Welcome to our charming country cottage nestled on the breathtaking Big Island of Hawaii in Kea'au. This idyllic retreat offers a tranquil escape from the hustle and bustle of everyday life, surrounded by lush greenery and stunning garden views, where guests can relax...
Villa Olina Charming 3-Bedroom Villa On the Golf Course Steps Away from Lagoons
Beautiful & spacious yet cozy and comfy Ko Olina Kai Welcome to your tropical haven in the coveted Ko Olina Kai community. This delightful 3-bedroom, 3-bathroom house rental offers a prime location just a 10-minute walk from the stunning Ko Olina Lagoons. Tailored for...
Hale Kona Kai #410 - Oceanfront Kona Condo
Get away from it all right in the heart of Kona! Feel the ocean spray as you watch for turtles on the lanai, or gaze at the tropical paradise through your bedroom window. While only steps away from the active downtown, this top-floor unit is on the ocean side of a...
Luxury Ocean View Condo, Recently Completely Updated!
Perfect Wailea Ekahi condominium, tastefully renovated! Ground floor center unit, #13B. Air conditioning in the living room and bedroom with state-of-the-art I-WAVE-M air filters installed in them to remove those airborne viruses. High-speed internet in the unit to help...
Marriott Maui Ocean Club 1BR 2 bath Available week of 12/22-29
Please push ask owner a question with your dates before using the book it now button. Web site calendar does not match what Marriott shows as available or take into account that Marriott timeshares have to be booked as full weeks and check in can only start on Friday,...
The Maui Escape - Spectacular 2.5 Bdr Penthouse -Oceanfront Resort-Owner Direct!
The Maui Escape is located with views of the upper pool and the spectacular surroundings. The villa's location is the perfect combination of being close enough to view the pool but far enough for privacy. At night the ambiance from the lanai is breathtaking with...
Ala Moana Hotel 13th FL R0 Studio - 2Double Beds 4Person
NEWLY RENOVATED 13th floor with Partial Ocean ViewCozy Hotel Studio | 2 Beds | 1 Bath | Sleeps 4 Stay in the heart of paradise! This bright and comfy studio is perfect for friends or family, with 2 beds, 1 bath, and space for up to 4 guests. Just steps from Ala Moana...
Exquisitely decorated 1bd oceanfront condo
Noelani 205 is a 1-bedroom, 1-bathroom condo on the 2nd floor featuring amenities such as panoramic ocean views, a remodeled kitchen, and a washer/dryer. The condo can accommodate up to 2 guests with a King-size bed in the bedroom. The spacious main living area includes...
SEE the SEA @ SEA VILLAGE RESORT nSUPER SPRING INTO SUMMER SPECIAL GETAWAY RATES
SEE the SEA @ Sea Village Resort Escape to Hawaii for a great vacation !!Great condo , Great Location, Great RatesFree onsite parking, gated oceanfront pool/hot tub (SLEEPS 2 MAXIMUM)Aloha and welcome to a special place aka NIGHTOWL HALE @ Sea Village Resort on Ali'i...
Mauna Lani Beach Club Pass! 906 Fairways at Mauna Lani
This vacation rental is professionally managed by ResorticaHawaiiFairways at Mauna Lani 906. Includes Mauna Lani Beach Club PassPlease scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom: Queen BedMauna Lani Beach Club Pass:...
Emmalani Court 322 - Golf Course & Ocean Views w/AC.
***DISCLOSURE 8/25/25: Please note that Emmalani Court will be undergoing a large-scale construction project fromSeptember 02, 2025 through approximately April 01, 2026• Construction activity may occur Monday–Friday, between 8:00am–5:00pm.• Guests may experience...
Newly remodeled gem in Hawaiian Shores
Spacious Custom built newly remodeled 3bd 2ba home with 2,144+ sqft of living space that has been beautifully remodeled/renovated for enjoying Island living.This home features vaulted ceilings, natural light with French Doors opening on to your spacious front...
Monthly Discovery Bay 1713 Ocean/City Views 1 Bd 1Ba
WAIKIKI / OCEAN VIEWS, 5 Minute Walk to Beach, Remodeled, Furnished and Fully Appointed. No smoking condo. Parking, Pool, Utilities, WIFI, BBQ, Gym, Sauna, Security, Washer/Dryer Included. Monthly.Excellent Views from Breezy Lanai, Tasteful and Clean. Monthly / contact...
Simply Stunning Condo, C202 is one of of the best!
A LITTLE ABOUT THIS CONDO... Lokelani C202 - Welcome to our coastal paradise on West Maui. This newly remodeled and updated oceanfront condo, just 45 feet from the Pacific, offers stunning views of Molokai, Lanai and Hawaiian sunsets from within and from its two...