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.
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...
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
The Hualalai Resort will host the annual Chairman’s Club event from December 1–6, 2025. Please note that access to certain resort amenities may be limited or restricted during this time for residential rental guests. We recommend inquiring prior to booking if your...
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 ResorticaHawaiiPLEASE NOTE: The swimming pool will be closed for Maintenance Mon-Fri from 8:30am-4:30pm Oct 6-27, 2025. Dates may be subject to change due to unforeseen delays.Fairways at Mauna Lani 906. Includes Mauna...
Emmalani Court 322 - Golf Course & Ocean Views w/AC.
Emmalani Court is a hidden gem in Princeville on the North Shore of Kauai. It is only 42 units and adjacent to the 8th hole of the top rated Robert Trent Jones Jr designed Makai golf course. This well maintained complex is located within walking distance to the...
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...
Beautiful Kukui'ula Home With Great Lanai Space
New pool just added! This home has it all, private hot-tub, brand new pool, fire pit, 2,000 sqftlanai, and enough room for the whole family with over 3,000 sqft of insideliving space! - 5,000 soft totalThis home is special with it's open indoor/outdoor main living area...
Newly Remodeled Luxury Condo with Ocean and Fairway Views
Beautiful newly-remodeled unit in one of the most sought-after associations on the North Shore. We invite you to enjoy the peaceful, old-Hawaiian feel of Kauai’s North Shore and the upscale yet understated elegance of Princeville with a visit to our beloved home....
Sands of Kahana Resort #345 - Vacation West Maui
★ Completely Remodeled in 2025★Air Conditioned 2 Bedroom, 2 Bathroom at the World Renowned Sands of Kahana Resort★ Oceanfront Oasis in West Maui's Sands of Kahana Resort★ Huge Condo, 1,600 Sq Ft Property Highlights:Mesmerizing views of Moloka'i and Lana'i on the...
Ocean Front Condo with AC, Watch Sea Turtles from Our Lanai
Visit our remodeled ocean front get-away. The unit has been remodeled from top to bottom, from ceiling to floor. The master bedroom features a California King bed, night stands with reading lights, built-in cabinets for clothing storage, granite countertop, ceiling fan,...
Luxury Oceanfront Condo - Fabulous Ground Floor 3BR/2BA, Sleeps 6 - Lae Nani 511
At Lae Nani #511, you will feel truly relaxed, surrounded by lush tropical landscaping and listening to the soothing sound of the ocean’s waves breaking on the shore. The location of this three-bedroom suite is ideal, providing views of the ocean as well as gorgeous...
Heaven on Earth in Upcountry Maui
Welcome to The Star Lookout, a magical vacation cottage in Maui's Upcountry. Experience a taste of 'Old Hawaii' in our quiet, restful perch with privacy, sweeping views, magnificent sunsets, and oodles of stars. We are located at 622 Thompson Road, Kula, HI 96790.The...
Villas By The Cove, Plantation House · Dreamy Indoor-Outdoor Living Opposite a Sandy Beach
Welcome to a Cutting Edge Maui Beach Home that blends its Original 1940's Plantation Style Charm with Refined Contemporary Design and custom finishes. Located just steps away from sandy beaches on the desirable oceanfront Ili'ili Road, this romantic property mixes art,...
Glam Condo Located in Central Waikiki, Panoramic Ocean View, & Full Kitchen!n
♨ Glam Condo Located on the 42nd Floor With Panoramic Ocean View ♨Enjoy this fully equipt kitchen including a full-size fridge, wall oven, stovetop & dishwasher.✔ Located in Central Waikiki✔ 5 Min Walk From Shops, Restaurants, & The Famous Waikiki Beach✔...
Spectacular Diamond Head and Ocean View! Best location in Waikiki!
You'll love our 2 bedroom 1 bath unit on a high floor with the best views in Waikiki.Located a short 5 min walk to the beach and across from the world famous Hilton Hawaiian Village.Whether seated in the living room or relaxing in bed you'll be treated to a breathtaking...
Ocean Beach Home In The Heart Of Authentic Old Hawaii
STVR 19-360891, NUC 19-1179 From home to ocean in under a minute! This newly built custom home is just 200 feet from the ocean and located in the heart of authentic Old Hawaii - Captain Cook locale on the Big Island of Hawaii. An exceptionally comfortable residence,...
Kai Moena Estate - Kailua Luxury Beachfront Estate with Pool, Spa, AC, Sauna, Fitness Center & More!
Prices start at $100,000/month and will not be pro-rated based on length of stay. Please inquire to get an accurate quote.Property is currently for sale. The property manager will contact you to make arrangements to schedule showings at a convenient time. This luxury...
Beautiful Kapalua Oceanfront Retreat (989 sq.ft)
Restore and enjoy all Kapalua has to offer! This private condo's idyllic location is perfect for a romantic getaway, or a peaceful place to relax and restore. Take a walk along the beach boardwalk to spot sea turtles, barbecue or lounge at the pool, boogie board at the...
Pali Nui – Gorgeous New Kukui'ula Villa
Jaw-dropping, breathtaking, spectacular: sometimes even the highest superlatives can seem like low-key understatement. Pali Nui—this uniquely gorgeous new Kukui'ula villa—is distinctively designed and stylishly curated, with artful décor, tropical allure, and...
Centrally located | 15 minutes from North Shore | 30 Day Minimum
Live like a local in an upcountry cozy gem located in Wahiawa. The bungalow features a private entrance and gated driveway. It is centrally located near North Shore. This is the perfect place to unwind and enjoy the slow-paced living on the island!You will have access...
Puako Pau Hana, A Restful, Private Retreat located steps from the water!!
Puako Pau Hana is a great place to escape from all your cares! Located in the heart of Puako, you are literally just a few steps to the most beautiful little beach in Puako! Puako is known for it's magical old fashioned neighborhood feel and remarkable clear water,...
Bishop Suites at Executive Centre, 1-Bedroom Mountain View Suite + Full Kitchen
Unwind in Honolulu at this terrific condo. This cozy 1-bedroom retreat offers a living room with a comfy sofa bed, perfect for extra guests. Enjoy the convenience of amenities like a hair dryer, WiFi, washing machine, and AC. Relax in the gorgeous bathroom after a day...
Cozy cottage nestled on our 5 acre Organic fruit farm
The farm cottage is set at the top of our 5 acre exotic fruit farm. Enjoy your stay by touring the property and relaxing in our cozy home away from home. The cottage is equipt with everything you'll need without the clutter. From the living room, enjoy a view of the...
Ginger Room
Rejuvenate in the Rainforest at Ginger room, situated on 5 lush tropical acres in the heart of Volcano Village near Hawaii Volcanoes National Park. Our guests enjoy four spacious rooms with full walk-in closets, thick curtains, hardwood floors, and private bathrooms...
Hanalei Plantation Road Home - Dream Retreat with Pool & Ocean Views
Escape to this beautiful Hanalei Plantation Road home, nestled in a prized neighborhood. Enjoy sweeping mountain and ocean views over Hanalei Bay. With 4 bedrooms, a gym, pool, and ample indoor/outdoor space, it's a dream retreat. Upstairs, find a bright living/dining...
Pohinahina Place – Serene Hualalai Estate with Ocean Views & Private Pool
Pohinahina Place is your private resort retreat. With an incredible view of the Pacific Ocean and overlooking the 5th green of the Hualalai Golf Course, this property is located right in the middle of Hualalai Four Seasons Resort. This beautiful oasis is nestled on a...