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.
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,...
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!...
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...
Brand New, Luxury Volcano Hideaway, Minutes from National Park
Escape to this Brand-New Luxury Hideaway in Volcano.This brand-new, 575 sq ft fully furnished hideaway offers a romantic and luxurious escape in the heart of quiet Volcano. Nestled amidst native forests, häpu'u ferns, and wild ginger, this private retreat is just...
SEE the SEA @ SEA VILLAGE RESORT SUPER 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.
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...
Lahaina Shores Maui Dream Oceanfront Ocean Views
Your Maui Dream Awaits! Beachfront Condo in LahainaImagine waking up to the gentle rhythm of the waves, stepping onto your private lanai, and being greeted by breathtaking, unobstructed views of the Pacific Ocean. This isn't just a dream – it's your next vacation at our...
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...
3-bedroom townhome in peaceful Ewa Beach with AC
Enjoy a peaceful stay at this charming 3-bedroom townhome in Ewa Beach. This terrific property features 2 queen beds, 1 twin bed, and a cozy office space with a futon. With amenities like AC, iron, and a hair dryer, guests can relax and escape close to the ocean in this...
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!
♨ 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✔ Public...
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,...
Beautiful Kapalua Oceanfront Retreat (989 sq.ft)
Wake up to the sound of waves and sweeping views of Molokai across the channel from this beautifully designed 1000 square foot one-bedroom villa in the Kapalua Bay Villas. Perfectly perched along the dramatic oceanfront cliffs, this ground-floor condo offers...
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 delightful...
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,...
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...
Elua 1310 Ocean Front Condo - Family Managed - 50 Steps to the Beachfront/Walk!
(9/17/25) We just wrapped a full condo remodel of our oceanfront home and am bringing the unit back online!Elua 1310 is in the closest building to the beach with 120 degrees of unobstructed ocean views and sits next to the famous Wailea Beach walk.You are just steps...
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...
Wailea Ekahi 14F - Best Views - 3 Minutes Walk to Beach
"Comfortable luxury with a magnificent view," wrote a recent guest. Wailea Ekahi 14F is an upper-floor 2-bedroom 2-bath condo. Situated in a quiet tropical garden setting in the center of Wailea Ekahi Village, far from road and pool noise, with one of the three "quiet"...
🏝️Summer Deals-Cute Studio across the Beach, pool, hot tub, wifi🏝️
This Studio has been recently renovated and furnished for your beach getaway. You have a view of the tennis court from the lanai, while enjoying your breakfast or morning coffee. The unit comes with air conditioner to keep you cool after a day at the beach. In the...
Charming. permitted cottage, short walk to Paia town & beach. STPH 2013/0004
Nestled on Baldwin Avenue, our plantation style one bedroom cottage provides convenient and comfortable accommodations for 2 people, with the amenities of Historic Paia Town and Paia Bay just a few minutes walk away and all areas of the Island within easy driving...
🌺 Fairways 1706 Tranquility Villa 🌺 Renovated, includes Beach Access, Bikes 🌺
Your perfect vacation begins here! The Fairways at Mauna Lani is a private gated community of quiet luxury condominiums, the famed Farimont Orchid Hotel and the Auberge Resort Collection. While relaxing, it is also close to the heart of Mauna Lani shopping, golf, spas,...
Downtown Luxury Penthouse, Free Parking, Washer/Dryer
Welcome to your stunning getaway in the heart of downtown Honolulu! This spacious, High-Ceiling two story Penthouse is perfect for families, large groups, or anyone looking to experience the best of the city with comfort and style. With 8 beds distributed across 3...