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.
Secluded Ocean front getaway
Summary:Relax with the whole family at this peaceful home. Our newly renovated oceanfront property is the perfect island getaway. With ocean and mountain views from your doorstep yet just minutes from the best local food and famous attractions you will enjoy the perfect...
BMB 804 Modern Waikiki 1 Bedroom, 2 mins to Beach
Located in Honolulu, this delightful apartment is a dream. With 1 tranquil bedroom featuring a cozy queen bed, guests can unwind after a day of exploring. The bathroom offers a relaxing bathtub and a hair dryer for convenience. An additional living room space with a...
Waikoloa Hills,Two-Bedroom/Two-bathroom BBQ & more
Welcome to Waikoloa Hills Unit 606, a beautifully appointed two-bedroom, two-bathroom vacation rental offering comfort, convenience, and mountain views. Nestled in the heart of Waikoloa Village, this two-story retreat is perfect for families, couples, or friends looking...
Two-story condo with Mauna Kea view, saltwater pool, hot tub - near beaches/golf
Waikoloa Hills #105 - Pineapple ParadiseOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Wake up each morning to a view of Mauna Kea from your bedroom at this two-story condo in...
Ocean and Diamond Views from the Balcony
Legally permitted rental - 134 Kapahulu Ave #911** For your health and safety, we utilize additional Sterilization procedures between reservations.This unit features breathtaking views of Diamond Head, Kapiolani Park and Kuhio Beach. Enjoy Sunrise and Sunsets, movies on...
Carefree Hawaiian Monarch Studio | Pool + Gym
Take in city and partial ocean views from this beautifully renovated studio at the Hawaiian Monarch building. Located at the beginning of Waikiki, this unit offers ac, smart tv, wifi and cable a short walk from Fort DeRussy Beach Park, Hilton Hawaiian Village, Ala Wai...
Upgraded Condo Near Beach - Kamaole Sands 4108
Recently remodeled and with an open layout, this air-conditioned condo located in the quiet part of the Kamaole Sands resorts, is your perfect home-away-from-home. Great for preparing a full meal or warming up leftovers from one of Kihei’s trendy eateries, the fully...
New! Kailua-Kona Stunning House w/ Ocean Views & Infinity Pool
Welcome to Hale Luana, your dream vacation rental with extraordinary ocean views in a reimagined and refreshed Kona home. Located at the pinnacle of the highly regarded Iolani subdivision, this oasis offers the perfect island getaway with convenient access to Kailua...
Oceanfront Kailua-Kona Islander Studio w/ Lanai!
Switch into island time the second you land on the Big Island of Hawaii and get settled into your tropical home-away-from-home in the Kona Islander Inn. This Kailua-Kona vacation rental studio features 1 bathroom, a well-equipped kitchenette, a private lanai, and a...
Centrally Located 2 BDRM 2 bath Condo w/City, Diamond Head & Ocean Views
Aloha and Mahalo from Waikiki! This property is a 30 day minimum rental at The Windsor. Centrally Located near the main Waikiki strip and in one of the most convenient areas of Oahu. Featuring a fully equipped kitchen ready for you to cook, and great views from your...
Koana's Ocean Hale | Onsite Pool
Summary:Fall in love with the Big Island and all its splendors when you stay at Koana’s Ocean Hale, a charming 1-bedroom condo on Hawaii’s west coast. Nestled among the lush island landscape, you’ll be located alongside the beautiful Kona Country Club where the...
Cozy studio with a shared pool, hot tub and grill area, steps from the beach
Kona Bali Kai 263Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located in the beautiful area of Kailua-Kona, Hawaii, this charming condo at Kona Bali Kai offers a serene retreat...
KBM Resorts | FREE CAR | Mahana | Oceanfront | 2-Bedroom Condo with Stunning views! MAH-719
** 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...
Waikoloa Shores Beach Resort #132 Hale Kai
Aloha and E Komo Mai to Shores of Waikoloa Hale Kai #132! Step into the welcoming open-concept living area that blends modern amenities with gorgeous furnishings, bathed in natural light that enriches the vibrant tones of the entire retreat. Our Newly remodeled and...
Amazing Ocean and Diamond Head Views
Breathtaking ocean view while also being able to see Diamon Head! This beautiful condo in Waikiki Sunset boasts the comfort of central AC while bringing you right to the beach.. With close proximity to the beach shopping and restaurants it is a perfect place for your...
Ilikai Apt 2127 - Spacious Studio with Spectacular Ocean & Harbor Views
Breathtaking Ocean & Yacht Harbor Views | Ilikai Studio, Sleeps 4 | Waikiki Paradise! Step into your dream Waikiki vacation rental—a bright and breezy studio suite located in the legendary Ilikai Hotel. Perfectly situated on the 21st floor with stunning views of the...
Coconut Plantation 1080-1: Spacious 3BR Ko Olina Retreat w/ Wrap-Around Lanais
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Welcome to Coconut Plantation 1080-1 by...
Kihei Akahi C-410 | Ocean Views, Near Area Fun!
Welcome to Paradise! Live out your Maui vacation dreams at Kihei Akahi C410, a fourth-floor upgraded condo in Kihei, HI. This gorgeous condo offers rest and relaxation for up to two guests with one bedroom and one full bathroom.The moment you step inside Kihei Akahi...
New listing! Poipu 3br Retreat with Pool and Gym
Poipu Retreat with Mountain Views and Resort-Style AmenitiesDiscover this breathtaking second-story sanctuary in the prestigious Pili Mai resort, where panoramic views of Kauai's stunning South Shore create the perfect backdrop for your tropical getaway.Nestled within...
Shores at Waikoloa Unit 111: 1 Br condo in the Tamarind Tower, sleeps 2
A Repair and re-tile project on the 2nd-floor walkway (catwalk) in the Tamarind Tower will start the week of April 21st, 2025, with plans to be completed late-June. While the walkway will remain accessible when under construction, there will be considerations for all...
Island Style W/Ocean View, Lanai and Fans–Kiahuna
Kiahuna Planation and Beach Bungalows #2072: Settle-in under tall ceilings, stunning ocean views, and a spacious open-concept design in this vacation suite. This space features warm and cool gray tones highlighted by tropical scenes and sets the standard for peaceful...
Kihei Akahi Condo w/ Free WiFi, A/C-Swim, Surf, and More
Kihei Akahi D601Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Step across the street and enjoy Kamaole Beach Park II, one of Maui’s best swimming and stunning beaches. Revel in...
Wailea Beach Villas PH105 - 3 Bedroom Garden View Penthouse
Welcome to Wailea Beach Villas Penthouse 105, where luxury living meets the breathtaking beauty of Maui. This elegant ocean view penthouse spans 2,500 square feet and features a spacious floor plan that flows seamlessly onto a generous lanai, providing the perfect...
Menehune Shores #209 – Oceanfront Tranquility and Your Perfect Maui Escape
Menehune Shores #209 – Two-Bedroom Oceanfront Retreat with Expansive LanaiWelcome to Menehune Shores #209, a beautifully designed two-bedroom, two-bathroom condo offering stunning ocean views and a rare oversized lanai. This oceanfront retreat combines modern comforts...
Ocean-View Condo w/ Pool in Maunaloa!
1 Mi to Papohaku Beach Park | Tennis Courts | Private LanaiLocated on the Western coast of Maunaloa, this 1-bedroom, 1-bath vacation rental condo places you in a perfect environment to connect with the serenity and natural beauty of the island. Enjoy the secluded Ke...
Wailea Elua Village 1511 - 1 Bedroom Garden View Condo
Wailea Elua Village 1511 is a premier vacation rental nestled in the heart of Wailea, offering a perfect blend of luxury, comfort, and stunning natural beauty. This exquisite one-bedroom, two-bathroom villa provides close to 1,000 square feet of elegantly designed...
Rare 2 Bedroom + Loft Townhouse on the North Shore
Affordable 2-Bedroom, 2-Bath + Loft at Kuilima Estates (next to The Ritz-Carlton O'ahu, Turtle Bay)Enjoy more space without the luxury price tag! This comfortable and spacious 2-bedroom, 2-bath loft is the largest floor plan in Kuilima East, giving you room to spread...
Royal Kuhio 1309 with King Bed, FREE Parking/WiFi, mins to BEACH!
Discover Waikiki Bliss at HOME Honolulu - Royal Kuhio 1309Embark on an unforgettable Hawaiian escape at our meticulously designed vacation rental, situated at the heart of vibrant Waikiki. Located at 2240 Kuhio Ave #1309, this King Studio promises an immersive 30-day...
2 mins Hon'l Beach, 1 Bed Condo with full kitchen, AC, WiFi, laundry, pool, BBQ
Experience Kailua-Kona like a local in this top floor, peaceful, cozy, 1-bedroom condo walking distance to Hon'l Beach and Ali'i Drive to downtown Kailua-Kona.Bask in Hualalai mountain views from the juliet terrace, and easily catch sunset beach views from the apartment...
Lovely Hawaiian decor with oceanfront views
Welcome to Paki Maui 310, a charming 1-bedroom, 1-bathroom unit that offers ocean views from your private lanai and ceiling fans throughout. This property does have elevators for easy access. Unit 310 can accommodate up to 4 guests. The bedroom features a queen-size bed...
Ocean View Studio with Kitchenette - Waikīkī Grand #910
Castle at Waikīkī Grand #910 - Make coffee in the morning in your coffee pot, warm up leftovers in the microwave, or cook a small meal on the hot plate all from your own kitchenette! Whatever your fancy, you'll have everything you need to warm up leftovers or to cook...
Stunning Fully remodeled Direct Oceanfront on the beach, AC, pool, spa
Welcome to your Oceanfront Maui condo with Pool and Hot Tub, perfectly situated for exploring all the wonders of Maui while enjoying the soothing sounds of ocean waves .From your porch you'll be treated to stunning sunrises and breathtaking ocean views. Relax by the...
Ilikai 427 Ocean / Sunset / Marina Views King Bed, Sofa Bed
OCEAN VIEWS! STEPS TO WAIKIKI BEACH. Sunset views. Walking distance to shopping mall, restaurants, shops, buses, rental cars, parks & Waikiki night life. The iconic Ilikai Suites are located at the gateway to Waikiki.The iconic Ilikai Suites are located at the gateway...
Lae Nani 313 Drastically Reduced Rates!
Rates have been drastically reduced to entice last minute travelers! This condo is very close to the beach. It is locatedon the ground floor so you can just walk to your beach without a staircase to obstruct you.You can relax on the lanai, amongst our beautiful...
Updated 2nd-floor condo in heart of Kona with lanai, pool, grills
Kalanikai 218Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This nicely updated, second-floor condo (no elevator) is in the heart of Kailua-Kona and is perfect for a romantic...
Ocean Views & ac W763! Sullivan Properties
Enjoy all that Kaanapali has to offer within walking distance. The 3 mile beach walk stretches from Sheraton’s Black Rock to the Canoe Beach just pass the Hyatt Regency Maui and your condominium at The Whaler is right in the middle. The location on Kaanapali Beach is...
Renovated Waikiki Suite, Walk to Beach + Parking
***PLEASE NOTE:DECK RENOVATION NOTICE:The building's recreation deck, including the pool and BBQ, will be closed for renovation starting April 7, 2025, with work expected to continue for approximately one year. Rates have already been discounted accordingly to reflect...
New Listing! Ground floor oceanfront blue oasis
Nohonani 101 is a spacious two-bedroom, two-bathroom condo that comfortably accommodates up to six guests. With a king-size bed in each bedroom and a queen sleeper sofa in the living area, there's plenty of room for families or small groups to relax and unwind. Although...
Kona Mansions#225 Top Floor, 2 story Unit w/Ocean views & Air Conditioning
Knutson & Associates is proud to be newly representing a spectacular new addition to our Vacation Rental Inventory. Kona Mansions#225 is a wonderfully appointed property that has a phenomenal location. Stunning ocean views, just steps from lively nightlife and the best...
Kailua Studio w/ Pool Access & Garden Views!
Indulge in paradise when you stay at this vacation rental studio in Kailua! Located at Kona Islander Inn, the home has a queen Murphy bed and 1 bathroom. Take advantage of great community amenities including a hot tub, or stroll across the street to sunbathe at the...
Island Surf 510B | Close to Beach & On-Site Pool!
Escape to the serene paradise of Island Surf 510B, a cozy tropical condo nestled in the heart of Kihei, Hawaii. This charming vacation rental offers a tranquil retreat for up to 2 guests, boasting 1 spacious bedroom and 1 bathroom all conveniently situated on one floor...
Coastal condo w/ breathtaking ocean views, shared pools, WiFi
Country Club Villas 234Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Experience the ultimate Hawaiian getaway at this stunning ocean-view condo nestled along the iconic Ali'i Drive...
Island Surf 209 One Bedroom One Bath with Ocean View
If you want to be within walking distance to all the best food and fun to be found in South Maui, this is the property for you! This stunning ocean view condo offers an unparalleled blend of comfort and luxury. As you step into the spacious, sunlit living area, you’ll...
OceanView Studio Waikiki Legal
About this spaceIndulge in a breathtaking ocean panorama from your recently renovated lavish studio situated on the 25th floor of the magnificent Waikiki Beach. This condominium is designed for discerning travelers seeking a roomy,and contemporary space measuring a snug...
NEW LISTING, The Queens Bluff 3 bedroom, AC, Ocean View!
Experience the ultimate Hawaiian getaway at Queens Bluff, a luxurious vacation rental located in the heart of Princeville, just steps away from the renowned Queen's Bath. This exquisite home offers the perfect blend of comfort, elegance, and breathtaking natural beauty,...
Kolea 1B | 3 Bedroom Kolea Vacation Rental with Easy Hilton Waikoloa Access
Kolea 1B is situated on the Hilton Waikoloa side of the Kolea property and offers a nice open view with some view of the blue waters of the Pacific Ocean. This expansive three bedroom vacation rental is great for families. Once you enter the villa through the large...
High Upgrades and Views W/TV and Washer/Dryer-Kanaloa
Kanaloa at Kona unit #2901: Whether you’re looking for a romantic retreat or a place to unwind and rejuvenate, this one-bedroom suite will satisfy your desires. Gaze out at the stunning Pacific Ocean from your furnished lanai that seats four guests and features a wet...
NEW! Stylish and Cozy Studio near Waikiki Beach!
Enjoy easy access to beach. Ala Moana shopping mall and central Waikiki area. Ihop restaurant and ABC store just next to the hotel. Across the street from Hilton Hawaiian Village. Hotel pool, gym, laundry facility, BBQ grill and more.Aqua Palms Waikiki ranks as one of...
Hale Kahanalu "House by the Surf"
Fall Special! Book 5 nights get the 6th night free! Just 175 yards from Poipu Beach, Hale Kahanalu "House by the Surf" is a 720 sq ft corner apartment perched on the top floor. This cozy unit in an intimate 8-unit complex puts you steps from one of Travel Channel's...
Marine Surf Waikiki w/ Beach Gear & Parking!
Summary:The Marine Surf Waikiki Condominiums are located just a block from Ft DeRussy Beach Park, The Royal Hawaiian Village, and International Marketplace for shopping galore, dining and nightlife. Maximum occupancy strictly enforced in accordance with local...