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.
Elegant Kamilo Home - Private Pool, Guest House, Gym Access
Built in 2016, KaMilo 329 is a 4 bedroom, 4.5 bath single story resort home. The Hoku B home model is the largest available floor plan in the KaMilo community with 3,529 sf of living space, including 627 sq. ft. of covered outdoor lanai space. This single-story detached...
What do you get when you combine unrivaled oceanfront views from a private lanai with gorgeous, high-end interiors? You get Sea Village 4207 and one amazing Hawaiian vacation! Bring your ohana – family – and experience the Big Island of Hawaii. Inside, gorgeous...
Bright, Airy Condo w/Epic View! Wood Floors, Lanai, Full Kitchen, WiFi–Kaha Lani 225
Castle Kaha Lani Resort #225 - This spacious 1,183 sq. ft. two-bedroom vacation condo, located on the second floor, overlooks the shores of Kauai’s east coast. Unit 225 offers a full kitchen, separate living area and bedrooms, and convenient touches such as ceiling...
Bright Ocean View! A/C, Kitchenette, WiFi, Flat Screen+More! Waikīkī Shore #1004
This uniquely appointed deluxe studio unit with Waikīkī beach views of the Pacific Ocean is bright and airy. Enjoy a larger kitchenette with everything you need to cook your own meals, a furnished lanai perfect for enjoying your morning coffee or evening glass of wine,...
King Bed Suite at The Waikiki Grand - Just steps away from Waikiki Beach
Positioned on the quiet side of the property with city skyline views, Studio suite 604 is spacious bright and offers a comfortable King size bed with fresh white cotton linens, great A/C and free WiFi.The studio has a fully equipped kitchenette with apartment size...
Directly Beachfront | Country Cottage
The Sand Dollar Cottage - NUC #: 90/TVU-0632Ultra High Speed Internet - Desk/Work SpaceOf the 26 charming duplex cottages in the gated Mokuleia Beach Colony, only five actually face the ocean; and this is one of them! You’ll wake to the sound of waves, sit on your open...
Say Aloha to Island Life! Pool View Suite w/Kitchen Ease, WiFi–Kamaole Sands 6308
Blue skies and swaying palms paint the scene as you sip morning coffee on the lanai of this air-conditioned 884sf suite with full kitchen and washer/dryer. It’s easy island living with homey touches like WiFi, flat screens, ceiling fans, DVD and cool tile floors. Sleeps...
Spacious 2 Bedroom Oceanfront Condo with Full Kitchen & 'Wrap around' Lanai
Legally permitted vacation rental - 2947 Kalakaua Ave #501** For your health and safety, we utilize additional Sterilization procedures between reservations.Suite 501 at The Diamond Head Beach Hotel - ++New Flooring and Window Treatments added December 2021.++My place...
Plantation Hale Suites A7, Garden View, Ground Floor, AC, Walk to Beach
Plantation Hale Suite A7, Ground Floor, Garden Unit. Kapa`a, Hawaii, Royal Coconut Coast. Walk to the beach, shops, restaurants, grocery stores, and more! Accommodates up to 4 guests, including children and infantsWailua, Kauai Vacation Rental near to shops,...
Great Views+Roomy Design! 2-Story w/Lanai, New Kitchen, WiFi–Kamaole Sands 3403
Families appreciate the cool colors and design of this two-story, 1,102sf condo with upstairs loft. Touches include a furnished lanai overlooking the swimming pool, open kitchen, air conditioning, ceiling fans, DVD, WiFi, flat screens and a washer/dryer. Sleeps 6 in 1...
STAY HERE for BEST OCEANFRONT VIEWS in KONA, HI
NEWLY REMODELED CONDO. This is the REAL DEAL - A DIRECT OCEANFRONT CONDO in a OCEANFRONT COMPLEX. Not an Oceanview Condo in an Oceanfront Complex!!Stay in our beautiful remodeled and well appointed OCEANFRONT 1-Bedroom Condo (sleeps 2-4). Condo is located in the popular...
Keauhou Kona Surf & Racquet 188: Renovated Oceanfront Retreat
Welcome to Keauhou Kona Surf & Racquet 188 by Gather, a fully renovated oceanfront townhome nestled along the stunning Kona Coast of Hawai‘i. This two-bedroom, two-bathroom retreat spans 921 square feet across two levels and accommodates up to six guests. Offering...
Beautiful Renovated Oceanfront Condo 🐬 Incredible Views From The Lanai! 🌅 Hale Kona Kai 407
Unit #407 is an ocean-front, comfortable, stylish, eco-conscious escape that features the newest technologies and conveniences for today's travelers.The condo is an absolute oceanfront condo with a lanai (balcony) that offers beautiful ocean views. Both bedroom & living...
Anahola Palms - Beachfront Home on Anahola Bay
Located northeastern side of the Kauai on Anahola Bay, this is the perfect beach spot for a gathering of family and friends. Mornings start with oceanfront sunrises and your day continues with beach activities right outside your door. Evenings are backyard barbeques and...
Kona's only Oceanfront pool! Pineapple Pl Reimagined! Cozy 2/1 Condo, sleeps 6,
Aloha!Welcome to Pineapple Place Reimagined! Our 2 bed 1 bath condo in lovely Kona sleeps 6, with access to an amazing oceanfront pool! In fact we just learned its the only residential ocean front pool in Kona! So therefore its the best pool in Kona! It's our tiny slice...
Beautiful Maui Banyan, South Kihei-2br, 1br or studio.
It's time to get away! Our beautifully updated condominium offers the ultimate flexibility, available as a 2-bedroom, 1-bedroom, or studio rental to suit any traveler.Beachfront Living at Its BestLocated directly across the street from the stunning Kamaole Beach II,...
Oceanfront 3rd Floor Mana Kai Condo
Hawaii Tax ID: TA-081-303-9616-01TMK: 390040230025Relax and enjoy sunrise over Haleakala and sunset over the ocean from your lanai of this third floor condo.Bedding Configuration:A side Bedroom: 1 King BedA side Living Room: 1 Full Sofa SleeperB side Bedroom: 1 King...
Recently Updated, Diamond Head Studio w/ Gr8 Ocean Views
Legal Vacation Rental - Diamondhead Beach Hotel2947 Kalakaua Ave #1005** For your health and safety, we utilize additional Sterilization procedures between reservations.2 Double Beds, Microwave, Fridge, Coffee, Pacific Ocean and Diamond Head ViewsPeace and tranquility...
Breathtaking Diamond Head and Sunrise Views! FREE Parking & Wi-Fi, Central AC
Ohua #7E – 250 Ohua Ave.(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)You'll create wonderful vacation memories in this beautiful vacation rental with breathtaking Diamond Head views! 6-person max. Small pool on property. Close to world-class...
Alii Villas #135: Ground Floor, Oceanfront, Remodeled, AC, Incredible Sunsets
Oceanfront Luxury 2 bedroom, 2 bathroom Condo at Alii Villas – Your Perfect Hawaii Getaway. Unit#135 is an incredible unit located in the southern-most oceanfront building and is unique in that it has south-facing coastline views and north-facing city and Kailua Bay...
IC 43th Floor Studio with balcony to enjoy Mountain View
IC 43th Floor Studio with balcony to enjoy magnificent city, mountain and partial ocean views. The studio design inspired by stunning ocean waves color - aqua blue.The studio has everything you might only wish for your comfortable stay. As you step inside, there is a...
Island retreat at Kiahuna Golf Club - Poipu Athletic Club pool & hot tub access
Hale Moana KaiOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Experience the tropical vacation of your dreams at this stylish and spacious home overlooking the Kiahuna Golf Club....
KKSR#37 Spacious 3 BED Townhome with AC, Sleeps 6, Close to the Pool
Knutson & Associates Property Management is proud to represent this wonderful 3 bedroom townhome that sleeps 6! Have a larger group? We manage the 3 bedroom townhome right next door! Townhome#36 sleeps 8, for a total group of 14.Air conditioning is available to cool off...
Stunning ocean views & direct beach access (516)
This gorgeous ocean view studio located in the popular but low-density beachfront Maui Kaanapali Villas Resort features a gourmet kitchen with stainless steel appliances, two ultra-comfortable Queen size beds, a private balcony, and spacious living areas. Enjoy coffee...
#18 Near VNP & Punalu`u Black Sand Beach- Na`alehu, HI
#18 The perfect studio for two guests on the front side of the unit for stunning ocean views and lots of privacy! High Speed Internet. Well appointed unit with kitchenette, washer/dryer unit....the perfect getaway to relax, unwind, explore!!This unit is a studio unit...
Mellow Kuhio Village Studio | Private Lanai
Take advantage of the amazing location of this Kuhio Village studio, right in the heart of Waikiki. In addition to the full bath, quaint kitchenette/dining area for 2, and private lanai with outdoor furniture, this unit features a flatscreen tv, wifi/cable, and ac....
Beachfront | Sunsets & Sea Turtles - Fall 2022 rate $8700/mt
Ultra High Speed Internet - Desk/Work Space - * Monthly Special Rate. - Tax/fees extra. New VRBO Listing! Reviews can be found on our direct website and other platforms. Please contact us with any questions. Hale KipukaExquisite Beachfront Gem sitting on stunning...
Poipu Makai B-1, A/C - Oceanfront - Enjoy the view!
Poipu Makai B-1 is beautifully furnished with Hawaiian decor and local art. You'll enjoy indoor-outdoor living here on your lanai and lawn with views of spectacular sunsets, humpback whales off shore (in season), and sea turtles and dolphins. This scenic vista includes...
Hawaiian Aloha spirit, Relax, play in beautiful Ko Olina. Paradise awaiting.
Aloha, Welcome to your home away from home. There is so much do to and see in beautiful Ko Olina. It's a place where you can Unwind, Explore, Dine, swim, snorkel feel right at home and relax. A place where you can celebrate a special occasion or milestone in your life's...
2 bedroom fully furnished and all included in downtown Kona with swimming pool
This condo is close to everything. 5 minute walk from the ocean.Renovated 2 bedroom apartment in the heart of Kona.You can walk everywhere.2 queen-sized beds with couch and one extra rollaway bed to accommodate up to 5 people (best suited for 4 people.) The bed linens...
Corner Unit with Gorgeous Ocean View! #2302
**Notice regarding renovations on building exterior walls**From 9/03/2024, to 12/02/ 2024, there may be noise due to renovations being completed on the exterior walls of the building. Due to this project, the pool will be closed from 10/14/2024 to 11/15/2024 and...
ALOHA Authentic Hawaii Condo C-7
Comfy, tropical 'Home away from Home!' Decorated in Hawaiian Style, is bright, cheery. comfy and filled with 'ALOHA!' for a restful, romantic &/or adventurous stay.LOCATION is so important on Kauai. Yes, we're along the scenic & historic, Kauai's east side, The Royal...
Waterfront resort condo w/ private patio, shared heated outdoor pool
Hale Ono Loa 116Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'A tropical haven awaits at this majestic resort condo just a couple of minutes away from Honokōwai Beach Park! Step...
Full-Kitchen, Lanai, Washer/Dryer–KSM #6309
On the third floor overlooking the pool and jet spas, this 818sf suite is all about easy living. As guests walk into the space they will be greeted with tasteful tan rattan furniture and teak-inspired tabletops. Here guests can enjoy mornings discussing upcoming...
Hilo Hibiscus Vacation Home 3 bedrooms
Consider this house your home away from home while you visit Hilo. This fabulous property boasts 3 bedrooms, each with its own unique charm.Start your vacation at this centrally located home, surrounded by shopping centers, restaurants, parks, and beaches! If you are...
Nani Kai Hale 502, Great Oceanfront Location
Oceanfront Paradise in North Kihei | Updated 2BR/2BA with Stunning ViewsWelcome to your perfect Maui getaway at Nani Kai Hale, where contemporary elegance meets oceanfront living. This beautifully updated 2-bedroom, 2-bathroom condo offers breathtaking ocean views and...
Bright two-story condo w/washer/dryer, shared outdoor pool, & free WiFi
Princeville Mauna Kai 9Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Experience paradise firsthand at this family-friendly condo near the beach! Ideal for a family retreat, this...
Adorable Top Floor Maui Vista Condo
This loft style condo with its vaulted ceilings, large windows and new paint, is clean, bright and cozy. It has two queen size beds in both the master and loft bedroom.. The loft bedroom has a full bathroom with a shower and the bathroom downstairs has been remodeled...
Kihei Garden Estates G-102 | Steps to the Beach!
Indulge in the ultimate Maui experience at our charming one-bedroom, one-bath ground-floor condominium in Kihei, Hawaii. Just steps away from the beach, Kihei Garden Estates G-102 offers a serene oasis amidst breathtaking ocean views and stunning sunsets.Relax on the...
Top Floor South Kihei Retreat with Panoramic Ocean Views!
RARE FIND! Oceanfront Kihei Penthouse with a 32 ft. private lanai Experience the epitome of Beach Town living while relaxing in the welcoming comfort of our top floor, South Kihei vacation home. Indulge in breathtaking ocean and sunset vistas from your private double...
Kihei Surfside #512: Luxe Oceanfront Escape with Gorgeous Views!
Kihei Surfside #512 – Oceanfront Comfort with Bedroom Split-Duct AC and Expansive ViewsWelcome to Kihei Surfside #512, a spacious 1-bedroom, 1.5-bathroom oceanfront condo offering wide-open views of Maui’s southwest coastline and the neighboring islands beyond. Located...
Beachfront Beauty $5900 PER MONTH
This is the ultimate getaway for Hawaii visitors seeking a quiet oceanfront setting to relax and forget the hassles of life. Newly remodeled Eat at home and save money with a full kitchen and barbecue grill. Relax in the master bath Jacuzzi tub. Walk for miles on sandy...
Maui Resort Rentals: Honua Kai - 3 Bedroom Tandem Package, Fantastic Value + Partial Ocean Views!
This offering combines a spacious 2BR interior courtyard partial oceanview suite, Konea 345, with a 1BR partial oceanview suite, Konea 344, located directly across the hall. This package offers value-minded guests a fantastic alternative to the higher-priced 3BR suites...
KKSR#176 Direct Oceanfront Corner AIR Conditioned Townhouse, Close to Pool
**AC! NEW LUXURY VINYL PLANK FLOORING INSTALLED IN BEDROOMS AND STAIRS WITH FRESH PAINT**This is a gorgeous ocean front townhouse corner unit. Being an end unit with additional side windows allows for additional light in the unit, and because it is located at the end of...
Charming 1-Bed 1.5-Bath at The Shores Near beaches Dining and Golf
The Shores at Waikoloa on the sunny Kohala Coast is located in the Big Island resort area. This one-bedroom one and half bath has a Hawaii touch throughout the home. Full kitchen with all the gadgets and a dining area. This home is centrally located near dining,...
Maui Resort Rentals: Westin Ka'anapali Ocean Resort 2BR Direct Oceanfront Villa
Two-Bedroom Direct Oceanfront Villa at The Westin Kaanapali Ocean Resort. This 2BR/2BA 1400 sq ft villa features large lanais set off the primary bedroom and a guest room with direct oceanfront views of the Pacific and the neighboring islands of Lanai and Molokai. These...
Breezy Corner Studio with AC & Kitchenette. FREE Parking, Wi-Fi, near Beach!
Marine Surf #701 – 364 Seaside Ave.This air-conditioned corner studio features 2 lanais (balconies), great cross-breezes, and is right in the HEART of Waikiki, a short walk from Waikiki Beach, swimming and surfing, shopping, restaurants, and nightlife nearby! You'll...
Reduced Rates w/Amazing Sunsets and Oceanview's with AC at Puu Poa
Perched on an oceanfront bluff in Princeville, this modern, air-conditioned condominium offers breathtaking panoramic views of the Pacific and Kaua‘i’s iconic North Shore coastline. Watch the ocean transform throughout the day from nearly every room—including the living...
Spectacular Views! Gorgeous Home In Hilo With Pool
The Hilo Bay View Estate is a gorgeous European-style home located in the exclusive area of upper Wainaku in Hilo. This stunning home has spectacular panoramic views of the ocean and Hilo town. Watch the magnificent sunrises in the morning and star-filled skies at...
Waipouli B103 just got a spring makeover! 2BR/3BA/4BD ready for Kauai adventure!
Welcome to Pau Hana Kauai, a luxury first floor condo located in Kapa’a at one of Kauai’s top vacation spots, Waipouli Beach Resort. With 2 bedrooms and 3 bathrooms in almost 1200 square feet of living space, plus 3 private lanais, you'll find plenty of space for your...