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.
Corner hotel room with lanai, ocean views, outdoor pool, hot tub & grill
Hanalei Bay Resort 9206Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Hanalei Bay Resort 9206 is an air-conditioned hotel room that is perfect for solo travelers and friends or...
Elegant Kamilo Home - Private Pool, Guest House, Gym Access
Kamilo 329 is a brand new (construction completed in 2016) 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...
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...
Ground floor great for families!! Whaler #123
Whaler 123 is a spacious inner court, ground floor condo, with a King bed; 2 Doubles; and a Sofa Sleeper - ideal for families or couples looking for a peaceful environment to relax after a day in the water, out Maui sightseeing or on the golf course. | | The condo is...
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...
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...
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....
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...
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...
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...
PacSB303 Spacious Kihei 2BR w/Pool, AC & Steps to the Beach
Pacific Shores B303 NEW LISTING Enjoy your next amazing Maui Vacation at this 2Bedroom, 2Bathroom, Kihei Retreat. Steps to the Pool, Hot Tub, and Walk to the Beach! FREE daily activities included with your stay value up to $554! Complimentary admission, every day of...
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,...
Breathtaking Diamond Head and Sunrise Views!
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...
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
Aloha! Kick your shoes off, take a deep breath of fresh ocean air, close your eyes and listen to the birds singing!This Condo is at the end of the front row of units, with no unit above, affording the best views and privacy. Pool & BBQ are a short walk away across the...
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 KIPUKA Exquisite Beachfront Gem sitting on stunning...
Sweeping Views - Spacious 3 Bds!
“Ho`ohano” is a Hawaiian word that can be used to describe something pleasing or enjoyable, and believe us when we say that it’s the perfect word for this stunning 3-bedroom on Hawaii’s Big Island! Located in the desirable Waikoloa Village, fine dining and...
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. nParadise 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...
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...
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...
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 tandem package combines a large 2 bedroom interior courtyard partial ocean view suite with a 1 bedroom partial ocean view suite located directly across the hall. This package offers value-minded guests a fantastic alternative to the higher priced 3 bedrooms found...
Charming 1-bed 1.5-bath at The Shores near beaches
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
2 Bedroom Direct Oceanfront Villa at The Westin Kaanapali Ocean Resort. Two bedroom, two bathroom 1400 square foot villa featuring large balconies set off primary bedroom and guest room with direct ocean front view of the Pacific and the neighboring islands of Lanai and...
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...
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...
Recent Remodel and Sweeping Ocean Views for Miles
This top floor condo is a perfect location to map out your adventures for the day. Hawaii's best beaching, snorkeling, surfing, boogie boarding, scuba diving, kayaking, and whale watching make Kaanapali beach truly an ocean lovers playground. In condo 1216 you are just...
Coconut Plantation 1078-3: Spacious 4BR Haven, Quick Walk to Ko Olina Amenities
As of 07/14/2025Scheduled Maintenance Notice – Coconut Plantation 1078-3Please be advised of upcoming building maintenance:- August 28–Sep 08, 2025: Lanai painting and elastomeric deck coating. Expect noise, limited lanai access, and on-site workers. Please remove...
Top of the world views!
**Hale Mahina A403**This two-bedroom, two-bath condo features an open floor plan, giving it a penthouse feel. The living room and kitchen are sunken, leading to a large, spacious deck with an unobstructed view of the beach and ocean. The upstairs bedroom is a large loft...
Kahana Sunset E2 - Beautiful tropical oceanfront complex with sandy beach - DISCOUNTED rates
Kahana Sunset Resort offers guests the ideal location to enjoy Maui. This beachfront resort is the only complex situated on the secluded, sandy beach of Keoni Nu'i Bay with magnificent views of the islands of Lanai and Molokai. This two story condominium has two...
Hale Kamaole 152 Ground floor condo, easy access to best beach on Maui!
Great Ocean View. Newly remodeled and new furniture this year, 2025. End unit with a large extra window bringing in a lot of light to dining room and living area. Very comfortable couch and easy chairs. King bed in bedroom. Large flat screen TVs in both the living room...
Turtle Bay resort, Prime location, 18th hole
You won't find a better location at Kuilima. Our lovely ground floor unit is on the desirable 'East Side', right at the 18th hole. Out of the 330 condos here at Turtle Bay Kuilima, our condo is set closest to the beach, so we know you will find the location to be ideal....
GREEN Dancer’s Cottage TA-038-749-9520-01
Orchid Isle Manor is a 5 acre private estate tucked away in the Kona Coffee country on the slopes of Hualalai volcano, overlooking the small coastal town of Kailua-Kona. On this property there are 4 cottages available rent. Each cottage is a one bedroom studio with a...
The Beach Villas w/ Pool Hot Tub & A/C!
Summary:2-302 The Beach Villas at Kahaluu is the perfect place for guests to stay on the Big Island of Hawaii. The vacation rental has 2 bedrooms, 2 bathrooms, and an ocean view from the private lanai. Maximum occupancy strictly enforced in accordance with local...