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.
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. 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...
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!nnn
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 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...
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
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...
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...
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
Welcome to Coconut Plantation 1078-3 by Gather, a luxurious two-story resort townhome located within the exclusive Coconut Plantation at Ko Olina. This 1,715 sq. ft. retreat offers spacious living, island-inspired design, and the perfect blend of comfort and convenience...
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...
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...
Kauai, HI: 2 Bedroom with WiFi, Resort Pool, Near Golf Courses, Beaches & More!
Nestled high in the cliffs of Princeville, this Kauai resort blends natural and man-made pleasures into magnificent harmony. Take the opportunity to enjoy a meditative retreat at the on-site spa, or use the resort as a basecamp for your many Hawaiian adventures.These...
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....
Ocean front condo overlooking Maalaea Bay
Wake up to full view of Hale'Akala beyond Maalaea Bay in this completely updated 1 bed / 1 bath, 3rd floor condo. Enjoy your morning coffee while watching whales (in seasons) feed in the bay and Hawaiian green turtles play in the waves. This is why you have come to...
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...
New Listing: Oceanview Kaha Lani 223 with Lanai, Beach Access & Modern Comforts
BEAUTIFUL FULL REMODEL!The Location:Perfectly positioned to accommodate everyone's interests, the Coconut Coast is flanked by epic coastline threaded together by the Ke Ala Hele Makale coastal bike and walking path. Just a 7-minute walk along the path or the golden sand...
Ilikai Hotel - City-view Two-Bedroom Condo on the 19th Floor, Peek-a-Boo Ocean View!
*Construction Update* Spall repair and exterior painting will be ongoing outside of the unit from August through mid-October 2025. During this time, access to the lanai will be restricted during work hours: Monday through Friday, 8am to 5pm. Lanai access will be...
Walkable to town and Oceanfront with A/C!
Now Featuring: Air-Conditioning in the bedroom and living room!Conveniently located between the south and north shore is this wonderfully appointed one-bedroom, one and a half bath, ocean-view condo at Lae Nani. Tucked away off a quaint side street in Kapaa, Lae Nani...
Kona Bali Kai 362 – For 2 Guests
Summary:Escape to the Big Island and enjoy a relaxing stay at Kona Bali Kai, just minutes from the heart of Kailua-Kona. This community offers everything you need for a restful vacation—take a dip in the ocean-view pool, unwind in the hot tub, or head to your private...
Zen home with fast WiFi, washer/dryer, koi pond & large lanai
Seabreeze Hawaii Kai -A - 30-Night MinimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'You’re sure to find your zen at this slice of paradise. From a gorgeous lanai to a lush...
Ocean-view condo with private balcony, washer/dryer, & shared pool/tennis courts
Wavecrest C216Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Your peaceful Hawaiian getaway awaits at this second-floor Wavecrest Resort condo. Situated in a tropical part of the...
Ocean view condo with a pool, hot tub, gym & WiFi - snowbird-friendly
The Windsor Waikiki #3704 - 30-Night MinimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Soaring above Oahu on the 37th floor, this condo boasts panoramic views of it all - the...
First-floor condo w/ ocean view, washer/dryer, & outdoor pool
Poipu Kapili #60Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Breezes are regular visitors at this gorgeous corner condo by the sea, as are beautiful views of the sunset. Enjoy...
Waikoloa Colony Villas 1401: 2 bedroom, 2 bath located on the 10th Fairway
Posted 1/12/23: Phase IIIA Irrigation Project will start next week Monday 01/16/23. They plan to start at Building 15 and work their way back to Building 19, this is a slightly smaller section than the Phase II Section and we are hoping that it will get done quicker...
Cove park - Beautiful 2 Bedroom / 1 Bath. Close to beaches/restaurants/nightlife
Popular Vacation Rental near Kihei's best beaches! This highly sought after 2 bedroom, 1 bath corner unit at Kalama Terrace is close to Charley Young, Kamaole One, and the Cove beach parks. Located on the top floor, you'll enjoy ocean, Lanai and West Maui Mountain...
Charming Beach Suite w/Kitchen–Waikīkī Shore 416
Castle Waikīkī Shore #416: This one-bedroom, one-bathroom minimalist modern-contemporary suite will provide you, your family, or friends with plenty of space to relax in the heart of Waikiki. Relax on your furnished lanai as you take in the ocean breeze and views of the...
Clean & Stylish Kihei Kai Nani Condo
Clean and sleek condo in Kihei, Hawaii on the tropical island of Maui. Ideal for two couples or a family of four, your condo comes complete with a queen sized bed, a futon in the living room, linens, towels, cookware - all the amenities you could need for a comfortable...
Maui Sunset B220 ~ 2 BR, 2 BA, Full Kitchen, Ocean View Condo!
Two bedroom, two bath ocean view second floor condo. Good walking, windsurfing, kitesurfing beach fronts this oceanfront condo complex in North Kihei. A couple of minutes away from Kamaole Beach I, one of the great beaches on the sunny South shore. Air conditioning in...
Oceanfront home w/loft, shared hot tub & pool, WiFi, & balcony
Pali Ke Kua 209Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'*Under new Ownership!* Come enjoy some of the best views in the world! This vacation home has the location dreams are...
Remodeled Studio in Waikiki Amazing Location !! No resort fee<br><br><br>
Newly renovated, clean and spacious studio in Waikiki. Unit is on 10th floor of the Hawaiian Monarch Hotel/Condo building and comes with queen bed, kitchenette, full bath.Walk to Waikiki beach, Waikiki strip, convention center, restaurants, shops and many other Waikiki...
Ocean-view studio with lanai, pool & hot tub - steps to Banyans Beach & trolley
Kona Bali Kai #264Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Beautiful Banyans Beach is mere steps across the street from this thoughtfully updated studio condo in Kailua-Kona....