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.
Ground-Floor Condo w/Shared Hot Tub, Pool, Gym, Central A/C, Free WiFi, Patio
Waikoloa Fairway Villas H3Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome home to this wonderful spot in the Fairway Villas. As you can see, this is an easy and convenient...
Turtle Bay unit 6, 2 bedrooms w/LOFT - Kuilima Estates
*NEW A/C : LIVING ROOM AND PRIMARY SUITE (2024).Wish You Were Here... on Oahu's famous North Shore at the world class Turtle Bay Golf and Tennis Resort. Spacious 2 bedroom, 2 Full Bath west side condo also has a bonus loft (w/2 twin beds). Kitchen/bathrooms remodeled in...
Pali Ke Kua 106, Fabulous view near a bluffs edge
Near the edge of a bluff overlooking the ocean, this special condominium is a favorite with many guests who return each year. Comments in the guest book reflect how much they enjoy vacationing here in their "home away from home" and some have even said that this end...
Beautiful Condo in Ko Olina next to beach
Furnished two bedroom, two bath condo on the ground floor. Located in Coconut Plantation in Ko Olina Resort. It's across the street from the famed Aulani hotel. Access to four lagoons, first class shopping and dining and world class golf. Condo situated behind gated...
Quiet, Licensed, Clean & Affordable Cottage Studio with Kitchenette
This charming, affordable, and clean little unit is one of the few free-standing units within the Paniolo Complex. It is situated in a quieter area, as it faces the Prince Golf Course rather than the street. Being a single-level unit, there are no neighbors above to...
Cliffs 6-306 with Extraordinary views of the ocean and lush foliage
From the moment you enter The Cliffs 6306 and see the breathtaking ocean front view, you will feel the stress melting away. Perched on a bluff above the beautiful Pacific Ocean, this spacious corner unit with 18-foot floor-to-ceiling windows and two lanais offers...
🏖️Close to Complex Amenities | Ground Floor | Nice Unit | vrKCV
vrKCV - Casa de Emdeko 109, Professionally Managed by Kona Coast VacationsWelcome to Casa De Emdeko 109 – Your Ideal Garden View Getaway for Couples or Families!Nestled on historic Ali'i Drive in Kailua-Kona, Casa De Emdeko offers a perfect combination of comfort and...
Hale Kamaole 271 Second floor condo, easy access to best beach on Maui!
This Maui condo rental, has two bedroom’s plus a sleeping loft featuring Ocean, garden, and pool views ! Master bedroom has king bed. Unit has flat screen TVs & Blue-ray players in both bedrooms, a large flat screen/Blu-ray player in living room area. This unit has 3...
Kai Nalu, Spacious, Beachfront Home
Kai Nalu, which means "Ocean Wave" in Hawaiian, is right on the beach in Waimea, between the river and the historic Waimea Pier. Located on the sunny West side of Kauai, this spacious home provides a perfect setting for your holiday in paradise. Enjoy spectacular ocean...
Kalama Terrace P-307 - a charming 3rd-floor walkup near Kam 1 Beach with AC!
Welcome to Kalama Terrace P-307, a charming one-bedroom condo located in the heart of sunny Kihei. A short walk from Kihei's stunning Kamaole I Beach, this tropical retreat is an amazing value – it's clean, beautifully decorated, and has AC, smart ROKU TVs for...
In the Heart of Kauai, Great Location, Steps from the Beach and Shops
We are proud to offer you a clean and modern condo in the heart of Kapaa! This lower unit in Village Manor has just been remodeled and is optimized for the comfort of a family or group of four (up to 4). It has 2 bedrooms that are furnished with a queen bed, the other...
Hale Kona Kai 405 - Find your Beach with Kona Beach Properties
Hale Kona Kai 405 is on the top floor of the building and is beautifully updated. Central air conditioning keeps the unit cool and comfortable, especially on those extra warm nights. Updated wifi equipment and settings provide high speed wifi, a necessity for "working"...
Beachfront + Oceanfront Molokai Condo
Invitation to ParadiseWelcome. Enter and experience the Aloha Spirit you have come to the Islands to experience. Come listen to the Pacific Ocean speak to you. Come feel the sea breeze delight your senses. Come taste the air of Hawaiiana. Our sanctuary at Kepuhi invites...
Koana Breeze-Breathtaking Sunset & Ocean Views, Hot Tub Living at its finest!
This spectacular 2500 square-foot plantation-style home is perched on a hillside with breathtaking ocean views of Keauhou and Kailua Bays. Enjoy year-round outside dining with fabulous views of gorgeous Kona sunsets on the lanai, and enjoy drinks in the hot tub. We call...
Kanaloa At Kona | Enjoy Peace in Paradise!
Summary:Imagine having the privacy of your own little piece of paradise — that’s exactly what you’ll find in this uniquely located condo. Maximum occupancy is strictly enforced in accordance with local ordinances. Situated at the end of the building with stunning...
Royal Kahana 510, Direct Oceanfront 2B/2.5B, Spectacular Views, AC, Sleeps 6!
Indulge in luxury in this newly renovated condo, offering 1,287 sq ft of living space and breathtaking wrap-around lanais. Located in a premier beachfront spot between Kaanapali and Kapalua. The expansive living and dining area, seating up to six, showcases panoramic...
Hale He'e - Octocondo at Alii Drive
Welcome to Hale He’e, a perfect little slice of Hawaiian beauty. Enjoy the best of what Hawaii has to offer in our completely updated condo at Kona Makai - an oceanfront complex complete with tennis courts, pool, spa and exercise room.This rarely available 798 sqft, 2...
Clean Comfortable Condo that is Steps to the Beach, Affordable w/Free Parking
Our second-floor unit is spacious with vaulted ceilings and an air-condition unit in the living area. The condo is a one bedroom that is equipped with all you need to enjoy a relaxing vacation in a tropical setting. We have free Wi-Fi , 2 wall hung LCD TV's, a 60" LCD...
KKSR#183 DIRECT OCEANFRONT REMODELED TOWNHOME. RIGHT ON WATER!
Gorgeous Direct Oceanfront Remodeled Townhome, truly stunning! Townhome#183 is very special, featuring all one could want in their Vacation Rental. It has two bedrooms & two bathrooms and is configured to accommodate up to 6 guests with a King bed in the ocean-facing...
Emmalani Court #221 - offered by Na Pali Properties, Inc.
Emmalani Court is a 42-unit, two-level luxury condominium complex located on a bluff over the ocean in beautiful Princeville, on Kauai’s north shore. Unit 221 is at the quiet end of the complex - the closest two bedroom to the ocean - and offers nearly 1500 square...
Ocean Views In Paradise
THIS IS A NO SMOKING/NO DRUGS UNIT/PROPERTYCLEANING FEE covers disinfecting and cleaning, laundering etc of unit before AND after. Should you assist (at time of checkout) with tossing all your excess food and bringing your bedding and towels to me, I will refund $50 of...
Secluded, spacious new geodesic home on the Big Island, Hawaii.
This stunning geodesic luxury 2,000 sq feet home complete with a full range of amenities, rests on 2 private acres enveloped by the lush beauty of the rainforest. Immerse yourself in the serenity of the tropical gardens, where the melodious coquis will gently lull you...
Newly Remodeled Oceanview 1BD/2 Bath at Popular Kamaole Sands
Welcome to Nani Kai which means 'beautiful ocean' in Hawaiian. We are located at the most popular and sought after condominium complex on Maui, Kamaole Sands. What makes Kamaole Sands Maui's best and most popular resort-like condominium complex are the amenities which...
🏖️100 feet to the Beach! | Spacious Private Home with Pool | vrKCV
vrKCV - Keiki Beach 6 at Kona Bay EstatesKeiki Beach Hale - A Premier Island Retreat in Kona Bay EstatesNestled just 100 feet from the beach in the exclusive Kona Bay Estates, Keiki Beach Hale offers an unparalleled vacation experience. This luxurious 5,000 square foot...
LOCATION LOCATION! Hawaiian Theme Condo with Hot Tub, Pool & Beach!
LOCATION, LOCATION!!! Hawaiian Themed Garden Condo with Hot Tub and Pool right across the street from a nice sandy beach for watching the gorgeous Hawaiian sunsets!Experience a blend of modern decor & Hawaiian beach charm in this beutifully appointed condo. Located in...
Maui Resort Rentals: Honua Kai Konea 632 – Upgraded 6th Floor Corner 2BR, Partial Ocean AND West Maui Mountain Views
Konea 632 is a luxurious 2BR/2BA suite boasting an impressive 6th-floor corner location. It offers the best of both worlds with sweeping views of the majestic West Maui Mountains as well as partial views of the Pacific Ocean and Maui's neighbor island Molokai from the...
Amazing pool, secure parking, walk to beach, shops, restaurants and much more!
"Thank you Sandra for everything! We absolutely loved staying at your condo and would happily stay again. It exceeded any expectation. Thank you for also being so communicative and inquisitive throughout our stay. Much appreciated!" - CynthiaThe Waikiki Landmark's...
3-bdrm Oceanview Condo at Makahuena -Walk to Poipu Beaches- NEW Split A/C SYSTEM
Located in the "almost always" sunny, resort town of Poipu, on the gorgeous south shore of Kauai, this oceanfront complex is situated on the southernmost point of the island. From the edge of the dramatic cliffs, just above the crashing waves, you can watch the sunrise...
KV F405 New Listing Location is Key for Your Maui Getaway Condo w Ocean Views
FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch (seasonal), Dinner Sunset Sail, Snorkel Sail, Alpaca Farm Tour, Pineapple Farm Tour, and All Day Electric Bike Rental. (W1)*One ticket per...
. Designer Remodeled. All Ground fl, Lovey tropical flower gardens.n
PARADISE DREAM WORLD. MAUI KAMAOLE- - Professionally decorated by a noted San Francisco designer. You will feel the relaxing atmosphere of "Magical Hawaii" with the New and lovley interior with 22 acres of lush tropical flower gardens .This is the last phase of Kihei's...
Private space in paradise
Nestled in the magical and untouched area of the fabled North Shore of Oahu, our charming private countryside beach cottage is a 5-minute walk to a private white sandy beach, surf, fishing and the best places to eat on the island. 1 bedroom, 1 full bathroom, sleeps 4 ....
Renovated 2nd-floor condo with ocean/garden views, lanai, on-site hot tub & pool
Sugar Beach Resort 203Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to Sugar Beach Resort #203! This attractive and newly renovated oceanfront condo has access to a...
Maui Resort Rentals: Honua Kai Hokulani 732 - 7th Floor 1BR w/ Expansive West Maui Mountain Views!
Hokulani 732 is a luxurious 7th-floor one-bedroom suite that offers expansive vistas of The West Maui Mountains with their frequent afternoon rainbows. The suite is ideally suited for small families and couples who are looking for luxurious and spacious accommodations...
Maui Sunset BR, 2BA Condo B-307 - New King Bed
Maui Sunset is the perfect vacation home on Maui. Your island days can be filled with recreation and fun. Swim in Maui Sunset's beautiful pool with a shallow end for small children or just relax on a chaise lounge by the pool or in the jet spa. This lovely resort also...
🌴Kona Alii #710 Wonderful top floor penthouse in the heart of Kona🌴
Ocean view penthouse overlooks downtown Kailua-Kona Stay right in the heart of Kailua-Kona a stone's throw from the ocean, restaurants andgift shops. This beautifully remodeled penthouse includes a high end kitchen, a large lanai anda private sundeck that overlook the...
Fairway Villas | Lanai Overlook
Summary:Come stay at this golf course front, tropical villa at the Waikoloa Beach Resort! Spend your days relaxing by the pool, golfing, kayaking, snorkeling, or going on glass-bottom boat tours! The Kings' Shops are within a short distance, where you can find delicious...
Spectacular Views from 7th Floor Oceanfront Whaler Condo Unit 751
Enjoy this elegant and luxurious seventh story condo (Unit 751) as your home on the beach. It’s right on the water’s edge in Maui's premier vacation area 'Kaanapali Beach.' Relax on your wrap-around lanai as you enjoy unobstructed views of the beach, ocean,...
Ocean-Front jewel & amazing views, here the ocean is your backyard.
Our jewel condo is a 5 Star rated by our amazing guests for our spectacular oceanfront ground-level condo. Only 15 feet away from stepping into the ocean, and the unobstructed 180% ocean views of Molokai & Lanai islands with memorable sunsets & whale watching in season...
Waikiki Fully Furnished w/pool - walk to beach!
Waikiki Fully Furnished Ready-to-rent Condo.Centrally located in the heart of Waikiki, Honolulu. Minutes away from the prime strip of Waikiki Beach, Waikiki Market, Waikiki International Market place, Honolulu Zoo, Kapiolani Park, Waikiki Shell, shops, restaurants, bus...
Pili Mai 15H - Central A/C, Pools, Gym
PILI MAI 15H AT KOLOA KAI VACATION RENTALSModern Luxury Meets Island CharmDiscover the perfect blend of contemporary comfort and tropical tranquility at Pili Mai 15H, a stunning two-bedroom, two-and-a-half-bathroom condo set amidst the lush greens of the Kiahuna Golf...
Maui Resort Rentals: Honua Kai Hokulani 815 - Top Floor Deluxe 2BR, Expansive Corner Floor Plan, Stunning Ocean Views!
As one of the finest two-bedroom suites available to rent at the entire Honua Kai Resort, Hokulani 815 boasts an exceptional 8th-floor penthouse corner vantage point and is among a class of the most sought-after 2 bedroom floor plans at Honua Kai.What distinguishes this...
Maui Resort Rentals: Honua Kai Konea 1032 – 10th Floor "Penthouse" 2BR w/ Mountain & Partial Ocean Views
Konea 1032 is a remarkable two-bedroom, two-bath suite boasting an impressive 10th-floor "penthouse" corner location. It offers the best of both worlds with views of the tranquil blue Pacific Ocean as well as the majestic West Maui Mountains. Oversized picture windows...
Luxury Oasis Resort Villa
This newly renovated luxurious Villa is nestled in the quiet neighborhood of Ko Olina Hillside. This Villa has 3 bedrooms/1 sleep sofa and can sleep up to eight guests. Choose to spend your days on the Ko Olina Championship golf course or at one of the 4 lagoons located...
1202A Cliffs RESORT, 159.00 5/2-5/7 Super Blow Out Sale with 10 Star Reviews!
*Our NEWLY Remodeled Modern Timeless Studio* at The Cliffs Resort in Princeville-Kauai, the north side of the island, where Majestic Views are endless in every direction, is for travelers that will spend most of their time outdoors and come home to relax... We are close...
SPECTACULAR OCEAN VIEW! A/C, Wi-Fi, Pool, FREE Valet Parking, Steps to Beach!
Waikiki Beach Tower #2001 – 2470 Kalakaua Ave.If you'd like to be directly across the street from the best swimming and surfing beach in Waikiki, then this two-bedroom, two-bath Waikiki Beach Tower condo with 1150 sq.ft. interior living space (and a large 160 sq.ft....
Welcoming Condo with Ocean View | Pono Kai Resort | PK-G104
Pono Kai's pool will be closed for repairs September 2025 through November 2025.The Kapaa Public Pool, located less than one mile from the resort, is open to the public.🌺 Ocean View Escape at Pono Kai Resort 🌺1 Bedroom • 1 Bath • Sleeps 4 • Prime East Shore...
Come explore the peace & beauty of Maui. Across from Charley Young Beach!
DREAMING OF HAWAII? We invite you to stay at our family-owned Maui Vista condo (Building One, unit 124) in sunny, South Maui. This one bedroom, one bathroom 1st floor condo is across the street from Kamaole I beach, aka Charley Young Beach, one of the best beaches on...
PRIVATE OCEAN FRONT ESTATE ON TURTLE COVE, NAPILI. nMOST SPECTACULAR LOCATIONn
THE MOST MAGICAL PLACE ON MAUI! SNORKEL WITH TURTLES, WATCH SURFERS FROM YOUR LANAI AND ENJOY EXQUISITE DIRECT OCEANFRONT DINING, TRULY A TROPICAL PARADISE!!Jacuzzi, Pool Table, Dry Sauna .....
Ocean views just steps to the beach
Kahana Reef 208 is a 1-bedroom, 1-bathroom condo that comes equipped with a modern split A/C system in the living room and pool/ocean views. There are elevators at this property. Unit 208 can accommodate up to 4 guests. The master bedroom is thoughtfully designed with...
Beach Bungalow, Walking Distance to Everything
Our completely remodeled tropical retreat is located in the highly desirable area of South Kihei, which is renowned for its beautiful beaches and proximity to restaurants and shops. This ground floor condo opens up to a lanai with a tropical garden view – the perfect...