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.
🍍Oceanfront Condo & Walking Distance to Beach and Town! 🏖 - Hale Kona Kai 207
Real and Total oceanfront condo with a lanai (balcony) that almost hangs over the beach. See the ponds below where the turtles and the eels want to come and feed. Let the sounds of the sea make you sleep after a day of sightseeing or relaxation; all bedrooms and living...
Waikiki Luxury 2 bedroom Condo (30 Nights Minimum Stay)
Conveniently located in Waikiki with luxury amenities, conveniently located close to all of your favorite restaurants and activities. The beautiful Allure building offers resort style living with a fitness center, pool & spa, and BBQ deck, also has a 24/7 security staff...
Summer Specials Plantation Hale D2 "The Palm Shade Stay" – Newly Renovated with AC
Welcome to The Palm Shade Stay, your breezy home base on Kauai's lush Coconut Coast. Nestled among swaying palms at Plantation Hale, this freshly updated ground-floor condo features brand-new furnishings, fresh paint throughout, and a newly renovated bathroom—bringing...
Affordable, Near Kaanapali Beach and Whaler's Village - Maui Eldorado #K105 - Quam Properties
Maui Eldorado Resort is located in the heart of Kaanapali on the golf course. Easy walk or free shuttle to private beach cabana for Eldorado guests only. Whalers Village is also within walking distance with world-class shopping and restaurants. This spacious 1 bedroom 2...
Turtle Bay Sea Shells
Ground Floor Unit. (Stairs from parking lot and down into unit.) Really cuteunit with Hawaiian décor and tasteful artwork. Window Air Conditioning in bothbedroom and living room keeps the unit cool and comfortable. ComfortableCalifornia king bed. 42" flat-screen TV....
Wyndham Waikiki Beach Walk|2BR/2BA King Balc Suite
Summary:This tropical escape boasts an impressive 7.7 acres of on-site fun. The family-friendly resort is only a block from popular Waikiki Beach and serves up a game room, children’s activities, and an outdoor pool.We understand the importance of an ocean view for...
3BR on the ocean in Sunny Poipu + Athletic Club
Poipu Shores is Kauai's premier oceanfront complex with unparalleled shoreline views. Enjoy whale watching and searching for sea turtles from your private lanai or bask in the sun by the oceanfront swimming pool.Unit 301-B is a newly renovated 3 bedroom, 2 bath family...
Updated tropical condo with great location, pool access, and central AC
Bamboo Bungalow at Napili RidgeOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Come home to this beautiful, ground-floor Maui bungalow where you'll find a refreshingly updated living...
Kauhale Makai 535 | Surf, Snorkel, Kayak and More!
When you stay at Kauhale Makai 535, you'll see firsthand why Kihei was once so popular with Hawaiian royalty! This 2 bedroom, 2 bathroom Maui retreat can accomodate up to 4 guests making it perfect for any island escape!Sleek and stylish, Kauhale Makai 535‘s living...
Spacious 2 Bedroom Condo - Kaanapali Plantation 52
Begin the day with ocean views in a tropical garden setting from Ka'anapali's North Course across the street from North Ka'anapali Beach. This space has 2 bedrooms, and 2 bathrooms, both bedrooms feature comfy king-size beds. Perfect for 2 couples or a family of 4. This...
PRICE Drop!!!True Oceanview Waikiki Studio B
Enjoy paradise views on the 30th floor (3002-B, E Komo Mai) in beautiful Waikiki beach. This studio condo is situated close to Convention Center, restaurants, family-friendly activities, the Ocean (minutes), and nightlife. out over the magnificent Ocean and Fort DeRussy...
Plantation Hale J11 | Condo in Kapaa with Central AC, Pool & Hot tub
Plantation Hale J11Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to Your Kapa’a Getaway at Plantation Hale! Wake up to stunning mountain views, soak in the Hawaiian sun...
Top-level condo with pools, hot tub, grill, W/D - close to beach access
Maui Kamaole D207Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Luxury and privacy meet at this Kihei Condo, located in the condo resort known as Maui Kamaole®, and just minutes...
NEW LISTING 3 PENTHOUSES, 2 SideBySide Spectacular Ocean Beach Front 6 Bed 6 Ba
Now with Air Conditioning! Yes we now have Daikin AC systems in each Bedroom, and Living room. New Listing, other listing 5 Stars all the time. Spectacular Ocean Beach Front Maui Penthouses 6 Bedrooms 6 Baths. Our MauiPenthouses are the Ultimate Maui Vacation Rental....
Beachfront Condo in Punaluu. Updated! Clean beaches to walk/swim! Escape Crowds!
Escape the crowed city, and come enjoy some time in the country. Relax in our updated island style condo in the iconic Pat's at Punaluu beachfront residence. This tastefully decorated unit has been fully outfitted with most everything you could possibly need, including...
Kahana Sunset A6 - Direct Oceanfront Great Rates For Winter 2024 - Magical Maui Sunsets!
Kahana Sunset Resort is the only beachfront resort situated on the secluded, sandy beach of Keoni Nu'i Bay with magnificent views of Lanai and Molokai. This direct oceanfront 2 bedroom 2.5 bath, is spacious two story condominium. Spend the day relaxing in the sun and...
Peaceful Top-Floor Condo w/ Unbeatable Views & Plenty of Island Charm
Located in the heart of Kauai's North Shore, Sealodge D7 offers a little bit of everything you need for the perfect family getaway: peace and privacy thanks to the top-floor location, unbeatable island ambiance thanks to the beautiful landscape and incredible ocean...
Beautiful, Spacious, Garden View Studio with Kitchenette. Wir Sprechen Deutsch.
This lovely, tiled, spacious (300 sq. ft.) studio with large covered lanai and tropical garden view is one of several studios in our Guest House. Wake up in the morning to birds singing and pick papayas from your lanai. Our studio has a comfortable queen bed, sleeper...
Serene Ocean View Retreat in Keauhou Palena
Welcome to your ideal getaway at our cozy ocean view condo in Keauhou Palena! Nestled on the serene 16th fairway of the prestigious Kona Country Club, this ground floor unit is perfect for those looking to relax and unwind.This charming 2-bedroom, 2-bath condo offers a...
Views, On Golf Course, New Flooring & Appliances
Welcome to your peaceful island retreat in Waikoloa Village – a serene escape for relaxation & exploration under Hawaii’s blue skies:- Sleeps 4 | 2 bedrooms | 3 beds | 2.5 baths- Heated pool, hot tub & tennis courts- Private lanai w/ Mauna Kea & golf views- Fully...
Luxury Studio With Amazing Ocean And Night View!
Luxury Studio with Amazing Ocean View and Sparkling Night View from 29th floor on Kuhio Avenue!!Enjoy a luxurious studio at Aston Pacific Monarch. Great location! Only 5minutes from the world famous Waikiki Beach, restaurant, and shops.Spacious apartment-style...
Kona Reef B32: Oceanfront Condo w/ Pool, Lanai, New AC, Beach Access & Prime Ali
Welcome to Kona Reef B32, a beautifully appointed one-bedroom, one-and-a-half-bath ocean-view condo along scenic Ali‘i Drive in Kailua-Kona, Hawai‘i. With 630 square feet of well-designed living space, this top-floor retreat pairs modern comfort with tropical...
Single-Story Shores Golf Villa 19 - 3 Ensuite & Loft
Summary:Maximum occupancy is strictly enforced in accordance with local ordinances.The Space:Shores at Waikoloa Golf Villa 19, located along side Golf Villa 20- are the only single-story standalone condominiums in all of Waikoloa Beach Resort that are available as a...
Private ocean view oasis with dream pool, rooftop deck, vaulted ceilings
Kona ParadiseOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Escape to your own private retreat at this open-concept two-bedroom bungalow, perfectly perched in the hills above Kona...
Hale Kauka ~ House of the Artist - Kuilima Estates East
Welcome to Hale Kauka, an exquisite Artist's Retreat nestled on the prestigious Fazio Golf Course at The Ritz-Carlton, Turtle Bay. This enchanting one-bedroom, two-bathroom haven offers a serene escape for up to four guests. The master bedroom features a plush king bed,...
Toast Paradise! Ocean View Suite w/Kitchen, Washer/Dryer – Waikīkī Shore #1202
This ultra spacious deluxe two-bedroom two-bathroom suite offers expansive views of the Pacific Ocean from your furnished lanai. From the moment you step inside you’ll feel like you’re in paradise. Enjoy a full-size kitchen with white wooden cabinetry, stainless...
Updated waterfront condo with ocean views, heated pool, & private lanai
Poipu Shores 403AOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Experience heaven on earth at this renovated oceanfront condo. Enjoy million-dollar ocean views from the large lanai...
Sea Breeze Retreat at Turtle Bay - Kuilima Estates West
Aloha and welcome to our Sea Breeze retreat, a 2-bedroom, 2.5-bath condo at Turtle Bay! Step outside the living room onto a beautifully manicured lawn overlooking the Fazio Golf Course. This gated condo offers the perfect blend of relaxation and convenience, just a...
29th floor studio with two full size beds
29th floor studio with 2 full beds, AC, small kitchenette. Panoramic windows and a balcony, right next to the Ala Moana Shopping center, beach. Enjoy Mountain and ocean views.The studio has everything you might need for a convenient like home stay :)A kitchenette to...
Turtle Bay Wicked Wahine by RedAwning
Perfectly located on the 1st tee of the Fazio Course with the Turtle Bay ClubHouse out your back door and beautiful sunset views. The lovely 2 bedroom witha loft and 2 bathroom unit has tile flooring throughout. Walk-in showerupstairs and tub/shower downstairs....
Kauhale Makai 506 | Stunning Ocean Views!
Guests rave about their accommodations and view from Kauhale Makai 506. You have a great view of the ocean from your balcony. This condo has hardwood floors, modern furniture, and all the little extras that will make your stay extra special. Plus, the Kauhale Makai...
Maui Vista #1323: 1 Br, Walk to Kamaole Beach Park I (Charlie Young)
This one-bedroom condo can accommodate up to four people with a queen bed in the bedroom and a pull-out sofa bed in the living room. The fully equipped kitchen is perfect for preparing meals to dine-in or to take with you while on the go. The living area is an open...
Garden view corner condo with wraparound lanai & pool, walk to Poipu beaches
Waikomo Stream Villas 120Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Airy Tropical Retreat with Wrap-Around Lanai – Excellent location!Welcome to your peaceful island hideaway...
Splendid Condo w/Pool Views, Lanai, Free WiFi, Shared Pool, Hot Tub, & Gas Grill
Makahuena 2202Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!' Welcome to your modern getaway! This freshly updated condo underwent a full renovation in 2025, featuring completely...
Deluxe Condo with Recreation Deck View, Free parking & WiFi by Koko Resort Vacation Rentals
Family-Friendly Waikiki Condo – 1 Block from Beach, Pool, & Free Parking! The pool and all associated amenities will be closed starting April 7, 2025,for an estimated duration of 10 to 14 months to accommodate the RecreationDeck renovation project. Perfect for...
Ground-floor zen studio with garden-view lanai, AC, beachside pool/hot tub
Islander on the Beach 171Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Discover the perfect ocean getaway at Islander on the Beach, a 6.5-acre oceanfront resort with stunning...
Wailea Ekahi Village 9A - 1 Bedroom Garden View Condo
Welcome to Wailea Ekahi 9A, a charming vacation rental nestled in the heart of Wailea. This meticulously maintained one-bedroom, one-bathroom condo offers a perfect blend of comfort, style, and convenience, making it an ideal retreat for couples or small families...
Stunning ground floor condo with ocean-view lanai - steps to the beach
Islander on the Beach 164Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Experience the ultimate oceanfront living at its finest in this stunning condo located in Kapaa, HI. Just...
OCEANFRONT*Deluxe Ocean View NEAR Sugar Beach!
Indulge in the serenity of this picturesque gem! Embrace the enchantment of a mesmerizing full-on ocean view coupled with a charming partial mountain view in this delightful, 559 square foot condo. Your beautifully tiled lanai invites you to soak in the scenery,...
Tranquil Island Escape | Walk to Kehena Beach | Washer & dryer, WiFi
Tranquil Island Escape at Kehena BeachOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'A tranquil and tropical retreat awaits at this stylish two-bedroom, two-bath home, boasting a...
Top-floor oceanfront condo with AC, water views, & pool access - steps to beach
Menehune Shores 626Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'We donate 10% of our rental proceeds to the Pacific Whale Foundation, supporting victims of the Maui...
Maui Resort Rentals: Kaanapali Ali'i – 5 Total Bedrooms, Luxuriously Remodeled, Oceanfront Royal Penthouse Offering, Sleeps 14!
This premier 11th-floor offering brings together one of our most sought-after 2BR royal oceanfront suites with a luxuriously upgraded 3BR neighboring oceanview suite to provide an unmatched top-floor pairing boasting breathtaking vistas of the Pacific Ocean. For a...
KR 117 Renovated OceanFront 1BD w Ocean Views
Kahana Reef 117 Freshly Renovated OceanFront Ground Floor with Epic Ocean Views & Sunsets 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...
Hale Kamaole Condo w/Private Washer/Dryer, Shared Pool, Free WiFi
Hale Kamaole 110Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Hale Kamaole is a South Maui condominium complex located across the street from Kamaole Beach Park III, one of the...
Upgraded 1BR Condo Ocean View - Sleeps 6
Hello and thank you for taking the time to visit our listing. We tried to create a home away from home for you in lovely Waikiki.This unit is on the south east corner of the 14th floor (Tower I). Corner units are larger (10%) than middle units in the Banyan. The kitchen...
Your Island Sanctuary: Spacious Ground-Floor Condo at Wailea Elua #2201
Wailea Elua #2201 – Spacious Island Comfort with Partial Ocean ViewsWelcome to Wailea Elua Village #2201, a beautifully upgraded ground-floor condo nestled within one of Wailea’s most exclusive beachfront communities. This spacious two-bedroom, two-bathroom retreat...
Ko Olina Kai 1065E: Elegant 3BR with Luxury Lanai, Near Lagoons & Golf
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 Ko Olina Kai 1065E by Gather, where...
The Pacifica Inn The Gecko and Volcano Room
Welcome to The Pacifica Inn located in Volcano on the Big Island of Hawai’i. The Pacifica Inn is a special little place out in the middle of the Pacific Ocean where you can experience peacefulness and tranquility. Come and enjoy the beautiful Hapu’u trees that...
𝐅𝐢𝐧𝐝𝐢𝐧𝐠𝐌𝐞𝐢𝐥𝐢 GorgeousBeachfront KoOlina Resort+Amenities.STUDIO unit
𝐕𝐢𝐬𝐢𝐭 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 to enjoy 𝐄𝐱𝐜𝐥𝐮𝐬𝐢𝐯𝐞 𝐒𝐚𝐯𝐢𝐧𝐠𝐬 on this stylish 𝐒𝐭𝐮𝐝𝐢𝐨 𝐒𝐮𝐢𝐭𝐞 at the stunning 𝐌𝐚𝐫𝐫𝐢𝐨𝐭𝐭’𝐬...
Ocean View Studio Steps to Beach - Pool, Spa & Pickleball - Free parking & Wi-Fi
SPECTACULAR OCEAN VIEW! FREE PARKING!Come enjoy this 2nd story condo with its direct ocean view. Feel the gentle ocean breezes and watch the waves as they rush across the reef to the sandy beach and shore.This gorgeous studio is across from the 'Humpback Whale Marine...