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.
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 area...
Alii Villas#304 Nicely Appointed Top Floor Condo with Garden & Ocean Views
Alii Villas, Unit#304 is a fantastic option for your Hawaiian Adventures. Discover your perfect island retreat in this charming top floor garden view condo nestled in the heart of Alii Drive. With lush tropical landscapes right outside your window and serene, peek-a-boo...
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 by...
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...
Honoli'i Oceanfront Hale
Welcome to your dream vacation home in Honolii, Hawaii! This charming 1950s A-frame retreat is nestled right on the oceanfront, offering breathtaking views of the Pacific Ocean. With three bedrooms and two and a half bathrooms, this spacious getaway provides the perfect...
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...
Tropical downtown suite w/private hot tub & gazebo, washer & dryer, patio
Kailua View Estates -HoeneOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'A serene paradise located just two minutes from downtown, this thoughtfully upgraded five-bedroom, five-bath...
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 steel...
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...
LOOK! Kai Cottage coastal getaway in Pauka'a!
Kai Cottage in the quiet Pauka'a neighborhood a few minutes drive north of downtown Hilo is the perfect vacation spot for exploring Hilo, Volcano and the eastern coast of Hawaii Island. This plantation era cottage, built in 1966, is designed to take advantage of coastal...
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...
A piece of paradise located in the heart of South Kihei.
This 1 bed, 1 bath condo located in Kihei Alii Kai is a meticulously designed living space that offers both comfort and convenience. Located in the beautiful area of Kihei, this condo provides a peaceful and relaxing environment.As you step inside, you'll be greeted by...
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 at...
Iconic Diamond Head! Great for Family!
Waikiki Sunset #1414 – 229 Paoakalani Ave.Enjoy a fabulous view of majestic Diamond Head from this 14th floor, two-bedroom, one-bath condo with central AC (604sf plus lanai with table and chairs). 6-person max!Just 10-minute walk to the best swimming and surfing beach...
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 families...
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...
Turtle Beachfront, snorkeling, free parking, wash-dryer in unit, Air Condition.
Newly remodeled kitchen and bath in this condo with an ocean view and located on a beautiful beachfront that has the best snorkel and swimming beach protected by a reef, with lawn like carpet and a Sandy beach where you can swim with turtles or just sunbathe, kayak or...
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...
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...
Spacious corner oceanfront 6thFL island getaway in Kahana!
Discover your tropical paradise in this stunning 1 bed/1 bath Hawaiian-themed condo! Slip into bliss on the luxurious California King bed, promising you the sleep of your dreams. Enjoy movie nights on the wall-mounted TV or step out onto your private lanai, where...
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
Welcome to Ko Olina Kai 1065E — Your Relaxed Island Retreat in Kapolei, HI Tucked within Ko Olina’s prestigious gated resort community, Ko Olina Kai 1065E offers 1,427 sq ft of light-filled, coastal-inspired living. With 3 bedrooms, 2 baths, and seamless indoor–outdoor...
Beautifully appointed ground-floor Kaanapali condo
Kaanapali Shores 104 is a ground-floor, 2-bedroom, 2-bathroom condo with central air conditioning that can accommodate up to 6 guests. Ocean views abound and the beach is only 50 steps from your lanai. Inside, an open-concept layout and Hawaiian-inspired decor with a...
𝐅𝐢𝐧𝐝𝐢𝐧𝐠𝐌𝐞𝐢𝐥𝐢 GorgeousBeachfront KoOlina Resort+Amenities.STUDIO unit
𝐕𝐢𝐬𝐢𝐭 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 to enjoy 𝐄𝐱𝐜𝐥𝐮𝐬𝐢𝐯𝐞 𝐒𝐚𝐯𝐢𝐧𝐠𝐬 on this stylish 𝐒𝐭𝐮𝐝𝐢𝐨 𝐒𝐮𝐢𝐭𝐞 at the stunning 𝐌𝐚𝐫𝐫𝐢𝐨𝐭𝐭’𝐬 𝐊𝐨 𝐎𝐥𝐢𝐧𝐚 𝐁𝐞𝐚𝐜𝐡 𝐂𝐥𝐮𝐛, 𝐎ʻ𝐚𝐡𝐮’𝐬 𝐩𝐫𝐞𝐦𝐢𝐞𝐫 𝐁𝐞𝐚𝐜𝐡𝐟𝐫𝐨𝐧𝐭 𝐑𝐞𝐬𝐨𝐫𝐭.Unlock 𝐌𝐞𝐢𝐥𝐢 𝐌𝐞𝐦𝐛𝐞𝐫-𝐎𝐧𝐥𝐲 𝐑𝐚𝐭𝐞𝐬 & 𝐔𝐩𝐠𝐫𝐚𝐝𝐞𝐬:𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 𝐄𝐱𝐜𝐥𝐮𝐬𝐢𝐯𝐞 𝐒𝐚𝐯𝐢𝐧𝐠𝐬 ($500–$1000 𝐎𝐅𝐅 𝐬𝐞𝐥𝐞𝐜𝐭 7-𝐧𝐢𝐠𝐡𝐭 𝐬𝐭𝐚𝐲𝐬)...
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...
Ocean Views, High Floor, AC, W/D, Wi-Fi and parking!
Chateau Waikiki #2910 – 411 Hobron Ln(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)Beautiful ocean views and more from this 29th floor condo with 540 interior sf plus lanai/balcony, all on a quiet street away from the noise and crowds! Close to...