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.
Exceptionally Pristine Haleiwa North Shore Beachside Retreat
FIND PEACE & ESCAPE FROM STRESS HERE. -This is considered one of the best North Shore neighborhoods! Avoid most of the North Shore's traffic mess by not having to drive past popular "Turtle Beach". The large Winter surf is here! Check it out just minutes away down a...
Poipu Pili Mai 9B, Flexible Cancellation, 4 bdrm, AC, Sunset/ Golf Course View
This is a 3 story building with our 2 story unit located on second and third floors with entry to condo up a flight of stairs. We have four bedrooms, 2 on the second story (the condo's main floor) which are Master suites. While upstairs on the third floor there are two...
Gorgeous Fairway View Home w/Shared Pool, AC & Relaxing Lanai: Kamilo #123
Mauna Lani KaMilo #123 – A brand-new designer home in the heart of Mauna Lani Resort, Kamuela, offering over 2,400 SF of luxury living space. Whether you’re here to relax or entertain, this 4-bedroom, 3.5-bathroom home accommodates up to 10 guests, with ample room...
Exceptional Kona Reef Condo: Full AC, Oceanfront, Easy Walking Distance to Town
*New Listing* Oceanfront, fully updated one-bedroom condo in the Kona Reef Resort. AC throughout the entire unit.Perfectly located just a 5-minute walk from dozens of shops, restaurants, and beaches.As you walk through the door and see the deep blue ocean waves out the...
Alii Cove G3 Beautiful Ground Floor Spacious 2 Bedroom with AC
Alii Cove#G-3 is an excellent beautifully furnished option for your Vacation. This spacious 2 bedroom, 2 bath unit has fantastic features that many guests enjoy. A perfect option for up to 6 people. ~No stairs! Walk right into the unit, there are 2 assigned parking...
Beautiful, renovated Home. Discover the North Shore of Oahu. Great location.
Aloha!My name is Lindsey and I was born and raised right here in beautiful Laie, HI located on the world famous North Shore of Oahu. This is our personal family home and we will go going on vacation. I love this town so much, that once I got married and started a...
Kona Reef: B-15: Direct Beachfront, Pool/Hot Tub, Air Conditioning, Elevators
*This unit will not have Lanai Access during 1/2/2026 - 2/2/2026 for Spalling Repairs, The rates for this time are being discounted by 50% for this inconvenience.* Located on the second floor, Kona Reef#B-15 offers stunning year-round views of golden sunsets and easy...
Spacious 2Bedroom/2Bathroom Oceanfront Condo with Central-AC
This spacious end-unit ground floor condo at Royal Kahana Resort is the perfect place to relax and unwind on your Maui vacation. With two bedrooms and two bathrooms, it can comfortably sleep up to six guests. The condo features a fully equipped kitchen, a washer and...
Beauty, comfort, and value describe this one bedroom condo in sunny Poipu!
Beauty, comfort, quality, and value are what best describes this spacious renovated one bedroom condominium in sunny Poipu! This is a real gem with stunning ocean and mountain views from the lanai that backs up onto Prince Kuhio Park, a lush, quiet open space that meets...
KBM Resorts | FREE CAR | Napili Bay | Oceanfront | Stunning Studio Villa, Turtle views! NAB-107
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Top-Floor Luxury: Rare 3 Lagoon View, 2 Lanais near Disney Aulani, Avail Jun15th
Nov 6th, Jan 4th next available. Note: We are the homeowners. Not managed by Vacasa or other troubled rental agencies.Our upscale beach home is ideally located on lagoon two, boasting some of the most spectacular ocean views at our resort from our two ocean facing...
Seaside Retreat Condo
Welcome to your retreat by the sea. A great ocean view Overlooking Kahaluu Reef Bay. AC & centrally located in the heart of Kailua-Kona right on Ali'i Drive. Free Digital guide with booking with lots of local recommendations. Designed for comfort and thoughtful details....
"Oceanfront Oasis with Captivating Views: Royal Mauian 317 - Make Memories !
Royal Mauian #317 – Upgraded Oceanfront Retreat with Stunning Sunset ViewsRoyal Mauian #317 is a beautifully upgraded two-bedroom, two-bathroom condo offering the perfect blend of modern comfort and breathtaking oceanfront scenery. With split-duct air conditioning, a...
Steps to Beach Family Friendly in Private Setting Lots of Grass to Play On
Kolea 15G at Waikoloa Beach Resort -- Amazing Location -- 5 minutes walking to the beach -- Heated Infinity Pool and Hot Tub with Ocean View -- Contactless Check In & Out -- Fast WiFi -- "Free and Clear" hypoallergenic detergent is provided -- Our Calendar is always up...
Sunny Side Waves-Beachfront Property-Ground Floor, Corner Unit-Sleeps 5-Remodel
Remodeled ground floor, corner unit in exclusive Bld 11. Steps from Poipu Beach! Only oceanfront condos in Poipu! One of only few air conditioned units (located in bedroom)! New cal-king bed in primary bedroom, queen sleeper sofa & twin in the living room. Expansive...
Relaxing 2bd condo with attractive amenities
Welcome to Maui Vista 3403, your perfect island retreat on the beautiful shores of Maui. This 2-bedroom, 2-bathroom condo is thoughtfully designed to accommodate up to 6 guests, making it an ideal choice for families, couples, or friends traveling together. As you step...
Newly remodeled with AC, gorgeous ground floor condo 87, 3 min walk to beach
Newest addition to our Kiahuna Plantation condos! We just purchased and started renting condo #87. For reviews, please look up our other units - VRBO 1300156, 1587209, and 2160974Dual AC in living room and bedroom.Fully remodeled 1bd/1b condo inside the stunning Kiahuna...
Steps from the Sand ! Stunning Curated Interior Mahana at Kaanapali. Fully AC!
The Mahana at Kaanapali Unit 317, Lahaina, MauiWe are trying to capture the essence of resort living with the cool and casual style of Tommy Bahama's new lines of furniture. Fully stocked gourmet kitchens with brand new appliances, bathroom with dual sinks (a rarity...
122 Hainoa – Designer Oceanview Estate with Pool & Spa at Hualalai
Important Resort Notices* Hualālai Spa Enhancements (Sept 15 – Mid-Nov 2025): Outdoor aqua-thermal areas will be temporarily closed. Massage and facial treatments will move to the Makaloa Villa, with full access to saunas, hot tubs, and pools maintained.*...
Ohana Kamalani: Lavish Fairwayfront Home w/Pool, AC & Stunning Sunsets!
Nestled in the heart of Princeville along the renowned Makai Golf Course, Ohana Kamalani by Gather is a spacious three-bedroom, three-and-a-half-bathroom home designed for comfort and relaxation. With Bali Hai and ocean views, a private pool, and air conditioning...
BRAND NEW REMODEL-OCEAN VIEW-GROUND FLOOR-LARGE LANAI-AC-MODERN FINISHES
Book with confidence, this brand new, completely remodeled 1 bedroom, 2 bathroom (818 sq ft.) condo at Kamaole Sands where even the lanai doors and windows have been replaced and no detail has been overlooked. This condo is managed by PMI Maui, a local Real Estate...
Luxury beachfront villa on a world class beach in Kailua, HI
As you enter the electric remote gate into this luxurious villa you will feel this sense of peace and calmness come over you.This luxurious Kailua Villa is located on the ocean which is hidden in the best part of Kailua. Wake up every day to the most amazing sunrises...
Kai Malie: Great House Across from Beautiful Anini Beach
At Anini Beach, among many listings on Vrbo, there are only 25 houses for rent, including this, that are actually in the beach neighborhood. It is also permitted by the County as 4217. The North Shore of Kauai has the third largest barrier coral reef in the world,...
Ground-Floor Condo w/Shared Pool, Hot Tub, Free WiFi, and Central AC
Pili Mai 15AOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Ready to experience a new Hawaii? Surrounded by the beautiful Kiahuna Golf Course with views of the mountains and ocean in...
Stunning 3br/2ba, Sleeps 8, Direct Ocean Front, 3rd Floor Condo, A/C, Pool
Welcome to Hale Honu (House of the Sea Turtle)! Panoramic ocean views and beautiful sunsets await you from this spacious 3-bedroom, 2-bathroom ocean front home at the Sands of Kahana. This upgraded beachfront condo is literally steps away from the ocean on the 3rd...
Your Hawaiian Vacation Starts Here! II
Welcome to Kona Shores, a charming complex situated on Alii Drive, along the Hawai‘i Scenic Byway (Ala Loa Foot Trail). Just one mile from downtown Kailua-Kona, this well-maintained ground-floor condo offers easy access to shopping, restaurants, and beautiful...
Ma'alaea Surf, Unit F6 2 BR Beachfront Condo, AC, Wifi, Pool, TV, Kitchen
Ma'alaea Surf, Unit F6 is a townhouse unit situated on the second floor offering guest total privacy. With the latest in contemporary upgrades, this gorgeous unit features a fully furnished modern kitchen and the convenience of a second bedroom and bath. It features...
Rainbow & Bali Hai views, Walk to the Beach, , Sleeps 6, 2 baths, close to shops
Aloha from Surf Sun Rainbow House — Your Relaxed Kauai RetreatEscape to this charming, local-style 3-bedroom condo nestled just off the beaten path in serene Princeville. Designed for comfort, convenience, and that laid-back island feel, our duplex invites you to...
❤️PiH❤️ PARADISE GARDEN HALE ★ Hilton Pool Passes ★ Large Back Yard ★ Enjoy Bikes
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to Paradise Garden Hale, a part of our Hawaiian Luxury Collection. Paradise Garden Hale at KaMilo is a wonderful new single level 3 bedroom home. We pride ourselves on providing some of the most sought after...
Stunning oceanview property minutes from dolphins
Please check out our cottage on the same property for smaller groups: Vrbo 953957 This Unique property showcases a 153 foot ocean facing deck with luxurious indoor/outdoor Hawaiian style living. Everything is completely redone and modernized. You could be swimming in...
Kona Makai Building #1
Stunning ocean views from the lanai, ocean front from the bedroom, the sounds of the surf on the rocks, and the spirit of Aloha welcomes you to our home in Hawaii. Kona Makai is a beautiful oceanfront complex with well maintained gardens, swimming pool, hot tub, gas...
Maui Resort Rentals: Honua Kai Konea 308 - Spacious 2BR/1BA, Gorgeous Partial Ocean and Lush West Maui Mountain Views!
Unquestionably one of Honua Kai's best values, Konea 308 is a rare two bedroom, one bath suite that offers the space and privacy of an additional bedroom without the price tag of a standard two bedroom, two bathroom. Enjoy beautiful partial ocean views from its spacious...
Maui Resort Rentals: Honua Kai Konea 531 - Gorgeous 5th Floor Ocean View Studio
Boasting an ideal vantage point overlooking the Konea Towers lush interior courtyard, this luxurious oceanview studio suite will impress from the moment you enter. From its optimal orientation toward the ocean to its excellent 5th-floor location, your group will enjoy...
🏖❤️Gorgeous🌴 2BD/2BA LUXURY CONDO, 180 REVIEWS, Updated & Painted🏝❤️
Newly painted interior, New coffee table, two new chairs, new kitchen lights, tile floors.🌺 You are renting directly from the owners Bob & Family. We would love to have you stay in our condo. As our guest, you have full access to all resort Amenities at Honua...
⛵️Mahana 1217 OCEANFRONT PENTHOUSE 1 BDRM/1 BATH Condo/12th floor/Legal Rental⛵️
The Mahana at Kaanapali is an OCEANFRONT resort located on the NORTH BEACH section of the famous Kaanapali Beach on West Maui. We are located just north of Duke's restaurant and several miles from the recent Lahaina fire. Our resort had no damage as a result of the...
Executive Luxury Luxury Home in the Safe Gated Community
Effective October 23, 2022 we will not accept rental for less than 91 days because we have to comply with the new law of city and county of Honolulu. In an exclusive Gated Community, this home is safe, quiet and situated in just on top of the hill for peaceful enjoyment...
Luxe Maunalani Resort Condo w/ Pool + Beach Access
Just minutes from the stunning beaches of South Kohala, this 3-bedroom, 2-bathroom vacation rental condo offers the perfect retreat for your island getaway. With a spacious lanai, community pool, and sauna, you'll have everything you need to relax and unwind. Spend your...
Large 3 Bedroom Ocean Front Villa on 7th floor, Lahaina Tower
Come to the gorgeous Maui Ocean Club and vacation in beachfront style! Marriott Vacation Clubs offer a luxurious and relaxing way to vacation while enjoying all the conveniences of home. Located in the Lahaina tower, this very large 3 bedroom/3 bath corner villa has...
399+ 13 years same ownership: Accountable
We're Accountable 24/7. This condo, however, is not a hotel. We will service immediately whatever needs attention. Our Cancellation Policy Protects both the guest and us. If a guest cancels their reservation outside 60 days, we'll refund their money immediately less...
Beautiful 2 Bedroom Oceanfront Condo Makena Surf F307 - Luxury Awaits!
Surround yourself in luxury while enjoying privacy and seclusion all while being close to world class dining and shopping. Enjoy unparalleled views and seamless indoor/outdoor living with a top notch beach steps away and some of the best snorkeling on island directly in...
Modern, Romantic Vibes in the Tropics
The SpaceCome enjoy this newly updated, spacious end-unit condo in beautiful Turtle Bay. It is as comfortable as it is beautiful. Whether it's breakfast in bed or a drink on the lanai swing, you may not want to leave. Everything has been updated, including hand-picked...
Relax by the sea! Two bedroom retreat near Kailua Pier - 11 min
Discover your tropical retreat at our enchanting two-bedroom holiday house in Kailua-Kona. Paradise is ready for you. Nestled just a short 11-minute drive from the vibrant Kailua Pier, you'll be perfectly positioned to explore the island's top attractions, including the...
Hale Ho'ouluulu – Luxury Poipu Villa with Infinity Pool & Ocean View
Wherever you look, this stunning Kukui'ula villa inspires admiration, and sparks delight. First, there’s the expansive view: an enchanting parfait of rolling hills and verdant orchards in the foreground, the glittering sea beyond, and impossibly blue skies overhead....
Beautiful Villa just steps from Pool. Long Term and Senior Discounts Available.
The Waikoloa Colony Villas is part of private gated community of luxury townhomes. It is on the South Kohala Coast within the world renown Waikoloa Beach Resort.It is centrally located with the best beaches and weather on Hawaii's Big Island. BEAUTIFULLY DECORATED UNIT...
Kaanapali Alii | 263
**Experience Luxury at Kaanapali Alii 263: Your Dream Maui Getaway**Welcome to Kaanapali Alii 263, a stunning luxury vacation rental nestled in the heart of Lahaina, Maui. This sixth-floor oceanfront condo spans 1,843 square feet, offering a perfect blend of elegance...
Four Seasons Hualalai 5BR Ocean Estate
Escape to your own private paradise at this stunning newly renovated expansive 5 bedroom, 5 bathroom 6500 square foot ocean adjacent estate, a beautiful custom home on 3/4 of an acre, nestled within the exclusive Four Seasons Resort Hualalai. Experience the height of...
LUXURIOUS, REMODELED MAUNA LANI VILLAGES TOWNHOME! VIP BEACH PASS INCLUDED!
BEST KEPT SECRET IN MAUNA LANI - Mauna Lani Villages 329 is a modern, highly renovated three bedroom townhome located right in the middle of the exclusive Mauna Lani Resort, where guests are able to access private beach clubs, secluded oceanfront trails and restaurants...
Luxury Alii Cove Ocean View Townhome In Kailua Kona
This 3 bedroom, 3 Bath luxury townhome is located in the gated Alii Cove Condominium complex. This location provides a short walking distance to the of town of Kailua Kona where you will find fine ocean front dining, shopping, St. Michael’s Church, and coffee shops...
Whispering Palms - Tranquility and Elegance
WHISPERING PALMS AT KOLOA KAI VACATION RENTALSTranquility and Elegance in Poipu’s Kiahuna Golf VillageWelcome to Whispering Palms, your luxurious Hawaiian retreat in the heart of sunny Poipu! Perfect for families, multi-generational groups, or friends traveling...
Beautiful Ocean View High-Rise in Ka’anapali 🌴😎⛵️
Experience breathtaking ocean and resort views from one of the best vantage points in the entire Kaanapali Shores Resort. This unit is unique in that it is one of only eight studio units that are placed in the inner courtyard (the other face neighboring properties and...