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.
ALII COVE#S-1: BEAUTIFUL 2 LEVEL SPACIOUS 3 BEDROOM WITH AC!
Alii Cove#S-1 is an excellent beautifully furnished option for your Vacation. This VERY spacious, 2 story 3 bedroom, 3 bath unit has fantastic features that many guests enjoy. A perfect option for up to 8 people! ~Largest Floor Plan in Alii Cove. Living Area, Main...
Stunning Ocean Front Views, Wailea, Polo Beach Club Condo - unit 303
Welcome to your tropical escape at Polo Beach Club, our cherished slice of paradise! Having fallen in love with this magical location years ago, we are thrilled to be able to share our beautiful condo with you. Nestled at the tranquil south end of Wailea Beach Walk,...
Family friendly Quiet Kailua Beachside lane, steps to lane private beach access
Only steps to beach through private street gate, and a short 1.5 mile bike to Kailua town. 2 bedrooms, family room, and kitchen on 2nd floor; laundry, 1 bedroom and bath on 1st floor. Washer/Dryer, Basic Cable, and Wifi includded. Small pets ok. Monthly rentals only -...
Waikiki Condo Has 2 Bedrooms & 2 Baths, with 1 free parking space.
This Waikiki condo was newly remodeled in June 2023, with 2 bedrooms, 2 full baths. The full kitchen has an oven, stove range, microwave, dishwasher and refrigerator, and includes fully stocked, large living room has a queen size sleep sofa/futon and 2 single full-out...
5 Star Upgraded Oceanfront 2 BR condo w/Amazing views & AC-Sands of Kahana 326
Imagine your next vacation in paradise and now imagine you are able to rent a condo that has all of the comforts of home and the views dreams are made of. Sands of Kahana unit 326 on the second floor of the oceanfront building 3 (feels like 3rd. Floor due to first...
Family fun! Recently remodeled. Closest Unit to the Amazing Pool
Welcome to Kaanapali Royal’s H-102 vacation rental. Completely remodeled in June 2019. 2 bed 2 bath condo with a queen sleeper sofa in the living room and a twin sleeper in master sitting area..Everything is brand new. The unit was remodeled from top to bottom. Onsite...
Purple House in Paradise
Our 700 sq. foot 2 story home, Miloli'i Beach Bungalow, is located 33 miles south of Kona in Miloli'i. If you are looking to get away from the hustle and bustle of the city, you've come to the right place. Our little house in paradise, 550ft from waterfront local...
Just 40 Steps to the Most Beautiful White Sand Beach in the World
Tropical Trade Winds and Unsurpassed Views are from our Beach Front Home. Opens up for full enjoyment of Hawaii's Climate. Our rap-around Lanai overlooks the beautiful beach, Kailua Bay, and Offshore Islands.Kailua is a small upscale town with excellent retail stores....
Fully Remodeled Modern Island Style!
Aloha and welcome to our condo, the Palms at Wailea 606. We’re looking forward to hosting you and making your vacation fun and enjoyable.The Palms at Wailea is an upscale community that offers you great shopping, dining, golfing, world-class resorts, and beaches all...
bright 3 bed,3 bath, pool, hot tub, tennis, breeze
Summary:Relax with the whole family in this lovely 3 bedroom 3 bathroom condo that overlooks the Waikoloa Village Golf Course and Kohala Mtn. Complex has a large swimming pool, hot tub, exercise room. tennis court and pickleball court. Barbecues within steps of the...
Maui Resort Rentals: Honua Kai – 3 Total Bedrooms + Den w/ Lush West Maui Mountain Views!
This exceptional four-bedroom plus den offering combines three spacious neighboring suites to create the perfect gathering place for any large group or family. Boasting an incredible oversized lanai and spacious interior, Konea 212 is a luxurious two-bedroom mountain...
Makena Surf F206 Beachfront Resort - 2 Bedroom Oceanfront Condo
Makena Surf F206 is a delightful retreat for your Maui vacation.The interior design features a harmonious palette and finishes that highlight organic beauty. The calming ambiance is enhanced by subtle Venetian plaster walls, cool travertine tile, and plush carpeting,...
Hale Leilani - Adventure Awaits
Relax and enjoy our pleasant and welcoming well equipped Home away from Home. Here you will find real Hawaiian flair within a cute renovated Plantation style Home. Location is prime - 5min to the Beach Parks, 3min to the Airport & 7min to Downtown. Our private House...
Exquisite Oceanfront Wailea Beach Villas B202
Wailea Beach Villas has been ranked #4 in Hawaii by Condé Nast Readers. This recognition places WBV among the very best resorts in Hawaii, and the best on Maui!This property is hotel zoned, and not being affected by the recent proposed legislation.Be one of the first...
Kaanapali Royal B-102 - Remodeled - Golf Course Living - Free Fun
Completely remodeled December 2021 - With more than 1,500 sq ft of air-conditioned living space, this gorgeous condominium is ideally located directly on the Kaanapali Golf Course. Kaanapali Royal B-102 features: • Located on the 16th hole of the championship...
Hale Kahili Nui – Poipu Beach Estates Luxury Villa
For those desiring larger accommodations, Hale Kahili Nui able to be combined with Hale Kahili Ohana for a Hale Kahili 8 Bedroom Estate experience.Amazingly spacious and extraordinarily appealing, this newly constructed 2-story villa is conveniently located in Poipu...
Fantastically Remodeled Condo with Huge Ocean Views
Aloha! Welcome to magical, mystical, mythical Maui. My intimate, meticulously maintained one bedroom two bath condo is located on the 1st hole of the legendary Wailea Old Blue Golf Course. If you are searching for a first class yet budget friendly Wailea resort...
Modern Oceanfront Cottage
Wake up to the sound of waves and step straight onto the sand at this stunning 3-bedroom, 1.5-bath oceanfront retreat. Perfectly positioned right on the beach, this home offers the ultimate island getaway with a spacious converted basement, comfortable furnishings, and...
Beautiful Plantation at Princeville
Lovingly maintained home! Bright and airy, ground level condo with attached one-car garage in a desirable community in Princeville on the North Shore of Kauai. This unit is the essence of aloha and comfort. Brand new linens, new boogey boards & cooler chest. The...
Aloha Condos, Kanaloa at Kona, Condo 203, Fairway Front, AC
Prime fairway front location - great for bird watching or watching golfers along the 11th fairway of the Kona Country Club Ocean Course. Peaceful and spacious with lovely Hawaiian decor, this condo is the perfect escape for two couples or a family. Top Floor Condo with...
Aston Waikīkī Beach Tower by Gather 2BR Condo w/ Oceanview, Pool & Lanai
Overlooking Waikiki’s sparkling shoreline, Aston Waikiki Beach Tower by Gather is a bright and stylish two-bedroom, two-bathroom retreat set in the heart of Honolulu’s most iconic district. With sweeping ocean views from your private lanai and modern resort...
KBM Resorts | FREE CAR | Honua Kai Konea | 1-Bedroom Condo, Steps to Beach! HKK-236
** 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...
Luxury! 3Bd Ocean Beach front in Paradise! Hyatt Residence Club
AMAZING! LUXURY! BEST OF THE BEST 3 Bed, 3 Bath in Maui!! Ocean Beach front Paradise!!THE UNIT IS AN UPPER FLOOR 3 BEDROOM, 3 BATH WITH SPECTACTULAR OCEANFRONT VIEWS OVER THE PALM TREES! There are only 6 upper floor 3 bedroom units at this exclusive resort. Most...
Absolute OCEANFRONT; Walk to Beach/Kona Town, A/C, Oceanfront Pool, Elevator
Full refund if HI reinstates the traveler quarantine. Right on the ocean, newly renovated upscale condo. Unbelievable views from the lanai, living room, and bedroom of this condo. Close to everything! 1-2 blocks to Honl's beach, farmers market, restaurants, bars, and...
SUPER SALE in April! ~ QUALITY Villa ~ Very COMFORTABLE ~ Easy Access on parking level
Welcome to one of a few exclusive members of the Platinum Maui Vacations ohana, (familiy). We call this Kapalua Golf Villa, (unit 17 T-3&4), Hale O Ho'aloha. A Hawaiian phrase which roughly translates to English as 'Home of Friends'.We call this unit a 1.5 bedroom...
Blue Lagoon Estate at Mauna Lani Resort
Enjoy the best Hawaii has to offer in this luxury 10,000 sq ft Kona Coast tropical estate on The Big Island in the Champion Ridge enclave of Mauna Lani. Enjoy the private heated lagoon pool and spa and access to many of the Mauna Lani resort area amenities including a...
Molokai Island Retreat
Aloha and welcome to Molokai Island Retreat! Molokai Island Retreat is located on the highly desirable lush east end of Molokai (we are not on Maui) in the Wavecrest Resort. Our condo offers a breathtaking bird’s-eye view of the ocean, with stunning vistas extending...
Luxury family friendly home within walking distance to Poipu Beach.
Honu House is located in sunny Poipu on the south shore of Kauai. This home was completed in March of 2019. Honu House is an open concept home with beautiful koa wood floors and 10' ceilings throughout, boasts 2 master suites on the main level with plush king size beds...
Ocean View Condo | Pono Kai Resort | PF-G102
Pono Kai's pool and spa will be closed January 6-31, 2026 for the instillation of the new pool deck fencing.The Kapaa Public Pool, located less than one mile from the resort, is open to the public.Experience the beauty of Kauai in this charming 1 bedroom, 1 bathroom...
Private Cozy Studio walking distance to beaches, shops, restaurants and bars
This studio is perfect for the vacationers who wants to spend their time out and about exploring the island and still have a very nice, comfortable place to come home to. It's on the 4th floor of The Island Surf in South Kihei and within walking distance of many shops,...
REMODELLED, prime OCEAN VIEW at Maui's #1 Kaanapali beach J221
Enjoy a prime ocean and golf course view, while sipping your morning coffee from the privacy of your own lanai.Bright Hawaiian style decor adorns this comfortable and relaxing suite. Perfect for a couple seeking a 5 star relaxing suite in Kaanapali. Tastefully...
Poipu Sands 437: Updated Spacious 2BR Ocean View Condo, A/C, pool, tennis, beach
Welcome to Poipu Sands 437! This top floor ocean view condo is spacious, updated and comfortable, with a 300+ sq ft lanai overlooking the cliffs of Shipwreck Beach, perfect for turtle, dolphin and whale watching (in season). There are two bedrooms, two bathrooms, a...
Lovely 2 bed 2 bath Maui Kamaole 2 story condo with views
With its superior location at one of the top-rated resorts in Southernmost Kihei, just a block from Wailea, this 2-bedroom, 2-bath luxury condo sleeps up to six and features Tommy Bahama furnishings, two resort pools and hot tubs, two tennis courts, and lush gardens....
Maui Resort Rentals: Honua Kai – 5 Total Bedrooms, 9th Floor Stunning Deluxe Ocean and West Maui Mountain Views!
This phenomenal nine-floor offering pairs two kitty-cornered residences for nearly 2800+ sq ft of combined interior living space. Your group will enjoy five luxurious bedrooms and bathrooms, two modern kitchens, and two expansive lanais featuring unparalleled views of...
Puako Beach Luxury Oceanfront Home- 3 Guest Suites
Say aloha to this gated oceanfront retreat! Beach access is a short 5-minute walk away, but your vacation begins as soon as you step on the grounds of this stunning property. Upon arrival, you’ll be greeted by a beautiful entryway of Balinese design. Once inside,...
Stunning Modern Condo Across Street from Turtle Beach, Learn to Snorkel or Surf!
Beach Villas at Kahalu’u is one of the newest condo complexes built along the lush Kona Coast on Alii Drive. It is located directly across the street from historic Kahalu’u Beach Park. Hawaiian people once fished and surfed here, and chieftains bathed in pools that...
Kolea 6E ~ Oceanview Three Bedroom Kolea Villa
Along with ample living space, Kolea 6E offers a nice ocean view of A'Bay over one of the few vacant lots remaining at Kolea. This villa is great for families as well as those just looking for a peaceful getaway in Hawaii.As you enter the villa you will be astonished at...
Mahana 1204 Oceanfront Penthouse. Top floor whale watching - direct beach access
1204 has it all: luxury accommodations with panoramic top-floor views, beachfront, and direct beach access.Experience the ultimate Maui getaway, perfect for small families and couples. Whether celebrating a romantic honeymoon, special anniversary, or birthday, unit...
Ultimate Luxury,Ocean Views,Walking Distance to Beaches!Kapalua Bay Villa 33B3-Quam Properties
Welcome to Kapalua Bay Villa 33B3, your private slice of paradise where the ocean greets you from every room and the spirit of Maui surrounds you in comfort and style. Perched above the sparkling waters of Kapalua Bay, this 1,750-square-foot luxury townhouse villa...
Top Floor, Retreat w/Mtn Views & Beach Access, 1538
Unit 1538 is a cozy and inviting retreat perfectly suited for a relaxing getaway. This spacious studio features a comfortable king-sized bed, a full kitchen, a washer/dryer, and a large bathroom with a walk-in shower. The room is also equipped with a large flat-screen...
Ocean Edge Bliss w/Island Decor, Kitchen Ease, Lanai, Flat Screen, WiFi–Kaha Lani 327
Castle Kaha Lani Resort #327 - Comfy and casual, this 739 sq. ft. suite boasts a Pacific Ocean view that’s hard to beat! End a dreamy Kauai day with cocktails and fresh catch prepared to perfection in the full kitchen. Touches include a flat screen, WiFi, ceiling...
New Listing: Bright corner condo in Kihei
New Listing! Sunlit Corner Penthouse in Kihei – Maui Banyan P409Escape to paradise in this bright and breezy 1-bedroom, 1-bathroom corner unit penthouse condo at Maui Banyan, ideally located in sunny South Kihei. Nestled on the top floor with elevator access, this...
Poipu Sands 126 By Parrish Kauai
Our luxurious Kauai vacation rentals at Poipu Sands offer spacious layouts, large covered lanais, a private heated resort swimming pool, community gas BBQs, on-site tennis courts, and more.Centrally located in Poipu, adjacent to the Grand Hyatt Resort & Spa as well as...
Magic Sands Ocean Front Condo. Kailua-Kona
This studio is oceanfront with stunning views. The popular Magic Sands beach is right next door. Bar and restaurant downstairs and bike rentals across the street. Close to Kailua-Kona town and other popular beaches including the famous snorkel beach Kahalu'u.This unit...
OCEANFRONT High Floor RENOVATED Maui Kai 806 Condo Private OPEN Lanai KING BED
OCEANFRONT High Floor RENOVATED Maui Kai 806 Condo Private OPEN Lanai KING BEDExperience true oceanfront at low welcome back pricing!Recent Cal KING bed and appliances!MK806 is an oceanfront studio condo apartment with a perfect ocean view that has been completely...
Oceanview Kihei Akahi D210: Updated 1BR/1BA, Perfect for everyone!
Unit D-201 has been completely remodelled and refurnished with modern, beachy decor. Fully renovated kitchen is wide open and includes views from the large, stone island and is fully equipped for the home chef! Dining table for 4 inside is perfect for game night....
Maluhia at Wainani - New Poipu Home with Private Pool & AC
Maluhia at Wainani is a fresh and stylish modern villa with all the amenities one desires while on vacation. Tucked back away in the quiet part of Poipu, but still perfectly located near the beach, this home is the idea vacation spot. Centrally located in Poipu Beach...
New! Luxury Split-Level Retreat at Pili Mai
Luxury Split-Level Retreat at Pili Mai #15E | Poipu ParadiseProperty OverviewWelcome to this stunning split-level home at the prestigious Pili Mai Resort in sun-soaked Poipu, Kauai. This immaculately maintained 3-bedroom residence offers the perfect blend of Hawaiian...
Luxury Beachfront Home in Haena AC, Pool TVNC5141
Mana Kauai Island Vacations Presents Holo Makani! The gated estate of Holo Makani is located in the sand on a dramatically beautiful and pristine beach on Kauai's North Shore coast line. Enjoy the lull of the ocean and the gentle trade winds coming in off the water...
Ocean View - King Bed✨nSelf Checkin and Out - Private Entry and Private Lanai
For The Island Adventurer✨Vast Ocean View!Facing the Pacific Ocean & Kailua-Kona Bay*Private Entrance*Self Checkin/Checkout*King Bed 4" topper - 30” elevated w/step up*Lanai/Patio ~ Outdoor Shower with Hot H20*FAST STARLINK Satellite for multiple devices *Beach+Bath...