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.
Dream Spot #103 Luxury, Views, and Paradise Await!
A LITTLE ABOUT THIS CONDO.....Welcome to Polynesian Shores 103, your perfect Maui getaway! This charming garden-level condo offers breathtaking ocean views and easy access to the pool and hot tub, right outside your door. Unwind on your private lanai as you soak in the...
Beachfront Cottage on North Shore Oahu, Sleeps 4, $295/Night
You've found Hawaii’s Best Kept Secret! (And YES WE HAVE A LICENSE TO RENT SHORT-TERM! SEE BELOW) The cottage is adjacent to a whole mile of deserted beaches, where you’ll discover isolated sandy coves, driftwood and shells, and forested pastures filled with polo...
Spacious 2BR Partial Ocean View O410 Resort Living at Ko Olina Beach Villas
Luxurious Condo - 2 bedroom(1 King size bed, 2 twin-size beds, and a pullout sofa bed.) , 2 bath, full kitchen Sleeps 6This 2-bedroom luxury villa is located on the 4th floor of the Ocean Tower facing the Aulani hotel and mountains . It is easy to access to the pools,...
Close But Far.... Cool da Heels
Aloha travlers! I'm very happy to see that you made it through these last couple of months, it certianly has been one for the history books! If you are feeling the urge to venture out, Hotel Pa'amalu may be the very place for you. We are now accepting reservations from...
Gorgeous 2 BR Plantation Style Home in Princeville
Our lovely Hawaiian plantation style home located on Kauai’s north shore, is surrounded by tropical flowers and plants, and features open beam ceilings and a wrap-around covered lanai. The garden view from the lanai, plus distant mountain views make it a soothing,...
Discover Kamaole Sands 3-101 - Premium Ground Floor Renovation, Split AC, Wi-Fi
Step into the spirit of Maui at Kamaole Sands 3-101, a beautifully remodeled, ground-floor 1-bedroom, 2-bath retreat in sought-after Building 3. Surrounded by the resort's lush tropical gardens, this condo offers the perfect blend of privacy, tranquility, and...
Steps to White Sands Beach, Affordable Tranquility!
**NO ADDED CLEANING FEES! Spend your vacation in Paradise! Our guests enjoy the convenience of the centrally located White Sands Village Condominiums on famous Alii Drive in Kailua Kona. We are four miles south of Kailua Bay and two miles north of Keauhou. White Sands...
Kihei Beach #102 - Stunning Beach Front 2 Bdrm Condo
Kihei Beach #102 – Ground-Floor Two-Bedroom Beachfront CondoWelcome to Kihei Beach #102, a fully remodeled two-bedroom, two-bathroom condo with the convenience of ground-floor entry. Located just steps from Maui’s famous Sugar Beach, this condo offers a perfect...
Ho'okipa Hale in Kona: Wade Pool, Pacific Views & Stunning Sunsets
Welcome to Ho‘okipa Hale, a three-bedroom, three-bathroom retreat in scenic Kailua-Kona. This private home blends the comforts of modern living with the beauty of tropical island surroundings. With panoramic ocean views, a lush fruit-filled garden, and a serene wade...
Hawaiian-inspired 1BD Villa in Kapalua
Welcome to Kapalua Golf Villa 15T1, where the laid-back luxury of Maui meets the sweeping greens of the Kapalua Bay Course. This beautifully appointed one-bedroom, two-bathroom condo is the perfect retreat for couples, small families, or friends looking to experience...
Unbeatable Deal with Spectacular Views on Maui!
**Valley Isle Resort 609**Located on the 6th floor of the lush, oceanfront Valley Isle Resort, this 1-bedroom, 1-bath condo offers panoramic views of the ocean and the islands of Moloka'i and Lana'i. Enjoy the best sunsets imaginable and prime whale-watching...
Princeville's Sh'Zen: Best Bali Hai, Sunset View
Princeville's Sh'Zen is a luxurious three bedroom, three bath home on a very private third of an acre of lush tropical gardens and pool. . Spectacular endless ocean views over the seventh tee and sixth green of the world famous and newly remodeled Makai Golf Course and...
Breathtaking Luxurious Pacific Island Home
Nestled in the gated community of KaMilo, located within the upscale world class exclusive Mauna Lani Resort on the Big Island of Hawaii is this breath-taking 4 bedroom 3.5 bath home. This stunning gated community is one of the Big Island’s newest neighborhoods and...
Ocean View - Pili Mai 12G - 2 Bedroom Suite Sleep 8 - AC, Pool & Fitness Center
Our "Ha'upu Hale" is a beautiful, brand new, two-bedroom townhome located at the Pili Mai resort in Poipu, Kaua'i with AC, Pool, and Fitness Center. Enjoy Ha'upu Mountain Views, and be entranced in beautiful sunrise views surrounded in serene Kaua'i harmony!The...
Tropical Oasis, Oceanview, new remodel, 3 bed, 3 bath, w AC, pool.
Aloha and Welcome to our Beach Home, a stunning two-story townhome with three bedrooms and three bathrooms. It has undergone a complete renovation and is newly furnished, highlighting a contemporary tropical beach house design. The downstairs kitchen, living room, and...
Keone = Sands - Ocean views, walk across grass to sand and sea, no stairs
Keone is the downstairs level of a beach house duplex. There are two bedrooms, one bath, a kitchen, dining area and living room (Standard Occupancy is 4*). There is a good sized covered lanai and great ocean views from the living room and the lanai. Just step off the...
AIR CONDITIONED HOME FEATURED ON TV - CLOSELY LOCATED TO BEAUTIFUL N SHORE BEACH
Newly installed AIR CONDITIONING provided throughout the house to provide added comfort to this already comfortable and luxurious home. This spacious home is within walking distance (or short drive) to Queen's Bath, Hideaways, Anini & Pua Poa Beach. The beautiful lanai...
*Oceanfront* Menehune Shores 411
Enjoy amazing sunsets from your private lanai, or the comfort of the sleeper sofa in the living room. TVs in living room & bedroom.Fully equipped kitchen with all major appliances, cookware, dining ware, and utensils. Take a stroll or find a perfect spot to relax on the...
COMPLETELY REMODELED-OCEAN VIEWS-LUXURY FINISHES-METICULOUS CLEANING-AC
Book With Confidence, This Stunning, 1 Bedroom, 1 Bathroom Condo (655 Sq Ft.) At Kihei Akahi Has Been Completely Remodeled. This Condo Is Managed By PMI Maui, A Local Real Estate Brokerage That Specializes In Vacation Rentals. We Are Located Within A Mile Of The Resort...
Panoramic Ocean Views - High End Remodel Nov of 2024 Central Air and King Bed.
Enjoy beautiful Maui sunsets, and spectacular ocean views while dining on the private lanai of this fifth floor Maui Vacation Condo. The condo is elegantly furnished in tropical prints and has a king size bed in the bedroom and hide-a-bed in the living room. The kitchen...
Amazing Hana Bay Beach Cottage Location! 5-Minute Walk to Hana town & beaches!
OCEANFRONT SPLENDOR IN PERFECT HARMONY WITH NATUREPerched on the dramatic bluffs of Hana Bay, Elua Cottage at Hana Maui Luxe offers a rare oceanfront escape surrounded by black lava cliffs, lush tropical beauty, and black, red, or golden beaches to enjoy. Whether you're...
2 Bed Cottage Along Beach and Bike Path in Kauai. Awesome Location! TVNC #4288
Live like a local at Oceanfront Rhythm, a professionally managed and operated vacation rental located -- as the name says -- on the oceanfront. This 2- bedroom, 1-bathroom classic Hawaiian historic home, is fully equipped with kitchen, living room, dining area, 2 King...
Oceanfront - Studio - Marriott's Maui Ocean Club: Molokai, Lanai, Maui Towers - Full Resort Access
Enjoy a luxurious stay for a fraction of the cost. Typical savings range from 30-70% when comparing our rates to direct resort bookings. All of our units are managed and maintained by the resort. Upon arrival, guests will check-in at the resort’s front desk using...
"Sunny Daze" Kapaa Sands 20 Ocean View
Welcome to Garden Breeze Retreat, a cozy ground-floor oceanfront escape at Kapaa Sands, where lush tropical gardens and sweeping ocean views create the perfect setting for your Kauai getaway. This peaceful retreat offers everything you need to relax, recharge, and enjoy...
Unique Oceanfront Condo with AC
This condo enjoys stunning views of the Pacific Ocean from its living area and kitchen. The crashing waves will lull you into complete relaxation after your days of adventures.This upper level unit enjoys high ceilings which give it an open and airy feeling. The kitchen...
!!! OCEANVIEW!!! 2Bdm Reno'd Top-Floor Kamaole Beach
This condo has the BEST OCEAN VIEW and sunset view in Kamaole Sands, a premiere condo complex situated on 15 acres of lush tropical landscaping in South Kihei, bordering Wailea. Located directly across the street from Kamaole III Beach, which has lifeguards, this...
Hale Kamaole 212 - Enjoy Your Beautiful Spacious Suite
Book with us and come to Maui to explore everything we have to offer!Beautiful condo conveniently located very close to world class beaches, shops, and restaurants! Gorgeous pool and ocean views second story unit with easy elevator access and lots of parking. Relax on...
Gorgeous 180 degree COASTAL VIEW Home! New SUMMER RATES!
20% off SPECIAL for upcoming season! We also have discounts with EARLY BIRD and LAST MINUTE too! Our home has been voted "TOP Vacation Rental" by TripAdvisor. (Also, Enjoy discounts with several excursions vendors: Fair Wind Charters, Hawaii Forest and Trail, zipline...
Large family home along the ocean and bike path in Kauai. Sleeps 7! TVNC #4247
Live like a local at Oceanfront Harmony, a professionally managed and operated vacation rental located -- as the name says -- on the oceanfront. This 4- bedroom, 3-bathroom classic Hawaiian historic home, is fully equipped with large kitchen, bar area, living room,...
Oceanfront Hawaiian-style Beach House
Throw a pebble into the Pacific Ocean from your lanai. Hale Aloha is an oceanfront private retreat located in the magical neighborhood of Puako, next to Mauna Lani Resort on the Big Island of Hawaii. Puako is one of the sunniest destinations in Hawaii with a unique...
Studio Kohala Big Island Ocean View
Nice studio with two lap around lanai, with ocean and North Kohala coastline view for miles. 5 mins from Kawaihae harbor and Mauna Kea beach & Hotel.Clean and quiet. Microwave. Toaster oven, small fridge. Coffee maker. High speed WiFi. Internet excellent connection,...
Top-floor beach corner unit - sweeping oceanfront views - beachside pool/hot tub
Islander on the Beach 354Our 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...
Kamaole Sands 4-401, Superior Comfort and Ocean Views
Your island paradise awaits you and your family at this 3-bedroom, 3-bathroom condo located in beautiful sunny South Maui in Kihei at the KAMAOLE SANDS resort. Situated on the top floor of the satellite 4 building, unit 4-401 offers guests tantalizing views of the...
❤️PiH❤️ HAWAIIAN DESTINY ★ Private heated pool/spa★ Beach Club ★ Views ★
Brought to you by Paradise in Hawaii Luxury HomesWelcome to Hawaiian Destiny, part of our Hawaiian Luxury Collection. Hawaiian Destiny at KaMilo is a wonderful home that sleeps 12 with a stunning backyard oasis including private pool and spa with stunning views of the...
OceanViewStudio, Full-Size W/D, Dishwasher, 55"TV, Hotel-Zoned, Beach across St,
This is a one of a kind, quiet, and gorgeous Studio; professionally decorated with Pier1 Furnishings and Local Artwork. New paint, tasty decor, and an Ocean/Garden view, create a soothing, colorful, and pleasant way to unwind at the end of the day. Split AC, keeps you...
Hawaiian Plantation Style Cottage In Resort Location
"Kuku's Nest" is a beautiful tropical home not just another rental. This condo is a large, remodeled, one bedroom accommodating two guests, ground floor unit, with full kitchen, luxury vinyl and tile floors, stainless appliances, fresh tropical colors, granite counters,...
VIEWS! Chic Vibes & Rainbows! 3bdr. Walk to Beach Quaint complex close to shops
Aloha from Surf Sun Rainbow House 2 — 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...
Enjoy Your Oceanside Dream at Kihei Surfside
Newly added split A/C system was just added!! Imagine sipping coffee from your private lanai overlooking the ocean! This beautiful second-floor condo features a Cal King bed in a private bedroom with a full bathroom. There is a comfortable sleeper sofa in the living...
Outstanding Location in Maui South Kihei & Wailea
Aloha! Your dream vacation starts with our beautiful new condo, located in Southwest Maui, in the town of Kihei. The Maui Kamaole complex borders on beautiful Wailea, known for excellent restaurants and world class shopping. The lush tropical grounds spread over 23...
PM 424 Beautiful BeachFront 2BD w Ocean Views
Paki Maui 424 Beautifully-Designed Condo With Breathtaking Ocean Views Sleeps Up To 7 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...
GORGEOUS Ocean and Diamond Head Views! Close to beach! A/C, Wi-Fi, Parking!
Waikiki Sunset #2910 – 229 Paoakalani Ave.Enjoy BREATHTAKING colorful blues of the Pacific Ocean and the lush greenery of Diamond Head and Kapiolani Park from this 29th floor, 1-bedroom condo (534 sf interior plus 67 sf lanai) with central AC and FREE Wi-Fi,...
One of a kind private Luxury beachfront Estate with oceanfront pool & jacuzz
TVNC #4224This is truly a one of a kind Hawaiian dream home. Stroll down the sand beach and find Hawaiian Paradise set on over an acre of beautiful tropical beachfront landscaping. This approx 5000 sq ft gated home has all the comforts one could need from a gourmet...
Maui Resort Rentals: Honua Kai Konea 351, 3BR w/ Direct Oceanfront Views + B.B.Q. on Balcony!
Upon first entrance to Konea 351, your senses will acknowledge that you've chosen one of the finest three bedroom direct oceanfront residences that Honua Kai has to offer. This 3 bedroom oceanfront Ali'i (Hawaiian word for royalty) residence commands a prime vantage...
Highly upgraded, Ocean View Kolea Penthouse
Kolea 2F is fully furnished and decorated by local interior designer Mealani Morgan and is located on the only condominium development within the Waikoloa Beach Resort. Penthouse includes access to the Kolea Beach Club with infinity pool, hot tub, gym, and sandy beach...
Beautiful Views, Walk To Beaches And Restaurants
Poipu Vista Villa is a custom designed home in Poipu Kai Resort. Ocean and mountain views are just the beginning for this Hawaiian paradise. The incredible design of this home literally brings the outdoors in, creating a place to relax in peace and privacy with...
Great condo within short walk to excellent beaches, shopping and dining.
This cute and cozy condo is in a small complex with a beautiful pool that is surrounded by gardens and a BBQ area. Kamaoloe Beach I is a four minute walk from your door. The place to go for restaurants and shops is known to locals as the Triangle, which is a 5 minute...
Hanalei Bay Resort 9305 (Hanalei Bay Hideaway) AC!
This separated one bedroom one bathroom condo with a loft including two twin beds, has full oceanfront views of Hanalei Bay with your own private lanai. Wake up in your king size bed with your clean crisp sheets and enjoy an amazing sunrise breakfast and a complimentary...
Steps to beach! Beautiful renovated 1 bedroom
Our renovated condo is located just steps away from one of the most beautiful beaches on Maui, Kamaole 2 beach. Our 1 bedroom, 1 bathroom condo is located at the Kihei Akahi in Building D which is at the back of the complex. It is on the 1st floor, one floor above the...
Ground floor, quiet, renovated 1 Bedroom 2 Bathroom condo
The condo has a large bedroom with king size bed and new mattress. There is also a new, queen size sofa bed in the living room. The two bathrooms are spacious and have been updated. There are showers only. The kitchen is equipped with stainless steel appliances. The...
Adventures in Paradise! Sandpiper229 condoA - Split AC, Nearest Assigned Parking
Aloha from the spectacular North Shore of Kauai, The Garden Island! Our multi-story tropical retreat features a light filled living room/dining and loft with vaulted ceiling, fully appointed kitchen, furnished lanai with outdoor dining, 2 king size beds and 2 en suite...