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.
Luxury Poipu Kai 3 Bedroom Villa with Pool and Tennis!
Listing provided by "The Vacation Rental Experts". Contact directly for more options!Enjoy tropical foliage and pool views with an exceptional level of luxury at this 1800 square foot villa. This stunning 3 bedroom, 3 bathroom condo offers all of the comforts of home...
3 HGVC Hawaiian Village Beachfront Resort and Spa!
Enjoy the glamour of this stylish, upscale place. Set among 22 acres of pristine Waikiki beachspace, Hilton Grand Vacations at Hilton Hawaiian Village provides visitors with spectacular amenities and an unrivaled position in the heart of paradise. Guests are treated to...
Marriott Ko Olina Beach Club 2BR Villa - July 4th or Thanksgiving on the Beach!
A beautiful Hawaiian Resort awaits your family and friends to celebrate Thanksgiving Week. Your charming 2 bedroom villa invites relaxation and restoration with two lanais offering island, mountain, and/or partial ocean views replete with the occasional rainbow or...
Palms at Wailea Villa 805 Garden View 2 BD 2 BA
- Ground floor unit- Kitchen includes stovetop, oven, microwave, refrigerator, dishwasher, coffeemaker, toaster, cookware and tableware- Spacious private 219 square feet deck- Master bedroom with 1 king bed- 2nd bedroom with 1 queen bed- Queen sofa bed in living area-...
Direct Ocean Front 1 BDRM 2Ba Whaler #601
Whaler 601 is a privately owned, beautiful, 1 bedroom, 2 bath, DIRECT ocean front, corner unit, with a wraparound lanai on the North tower on the 6th floor of the Whaler resort. Many listings say 'ocean front' but in reality, are common ocean views. The attached photos...
Kaanapali Alii | 183
Kaanapali Alii 183 is a luxurious oceanfront vacation rental nestled in the heart of Maui's renowned beach destination of Kaanapali. This spacious 1,800 square foot condo offers breathtaking views of the Pacific Ocean, the islands of Lanai and Molokai, and the pristine...
Maui Ka’anapali Villas #C258: One bedroom, one and a half bath loft with a garde
Maui Ka’anapali Villas #C258: One bedroom, one and a half bath loft with a garden view on N. Kaanapali Beach with Pool and Beach AccessThe space:Relax in the lush garden and pool views at this Hawaiian oasis in the serene Coconut building. This condo has been upgraded...
New Listing! Open Condo with Warm Wood Accents
Welcome to Koa Resort 2I — a beautifully appointed 2-bedroom, 2-bathroom condo that comfortably accommodates up to 6 guests. The spacious living room features a queen sleeper sofa for additional sleeping space. Please note that the second bedroom is a loft, offering...
Lani One’ā: A Handcrafted Island Sanctuary with Seaside Community & Aloha Spirit
This charming, elevated home in Pahoa, Hawaii, blends modern comfort with island charm. Painted in soft green hues that complement the lush tropical surroundings, this rental is perfect for a relaxing escape.
Kanaloa at Kona Ocean View 2 Bedroom
- Condos located on 1st or 3rd floors- Kitchen features stovetop, oven, refrigerator, microwave, dishwasher, coffeemaker, blender, disposal, cookware and tableware- Private balcony with wet bar- Master bedroom with 1 king bed or 1 queen bed and private bathroom with...
New Listing! Private Maui escape with Island charm
Welcome to Alaeloa 35 – Your Private Maui Getaway! Tucked within the peaceful, oceanfront enclave of Alaeloa in Napili, Alaeloa 35 is a charming 3-bedroom, 2-bath freestanding cottage that effortlessly blends island comfort with timeless Hawaiian charm. Surrounded by...
Waikiki Getaway! Pool, Near Honolulu Museum of Art, Parking!
Sandy beaches or exciting adventures--look no further than this Oahu property!This listing is for a room within a hotel.✦ Your room is 300 sq. ft, equipped with complimentary toiletries, high definition 40-inch TV, available with Premium cable.✦ Daily cleaning...
Westin Ka'anapali Ocean Resort Villas 1 Bedroom Villa Ocean View
The Westin Ka'anapali Ocean Resort Villas - whale watching, snorkeling, sailing, windsurfing and scuba diving just steps away, there are plenty of activities at our Maui beachfront resort near Lahaina - comes with Westin touches keeping in harmony with the Hawaiian...
30 Day Rental in Waikiki with Parking!
Welcome to Fairway Villa, your ideal retreat in the heart of Waikiki! This studio, available for a minimum 30-day stay, is perfect for remote workers, traveling nurses, or anyone needing a longer-term stay in Waikiki. The studio features a comfortable Queen-sized bed, a...
Peaceful Peacock Palace in Makaha
Nestled in the lush landscapes of Makaha Valley, backed by the beautiful Mountains with a 24 hour Oceanview, our enchanting retreat offers guests a unique blend of serene natural beauty and luxurious comfort. As you enter the gates, you are welcomed by the sweet...
Hilton Hawaiian Village Lagoon Tower 2BR 2BA sleeps 6--Ocean View
Consider this condo your home away from home while you visit Honolulu. Lagoon Tower offers 2 bedrooms and 2 bathrooms, ensuring a comfortable stay for guests. With amenities like a hair dryer, heating, WiFi, a washing machine, an iron, a fitness room, and AC, your needs...
Lahaina Condo Studio • 2 Beds • 1 Bathroom
Begin your Maui journey at The Westin Kāʻanapali Ocean Resort Villas. Our dedicated guest services team helps plan amazing island trips, such as volcano visits or waterfall treks. Your pre-arranged activity passes await you upon check-in. Unwind in your private villa...
New! Lae Nani #621, AC, Ocean View, Tropical Oasis, Steps to Beach and Town
Lae Nani Resort Kauai #621, Beautiful Ocean View Unit on a Tropical Beachfront Oasis. This Kauai Vacation Rental is conveniently located in Kapaa Town within walking distance to shops, restaurants, and just steps to beautiful white sandy beaches. Accommodates up to 4...
Entire House, Ocean front, White Sand Beach across the street.
Located directly across from a stunning white sandy beach, this home offers the perfect Hawaiian country retreat. Start your day with breathtaking oceanfront sunrises and end it with serene mountain-view sunsets—all from one property. Enjoy snorkeling, fishing,...
Kaimana Beach Hotel | Classic Queen | Beachfront Getaway
Tucked at the serene end of Waikiki, Kaimana Beach Hotel offers direct beachfront access, steps from Kapiolani Park and beneath Diamond Head. The Classic Queen is a cozy retreat with a plush bed and breezy island-inspired design. It's perfect for solo travelers or...
Waikiki Beach Walk Resort 2BR/2BA
Located on nearly eight acres of new Waikiki pleasures. If you're looking for a resort that packs a ton of nearby fun, be among the first to reserve your spot at the new Club Wyndham at Waikiki Beach Walk®, part of Outrigger's huge Waikiki Beach Walk project. This...
Kai Lani 21C: Spectacular Ocean Views, Upgraded 2BR Condo
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 Kai Lani 21C by Gather, a...
Snowbird-friendly home near the beach with patio, grill, outdoor dining area
Hale Olena Ohana - 31-Day MinimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Conveniently located just 26 blocks from the ocean, this snowbird-friendly home offers the perfect...
Royal Kahana Maui 415 Ocean View 1 Bedroom
- 4th floor condo with balcony- Tile & Vinyl plank flooring throughout- Fully equipped kitchen with– fridge, stove/oven, microwave, cookware, tableware- Tiled bathroom with walk-in pebble shower with grab bar- Queen sofa bed in living area- Central Air Conditioning-...
Oceanview Suite and Cottage
We are a 3 Acre Luxury Vacation Rental Property with an Award Winning Coffee Farm comfortably nestled on the slopes of Hualalai overlooking Kailua-Kona.This rental is composed of 1 Suite and 1 Cottage.We have a brand new split system AC and heating in every room and...
Stunning Oceanfront 1BR/2BA Retreat with Spectacular Views - Wailea Elua 1802n
Wailea Elua #1802 – Luxurious Oceanfront Retreat with Panoramic ViewsExperience upscale coastal living at Wailea Elua #1802, a beautifully renovated second-floor, 1-bedroom, 2-bathroom oceanfront condo located in one of Wailea’s most desirable beachfront...
Westin Nanea Ocean Villas Resort & Spa, Hot Tub!
A state of relaxation and repose - firsthand at The Westin Nanea Ocean Villas! Set on twenty-six acres of lush, tropical land and infused with a variety of Hawaiian design elements, The Westin Nanea Ocean Villas blends a top-notch vacation experience with the authentic...
Alii Park Place#N-202: Gorgeous Remodeled Top Floor 3 Bedroom unit with AC
Alii Park Place is one of the premier developments on Alii Drive. Tinguely Development group created this complex wanting to offer true quality living. It's clearly apparent this reigns supreme as you walk into the space. Unit#N-202 is beautifully furnished, and offers...
Oahu Dream! 3 Amazing Units, Pool, Minutes to Waikiki Aquarium, Waikiki Beach
Looking for a beachfront getaway in Waikiki? Look no further than this convenient property! Just minutes from the most popular attractions, the excitement of Waikiki is all around you! And with comfortable amenities and authentic Hawaiian hospitality, you'll have...
Private Napili Nest Near Beach
Tucked away, yet within minutes of Napili Bay, Kapalua resorts, golf, hiking and restaurants, Napili Nest is a private, remodeled and well-appointed end-unit studio with an A/C, a balcony, peek-a-boo ocean/garden view and thoughtful guest amenities. Located in a quiet,...
Princeville oceanfront 6 bedrooms! Breathing ocean views!
Listing provided by "The Vacation Rental Experts". Contact directly for more options!This listing is made up of THREE 2 bedroom ocean view units in Princeville. Great option for 3 families or several couples traveling together! Total of 6 bedrooms, 6...
Newly remodeled 2bd condo with ocean breeze
Mahina Surf 205 is sure to impress! Stunning tropical hues greet you the moment you walk in. New and modern furnishings, Maui-inspired designs, and artwork throughout the condo transport you to the perfect beachy abode where you can instantly unwind and enjoy the beauty...
Perfect location in the heart of Honolulu
Settle into the lap of luxury, where plush bedding assures pampered restfulness for the weary traveler. Honolulu rises to meet you with an Aloha welcome! Enthroned in the spectacular verdancy of Oahu, Honolulu provides a unique blend of urban vibrancy and unblemished...
Island Paradise home 5 min from the beach
Your family will be close to everything when you stay at this centrally-located place. Our Island Paradise home is just a short 5-minute walk to the beach, offering the perfect blend of convenience and relaxation. This fully furnished midterm rental offers 4 bedrooms, 2...
Royal Sea Cliff Kona 303 Garden View 1BD 1BA
- Ground floor condo near pools and BBQ grills- Covered lanai is 154 square feet/14 square meters- Tile floor throughout unit- Updated kitchen featuring granite counters and stainless-steel appliances- Bedroom with 1 queen bed- Queen sofa bed in the living room-...
Queen Bed | Outrigger Waikiki | Shopping & Dining in Central Waikiki! Gym, Pool!
Aloha, and welcome to your tropical playground on Waikiki Beach!This listing is for a room within a hotel.✦ Your room is 234 sq. ft, equipped with complimentary toiletries, high definition 55-inch TV, available with Standard cable, and Premium cable.✦ Daily cleaning...
Fairways Villas at Waikoloa E4 Golf View 2 Bedroom
- Front office is located at the Kings' Shops, 69-250 Waikoloa Beach Dr., Suite B-13. Office is open daily 9 am - 5 pm. - Kitchen features cooktop and oven, refrigerator, microwave, dishwasher, coffeemaker, toaster, rice cooker, blender, cookware and tableware - Master...
KBM Resorts | FREE CAR | Hale Honu At Montage Kapalua Bay, Sleeps 10! 3-Bedroom Condo with Daily Housekeeping, Spa!
Luxurious ocean view 3-bedroom, 3.5-bath Grand Residence at Montage Kapalua Bay, gourmet kitchen, spacious lanais, and convenient beach and pool access.** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and...
Discovery Bay 1 Bedroom Deluxe Ocean View, Near the Beach!
Experience island living with comfort and style in this 37th-floor ocean-view condo at Discovery Bay! This inviting 1-bedroom unit features a queen bed, sleek vinyl flooring, refreshed furnishings, and a modern design perfect for a relaxing getaway or extended...
Picturesque views of the ocean and Diamond Head
Mesmerizing panoramic views of Diamond Head, the blue Pacific Ocean, the moon and stars! This spacious corner condo is as close as you can get to the sand without being on the beach. Step back in time for this rare opportunity to stay for a while in the home of a...
New Listing! Chic, Cozy, and so Kaanapali
Kaanapali Shores 736 is a charming Studio condo with central air conditioning, comfortably accommodating up to 4 guests. Perched on the seventh floor, this unit features an open-concept design, creating a peaceful island retreat. After a day of adventure, relax on the...
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...
Kaanapali Alii | 192
Kaanapali Alii 192 is a stunning vacation rental located in the prestigious resort town of Kaanapali on the western coastline of Maui. This luxurious one-bedroom (plus den), two-bathroom condominium spans approximately 1,500 square feet, offering ample space and comfort...
Westin Ka'anapali--Spacious Studio with full kitchen-- full resort access
On beach with outdoor pool, near Whalers VillageGuests of this beach resort will appreciate convenient onsite amenities such as a hot tub and a fitness center. Air-conditioned accommodations at this resort offer safes and coffee/tea makers. Rooms open to balconies....
Gorgeous Lahaina Shores 302 – Modern Comforts, Scenic Views, Heart of Lahaina
* NEW PROMO: Stay 5 or more nights from September 1st - October 31, get 1 FREE!Lahaina Shores 302 – 1BD Mountain View CondoLahaina Shores is a charming boutique resort located directly on the oceanfront in the heart of historic Lahaina Town. Unit 302 is a 3rd-floor...
Christmas in Hawaii!!! 2 BR & 2 BA Ocean View in Ko Olina on the island of Oahu
Marriott Ko Olina Beach Club is surrounded by clear blue waters and a picturesque lagoon. Just steps from the ocean on the island of Oahu. Soak up the sun by one of our three outdoor pools, work out in our state-o-the-art fitness center. During your stay enjoy...
Bright 3-bedroom tropical house in Waimanalo Beach Lots
Welcome to our tropical home, a bright and breezy retreat just one block from Oahu's most beautiful beach: four miles of soft sand and gentle waves await you! From the house and patio, you’ll enjoy breathtaking sunset views over the Ko’olau mountains. From the sandy...
Fabulous Renovated Honolulu Loft with A/C
*** Disclosure: All rooms are renovated in a similar fashion. Furniture style may vary in pictures and in the unit. Functionality are all the same. Queen size bed in bedroom, sofa bed in the living room. Free WiFi, free tandem parking allowed to park two cars. Pets...
Spacious 5 bdrm Home steps from Hukilau Beach, AC, Ocean Views, 30-day
This home has a casual Island feel but with updated features. It was fully renovated 8 years ago and within the last 2 months we have given it a mini makeover. We love how spacious and private it feels and also its location right across the street from one of the best...
Royal Sea Cliff Kona 314 Oceanfront 2 Bedroom
- 3rd floor condo located on southwest end of building close to elevator and parking- Private covered balcony and open sundeck- Tile floors throughout- Renovated kitchen with new cabinets and countertops features stovetop, oven, refrigerator, microwave, dishwasher,...