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.
1 bedroom 1 bath guest house. 1 queen bed. Comfortably sleeps 2. Walking to shopping, surf, beaches. Close to Waikiki. Private access. Kitchenette. Air conditioning. Access to shared home gym/ treadmill and yard. Ample parking available.
2 Spacious Room Perfect For Family Stay with Balcony | Free Breakfast
Unwind in a spacious suite with private lanai, deep soaking tub, free WiFi, and plush bedding. Enjoy continental breakfast with Kona coffee, then stroll to Waikiki Beach or nearby shops. After exploring, relax by koi ponds or dip in the pool. Perfect for couples,...
Lahaina Shores PH5 Penthouse! Enjoy Stunning Ocean Views, Pool, Hot Tub
Lahaina Shores PH5 NEW LISTING Spectacular Direct Ocean Views from this 1Bedroom West Maui Penthouse 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...
New listing: Oceanfront Oasis on Maui - Ocean View Aston Kaanapali Shores 606
Welcome to Kaanapali Shores 606 – Your Oceanfront Oasis on MauiNew Listing! This condo was previously managed by the front desk program and just transitioned to private management—so no guest reviews yet, but it’s the same great unit with even better service.Step into...
Dreamy Waikiki Condo, Steps to Beach, Free Parking
Aloha! Welcome to our stunning boutique corner unit condo steps away from Waikiki beach! The location is truly best in class. Dine, swim, surf and shop all within walking distance. This unit is a 100% legal VRBO rental. You will be staying at a beautifully renovated...
Kaanapali Alii 11022 Bedrooms | 2 Bathrooms | Sleeps 4 | Ocean View________________________________________Welcome to Kaanapali Alii 1102, an elegant one-bedroom ocean-view condo, with a fully enclosed den that comfortably serves as a second bedroom. This residence...
Gorgeous 6 bedrooms for 16 Lahaina Maui ocean view penthouse
Gorgeous 6 bedrooms for 16 Lahaina Maui ocean view penthouse! This gorgeous 6 bedrooms 5 baths for 16 is made up of two separate 3 bedroom ocean view penthouses! The complex features 2 pools, cabanas, tennis courts, putting greens, shuffleboard and plenty of gas BBQ's...
Complete Renovation - Everything Brand New | Wailea Ekahi 6F
Wailea Ekahi Village 6F is a premier vacation rental located in the heart of Wailea, Maui. This one-bedroom, two-bathroom condo located within the resort community of the Wailea Ekahi Village, a low-density collection of condo clusters set across 34 acres of beautifully...
2BR just 1.6 mi from the Ironman Run Course
Perfect for Ironman! Nestled in Kailua-Kona, this spacious, professionally managed suite offers modern amenities with a Hawaiian touch. Just 1.6 miles from the Ironman starting point, nearby beaches, and local attractions, it’s the ideal spot for athletes and families.•...
Charming cabin in Pāhoa for a peaceful getaway
Unwind in Pāhoa at this peaceful cabin. With a cozy living room featuring a comfortable queen bed, guests can relax after a day of exploring. The bathroom offers a refreshing rainfall shower and skylight for a wonderful start to the day. Experience what Pāhoa has to...
Pili Mai 13M - Golf Course Villa in Poipu by Coldwell Banker
Pili Mai 13M - Golf Course Villa in PoipuThis beautiful, ground-floor villa in exclusive Pili Mai Resort combines modern luxury with all the conveniences of Poi'pu.Nestled within the exclusive Pili Mai Resort, this lovingly maintained 3-bedroom, 3-bathroom sanctuary...
Marvel at Panoramic Views from Your Island-Style Suite w/ Balcony & Living Area
Our villa offers sweeping Pacific Ocean views and island breezes from a private lanai. Enjoy bamboo linens, a gourmet kitchen, and access to the oceanfront club with lagoon pool and seaside dining. Steps from Waikoloa Beach Resort golf and minutes to Hapuna Beach,...
Your Holiday Paradise! Marriott's Kauai Beach Club Garden Suite
Listing Summary:Escape to paradise this holiday season! Secure your spot at the luxurious Marriott's Kauai Beach Club, perfectly located on the golden sands of Kalapaki Beach. This elegant Garden View Parlor Suite is your ideal home base for exploring the Garden Isle....
Royal Kahana Maui 120 Garden View 2 Bedroom 2 Bath
This inviting two-bedroom garden-view unit provides a serene setting surrounded by lush greenery, ideal for families or small groups looking to unwind while staying close to Maui’s beautiful coastline. Unit 120 Garden View 2 Bedroom 2 Bath• First floor condo in a garden...
Amazing views! Exclusive & peaceful Hawaii Kai. Walk to ocean & hikes, Pool, AC,
A pristine, quiet neighborhood on the backside of Hanauma Bay, your Honolulu/Oahu adventure begins at this lovely 4-bedroom house. With 2 king beds, 1 full bed, and 1 queen bed, this newly rebuilt property is perfect for families or small groups of friends. Three of the...
Deluxe Garden View w/WiFi & A/C-Maui Banyan
Maui Banyan T108A: Tasteful artwork, chic floral patterns, and rustic island color tones set the mood in this wide-open 1st-floor unit that boasts sleek hardwood flooring and oversized garden-facing windows. The functional layout is furnished with premium furniture that...
Hale Nalu (Lower Level) by Gather: Oceanfront w/ Lanai, Grill & Views
At Hale Nalu (Lower Level), the Pacific Ocean stretches out from your backyard while the famous beaches of O'ahu’s North Shore frame your days. This three-bedroom, two-bath home offers relaxed beachfront living with its own full kitchen, living spaces, and covered...
Peaceful Ground Floor Unit- Hale Kaileia Kai with Infinite Pool & Hot tub
Welcome to your serene island hideaway at Fairway Villas #C2, in the beautiful Wāikoloa Beach Resort on the Kohala Coast. This spacious 2-bed, 2-bath ground-floor villa (1,170 SF) blends modern comfort with relaxed resort living. Enjoy golf course + Mauna Kea views from...
Stunning Studio w/Pool & Includes Free Dedicated Parking Space
Welcome to this charming studio in Honolulu. Guests will find a tremendous living area featuring a comfortable queen bed and sofabed (for 3rd guest), perfect for relaxing after a day of exploring. The bathroom includes a refreshing shower and a handy hair dryer for...
Ideal Long term remote work space close to the beach
Enjoy the sound of the birds and the convenience of being in Lahaina. Workout facility, community pool and short walk to the beach. Spacious kitchen with eat in counter. Van also available for additional fee and long term rentals. Pet friendly community.
KBM Resorts: Napili Point, NAP-B26, 1 Bedroom Condo w/ luxury amenities, Includes Free Rental Car!
** 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...
Live Local Redwood Pole house panaramic Ocean views quiet convienent nbrhood
. Wailupe is on mountain side , 5 blocks facing ocean. enjoy tennis, bball/park across street, great views. Convenient location to town, Waikiki 4 miles away. Two bedrooms in large great room. Main bedroom has a queen size bed, sons room has a twin, and living room has...
Maui Resort Rentals: Honua Kai – 4 Total Bedrooms + Den w/ Beautiful Ocean & Mountain Views!
Unquestionably one of Honua Kai’s best values, this exceptional 4BR plus den offering combines two neighboring partial oceanview suites with an adjacent mountain view suite. Together, the residences provide the perfect retreat for large groups or families seeking a...
Marriott's Ko Olina Beach Club | Two-Bedroom Villa
Summary:Find your happy place at a beautiful villa at Marriott's Ko Olina Beach Club, right on Oahu's gorgeous western coast. Imagine yourself relaxing on the beach, swimming in the clear lagoons, and enjoying all the great things the Ko Olina Resort & Marina has to...
Diamondhead / Ocean View Waikiki Condo on 38th Fl
Located central to Waikiki, just a block away from the famous International Market and mall, walking distance to the beach, restaurants, and more. The condo comes with a very spacious lanai (balcony) that invites the fresh Hawaiian breeze with 180° views, super comfy...
Ka’anapali Alii 4643 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean View________________________________________Welcome to Kaanpali Alii 464, a gorgeous two-bedroom condo with an additional enclosed den that serves as the third bedroom. The den has a queen bed that can...
Aqua Aloha Surf Waikiki 209 Moderate Studio with Partial City Views, Sleeps 2
Aqua Aloha Surf Waikiki 209 Moderate Studio with Partial City Views located just 2 Blocks to Waikiki Beach, (1) Queen bed, Sleeps 2, 219 Sq FtAqua Aloha Surf Waikiki brimming with island personality offers a range of accommodations that are perfect for couples and solo...
Family Retreat In Beautiful and Lush North Shore
Welcome to Mauna Kai 2B, your home away from home, situated between mountains and ocean. The whole group will enjoy easy access to all North Shore attractions from this centrally located condo. Surrounded by lush tropical gardens and a residential feel, this is the...
Maui Resort Rentals: Kaanapali Alii - 4BR Retreat with Ocean and Mountain Views!
Suite 241 is ideally situated within one of the resort’s most desirable interior columns, showcasing sweeping views of the Pacific Ocean, the island of Lanai, and the impeccably landscaped Kaanapali Alii grounds below. These captivating vistas extend effortlessly...
Ocean View Queen Room at Kaimana Beach Hotel | Right on the Beach
Nestled between the iconic Diamond Head and Waikiki Beach, Kaimana Beach Hotel combines coastal charm with easy access to local attractions. The Ocean View Queen offers partial ocean views and a relaxed island atmosphere. It's a perfect hideaway to watch the waves and...
2BR+Den High Floor Ocean View Free Parking
Enjoy ocean and city views from this spacious 2BR+Den condo 798 sqft/74 sqm at high floor with floor-to-ceiling windows. Save $$$ with secured free parking in the building plus free wifi and fully equipped kitchen. Walk to the best restaurants and bars, Chinatown, and...
Amazing Kauai 2 BR Condo Ocean View Location ~ Beautiful Interior ~
BEAUTIFUL Princeville, KAUAI, check-in, Saturday to Saturday: This is paradise on a bluff -Amazing Ocean View ~ Amazing Location ~ Amazing Interior ~ • Paradise Found..! Surrounded by Lush Tropical Landscape ~ On a bluff on the north shore of Kauai, The Cliffs Club...
Oceanfront Maui Retreat Steps From Sugar Beach
Kanaʻi A Nalu | Central Location | 4th-Floor Corner UnitWake up to the sound of the waves and end your evenings watching the sun melt into the Pacific. This oceanfront Wailuku vacation rental condo celebrates slow mornings, uncrowded beaches, and lanai sunsets. Stroll...
Just Listed! Oceanfront Paradise Views and Luxury
Relax and replenish at this lovely and clean hotel room at the sought-after Outrigger Kauai Beach Resort. Situated with amazing views of the pools, ocean, and tropical paradise of the unmatched landscape . See the sunrise from your private lanai over the Pacific while...
Wyndham Makai Club Cottages|Two 2BR/2BA Suites - Sleeps 12!
Summary:Explore all the beauty, fun, and heritage of the “Garden Island” from your private cottage, situated serenely along the first fairway of the Trent Jones-designed Makai Golf Course in beautiful Princeville.The Space:This listing is for two suites at Club Wyndham...
3 Ko Olina Beachfront Resort & Spa, First Class!
Marriott Ko Olina Beach Club is located on the stunning western shore of Oahu, offering a tropical paradise experience with breathtaking views and luxurious amenities. Upon arrival, guests are greeted by beautiful waterfalls and fountains, setting the tone for the...
Kapalua Ridge Villas | Ocean Views, Grass Lawn | KBM Resorts | 2 Units, 3 Bedrooms | KRV ML-2516
** 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...
Kihei Condo 8-363 - Steps to Kam II Beach and Sunsets
Welcome to your perfect Maui getaway at Kihei Kai Nani 8-363, where Aloha Chic design meets stunning sunset, sunrise and mountain views. This thoughtfully appointed 1-bedroom condo is at the back of the property, furthest from the main road, making it more peaceful....
Ilikai Hotel Condo with Ocean, Lagoon & Fireworks Views
Book with confidence! This property is professionally managed by Ali'i Beach Rentals, an award-winning property management company.Welcome to your island escape at the iconic Ilikai Hotel, where this beautifully appointed corner unit on the 8th floor offers stunning,...
Waikiki Compact Family Room 10Guests /2 Studio/ 2Full bathroom
This Waikiki Sudio/condo, nestled against an iconic backdrop, is truly one of the area's hidden gems! Close to everything, it offers modern accommodations, canal views from its upper floors, and free access to condo amenities: an outdoor pool on the 6th floor and...
Enjoy this 18th-floor 1br apartment with stunning ocean and Diamond Head views!
This newly renovated 18th-floor 1br apartment is the perfect retreat for up to 4 guests, offering beautiful diamond head, ocean and city views in the heart of Waikiki. Just a short stroll from world-famous beaches, you’ll be swimming, surfing, or snorkeling in no time....
Waikiki Gem! Renovated, Steps Away From The Beach!
Prime location and fully renovated studio! Revel in vibrant hues, new furnishings, and a lanai offering a peekaboo ocean view. Enjoy comfort with a kitchenette including basic cooking utensils and a luxurious bathroom. Explore our modern oasis, ideally located within...
Waipouli Beach Resort Courtyard View 1 BD 2 BA
Courtyard View 1 Bedroom 2 Bath- Spacious condo offers full kitchen to include granite countertops and includes Wolf cooktop and convection oven, microwave, 2-drawer Fisher-Paykel dishwasher, full size Sub-zero refrigerator, coffee maker, blender, toaster, cookware and...
Aqua Aloha Surf Waikiki 1208 Deluxe Studio with Lanai and Partial City Views
Aqua Aloha Surf Waikiki 1208 Deluxe Studio with Lanai and Partial City Views located just 2 Blocks to Waikiki Beach, (1) Full/double bed, (1) Twin bed + (1) Queen sofa sleeper, sleeps 4, 365 St FtAqua Aloha Surf Waikiki brimming with island personality offers a range of...
Charming Coconut Plantations 2/2.5 Townhome in Ko Olina Resort Community
Situated on the 13th fairway of the famous Ko Olina Resort, overlooking a beautiful pond inhabited by the graceful Ko Olina black swans, this fully furnished single level, 2 bdrm, 2.5 bath home feels like your own private oasis in an exclusive gated community. This...
Kainani Vacation Home 10: 5 BR Ocean View Home with Pool
Welcome to Kainani Vacation Home 10- where trade winds, golden sunsets, and effortless island living come together in one stunning home. With ocean and golf course views, nearly 4,700 square feet of indoor-outdoor living, and a layout designed for gathering, relaxing,...
** 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...
Royal Kahana Maui 410 Oceanfront 2 Bedroom
Step into your oceanfront two-bedroom retreat with expansive views of the Pacific, just moments from the beach. Ideal for families, couples, or friends seeking a memorable Maui escape. Unit 410 Oceanfront 2 Bedroom 2.5 Bath• 4th floor condo with large balcony with views...
Regency 620 - Beautiful 3 Bedroom Overlooking Regency Pool
Summary:Top-floor 3-bedroom, 3-bath home in Poipu Kai with central A/C, vaulted ceilings, two private balconies, and access to Regency pools and hot tubs. Walk to Poipu Beach, Brennecke’s Beach, and coastal trails.The Space:REGENCY 620 AT KOLOA KAI VACATION...
Comfortable, Spacious with Great Location in Waikiki!
1 Bedroom Ocean View on the 9th Floor of Discovery Bay! Fully equipped and furnished condo with complete kitchen including dishwasher and built-in microwave. Unit has been recently updated with new furnishings and artwork and new refrigerator and range. The remodeled...