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.
Poipu Ohana Vista - Spacious Home Near Beaches, Community Pool Access
POIPU OHANA VISTA AT KOLOA KAI VACATION RENTALSExperience the essence of Kauai’s beauty and relaxation at Poipu Ohana Vista, a spacious and versatile home ideally located between Poipu Beach and Shipwreck Beach. With breathtaking views of sunrises and sunsets just...
Best of all Worlds: Beach Block; Ocean, Park, & City at hand; Kitchen; WIFI
Legally permitted rental - 134 Kapahulu Ave #919Beautifully decorated extra-large studio with separate kitchen. Queen-size bed, and a sitting area with a futon sofa. On the top floor, with Diamond Head and Palolo Valley views through floor-to-ceiling sound-proofing...
Studio with stunning ocean views at Royal Kahana
Welcome to Royal Kahana 505. This well appointed studio condo features central air conditioning, California King bed, & dining areas both inside & on the lanai. Lay in bed and admire the ocean, whales, sailboats, & the island of Molokai. You'll truly feel the essence of...
Couples Getaway! Beach, Pool, Tennis, AC. Video Tour!
**Escape to Your Peaceful Maui Retreat**Welcome to your island hideaway! Nestled in a quiet, tropical corner of South Kihei, our ground-floor condo offers the perfect blend of comfort, convenience, and tranquility. With lush garden views and easy access—no stairs...
BEACHFRONT RESORT restaurants on site, Ocean & Pool Views!
Our unit is a privately owned hotel room located in the Outrigger Kauai Beach Resort and Spa.Beautiful third floor unit with amazing views of the ocean and pools. Comfortable King bed.The Outrigger Kauai Beach Resort and Spa is a beautiful Hawaiian resort located on 25...
Aston Kaanapali Shores #533: 1 Br Garden View at Ocean Front Resort
For the best use of indoor and outdoor living, this 5th-floor North Kaanapali vacation condominium opens to a large lanai with tropical garden views-perfect to enjoy your morning coffee or afternoon cocktail. This one-bedroom, one-bath features a comfortable living room...
Maui Kamaole G-202 - Spectacular Views, Updated and Elegant, Wi-Fi & Split-AC!
Welcome to your serene island sanctuary, Maui Kamaole G-202. A spacious two-story escape designed to elevate every moment of your Maui vacation. With sweeping ocean views, luxurious finishes, and an open, airy layout, this upscale condo offers the perfect blend of...
OCEANVIEW Studio Condo on world famous Kaanapali Beach! - Whalers 518
Immerse yourself in the luxury and beauty of Kaanapali Beach at this exquisitely remodeled studio condo at the iconic Whaler Resort, perfectly situated adjacent to Whalers Village. Located in Tower I on the 5th floor, this professionally designed retreat offers a...
Emmalani Pool House: Luxury 4BR Princeville Home
Welcome to Emmalani Pool House Escape to this exceptional Kauai vacation home on the stunning North Shore in Princeville. Situated on the Golf Greens, this beautifully upgraded residence boasts a 4-bedrooms and 3 Bathroom and breathtaking views of the golf course and...
Quiet, comfortable and across from gorgeous Charley Young beach
Clean, quiet unit on second floor with pretty garden view and shade on the lanai throughout the day so never too hot to sit outside. Perfect for morning coffee, lunch and evening libations! Quiet master bedroom with king size bed, no traffic noise, just birdsong. Large...
Beautifully Furnished 2 BR, 2 BA Recently Remodeled With Stunning Views.
This friendly, easily accessible and cozy non-smoking end unit is located on the ground floor with gorgeous views of the golf course and breathtaking sunsets. This spacious 2 BR, 2 BA condo was recently remodeled with new furniture and appliances! It accommodates...
First floor condo nestled between Prince Kuhio Park and tropical gardens.
Large, one-bedroom, first floor condo nestled between Prince Kuhio Park and tropical gardens. The living room has great views of the gardens and pool. You can see the ocean from your lanai and, at night, let the sound of the surf lull you to sleep. The kitchen is fully...
Ocean View ~ Pool, Jacuzzi ~ Fitness Center
Spectacular Ocean Views with the Comforts of Home ~ Pack Your Bags..! This is the Ideal Vacation Rental for a Party of Two. Special Occasions will be Most Enjoyed right here... $15.71 Per Day Parking Charged by the Resort upon check-in. Located on the Ocean Bluff. This...
Nihilani Family Condo 24C, New Modern Decor, Spacious and Beautiful!
Three bedrooms with 1 King bed, 1 Queen bed and 2 twin beds, and queen sleeper sofa, 3 full bathrooms, 2 lanai spaces, washer and dryer in unit, 2 car garage, spacious living, garden views, fun resort amenities.This spacious 3 bedroom, 3 bath townhome is a perfect place...
New Listing! Partial ocean views from Kihei condo
Island Surf 303 is a charming 1-bedroom, 1-bathroom condo located on the third floor offering a private balcony to relax and unwind. It comfortably accommodates up to 4 guests. The master bedroom features a queen-sized bed and plenty of closet space, allowing you to...
🏖️Walking Distance to Town | AC | WIFI | vrKCV
vrKCV - Kona Pacific C319, Professionally Managed by Kona Coast VacationsWelcome to Kona Pacific C319 – Your Tranquil Oasis in Downtown Kailua Kona!Nestled on the southern edge of downtown Kailua Kona, Kona Pacific offers you the perfect balance of convenience and...
Newly Renovated Maui paradise condo steps away from the beaches of South Kihei
Condo, 1 Bedroom, 1 Bath, (Sleeps 4)Enjoy this newly renovated (November 2023) quiet unit in Maui Vista, across the street from the fabulous beaches of South Kihei. Unit features high-grade appliances in the well appointed cooks kitchen and stunning hardwood custom...
3br w/so many extras! AC, fitness center, hot tub,, garage, more!
Plantation at Princeville 1322: This elegant air-conditioned Kauai vacation rental at The Plantation at Princeville is close to everything! You'll be just a few minutes drive from great beaches like Anini, Hideaways, and Hanalei. It's one mile to the Princeville...
Beautiful Kihei Kai Nani 162, 1BR Condo by Kamaole Beach 2, Cal King, Wi-Fi, W/D
Beautiful and clean 1-bedroom vacation condo in South Kihei Maui. Kihei Kai Nani complex is directly across the street from Kamaole Beach 2. Walk to restaurants, shopping and fun beach activities. Sleeps 2-4; Cal King bed and Queen sofa bed plus comfy recliner chair....
New! Poipu Paradise - Golf, AC, Pool
Imagine a perfect vacation rental in Poipu, Kauai, where you can relax in comfort and enjoy the best of island living. This 2-bedroom plus loft condo offers everything you need for a memorable stay.Poipu Paradise features two spacious bedrooms, each with comfortable...
Bali Hai- & ocean-view condo with lanai, AC, laundry, 2 pools & 8 tennis courts
Hanalei Bay Resort 6222Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Take in gorgeous views of Hanalei Bay and Bali Hai, and relax in this air-conditioned, second-floor condo at...
Direct Oceanfront. Tranquility and Seclusion ~ Best Oceanfront Value!
30 DAY MINIMUM RENTALPrivate oceanfront house located on Oahu's West (Waianae) Coast near Makaha Surfing Beach. Enjoy the deep-blue ocean and great sunsets from the lanai and large grass lawn. Nap to the sound of the waves. The property fronts coral reefs and is five...
Includes Beach Gear! Vista Waikoloa D302
This vacation rental is professionally managed by ResorticaHawaii Vista Waikoloa D302Please scroll down for detailed informationBedroom Configuration:Master Bedroom: King Bed with ensuite bathroomGuest Bedroom: Queen Bed with ensuite bathroomLiving Room: Twin Fold Out...
Kailuana Beachfront Estate: 5 BR Kailua Oceanfront Home
This property is professionally-managed by Private Homes Hawaii, LLC and is a licensed short-term vacation rental, Non-Conforming Use Permit Number 1990/NUC-1774 for the main house and 1990/NUC-1775 for the guest cottage. It is compliant with Hawaii State Legislation...
Home Away From Home! B104
A LITTLE BIT ABOUT THIS CONDO....Lokelani B104 is a newly remodeled one bedroom premium unit. It has cherry laminate living room floors, maple kitchen cabinets with granite counter tops and a new walk in shower bathroom. The bedroom is carpeted and contains cable TV....
Large private home with pool & ocean views - Inquire about dates!
This property is a legally established dwelling that is rented for periods of 30 consecutive days or more at any one time. Spectacular 4 bed 2 bath home with private pool and breathtaking ocean and mountain views. Situated on the ridge in the highly desired area of...
Poipu Ocean Vista, Inviting home, Panoramic Views
Located in desirable Poipu, this inviting, bright and sunny 2-level island home greets you with panoramic views of the brilliant blue ocean. Hardwood floors and high vaulted ceilings give Poipu Ocean Vista an open and airy feeling. Once you step into this attractive...
Aloha Condos, Kona Coast Resort, Condo 1-304, Ocean View
Aloha - Our "home away from home" has all the comforts of home with ocean views that are endless. This specatular top floor end unit is a spacious 1 bedroom/1 bath 1453 sq ft Island-style villa. Kona Coast Resort unit 1-304 is located at the highest point of the resort...
Inviting ground floor condo with private laundry
Introducing Kihei Resort 110B, your gateway to a tranquil and tropical paradise in the heart of Maui. This cozy 1-bedroom, 1-bathroom unit is designed for up to 4 guests, making it a perfect choice for couples or small families seeking a serene Hawaiian getaway.Situated...
Waikoloa Villas F-100: Lush Villa w/Shared Pools & Spa - Easy Golf Course Access
Welcome to Waikoloa Villas F-100 by Gather, a beautifully remodeled two-bedroom, two-bath condo set on the ninth fairway of the Robert Trent Jones Jr.–designed Waikoloa Village Golf Course. At 900 feet above sea level in South Kohala’s Gold Coast, this quiet retreat...
Lemon Tree - Spacious house, private with a salt water pool & mountain views!
Welcome home to Lemon Tree Hale! Brand new renovation, Instagrammable moments throughout the huge, comfortable house finished in a boho modern design. Perfect for remote work and groups of friends and families, the house features an upstairs office/den as well as...
Enchanting home with pool, hot tub, lanai, balcony, golf nearby, & washer/dryer
Makena-An Island ParadiseOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Aloha, and welcome to this relaxing and homey Hawaiian retreat on the island of Kauai. This vacation rental...
Hale Nalu ~ The Surfer House
This well-appointed unit has a half bath downstairs and two bathrooms upstairs. The master bedroom has a queen bed with a full bathroom with stand-up shower and window air conditioner. The second bedroom upstairs has two twins, and window air conditioner and a full...
Ho\'olei Villas Wailea Kapili - 3 Bedroom Condo Overlooking Pool
This residence has been given the Hawaiian name "Wailea Kapili", which translates to "a Wailea Gathering." It is the perfect accommodation for gathering with friends and family to enjoy the beauty of Maui. This Ho\'olei Residence is a spacious 2,426 square foot three...
Ocean Front Rare Beach View from Villa unit 21b3
Spectacular one bedroom OCEANFRONT Kapalua Bay Villa, unit 21B3. VIEW the ocean and LISTEN to the surf whether you are sitting on the sofa, eating breakfast or resting in bed. The sights and sounds are the same throughout the villa. It's as if you are on the helm of a...
Kailua Palms Guest House with Pool and Views! Parking and wi-fi included
Come bask in the gentle trades of the windward side at the Kailua Palms Estate Guest House, a fabulous two bedroom, two bath vacation guest house located in sleepy Kailua Town near Kailua Beach. The two bedrooms are spacious and comfortable. You will like the relaxed...
Lahaina Shores, Maui Oceanfront Resort.
This Premium studio apartment on the 4th floor was totally remodeled and upgraded. It features a full bathroom with walk in shower, full kitchen, queen size bed and a balcony offering beautiful mountain view. Other property amenities are AC, pool, jacuzzi, 24 hour front...
Konea 314 at Honua Kai Resort ~ Luxuriously Upgraded, Modern Furniture & Floors
Welcome to Konea 314 a luxuriously renovated 690-square-foot third-floor condo with a 135 sq ft private lanai, located in the Konea Tower of the Honua Kai Resort. This recently updated one-bedroom condo boasts beautiful porcelain tile floors and modern furnishings that...
Luxurious Guest home w/Swimming Pool Just Steps away from the Ocean/Beach.
Welcome to this exquisite Japanese-inspired retreat, a sanctuary of elegance and tranquility. This luxurious guest house seamlessly merges architectural sophistication with serene, peaceful vibes. Attached to the main residence yet offering complete privacy through its...
Gated Oceanfront Villa with private access to beach, heated pool & tennis court!
Welcome to Barefoot Kona @ Alii Point. Be one with nature in a family friendly 2 story oceanfront villa, located in an exclusive gated community of only 16 homes - with private access to a heated pool, tennis court and a beach where lava rocks meet the sea!A meandering...
Waikoloa Fairways 2-bed, 2.5-bath golf-front paradise with AC + spacious lanai
Turn moments into memories at this two-bedroom, two-and-a-half-bath Waikoloa Fairways property. A golfer's paradise as the property sits right on holes 3 and 4 at Waikoloa Village Golf Course, designed by Robert Trent Jones Jr. This property offers dual suites, central...
2 units back from Oceanfront, Views of Lanai Island and the beautiful courtyard
The Kitchen and foyer have been remodeled in 2020. Custom art work .The Whaler is located in the heart of Ka'anapali. Whalers village is right next door. There is shopping ,restaurants and convience stores. Golfing is nearby. The beautiful catamarans come right up in...
Cozy stay just 5 minute drive to Volcano National Park, Winery and Golf!
A warm room awaits in a home on a quiet cul de sac in the Volcano Golfcourse and Country club. Minutes from the entrance of Hawaiʻi Volcanoes National Park, Historic Volcano Village, golf course and Winery. A covered garage with private entrance leads to a completely...
Spectacular Oceanfront Views with Split AC -Wailea
Kihei Surfside #507 features Incredible views from the lanai, kitchen, dining, and living areas. Completely renovated featuring porcelain tile flooring, custom cabinetry, granite countertops, and a fully equipped kitchen with stainless steel appliances. Bath has a...
Breathtaking Ocean Views, Nestled Between Two Stunning Beaches! Royal Mauian 606
Royal Mauian #606 – Oceanfront Comfort with Modern UpgradesRoyal Mauian #606 is a beautifully upgraded two-bedroom, two-bathroom condo set on the sixth floor of one of South Kihei’s most desirable oceanfront properties. Offering direct access to the sandy shores of...
Fully Remodeled in 2021 All new Furniture
Fully Remodeled in 2021 All new FurnitureThis 2 bedroom, 2 bathroom condo (#602) is perfect no matter what you want out of your vacation. You will be located on one of the best beaches on Maui. Our unit has one of the top 6 locations at Mana Kai, being all the way in...
Panoramic Oceanfront Views - Royal Kahana 911
Stunning ocean front views from the 9th floor in this beautifully remodeled & tastefully furnished condo on Kahana Bay. A large wrap-around lanai, accessible from the living room and master bedroom, adds to the view. In addition to the HD TV & Blu-Ray DVD player in the...
Maui Resort Rentals: Honua Kai Konea 739 - Stunning 7th Floor Ocean View 2BR w/ Deluxe Corner Floor Plan!
As one of the finest two-bedroom suites available to rent at the entire Honua Kai Resort, Konea 739 boasts an exceptional 7th-floor corner vantage point and is among a class of the most sought-after 2 bedroom floor plans at Honua Kai.What distinguishes this column in...
Oceanfront 1 bedroom + loft with Beach BBQ & Pool !
With oceanfront views and an unbeatable location near shops and restaurants, Hale Kai puts you in a central position for the ultimate Hawaiian getaway. This unit features a private bedroom with king size bed, a private den upstairs with a sofa sleeper, and a pull out...
Real Affordable Luxury~1250 s.f Beauty~ Big Beachfront End Unit
This is a Beautiful and Spacious apartment in a truly unique location on Oahu...An uncrowded stunning beach on the Sunny/Dry Leeward side of the island. This 4th floor, 1250 sq ft. unit includes a private wrap-around lanai where you can relax and take in the...