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.
Kailua-Kona Estate – Luxury Mansion
Welcome to the largest home* on the Big Island! Highlights include the 100' infinity edge pool, new outdoor pickleball court, 16+ person movie room, and a ~2000 sqft great room.“The place is out of this world beautiful.” – Anca, 5-Star Review“The view...
COUNTRY CLUB VILLAS 242 - OCEAN & GOLF COURSE VIEWS
Enjoy panoramic coastline views and year-round sunsets from our wonderful two bedroom, two bath, bright, airy and tropically furnished corner condo overlooking the 17th fairway of Kona Country Club's Ocean Golf Course. An impeccably maintained golf courses surrounding...
Luxe Private Cliffside Oasis at Kalapaki Beach!
Discover the very best of Kauai from the comfort & convenience of this private oceanfront retreat! Experience kayaking, surfing & relaxing on Kalapaki Beach just steps away, or simply step outside to enjoy incredible ocean views overlooking Nawiliwili Harbor from your...
Two Hawaiian cottages with Diamond Head views - walk to Waikiki
Garden Cottage A & B - 30-Night MinimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Ideal for groups who want both togetherness and privacy, this pair of vintage-inspired Hawaiian...
Second Floor Condo with Free WiFi, Furnished Lanai, Shared Pool, Hot Tub, Tennis
Kamaole Sands 8-205Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Take a well-deserved break and relax at this second-floor getaway located across the road from Kamaole Beach Park...
Deluxe One BR w/ 4 Beds Waikiki Banyan includes Free Parking!
Waikiki Banyan Upper Floor Condo with Partial Ocean Views from the Lanai, Bedroom, and Living Room! Sleeps up to 4 with 2 Full Beds in the Bedroom plus 1 Full Sofa Bed in the Living Room (Note: 2nd Grey Queen Sofa not for sleeping). TVs in Both Rooms, FREE WiFi, and...
Gorgeous 12th floor central Waikiki Ocean View Studio Suite
2425 Kuhio Ave., #1201 ** Newly remodeled and updated :) **** For your health and safety, we utilize additional Sterilization procedures between reservations.This ocean facing 12th floor studio Suite offers two lanais (one overlooks pool & has an ocean view), in-room...
Rare 3 Bedroom heart of Downtown!
Prior to booking please read our "Host Disclosure"(Based on availability & length of stay, Parking Fee may be waived - pls inquire)This spacious unit is located in the same building as the Aston Hotel at Executive Center downtown Honolulu. You will treat yourself and...
Classic Hawaiian condo with WiFi, mountain views, pool, & hot tub
Pali Ke Kua #8Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Pali Ke Kua 8 is a ground-level condo that opens out to the expansive green lawn with gorgeous mountain views. Pali Ke...
Kalani Kai#104 1st Floor, Remodeled Unit in Heart of Kona Town! Best location
Very Unique Kalani Kai condo that's located in the heart of Kailua-Kona. Walking Distance to Everywhere in Town! Vinyl Plank Flooring throughout! No carpet! You'll appreciate a remodeled, fully equipped kitchen with quartz countertops, good quality cabinets, Dishwasher,...
Direct Oceanfront Newly Remodeled!
Hosted by VacaMauiWe chose Maalaea Banyans because of it's fabulous views sitting right right on the ocean.The unit was finished being remodeled in August 2023. Stainless steel appliances, split air conditioning, quartz countertops, and beach gear are some of the...
Kamaole Sands 1 BR Partial Ocean View #2-302
Celebrate another dreamy day in this 818sf suite overlooking tropical gardens and offshore islands. Relax on the lanai with Surfing Goat cheeses and Maui wine. Comforts include a full kitchen, washer/dryer, WiFi, flat screens, DVD, air conditioning and ceiling fans....
Oceanfront RARE Kaanapali premier cornerVU Penthouse2bb Resort
Brand New, $150,000 modern kitchen/vanities with surround Aquarium murals. Brand New sliding doors $35,000. New $10000 Morrocan Rug! Brand New Stainless Steel Refrigerator and New Stainless Steel Oven and new SS Hood. New red Kitchen-aid toaster, New Red Teapot, also,...
Garden view condo on beachfront resort with A/C
Hono Kai A16 is a 1-bedroom, 1-bathroom condo that offers 1 window A/C located in the bedroom, additionally, there is easy ground-floor access. Unit A16 can accommodate up to 4 guests. The master bedroom is equipped with a king-size bed and a ceiling fan. For additional...
Valley Isle 403 2B/2B Oceanview, AC - Spring Deals! Book April/May and SAVE BIG!
Overlooking a sandy beach protected by coral reefs, you will fall in love with the impressive oceanfront views and colorful sunsets that set the sky ablaze with a spectacle of colors. As if that's not enough, you will be conveniently located to the West Maui airport,...
Plantation Hale J16-AC: Ocean Facing Unit, King Bed, AC, Next to Marketplace
Plantation Hale Suites Unit J-16, Royal Coconut Coast, Wailua, Kauai Vacation Rental.*New luxury vinyl flooring and updated walk-in shower*One bedroom, 1 bath condo, 2nd floor end unit with a King bed and a queen sofa sleeper*Ocean facing unit with distant ocean views....
Kauai Mermaid Queen Sanctuary - Sleeps 16 - A/C!
Summary:Discover the epitome of luxury in our spacious and updated retreat boasting breathtaking mountain, waterfall, and ocean views. Situated within walking distance of beach trails and the enchanting Queens Bath, our home is gracefully backed up to the renowned Makai...
Oceanfront KUL716 - Beautiful Beachfront Corner Condo Great Ocean View!
**2025 Discounted Rates - Book Now! **Experience the ultimate Maui vacation in this beautiful oceanfront condo! Perched on the second floor, this one-bedroom, one-bathroom unit offers stunning views of the beach and the crystal-clear waters of the Pacific Ocean. As you...
Near Golf Course and Ocean, Large Lanai, Top Floor
Welcome to your peaceful Waikoloa escape - a tropical retreat made for relaxation & island ease! Enjoy sunny days, gentle breezes & comfort in every corner:- Sleeps 4 | 2 bedrooms | 2 beds | 2 baths- Shared pool, hot tub, tennis courts & gym- Large furnished lanai w/...
Wailea Ike by AvantStay | Walk to the Beach | Balcony w/ Views
Pack your swimwear and prepare for an unforgettable getaway at this newly renovated condo, where every morning greets you with stunning balcony views of lush landscapes rolling down to the ocean. This condo is within walking distance of the beach, the Wailea shops,...
Molokai Shores 131
Molokai Shores unit #131, on the ground floor: Stroll across a manicured lawn from the ground floor lanai of your renovated oceanfront suite to a gorgeous beach. The beach is perfect for a morning stroll or an evening of stargazing. Celebrate with an evening toast on...
Condo with expansive ocean views from the kitchen, lanai & primary suite
Makanui at Poipu Resort 222Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This two-bedroom, two-bath with two-bed bonus loft is a Hawaiian-themed oasis surrounded by lush tropical...
Honu Hale | Minutes away from the beach!
Summary:This two-bedroom condo in Kailua-Kona is the perfect getaway for small groups looking to make the most of their Hawaiian vacation. Maximum occupancy strictly enforced in accordance with local ordinances.The Space:This oceanfront complex has an amazing location...
Ocean/Diamond head view condo at Waikiki Banyan. Free Parking! Centrally located
Welcome to your perfect island getaway at the Waikiki Banyan! This 1-bedroom, 1-bathroom condo comfortably sleeps up to 4 guests and features stunning ocean views and an iconic view of Diamond Head from your private lanai. Whether you're enjoying your morning coffee or...
Kihei Akahi Resort C603 Beautiful Ocean View
"Escape to Maui and Experience Warm Aloha! Enjoy Last-Minute Deals Through March 2026!".Two Way Split AC in Living Room and Bedroom - Top Floor with Great Ocean View.Kihei Akahi C603 located on the top floor of building C at the Kihei Akahi Resort. Enjoy spectacular...
Oceanfront condo with balcony, great view, pool, hot tub - 50 ft to beach
Pono Kai Resort B208Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Gorgeously situated only 50 feet from the sandy beach in Kapa'a, this recently remodeled oceanfront condo at Pono...
Exquisite interior updates and stunning ocean view
Kaanapali Shores 849 is a 1-bedroom, 1-bathroom condo with central air conditioning that can accommodate up to 4 guests. Located on the 8th floor, you'll find an open-concept layout and Hawaiian-inspired furniture and decor. When it's time to rest, the bedroom features...
Updated Oceanfront Condo! Long clean beaches to walk & swim! Escape the Crowds!
Our Hawaiian Paradise Vacation awaits you here in our uniquely remodeled Hale. Be a part of our Ohana and escape to the Hawaiian countryside, leaving behind the hustle and bustle of Waikiki with its crowded beaches and enjoy a private serene beach with amazing views and...
Kihei Akahi D210: 1BR/1BA with Ocean Views, Updated Interior, and Prime Location
This property is hotel zoned, and not being affected by the recent proposed legislation.Kihei Akahi D210, Great location with views of the ocean! This 1 bedroom/1 bath is centrally located in Kihei and perfect for couples or small families. This condo has been nicely...
RENOVATED Studio By The Ocean!!!
Aloha Kakou! Thank you for checking out my unit near the beach. I have a kitchen to test out your cooking skills and a balcony overlooking the pool for your morning coffee and a glass of wine at night! Historic Kona town is steps away with open-air eateries,...
Beautiful Oceanfront Resort With Walk Out Lanai to the 4 Resort Pools and Beach
Our unit is a privately owned hotel room located in the Outrigger Kauai Beach Resort and Spa.This is a serine ground floor unit with 2 queen beds and a gorgeous view of the pools and resort. Walk out your lanai and walk straight to the pools and within a couple of...
Mahana 1111 • Direct Ocean Views & Beachfront
This is a legally permitted vacation rental and hotel zone according to the County of Maui ordinances.Mahana 1111 – Your Oceanfront Paradise on Kaanapali Beach Welcome to your stunning, direct oceanfront 2-bedroom, 2-bathroom luxury condominium located on the pristine...
Lofted Lahaina gem pool, ocean view, & high-speed WiFi
Mahina Surf 206Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Find peace and serenity by the water here in Lahaina and call this lofted getaway home for a little while! Whether you...
Wailua Bay View condo near surf & sand with pool, ocean views & W/D
Wailua Bay View 307Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Wailua Bay View Kauai vacation condos are exactly what you have been looking for. Located on the Coconut Coast,...
Kona Mansions#309 Top Floor,Beautiful, AC, Located in Heart of Town
Welcome to Kona Mansions, Unit#C-309! Beautiful Top Floor Unit in Heart of Kona Town, Walk to everything! Located in downtown Kailua, this front row, third-floor unit has spectacular ocean views in Kona Mansions condos. Walk to Ali'i Drive and experience great...
Beautiful Ko'olau Mountain Views! AC, one FREE Parking and Wi-Fi!
Waikiki Sunset #1211 – 229 Paoakalani Ave.Enjoy majestic Ko'olau Mountain views by day and sparkling city lights at night from this 12th floor, one-bedroom condo (546 sq.ft. plus 55 sq. ft. balcony/lanai with table and chairs) with central A/C, and it’s just 2...
Stunning, Fully Remodeled, Luxury Condo
This renovated and tastefully decorated 650 sq. ft. condo provides 1 bedroom and 2 bathrooms. Spacious and airy with a modern Hawaiian feel, take the time to relax in this oasis after a nearby yoga class or long beach walk. Beautiful pathways guide you through tropical...
Shores at Waikoloa Beach Resort 315
Summary:This tropical top floor penthouse offers beautiful resort views and peek a boo ocean views that look towards the Hilton Waikoloa hotel. The Waikoloa Beach Resort features luscious greenery, koi ponds, a shared swimming pool, a fitness room, and BBQ stations to...
Cozy Condo Located in the Heart of Kihei
Hawaii Tax ID: TA-054-572-6464-01TMK: 390180030141Aloha and Welcome to Maui Vista 2220! Discover the perfect blend of comfort, convenience, and island charm in this 1-bedroom, 1-bathroom condo located in the heart of Kihei. Whether you're seeking beach days, island...
Rolling surf, gentle trade winds, and unparalleled ocean views await you!
Seabreeze #7 – 3065 Kalakaua Ave.(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)Enjoy 180-degree unobstructed panoramic views of the Pacific from this oceanfront property on Diamond Head's coveted Gold Coast.You'll have the entire 7th floor to...
Ocean & Diamond Head Views! Full Kitchen, Lanai, 1 Free Parking! Sleeps 6
Waikiki Sunset #2514 – 229 Paoakalani Ave.Popular 2-bedroom, 1-bath condo (604 sf plus 56-sf lanai, sleeps 6) positioned on the 25th floor in the preferred corner end suite stack with central A/C and spectacular views of Diamond Head, Kapiolani Park, and the Pacific...
Incredible Kekaha Beachfront Estate for 10!
Listing provided by "The Vacation Rental Experts". Contact directly for more options!Main Home: This custom home is on a ocean front estate. It has three bedrooms and three bathrooms. The home has large sliding doors that disappear into the walls so you won't know where...
Captivating Ocean Views at Spectacularly Located Makena Surf Resort #C-205
Makena Surf C205Makena Surf Resort, located in the exclusive Makena area, offers a secluded beachfront retreat surrounded by lush tropical landscaping. This gated property features six two- and three-story buildings, each designed to maximize stunning views of the...
Large corner unit Condo in the heart of Waikiki. Easy walk to the beach!
Large recently updated condo only 3 blocks from the beach. Room for up to 4 people with one king size bed in the bedroom and two twin size futons in the living room. Quiet corner unit with a well stocked kitchen, fast wifi, and cable TV. Located in the Hawaiian King...
Aston Kaanapali Shores - 2BR Garden View - NO Resort or Cleaning Fees
All of our guests have complimentary access to our Maui specialist and support team during their stay.*This condo is in the Aston rental program and is subject to a $10.95/day parking fee to be paid to the front desk on property. {A valid credit card is required to...
3 Bedroom Suite w/Loft – Kamaole Sands 1401
Kick back and relax in this 1,577-square-foot, two-story, condominium with a stylish kitchen, cool tile floors, and tropical décor. Located on the 4th floor, its lanai offers expansive views of the resort’s lush, tropical gardens and partial views of Kamaole Beach...
8th floor 1bd with great oceanfront views
Enjoy panoramic ocean views from this gorgeous oceanfront condo, Maui Kai 801! It doesn't get more oceanfront than this! Here you will enjoy spectacular sunsets year round, whale watching during winter months, and spotting turtles swimming below while drinking your...
Located in the Heart of Waikiki! Free parking & W/D in the unit!
The Marine Surf Condominium is located right in the middle of Waikiki. This is a breezy and cozy corner unit at Marine surf. The unit was renovated in May 2011. This unit has a unique layout of 1 full bath and 1 half bath for guest convenience. Enjoy the mountain view...
Largest Private Patio on the Ocean and Air-Conditioning
Newly remodeled unit just made available for rentals. This was our home in the 70's and now our vacation home. We want you to enjoy old Hawaii the way we did when we were first married. This is a quiet get away from the hustle of Waikiki but can be reached in under an...
The Drifter - North Shore Loft - Relaxed Luxury
Welcome to The Drifter!! Part of the Kuilima Estates East community, the unit was designed with the goal of offering a “Relaxed Luxury” experience. Meaning, to provide guests with an elevated design aesthetic with a feel-good comfortability. The unit is a loft-style...