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.
Oceanfront Home w/ Incredible Lanai, Great Ocean View, WiFi, Washer/Dryer
Hale AikalaniOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'The open waters of the Pacific Ocean are right in your backyard at this modern and comfortable home just outside Pahoa,...
Hale Kainani #6 E Komo Mai: Secluded Luxury Home w/ Pool, Spa, AC & Ocean Views
Hale Kainani 6E Komo MaiSet within the exclusive resort community of Kukui`ula, this luxury Poipu vacation rental offers the ultimate location for your group getaway. The home is brand-new, finished and furnished in comfortable elegance with natural tones for a peaceful...
Luxurious 4BR/3.5BA House: AC, Short Walk To Beach
Discover Elegance at Poipu: The Ohana House hosted by BlueTideVillas.Step into the luxury of the Ohana House, a 2,800-square-foot haven nestled on a half-acre oasis, boasting a sprawling private lanai—perfect for savoring your favorite tropical drink. Celebrated as...
New Upscale Kona Retreat, Ocean Views, Pool, BBQ
Welcome to paradise in Kailua-Kona, Hawaii! 🌴 Escape to this stunning 3-bedroom, 2-bathroom oasis boasting breathtaking ocean views and a private pool for the ultimate Hawaiian getaway. Wake up to the panoramic views of the Pacific Ocean right from your private...
Breathtaking Transformation! Luxury 3-BR Oceanfront Condo
When you walk into this oceanfront townhouse the first thing you notice through its expansive windows is the shimmering sea, which is so close it seems to fill up the room. Your eye is drawn across the channel to the neighbor islands of Lana`i and Moloka`i, green...
Wailea Ekahi Village 19B - 2 Bedroom Ocean View Condo
Wailea Ekahi Village 19B is a two-story, two-bedroom, two-and-a-half-bath townhome that comfortably accommodates up to four guests. This beautifully designed residence features island-inspired décor, creating a cozy and inviting atmosphere perfect for families or...
Kona Coast Condo w/ Lanai & Outdoor Kitchen!
Plan your next tropical getaway and book this Kamuela condo for a week of beach exploration from the comfort of a tropical sanctuary. Located just a mile away from Holoholokai Beach Park, this 2-bedroom, 2.5 bathroom vacation rental lets you experience authentic Hawaii...
Ocean Front! Stunning Remodel in 2024! 102 Kona Riviera
Ocean Front Stunning Remodel in 2024Kona Riviera #102Bedroom Configuration:Master Bedroom: King Bed Living Room: Sleeper SofaAmenities:Beach Equipment: All of our vacation rentals include beach towels for the maximum occupancy, four beach chairs, two boogie boards, one...
Villas By The Cove, Penthouse II · Ocean View Penthouse Steps from the Beach
Welcome to the newest addition to the Villas by The Cove, our Oceanview Penthouse II. This modern home has stunning ocean views, three bedrooms and three full baths, private gated parking, private lanais on both levels, and a large shared pool and bbq pavilion.The open...
Enjoy sunsets-Beautiful Oceanview Pac Shores perfect for couples and families!
Book dates now to Dec 21 to receive an additional 15% discount. Book for 7+ days receive additional 10% discount.Start your mornings on the third-floor lanai for sunrise and end the day at Charley Young beach for spectacular sunsets. Watch turtles cruising the waves and...
Gorgeous Wailea Elua 2Bd+2Ba 1st Floor, Ocean View Paradise Condominium #2301
New living room furniture and lanai furniture - Absolutely Lovely! Wailea Elua Village #2301 is a premier vacation condominium located in Elua Village which is directly on the sugar sand of Ulua beach in Wailea. This impressive vacation condominium is constantly in high...
Luana Kai B212 Ocean View. South Maui WeathernRelax...Steps to the Beach!
Beautiful single level condo in South Maui! Our unit is located on the second floor with an ocean view, recent updates, close to shopping, beaches and activities. The view can be enjoyed on our expansive double sized lanai for casual dining. You will feel at home with...
Beach Front Estate With Guest Cottage Sandy Beach Heated Pool/Spa:Please Inquire
30 Night ContractShare the romance and beauty of the North Shore with your entire family: 2 separate fully appointed living spaces with high end amenities great your every moment of your vacation.Swing open the gate to our Sandy Beach, sink your toes into the white sand...
Steps to Beaches, 2 King Suites, Private Pool, AC!
Spacious villa in Keauhou Resort just one block from He'eia Bay and two blocks from Keauhou Bay. Walk to Kona Country Club's ocean golf course, with resorts, shopping, and dining nearby. Perfect for relaxing with family and friends, featuring designer furnishings,...
Kolea Penthouse16F"ALWAYS-ON-MY-MIIIND". DIRECT BEACH ACCESS, Beach gear & More
PROPERTY DESCRIPTION: KOLEA PENTHOUSE VILLA 16F - 2BR, 2BA- TOP (3rd) FLOOR with a 3-Mountain Views, elegant tropical decor, and direct beach access. Sleep 4.Experience the finest in luxury at Kolea. This beautiful 2-bedroom, 2-bath Penthouse villa is outstanding....
La Bella’s Bed & Breakfast-Honu (Turtle) Suite-Walk to beach-In Kailua (O’ahu)
No detail is overlooked at this charming and luxurious home. La Bella’s Bed and Breakfast is the place to be if you are looking for a short walk to the beach, a beautiful garden to enjoy, great host family and close to amenities. Our luxury bedding and upgraded style...
Experience Unparalleled Oceanfront Luxury at Puu Poa Condo with a 5-star rating.
Welcome to your tropical paradise vacation! Immerse yourself in the breathtaking beauty of Kauai’s North Shore with spectacular oceanfront views and stunning sunsets from our elegantly designed, ultra-luxurious condo.Highlights:Location: Steps from a secluded,...
Modern 1BD Condo with Pool Steps from Beach
Summary:Discover the allure of Maui with this chic and comfortable one-bedroom condo, a perfect retreat for those seeking both relaxation and adventure. Newly remodeled in December 2023, this fifth-floor gem offers stunning ocean views and is just steps away from the...
Studio Premium Villa - Ocean View at Westin Ka'anapali Ocean Resort Villas
Settle into the lap of luxury, where plush bedding assures pampered restfulness for the weary traveler.If the majesty of Maui’s beaches and mountains weren’t enough to sell you on a trip to Hawaii, perhaps the allure of this world-class wellness resort will tip the...
Sandpiper 129A - Updated, modern, comfortable 1 bd
Clean, modern 1 bedroom, (King bed + queen sofa sleeper), 1 bathroom condo with assigned parking, pool, hot tub, and bbqs on site. Close to beaches, shopping, dining, golf, hiking, parks and more. Located in Sandpiper Village, which is centrally located in Princeville,...
Happy House on Exquisite Kailua Beachside Property!
Kailua Beachside: Charming beach house steps from the white sands of beautiful Kailua Beach. Nestled in a large, private garden property, enclosed by stone walls with palms, banana trees and beautiful tropical gardens. Very safe and fun for kids, great for families,...
From 185 nt Aloha Summer Sizzle 2025 incl AC, 5 Star Luxury on the Big Island
Island breezes, fragrant blossoms, privacy - Na Hale O Keauhou, Hawaii's Best Kept Secret. This private 2 bedroom, 2-1/2 bath, 2 story town home is located in a 5 star, gated, luxurious resort complex with breathtaking, panoramic views of the ocean and mountains. Within...
Keauhou Punahele B207 2 bedroom 2nd floor no stairs, fantastic views!
Keauhou Punahele B207 Oceanview Escape at Keauhou Punahele – 2BR/2BA Vacation Rental with no stairsRelax in paradise at our beautifully appointed 2-bedroom, 2-bath condo in Keauhou Punahele! Overlooking the sparkling pool and the stunning Pacific Ocean, this spacious...
Maluhia Wai - Modern 2 Bd Condo w/Pool, A/C, Wi-Fi
Wai Maluhia awaits! FIRST TIME OFFERED This newly renovated condo is like no other in Hilo. IF you are looking for the best East Hawaii experience look no further. New furnishings, modern decor, and upscale luxury are all features you will appreciate. This corner condo...
Penthouse View in Lanikai LANIKAI NUC 90/BB -0108 Most comfortable for 2 or 3.
Welcome to the monthly rental Penthouse in Lanikai! We have been sharing our piece of paradise for over 20 years.! Everyone deserves to experience the Hawaiian lifestyle! Sunrises, moonrises, walks, bike rides, and daily runs on the beach. We have guests from all over...
Top Floor, remodeled, oceanview & steps from beachn
Welcome to Kihei Ali'i Kai A404. This remodeled, top floor, ocean view, 2 bedroom 1 bathroom condo is your perfect Maui getaway. Enjoy sunsets & ocean views from your large private lanai. The condo has a fully equipped kitchen, new AC, new towels & linens, & beach gear...
Aolani Coffee Cottage | #1 AirBnb | Condé Nast | AC
🌺 Aolani Coffee Cottage | Private Hot Tub + Ocean Views + ConciergePeaceful Holualoa Farm Stay | 12 Min to Kona + Beaches | Luxury EscapeAbout This SpaceWelcome to Aolani Coffee Cottage, a serene and stylish retreat nestled in the heart of Kona’s lush coffee belt....
Hawaiian Haven @ KoOlina Kai
This gorgeous 3-bedroom, 2-bath villa is located in Hawaii's premier KoOlina Beach Resort in the gated community. Your vacation starts as you enter the gate, surrounded by beautiful palm trees and the gorgeous KoOlina LPGA-level golf course. Convenience is at your...
April & May 15% discount Oceanfront with Spectacular View #101 Napili Bay, Maui
Spend your next vacation in our oceanfront studio condo on beautiful Napili Bay. You can't get closer to the ocean anywhere on the island!! Our studio has been upgraded completely to include a wall-mounted 42' flat screen tv with blu-ray DVD player, double pillow-top...
💕Hale Mele💕 Polynesian Pod Style with Pool/Hot Tub, Gazebo, Golf Cart & Ebikes
Welcome to Hale Mele — A Premier Hawaiian Retreat on the Big Island’s South Kohala CoastEscape to Hale Mele, an extraordinary luxury residence situated within the exclusive, gated community of Champion Ridge on the radiant South Kohala Gold Coast. Recognized by...
Spectacular Views of Hanalei Bay 2 bedrooms
UNIT 9201/2Kauai’s Most Breathtaking Views at Hanalei Bay ResortWelcome to your Kauai paradise. Units 9201/2 are located in the renowned Bamboo building which features the most stunning views of Hanalei Bay and Bali Hai. This spacious fully air conditioned 1350 square...
Rare Find w/ 2 AC! Newly renovated condo #128, ground flr, 3-4 min walk to beach
Brand New AC in living room and bedroom. One of very few units in Kiahuna with 2 ACs.Fully remodeled 1b/1b condo inside the stunning Kiahuna Resort. The perfect spot for romantic getaways or family trips. We have everything you need:-AC in living room and bedroom (and...
Absolute Ocean Front Home at Sea Level Hale Hokulani "House of the Heavenly Star
HAWAII LAW COMPLIANT !!We received the original and the renewals of the highly sought after short term vacation rental seal of approval/certificate from the County of Hawaii meeting all their stringent requirements. When you rent our home you receive the entire home...
Tropical Garden Family Home & Penthouse - Sleeps 8 Walk to Beach, BBQ, Hot Tub
• 2 fully stocked kitchens • Outdoor hot tub and private jacuzzi tub in the penthouse• Fully fenced yard and lush tropical garden• Top-of-the-line amenities.• Have fun with the whole family at this stylish place.• Feel free to message us with questions or...
Ocean-view condo, ground floor - pool, hot tub, full kitchen & ocean-view lanai
Polynesian Shores 118Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Conveniently located on the ground floor, this thoughtfully appointed condo presents pure oceanfront bliss....
Hamakua Coast Home- Ocean views, private, clean and friendly
Our secluded ohana (guest home) features a grand, unobstructed view of the Pacific Ocean. The gentle breezes and typically sunny days of our small local neighborhood make this charming hideaway perfect for guests seeking tranquility, privacy, and convenience in a...
Beautiful, spacious 4 bedroom/4.5 bath home with Ocean views, A/C, and sauna
Situated on an ocean bluff this gorgeous home features 4 bedrooms and 4 ½ baths to comfortably accommodate up to 8 guests with its 1 California King Bed and 3 Queen beds. With upscale finishes throughout and fantastic views everywhere you look, this home is truly...
Vintage tropical townhouse close to pool
In addition this resort is a golfer's paradise being that the unit is situated near the Waikoloa Beach Golf Course. Enjoy all the conveniences of our townhome, right at your fingertips. On the bright side the vaulted ceiling in this condo allows natural sunlight to...
3 bedroom amazing location ACN4
Welcome to our beautiful Alii Cove Townhome! This Gated Community is located on Alii Drive across the street from Hon'ls Beach and a five minute walk to the Village of Kailua-Kona, where you will find numerous restaurants, shopping, entertainment and other activities....
New Listing! Waikoloa Fairways 2-bed, 2.5-bath unit with pool, BBQ, and lanai
New Listing! Relax at this two-bedroom, two-and-a-half-bath Waikoloa Fairways unit in the heart of Waikoloa Village. The primary offers a soaking tub. Enjoy the open living layout, outdoor wet bar, and large lanai. Pool, hot tub, and BBQ at the complex.Upon entry, you...
Super Luxury, Direct Oceanfront, 20 yards From Ocean, Whale Watchers Paradise
In Hawaii's lush tropics, discover your dream home at this stunning 2-bedroom retreat. Nestled just an 11-minute walk from the picturesque Maalaea Harbor, you'll be perfectly positioned to explore the stunning West Maui Mountains and the pristine Wailea Beach, just a...
Wailea Ekolu 1106 May & June Deals at Remodel Condo for Peaceful Island Getaway
The Stice Team — Powered by Gather Vacations. Maui Born and Raised Professionals. Your Local Experts in Crafting Unforgettable Stays.Welcome to Wailea Ekolu 1106, a newly remodeled 2-bedroom, 2-bath upper-level townhome tucked into the serene Wailea Ekolu Village on...
Third floor resort studio - ocean-view lanai - steps to beachside pool, hot tub
Islander on the Beach 340Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Experience the ultimate oceanfront retreat at this premium top-floor condo in Kapaa, Hawaii. Situated in the...
Bright and Upgraded, Lanai Steps away from Coconut Grove!
Aloha and welcome Hale Ho'omana'o 19E at Hali'i Kai in the Waikoloa Beach Resort. Enjoy the serene Coconut Grove area with delightful hammocks for you to experience the perfect blend of tranquility and comfort. Hale Ho'omana'o in Hali'i Kai is a stunning condo...
Kihei Holiday Stunning Ocean View #309 2bd/1ba condo, 1 min walk to the ocean.
***Notice (July 2025) regarding Short Term Rentals on Maui: Kihei Holiday Condominium is legally zoned (H-1/H-M) for short term vacation rentals and is not affected by the new rules in Maui County for many other properties! Your booking is safe with us!!!Maui Ocean...
Kona By The Sea 323 - Exceptional Kona Sunsets
Unit 323 is the perfect vacation rental for those seeking a longer stay. With its super-fast Wi-Fi, it's an ideal choice for remote workers, providing a stunning backdrop of the Kona Coast for their work-from-home endeavors. Recently upgraded, Unit 323 boasts brand-new...
Enjoy luxurious furnishings and a short walk to the beach from this villa!
Kolea 9A was newly remodeled in 2024. Just a few minute walk from the Kolea Pool & Beach Club, Kolea 9A is conveniently located within Kolea. Also located on the ground floor this villa offers a nice lawn area in front for the children and is surrounded with lush...
Beautiful and Serene Maui Kamaole Condo I-209
This ocean view, two-bedroom, two-bath condominium is located near the front of Maui Kamaole and is located up one flight of stairs on the second level. Inside you will notice it is designed in the style of a townhouse with the master bedroom on the main floor and a...
Hale Nalu: Tropical Cottage in Poipu-Walk to Beach
Scenically situated on the Green Belt pedestrian pathway, this enchanting island-style home combines the casually elegant charm of a country-plantation retreat with an ideally convenient location. Not only is it close to everything—an easy stroll to beaches and...
Dream Hawaiian Getaway at Stunning Oceanfront Maui Sunset!
Welcome to your dream Hawaiian getaway at Maui Sunset, a stunning oceanfront complex known for its lush, beautifully landscaped 5-acre grounds. This newly updated 1-bedroom, 2-bathroom condo offers everything you need for a comfortable and unforgettable stay.Step into a...