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.
Kapalua Ridge 1421 40%Off May Deals for Relaxing Getaway at Remodeled Condo
The Stice Team — Powered by Gather Vacations. Maui Born and Raised Professionals. Your Local Experts in Crafting Unforgettable Stays.Welcome to Kapalua Ridge 1421, a masterfully re-imagined 1-bedroom, 2-bath townhome perched on the second floor of Kapalua Ridge Villas...
Sunset Makai Hale By Parrish Kauai - luxury oceanfront home w/ pool
This extraordinary 4 bedroom, 4 bathroom luxury home is one of the finest Kauai oceanfront rentals on the island. The grand entrance opens to expansive cathedral ceilings showcasing the magnificent oceanfront living areas surrounded by tropical atriums, lava rock...
Aloha Kai Suite at Wailea Beach Villas. Penthouse 205. Ocean View. 3 BR / 3 BA
Wailea Beach Villas voted as one of the top 100 USA Hotels by the Conde Nast Traveler Readers Choice Awards!Luxury awaits in this exquisite three bedroom, three full baths, 2500 square feet Penthouse Villa J205 with gorgeous ocean view. Our Aloha Kai Suite is elegant...
Wailea Ekahi Village | 39A
If you’re seeking privacy and relaxation, Wailea Ekahi Village 39A offers a secluded Maui retreat nestled behind a lush row of towering tropical plants. This hidden gem provides a tranquil oasis perfect for unwinding after a full day exploring Maui's scenic...
Wailea Grand Champions | 95
Do your Maui vacation right! Wailea Grand Champions 95 is surrounded by tropical landscaping and rolling green fairways, that serve as a constant reminder that you are vacatioing in paradise. This vacation rental offers a perfect blend of comfort and luxury, making it...
Maui Parkshore 208: Beautifully renovated 2 bedroom ocean view condo on Maui
**Please note that the pool will be closed from Wednesday, September 4 through Thursday, September 12 due to pool deck maintenance**This attractive 2-bedroom, 2-bath S. Kihei vacation rental overlooks the pool area and offers ocean views beyond. Recent renovations in...
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 Keoniloa: Tropical Charm + Pool in Poipu
This sophisticated, spacious, stylish, newly remodeled tropical villa seems to exist in an enchanting, resort-like world of its own, yet it's just a few minutes from world-class beaches and all the other attractions of Poipu, Koloa and the South Shore. From top to...
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...
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!
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 spot whales offshore during the winter season.Two bedrooms and two bathrooms provide space and privacy for...
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
30 Day Minimum Stay Required Share 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...
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....
Beautiful Beachfront Resort with Best Ocean View Room On Property pools/hot tub
Our unit is a privately owned hotel room located in the Outrigger Kauai Beach Resort and Spa.This is a Beautiful forth floor room with a king bed and sitting area. Spectacular views of the ocean and resort pools.The Outrigger Kauai Beach Resort and Spa is a beautiful...
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...
Wailea Elua Village | 1001
Wailea Elua Village #1001 is a stunning oceanfront sanctuary that has recently undergone a complete transformation. For discerning travelers who enjoy the best of Wailea, the extended outdoor living space allows you to enjoy panoramic ocean views while relaxing with a...
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...
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 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 the world return...
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, brand new AC system,, & beach gear for...
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 Escape🏡 About This SpaceWelcome to Aolani Coffee Cottage, a serene and stylish retreat nestled in the heart of Kona’s lush coffee...
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 water anywhere on the island!! Our studio has been upgraded completely to include a wall-mounted 42' flat screen tv with blu-ray DVD player, new double...
💕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...
Mauna Lani Point B101 Luxury Vacation Home
Welcome to Mauna Lani Point B101, your serene escape where you can unwind with stunning ocean views and enjoy direct access to the world-class Mauna Lani Golf South Course, just steps away. This beautifully renovated residence boasts an open floor plan that seamlessly...
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...
Kona Alii Penthouse with Village and Ocean Views
This beautiful condo is located in the heart of downtown Kailua-Kona. Two bedrooms with private baths, and king size beds and flat screen TV. The loft bedroom opens to the private sun deck with stunning panoramic views.The kitchen is fully equipped with everything you...
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....
Worldmark kihei in beautiful Maui , walking distance from beach
Tropical yet sophisticated, this Maui resort just steps from the beach delivers the experiences that’ll create memories you'll treasure for a lifetime. Take in this serene island’s historic, natural, and contemporary bests.
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...