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.
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...
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...
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...
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, 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 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 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...
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...
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
Kona by the Sea is an absolute oceanfront property. Unit 323 is a spacious 1 bedroom - 2 bath well-lit condo with many beautiful upgraded features.. The kitchen is well stocked with everything you might need for an extended stay. Enjoy a great view of the ocean looking...
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...
Stunning oceanfront view with private lanai
Kulakane 212 is a stunning oceanfront condo that features spectacular ocean views! This beautiful 1-bedroom, 1-bathroom condo is on the 2nd floor and can accommodate up to 4 guests . Please note this resort does not have elevators. Enjoy Maui's blue waters with a cup of...
★Jump Start The Road to Hana at The Lookout House! Private Hot Tub + Pool Access
The Lookout House at Huelo Point Lookout in Maui is the perfect home base for exploring the island. The location of the house off the Hana Highway makes it a great starting point for your Road to Hana adventure. The famous scenic drive to Hana is a must-do activity for...
Right on the water in West Maui.
Looking for a getaway that is right on the water with a full ocean view on the west side of Maui? This condominium has a full kitchen with stainless steel appliances including a dishwasher to create your own meals and save money on your vacation. Features a king size...
Stunning! Fully Air-Conditioned Penthouse Level Ocean Front 1 Bedroom - #609
Simply Exquisite! The photos say it all!This fully air-conditioned penthouse level unit is sure to make your stay in Paradise a romantic and memorable one! Recently remodelled and expertly finished by the best tradesmen, it boasts travertine marble flooring throughout,...
Romantic Cottage, Stunning Ocean Views, Whales are jumping!
James Cottage is a historic home that has been completely restored for our guests to enjoy. Located with in The Historic Puakea Ranch, your bungalow was once home to the paniolos who lived and worked at Puakea 100 years ago. Ocean views, light filled, airy and...
1 Bed/2 Bath Condo with Sensational Ocean View
Welcome to paradise at Maui Kamaole's J115. The breathtaking view from our condo will entice you to stay here. You'll want to return because it's a clean, quiet, well-appointed, well-equipped retreat with plenty of extras. You'll love the gentle trade winds that sneak...
Luxury Mahana 1bd/2ba-Beautiful Remodel- Incredible Views-Free Parking/WiFi
Mahana 715 is a 1BD/2BA condo featuring the best direct beachfront location, panoramic Pacific Ocean views, year round sunsets, and seasonal whale watching at its finest. The Mahana is one of a kind with its close proximity to the water and there is truly nothing like...