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.
Ocean View Upgraded Top Fl HOKU711 Shaded Lanai see condo comparison chart
**COMPARE MY CONDO TO OTHERS**Hokulani 711-Upgraded 2022 (new beds, headboard, and mattresses, all furniture replaced including the sofa bed with a supreme mattress top, table with optional bench to seat 6, carpet removed and replaced with LVP for a cleaner environment,...
Largest 3BR Villa in Turtle Bay Hawaii, nearest beach access!
Indulge in North Shore Luxury – Closest 3BR Villa to the Beach at Turtle BayWelcome to your ultimate Oahu escape — the only single-story 3-bedroom villa at Turtle Bay Resort, and the closest villa to the beach on the property. This expansive 1,700 sq. ft....
Luxury Kapalua Ridge Villa Featuring Sparkling Ocean, Island and Coastal Views!
Property Highlights • Five minute walk from three world-class beaches, including Kapalua® Bay, rated the "Best Beach in the World" by Dr. Beach, and “Best Beach in the US,” by Conde Nast • Large lanai for optimal outdoor living space • Better-than-Gold...
Kalo Homes ~ Tropical Makaha Sanctuary
Imagine waking up to breathtaking views of the ocean, mountains, and valley, while surrounded by lush tropical landscaping. You can unwind in the Jacuzzi or fire up the Traeger grill for a tasty BBQ. We`ve got you covered with all the beach amenities you`ll need to...
Hualalai Palm Villa 130A
One of the largest floor plans of any villa at Hualalai, this spacious and centrally located 3 bedroom, 3 bath villa is ideal for your Hawaii getaway. Extra bedding available with a "bonus" living room on the first level. The down-stairs suite opens to a large lanai and...
Maui Parkshore #203 Ocean View, Great Location, Across from Kamaole Beach
Maui Parkshore #203 is a 2 bedroom, 2 bath unit on the second floor with a pool and ocean view, washer and dryer, fully-equipped kitchen, flat-screen TV, DVD player, and free wifi. The master bedroom has a queen bed, ceiling fan, flat-screen TV, alarm clock, and full...
One Hanalei, Luxury Home, walk to the bay! TVNC #1168
One HanaleiPermitted Vacation Rental Property - TVNC#1168Transient vacation rental is located in the tsunami evacuation zoneOne, meaning Sand in Hawaiian, is a family beach house, named after the owner’s mother Sandy and the beautiful sand beaches of Hanalei just...
Kalama Terrace Renovated Retreat, Centrally Located with AC!
Welcome to Kalama Terrace: Your Stylish, Centrally Located Kihei Retreat!Step into island living at Kalama Terrace, Unit P211—an inviting, fully renovated condo in the heart of Kihei. Perfectly situated just a short stroll from the sandy shores of Kamaole Beach and...
Na Hale O Keauhou | Beach Views, Hot Tub & Pool
Summary:Welcome to Na Hale O Keauhou #I1! Located in one of Keuhou’s newer neighborhoods, this one is a delightful Hawaiian getaway home. Enjoy nearby beaches and glorious sunsets, it’s perfect for vacationers looking to unwind and bask in the tropical sun. Maximum...
Spring Special! Fantastic Beachfront Wailea Ekahi 2/2
Welcome to my sunny Wailea Ekahi Paradise! This unit is a remodeled, expanded and wonderfully furnished 2 bedroom 2 bathroom ground-floor condo (Unit 43A) is the perfect spot for a family or group vacation! Keawakapu Beach is just a short walk away through beautifully...
Deluxe Two Bedroom Partial Ocean View Luana Kai C201
Unit C201 with AC is a deluxe, 2 bedroom, 2 bath with a partial ocean view. A fun view of the pool, ocean, West Maui mountains, The Pali”, and Ma’alaea bay. During the winter months you can enjoy the occasional appearance of whales from your lanai. There is a king...
Charming Oceanview Oasis: Wailea Elua 802 Surrounded by Lush Tropical Grounds
Wailea Elua #802 – Panoramic Oceanfront Luxury, Fully Remodeled in November 2024Welcome to Wailea Elua #802, a stunning second-floor oceanfront condo that redefines luxury in Maui’s premier resort community. Completely remodeled in November 2024, this 2-bedroom,...
Heavenly Waters Hawaii – Near Beach 69 in Puako
Heavenly Waters Hawaii is a tranquil oceanside tropical retreat in Puako, perfect for your next family vacation. This spacious three building estate includes a large oceanfront cliffside pool and hot tub to enjoy memorable Hawaiian sunsets. It is ideally situated on the...
Poipu Beach Plantation Style Cottage
This custom designed Hawaiian plantation style cottage is located just steps from Poipu Beach Park and Brennecke’s beach on a quiet dead end street. It is the perfect vacation retreat. Hale Honu was just completed in September of 2014 and was designed to fit in with...
Ocean View, Beach Front freshly remodeled 2bd 2ba unit!!!!!
Welcome to Kahana Village unit #11! This 2 bedroom, 2 bath ocean view/beach front property unit will provide everything you need while on your Maui vacation.This beachfront 2-bedroom condominium is one of the finest in West Maui. Comfortably sleeping up to six guests,...
Quaint Hilo Vacation Rental w/ Community Pool!
Near Restaurants & Shops | Free WiFi | < 1 Mi to BeachesExperience the ultimate island getaway at this Hilo vacation rental! Featuring a prime location just down the road from stunning beaches, downtown markets, hiking spots, and more, this 2-bedroom, 1-bath condo is...
SUMMER SPECIAL! AMAZING VIEW! Book Between May 25th - Aug 31 375/night!
Breathtaking views from our Unit 507 at The Whaler on Kaanapali Beach. 1 back from oceanfront! 1 bedroom unit has a king sized bed and a full size Murphy bed. 2 full baths. Sleeps 4 comfortably. Also a well equipped full kitchen.Relax on the spacious lanai while...
11th Floor 2 Bedroom Sans Souci condo w/ incredible bay views
Luxurious Monthly Rental Property:Relax in the comfort of this high floor Sans Souci condo with stunning ocean and bay views.Condo Features:2 King Size Beds, Full Kitchen, Free Wifi, Ocean Front, Ocean View, One complimentary dedicated Parking Stall is...
Villa 315: Ocean views every bedroom!
Our Villa 315 is Located on the Turtle Bay Resort! You can use the Ocean Villas pool and Jacuzzi, park for free, and pay no resort fees! You can also use most of the Turtle Bay Resort Amenities for a fee. You have FREE access to the 12 miles of hiking and biking trails,...
Kona Koa House by Gather: Oceanview 3BR Estate w/ Heated Pool & BBQ
Escape to Kona Koa House by Gather, a stunning 3-bedroom plus bonus room, 3-bath vacation home set within the prestigious Keauhou Estates gated community in Kailua Kona, Hawai‘i. Perched 500 feet above sea level, this luxurious single-level retreat spans nearly 3,000...
Puna Rainforest Retreat Hotspring - Purple Passion Cottage
The Purple Passion Cottage is located on a serene 20 acre estate with beautiful ocean and meadow views. The cottage is cozy and equipped kitchenette (range, oven, mini-fridge/freezer, microwave), full bathroom and two bedrooms. The main bedroom has a king bed with an...
Nohea Villa: Elegant Tropical Home w/ Mountain Views, Pool & Spa
The Nohea villa in Kamili'i village is an ideal destination for a visitor to the spectacular island of Kauai. While it could be said, that the open concept floor plans of the units in Kamili'i village are pretty much the same, Nohea's remarkable seat on top of the...
Paradise: Ocean View Cottage Solar Power Tropical Flower Gardens
Entabeni Cottage, sits above the Road to Hana overlooking the Pacific Ocean on the north shore of Maui, Hawaii. Maui County License & Permit: BBPH 2013/0006 and SUP2 2012/0011Entabeni Cottage is a fully-equipped, 830 square foot home, powered by the sun and beautifully...
Honu Hideaway Studio at Royal Garden | Lanai Oasis
This gorgeous Waikiki studio is located at the beginning of Waikiki with easy access to some of the best Oahu has to offer. At the luxurious “Royal Garden” building, guests are free to enjoy the gardens, pool, sauna, BBQ grills, fitness center, 24/7 laundry room...
Trev's Surfside Hideaway- Kihei Maui
Our Kihei Maui condo offers all the comforts of home in a peaceful garden style setting. Located just steps from the beautiful Kamaole 1 beach park and close to all amenities including some of Hawaii’s finest golf and shopping. Whether walking or driving everything...
Private Villa on 3 acres with Pool and Spa TVNC-4195
This spacious home is Located in the Seacliff gated community, adjacent to the Kilauea Point National Wildlife Refuge and the Kilauea Lighthouse.You will enjoy large panoramic windows throughout the home with extensive mountain and bay views. This well maintained three...
Paradise on park like estate with beautiful ocean and mountain view
Envision time on 45 acres of a landscaped park-like estate bordered by two streams - one is seasonal with a forty foot waterfall. Imagine picnicking by the stream or going for leisurely walks. The 800 plus square foot guest house provides privacy and space to relax....
Aston Maui Kaanapali Villas A101: 2 Br Premium on N. Kaanapali Beach Sleeps 6
At the heart of the Maui Ka’anapali Villas Resort, an opulent retreat awaits. This sprawling ground-floor condo boasts wide open spaces, with lofty ceilings, and walls adorned with fine Polynesian and Asian Pacific antique art. Soft creamy décor pays muted compliment...
Kaanapali Maui🐢⛰Hawaii<br>Amazing Pools/Jacuzzis 1 Bedroom Villa sleep 4 privately
Kaanapali Beach Club is an amazing property with a beautiful swimming pool with a great slide for the kids 🐚humongous hot tub 🛁seats 24 ,made out of lava🌋 stone beautiful gardens🌺 fitness room. Roof top Putt Putt a golf ! Ping pong table and kids bowling...
Vacation in a Tropical ParadisenNapili Shores - C121 Studio n
Napili Shores Resort offers luxurious condominiums in the tropical paradise of Napili Bay. The resort is located on six beautifully landscaped acres and has two pools and two restaurants on the property. It's a getaway spot you won't soon forget!Our studio is a comfy,...
Wailea Ekahi Village 25D - 1 Bedroom Garden View Condo
Welcome to Wailea Ekahi 25D, an exquisite vacation rental that embodies the essence of luxurious island living in Wailea. This one-bedroom, one-bathroom second-floor condo offers a enjoys elevated views of the 32-acre manicured grounds. Vaulted ceiling and tiled floors...
Cozy cottage 3 bedroom, 2 bath, AC, MOUNTAIN VIEWS
Recently updated, lovely 3 bedroom (king, queen, 1 twin), 2 bath, 2 story duplex condo located at the outskirts of Princeville on Hanalei Plantation rd. Central AC in all 3 bedrooms located upstairs. A 15 minute walk will get you to the ruins of the old Club Med and a...
Beautiful Sunsets with this Ocean View Condo! Mar 23 - April 7 Open!
This beautiful top floor, Grand Champs condo has one of the best ocean views in the complex. This fully updated 2 bedroom, 2 full bath condo has wonderful panoramic ocean views perfect for sunsets and whale watching. From the extra large, newly tiled lanai, you can see...
SUNSET PALMS! Pool, Tennis, A/C, Mins to Beach 5 Bed 4 Bath sleeps 14
It is our wish that you enjoy this home away from yours, as much as we enjoy living in it when we come to Kauai! This custom built home is the perfect vacation home for up to 5 couples or large families as it accommodates 12 people comfortably. Access to private pool...
Relaxation Bungalow with Hot tub, Sauna, Lush Garden, and Pristine Island Living
Escape to Hale Kalani, a charming 3-bedroom surf bungalow nestled in the heart of Princeville on Kauai’s renowned North Shore. Thoughtfully designed for relaxation and island living, this single-level haven features a private cedar barrel sauna, a brand-new hot tub,...
Resort Style with Hula Show, Fireworks and even Tiki Torches!
The Ilikai is the first hotel-resort condominium developed in Hawaii and is one of the original landmarks of Waikiki. It is best known for being featured in the Hawaii 50 TV series and is loved by tourist and locals alike. Conveniently located in Waikiki next to the...
Ilikai Oceanfront Rental
This property is a LEGAL SHORT TERM VACATION RENTAL located in the resort zoned, oceanfront, Ilikai Apt. Building! This gorgeous, bright and airy, 1bd/1bth oceanfront, ocean/lagoon view unit, located in the iconic Ilikai Apt Building was completely remodeled into a...
Panoramic Ocean-View/STEPS FROM BEACH/FreeParking/Best Location in Waikiki
Breathtaking ocean, sunset and city skyline views from the 21st floor! Enjoy walking distance to Waikiki Beach/Hilton Lagoon and Friday Night Fireworks! Ala Moana Mall with World class Dining/Shopping are steps away. Best location in Waikiki! Newly renovated condo with...
Whales! Luxury Oceanfront 20-foot Panoramic Views of Whales and Turtles
The Space:Notice - This home is in the HOTEL ZONE, so it will NOT be banned by the new law that will restrict short term rentals in the Apartment Zone.Our home is conveniently located at the prime location in the heart of West Maui. Wake up to breathtaking panoramic...
Dramatic Ocean Views, Wailea Ekolu 407, Perfect for Couples, Renovated, Split AC
Experience the essence of Maui at Wailea Ekolu 407, a luxurious 1-bedroom, 2-bathroom condo that offers breathtaking panoramic ocean views from the spacious living area, kitchen, primary suite, and oversized lanai. Nestled in the heart of Wailea, this elegant...
Romantic! Oceanfront Air Conditioned Condo #114
. . . . WELCOME! Enjoy Old Hawaii “Aloha” in modern comfort. #114 is a ground floor 1-bedroom oceanfront condo in the most romantic spot of West Maui. Your condo opens directly onto a landscaped lawn with heated swimming pool & BBQs. Your lanai directly faces...
Ocean Views and only Steps from Magic Sands Beach!
TAKE IN A VIEW OF LAʻALOA BEACH (aka Magic Sands) FROM OUR LANAI! The top floor condo is directly across the street from La'aloa beach park (aka Magic/White Sands) - at most a 5 minute walk from the front door. Try boogie boarding at the beach with one of the boogie...
Two Adjoining Luxury Homes in Mauna Lani - 12 bdr, 2 heated pools, 16,000 sqft
Blue Lagoon (7 bedrooms) and Blue Oasis (5 bedrooms) share a property line and a private putting course with gated paths connecting the two homes.With 12 bedrooms, 13 bathrooms, 2 heated pools and 2 hot tubs, these homes are dream setup for a large gathering, a wedding...
Studio Oasis in Waikīkī w/Kitchenette And A/C - Waikīkī Grand #404
Waikīkī Grand Hotel #404 on the fourth-floor: Begin the day with a fresh cup of coffee and breakfast favorites from your kitchenette. Essential kitchen items and takeout can be stored in your refrigerator. Food can be prepared on the two-burner cooktop or reheated in...
Luxury Home in Mauna Lani☀️🌴
Nestled in the Big Island's dream Kohala Coast, in the sought after Mauna Lani Resort, this showroom home is an absolute marvel. Sparing no expense on construction, design and furnishings, this property is truly one of a kind. The home is located in Nohea, in the heart...
Mauna Lani Terrace F302 - Luxury Ocean View Penthouse
The Mauna Lani Terrace is located within the world class Mauna Lani Resort. It is on the ocean and adjacent to the royal fishponds and between two beautiful white sand beaches. The water is crystal clear with one of Hawaii’s healthiest reefs, lava arches, schools of...
Awesome Beach - Elegant Villa - Tropical Oasis
Luxurious Villa - just steps to the beach! Aloha and welcome to our beautiful home, an elegant tri-level, three-bedroom vacation home steps away from two of Maui's most beautiful beaches and the world-famous Kapalua Resort. We invite you to enjoy a wonderful vacation in...
Ocean Views! Mauna Kea Resort. Beach Gear Include. Kumulani J3
This vacation rental is professionally managed by ResorticaHawaiiKumulani J3Bedding Configuration:Master Bedroom: King BedGuest Bedroom: Queen BedGuest Bedroom: Two Twin BedsMauna Kea Amenity Program-see all details below:PLEASE NOTE: The Mauna Kea Hotel and golf...
🏖️Beautiful Ocean View! | Central AC | Serene Surroundings | vrKCV
vrKCV - Nakukui Ekolu, Professionally Managed by Kona Coast Vacations Nakukui Ekolu at Kahakai Estates - The Piece of Mind RetreatDo you need a vacation? Not just a trip, but an actual vacation? That is what you'll find at the Piece of Mind Retreat. If you wanted to,...
Kona Reef D24 - Direct Ocean Front Condo - Private Lanai -nNext to Honl's Beach.
Welcome to our beautifully decorated ocean front condo in paradise - Kona Reef D-24. Our condo is our home away from home, so we respectfully request a maximum of 2 adult guests and no children under 18. Whether this is your first trip to Kailua-Kona or you are a...