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.
Luxurious Wailea Ekahi 19A - Ground Floor with Ocean Views & Easy Beach Access
Wailea Ekahi #19A – Spacious Townhouse Comfort Near Keawakapu BeachWelcome to Wailea Ekahi #19A, a rare and spacious 2-bedroom, 2-bathroom townhouse nestled within the beautifully landscaped Wailea Ekahi Village. Located just steps from world-famous Keawakapu Beach...
Stylish condo with private lanai, shared pool & hot tub - steps from the beach
Plantation Hale #C5Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your tropical oasis in Kapaa, HI! This charming ground floor, end unit condo is the perfect getaway for...
Kulanakauhale 11 – Elegant & Modern | Onsite Staff & Daily Housekeeping
This 4-bedroom, 4.5 bath private home combines pod-style architecture with traditional design to optimize the resort lifestyle for up to 8 guests. Surround yourself in custom contemporary resort furnishings and décor while enjoying expansive golf course and mountain...
Royal Sea Cliff Kona 711 Ocean View 2 Bedroom
- 7th floor condo with covered lanai- Maximum 6 persons including children and infants- King size bed in master bedroom- Queen size bed in second bedroom- Sofa bed with two recliners in living room- Updated kitchen – with fridge, stove/oven, microwave, cookware,...
Island Haven Hawaiian Monarch Studio | Ocean View
Thoughtfully designed ocean-view studio with flexible sleeping, storage and remote work options. This home offers ac, flatscreen tv, wifi, cable, dining for 4, and cute kitchenette. A prompt walk from Hilton Hawaiian Village, Fort DeRussy Beach Park, Ala Wai Canal and...
Beachfront 3 bedroom penthouse with easy beach access!
Enjoy easy beach access and an amazing view from this three bedroom penthouse at Kolea at Waikoloa Beach Resort. From the minute you walk into the villa you will be struck by the size and amazing view. The large great room has expansive views of the beach and ocean. The...
Recent RENO! Fits 6, FREE parking
You & your family or friends will be close to everything at this centrally-located oasis in Waikiki. A couple minutes to the beach, surfing, the lagoon, boating & fishing, hiking, restaurants of every kind, shopping galore, everything Hawaii has to offer for a tropical...
Modern & Tropical Oceanside Vistas
Summary:Newly remodeled (June 2022)1 br, 1 bath modern condo with upscale Hawaiian style. Located directly across from the beach in warm & sunny Kihei. Nestled in the exclusive and desirable Kihei Bay Vistas, you will be embraced in the tranquil grounds and ocean views....
One of a Kind Luxury
FEATURED IN ARCHITECTURAL DIGEST MAGAZINE! Are you ready to graduate from the Presidential Suite? Are you looking for the most relaxing vacation accommodation?*Specials not available during Peak Season*This OCEANFRONT CROWN JEWEL – A MODERN DIAMOND HEAD HOME –...
Hale Hau`oli ~ FAIRWAYS TERRACE H104 ~ 2 BR / 2 BA ~ Pool/Spa/BBQ ~ Gym ~
Summary:Hale Hau'oli - Located on the western slope of Mauna Kea our 2 bedroom 2 bath condo in Waikoloa Village sits on the Robert Trent Jones golf course (The Village Course). Enjoy the benefits of the 900’ elevation with warm days and cool mornings and evenings....
Remodeled Ground floor, Oceanview, AC, steps to Kam II Beach
Freshly remodeled unit top to bottom in a prime South Kihei location. ***Please note: This property is Hotel Zoned and NOT in danger of the possible upcoming short term rental ban.***The layout:Bedroom: King size bed with premium linens, blackout drapes, closet, new...
Ocean Front 3-bedroom house in phenomenal Anahola with WiFi
Experience Anahola like a local in this 3-bedroom house. This charming property features 2 queen beds and 1 bunk bed, perfect for families or friends traveling together. With amenities like heating, WiFi, and a hair dryer, guests will feel right at home. The 2 bathrooms...
Cozy 1-bedroom apartment in amazing Honolulu with WiFi, AC
Located at the riverbank of Ala Wai Canal, you can enjoy the beautiful river view from the balcony. This apartment is remodeled in 2023 with zero VOC paint on the walls for your kids’ safety. Near 7-11 convenience storeVersatile kinds of restaurants Chiba-ken...
Maui Resort Rentals: Kaanapali Ali'i – 4 Total Bedrooms, Luxuriously Remodeled, Premiere Ocean AND West Maui Mountain Views!
This phenomenal four-bedroom offering brings together a 2BR suite with a premier ocean view in one of the best interior stacks at the entire resort with a luxurious neighboring 2BR partial ocean view suite. Together the two neighboring 7th-floor suites offer a combined...
Royal Sea Cliff Kona 103 Garden View 1 Bedroom
- 1st floor condo located very close to the South pool and the BBQ grills- Covered lanai is 154 square feet/14 square meters- Tile flooring throughout unit.- Updated kitchen features all new, stainless steel range, dishwasher, and refrigerator- Bedroom with 1 king bed-...
Ridge Villas Fairway View 1 Bedroom at The Kapalua Villas Maui
Nestled in lush gardens and beside pristine beaches, our secluded sanctuaries offer tranquility. Enjoy world-class golf, snorkeling, award-winning spa treatments, and farm-to-table dining. Experience luxury in our fully-equipped villas, with stunning sunsets from your...
Maui Resort Rentals: Honua Kai Konea 326 – Luxurious 2BR w/ XL Balcony & Delightful West Maui Mountain Views!
Maui Resort Rentals is proud to bring you this 2BR Partial Ocean View Suite at the Honua Kai Resort, newly launched on May 12th, 2025 to start taking reservations for check-ins on June 21st, 2025!Konea 326 is a remarkable 2BR/2BA suite offering nearly 1,300 square feet...
Aloha Hale - 3-bedroom house in tropical Pāhoa near Hilo
Your group will be close to everything when you stay at this centrally-located home near Pahoa Town where you'll find local shops, a variety of restaurants, and the gateway to exploring the Puna District. The 3 bedroom 2 bath home is located in a quiet Hawaiian...
Charming 1-bedroom condo in lovely Kihei with WiFi, AC
Discover this fantastic 1-bedroom gem in Kihei. This cozy condo features a nice king bed, 2 bathrooms with a bathtub and shower, and convenient amenities like WiFi and AC. The serene atmosphere of this property will make guests feel right at home. You're sure to make...
Beautiful, Updated Condo Across the Street from Famous Charley Young Beach
Hawaii Tax ID: TA-140-731-5968-01TMK: 390180030175This beautiful and updated condo is right across the street from the famous Charley Young beach, within walking distance of several other beaches along the Kihei coast as well as many shops,...
Oceanfront 2BR Condo w/ Pool Access & Sunset Views
This is a legally permitted vacation rental according to current County of Maui Ordinance.Private Oceanfront Escape – Sea Turtles, Snorkeling, and Stunning Sunsets E komo mai (welcome) to Mālama Honu, your luxurious home away from home at Hale Ono Loa 121. Nestled...
Chic 1-bedroom in beautiful oceanfront resort with King Bed and AC
Welcome to Kauai, Hawaii! We are delighted to welcome you to Outrigger Kauai Beach Resort, a hidden gem nestled on the sandy shore of an exclusive east-side oceanfront property. Our resort offers a blend of luxury, convenience, and affordability, providing a serene...
Wyndham Paniolo Greens | 2BR/2BA King Suite
Summary:This resort is a lush, tropical retreat in the heart of Hawaii's Big Island featuring spacious suites with private lanais. There’s plenty to do on-site, including a swimming pool, spa, tennis court, and scenic barbecue areas.This listing is for a 2BR/2BA suite...
Recent remodel: quiet, new AC, WiFi, accross the street from Kam III beach
In south Kihei, this elegant top-floor condo is accross the street from Kam III beach, one of the best beaches on Maui. Great amenities & conveniences: WiFi, electric standing desk, washer/dryer, new and quiet AC, within walking distance to shops, restaurants, grocery...
Mauna Lani Point | C302
The view from Mauna Lani Point #C302 sets this Big Island vacation rental apart, offering an unforgettable experience from the moment you open the front door. Greeted by breathtaking ocean views, you’ll enjoy a front-row seat overlooking one of the most photographed...
Marriott Main Ocean Club- Stunning Studio Villa Lahaina/Napili Towers
Concierge Realty is proud to present luxury villas at Marriott Maui Ocean Club TowersWe are able to offer reservations in weekly increments with arrivals and departures Fridays, Saturdays and Sundays.Beginning Aug. 23, 2025, to Dec.16, 2025, Marriott’s Maui Ocean Club...
Secure Building at Entrance to Waikiki!
Waikiki is at your beckoning! Fully furnished with parking for your rental. Enjoy relaxing mountain view and a rooftop pool to soak in what paradise offers! Washer and dryer in unit along with air conditioning in this fantastic one bedroom unit!ULTRA SECURE building...
Westin Ka'anapali 1 Bedroom Villa at oceanfront resort (Guaranteed Week!)
Westin Kaanapali is a world-class destination at a luxury resort. All resort-view 1-bedroom villa reservations are equivalent - specific units are assigned at check-in. All listings describe the same property. The difference with this listing is that it’s a guaranteed...
Tranquil ocean-view condo just steps to water
Hale Ono Loa 401 is a 1-bedroom, 1-bathroom forth-floor condo featuring ocean views and a private lanai. This unit does not have air-conditioning. The condo can accommodate up to 4 guests with a king size bed in the bedroom and a queen sleeper sofa bed in the living...
Welcome to your Maui Escape!
Experience the ultimate getaway at a charming and centrally located condo in Kihei, just steps from the beach! Nestled in a small quiet complex, this tropical retreat offers a peek-a-boo ocean view, the perfect backdrop for your morning coffee or evening sunset. Enjoy...
MV 3214-Across from the Beach! So close to Everything!
* Across from the beach! * 4 more beaches within 1 mile* 1/2 mile to shops, dining and activitiesExperience Maui's magic in this charming 1-bedroom, 1-bathroom condo at Maui Vista. This cozy retreat offers comfortable accommodations for up to 4 guests, featuring a plush...
Discovery Bay 1 Bedroom Deluxe City View, Near the Beach!
Enjoy the vibrant energy of Honolulu from this stylish 1-bedroom condo perched on the 26th floor of Discovery Bay, offering sweeping views of the city skyline. Thoughtfully updated for comfort and convenience, this unit features a plush king bed, central air...
A Pool Ocean View Plus a Mountain View Hotel Room at 4 Star Oceanfront Resort
Welcome to Kauai, the Garden Isle, where local culture meets world-class hospitality. A full-service 4-star resort, escape to paradise at our tropical oasis nestled directly on Nukolii Beach on the Garden Isle's East shore. Experience the warmth of Hawaiian hospitality...
Cozy 3-bedroom apartment with WiFi in Centrally located Honolulu Salt Lake
Discover this 3-bedroom gem in Honolulu. This excellent apartment offers a peaceful retreat for guests. With 2 twin bed, 1 queen bed, and 1 Office. (The Office does not have a bed.) It comfortably accommodates everyone. The bathroom features a refreshing shower, and...
MKV A302 - Beach Front 2 bedroom with Garden Views
Book with us and come to Maui to explore everything we have to offer!Enjoy staying at this well maintained 2 bedroom 1 bath unit located at the Maui Kaanapali Villas. Boasting 2 pools, a spa, onsite restaurant, fitness center, activities center, and access to the...
Comfortable condo in town with ocean view, lanai & pool - walk everywhere
Kalanikai #319Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Experience the ultimate Hawaiian getaway at this charming third-floor condo in Kailua-Kona, just a short walk from the...
Beautiful Waikiki condo with a large private lanai & conveniently located
Aloha Towers 503Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Experience the best of Waikiki from the comfort of this spacious 2-bedroom, 2-bathroom corner unit condo located in...
Deluxe 2BR Oceanview Maui Condo...Ideal West Maui Locale!
Welcome to your own Deluxe 2-Bedroom Oceanview Maui Condo..Ideally Located in West Maui, just north of famous Kaanapali Beach. You'll love the stunning Tropical Grounds, set amidst swaying coco Palms, and just steps to small sandy beach. Take a dip in the Oceanview...
Hapuna Beach Residence B14 at Mauna Kea Resort
This brilliant, oceanfront, newly-constructed, ground level island masterpiece offers floor-to-ceiling sliding window walls that create indoor/outdoor living space, a state-of-the-art chefs' kitchen outfitted with professional-grade Wolf, Sub-Zero and Miele appliances,...
![Luxury Oceanview Wailea Retreat [Hōkū Hale]](https://media.vrbo.com/lodging/116000000/115230000/115220600/115220592/19b8a6ba.jpg?impolicy=ccrop&w=1000&h=666&q=medium)
Luxury Oceanview Wailea Retreat [Hōkū Hale]
Escape to Hōkū Hale, a serene oceanview retreat in the heart of Wailea. This designer oasis offers modern comforts, a private lanai with stunning ocean views, all situated on the fairway of a private golf course. Walk to world-class beaches, golf, and dining, or relax...
A luxury guest room in Marriot's Ko Olina Beach Club in Waipahe Place
A luxury guestroom in Marriot's Ko Olina Beach Club!Enjoy you stay at a beautiful beachfront resort with outdoor pool, spa, fitness center and restaurant. Whether your looking to relax in your private guestroom or prefer to lounge poolside with food and beverage...
King Bed Luxury Beach Studio Heart of Waikiki
About this spaceBrand new saltwater pool! This special place is close to everything, making it easy to plan your visit. Feel right at home in the heart of Waikiki's famous resort district. If you want to avoid having to have a car and prefer to walk across the street to...
Poipu Kai Regency 412 - Two-bedroom Garden View
Poipu Kai Regency 412 - Two-bedroom Garden View condo on the island of Kaua'i. Primary bedroom: King BedPrimary bathroom: full bath ensuite with shower/tub comboBedroom 2: 2 TwinsSecond bathroom: full bath with shower/tub comboSleeps: 4 peopleAC: NoneLaundry: in...
Top floor, direct oceanfront views, & remodeled Kaleialoha gem.
Welcome to Kaleialoha 413. This top floor, direct oceanfront condo features 180 ocean & island views. This condo has a remodeled kitchen & bathroom, AC in living area, 2 Flat screen TVs, new king bed with luxury bedding and more! Close to shops, dining, farmer's market,...
Mauna Lani Point | C303
The privileged third floor location of Mauna Lani Point C303 provides you with the most elevated and dramatic views on property. Once you open the front door to this vacation rental you will be greeted with the ocean and golf course views. Make your way out onto the...
Stay Inn a Volcano on a Volcano
Don't let your adventure stop at the national park! Come experience living in a luxurious volcano dome home where you will live in synergy with the natural exquisite surroundings. The cinder we used to build the whole dome comes from the local query produced from big...
Mauna Lani Point | J104
Welcome to Mauna Lani Point J104! As you step into this beautiful two-bedroom residence, you'll feel a sense of calm and be drawn to the incredible views of the Big Island scenery and Mauna Lani Golf Course.With its large lanai and outdoor space, you can experience the...
Park Lane Getaway by Gather: Spacious 2BR w/ Ocean view Lanai & Resort Amenities
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Welcome to Park Lane Getaway by Gather, an...
Oceanfront oasis with whale watching view
Welcome to your oceanfront getaway at Hololani A503, a 2-bedroom, 2-bathroom condo that offers ceiling fans throughout, panoramic ocean views from your private lanai, and a private washer/dryer. This property has elevators for easy access. Unit A503 can accommodate up...
🌴 Newly Renovated Top Floor Condo with Golf Course & Ocean Views 🌴
** Keep in mind that the "3rd bedroom" is a loft area. (See Photos) Enjoy ocean views from your vacation headquarters that lie right on the golfcourse. Country Club Villas offers a peaceful resort setting on the quiet end of Kona inKeauhou. Three pools are shared by...