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.
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, restaurants and a...
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 along...
Lodge at Kukuiula Cottage 15
The two-bedroom cottages at The Lodge at Kukui'ula on Kaua'i offer luxurious accommodations and exclusive access to the award-winning private club facilities and amenities of The Club at Kukui'ula, including the 18-hole Tom Weiskopf designed golf course, sprawling spa...
Kapalua Bay Villas | 3 Free Rental Cars | KBM Resorts | Large Master Suites | 3 Units, 3 Bedrooms | ML-2092
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Kksr#7-103 Ground Floor, Garden/Golf Course Views, Beautifully Remodeled
Relaxed Island Living at Keauhou Kona Surf & Racquet Club – Ground Floor 2BR/2BAWelcome to your Hawaiian getaway at Keauhou Kona Surf & Racquet Club, Unit 7-103. This beautifully remodeled 2-bedroom, 2-bathroom ground-floor condo offers comfort, style, and easy...
Maui Banyan T308 | Spacious 2BR w/ Garden & Mountain Views by Kamaole II
Sunny 2-Bedroom Condo with Garden Views – Across from Kamaole II Beach!Welcome to your perfect Maui getaway! It is ideal for anyone looking to unwind just moments from the beach.• Located just a short distance from the crystal-clear waters of Kamaole Beach Park II, one...
1 Mi to Beach, Remote Work Hub: Modern Kailua Gem!
Walk to Shopping & Dining | Furnished Lanai | Home Gym | Community Pool AccessFind your slice of Oahu paradise at this luxury Windward Harbour vacation rental! The 3-bedroom, 2-bath condo boasts inviting indoor and outdoor living spaces, making it easy to recharge after...
New Listing! Waikoloa Fairway Terrace-Golf Course
Welcome to your serene retreat at Big Island Fairway Terrace I-208, nestled in the heart of Waikoloa, Hawaii. This charming 1-bedroom, 1-bathroom vacation rental offers a perfect blend of comfort and elegance, ideal for a memorable getaway. The spacious 492 sq. ft....
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...
Fabulous oceanfront Poipu Point! 4 bedrooms for 12!
Located at the fabulous Poipu Point oceanfront resort! The 4 bedrooms, 4 baths for 12 is made up of two separate 2 bedroom 2 bath condos for 6, just steps apart! Dec 20-27, and Dec 27-Jan 3 is available! If you need more units, let us know. 4 bedrooms 4 baths for 12...
Top-Floor Ocean-View Condo; 2 min walk to Kamaole Beach III, 2 King Beds
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...
Waikiki Banyan | Free Parking | Ocean Tower Beach
Our High Floor Makai Tower (Ocean Tower) Condo at the Waikiki Banyan Resort is your Beach Getaway, just renovated with FREE garaged parking and the Beach one block away. Contactless Check-InNO Resort FeesNO Security DepositFREE Parking Garage with elevator straight up...
KÄÊ»anapali Golf Course Access + Pools and Tennis
Escape to paradise at Royal Lahaina Resort & Bungalows, set along Maui’s iconic Kaanapali Beach. Enjoy direct beach access, two oceanfront pools, on-site dining, tennis courts, and lush tropical gardens. Just minutes from Whalers Village and Lahaina Town, this resort...
The Islands at Mauna Lani F4
The Islands at Mauna Lani F4 has everything you could want in a vacation rental for a memorable stay on the Island of Hawaii. This ground floor two-bedroom condo that sleeps up to six guests is 2,189 square feet and enjoys peaceful vistas across a beautiful golf course...
Marriott Main Ocean Club- Stunning three bedroom villa in 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...
Serene 1bd ocean view condo, moments from shore
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...
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...
BEACHFRONT REEF TURTLES KAYAK NORTH SHORE
Monthly Rental as required by Honolulu County. Please inquire before getting scared off by the rental rate or Honolulu's system. Will consider discounts as VRBO's system does not work for Honolulu. Happy to share the True Spirit of Aloha here with web Aloha Beach...
Oceanfront • AC • W/D • Desk • Central Maui
Wake to the sound of waves and sip your coffee on the oceanfront lanai as the sun rises over Haleakalā. Spend the day by the pool watching sea turtles and in season, spot the whales breaching right in the bay. Walk to the Harbor for snorkeling or sunset cruises, and...
4 Star Beachfront Resort. AC. Restaurant. Pool. Gym. Spa. 4 rooms. Sleeps 11
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...
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...
Sheraton Kaua'i Resort Villas 2-bedroom villa with WiFi, AC in lovely Koloa
Welcome to this charming villa in Koloa. This amazing property features 2 bedrooms with king beds, 2 bathrooms (one with a soaking tub, and both with walk-in showers), and a beautiful living room with a sofa bed. Guests can enjoy amenities like AC, a washing machine &...
Laueki 5 – Ocean View Estate | Onsite Staff & Daily Housekeeping
This large, Hawaiian Style home boasts luxurious indoor and outdoor spaces and stunning ocean views overlooking the 4th hole of the Ke‘olu Course. Five bedroom suites accommodate up to 10 guests plus media room, infinity pool and hot tub and a private courtyard. Located...
Aqua Aloha Surf Waikiki 1005 Deluxe Studio with Lanai and Partial City Views
Aqua Aloha Surf Waikiki 1005 Deluxe Studio with Lanai and Partial City Views located just 2 Blocks to Waikiki Beach, (1) Full/double bed, (1) Twin bed + (1) Queen sofa sleeper, sleeps 4, 365 St FtAqua Aloha Surf Waikiki brimming with island personality offers a range of...
Hapuna Beach Residences B14 Four Bedroom
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 24th-Floor Waikiki Landmark Condo with Mountain & Ala Wai Scenic Views
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.*This property is new to our inventory, so reviews are coming soon. We can assure you this place is truly...
Kona Retreat • Ocean View, Pool & Walk to Beach
Welcome to your Downtown Kona Retreat! This top-floor 2BR/2BA condo offers ocean-peek views, a spacious lanai, and room for up to 6 guests. Enjoy a fully equipped kitchen, AC, pool, hot tub, and easy walkability to beaches, shops, and restaurants. Relax after a day of...
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...
NEW LISTING! Kapaa Condo with Pool and Hot Tub
Perfect Location! East Kauai Condo Escape to this delightful one-bedroom condo nestled in the heart of Kauai's stunning east side at the beloved Plantation Hale resort. Unit G6 offers the perfect blend of comfort, convenience, and charm for your island adventure.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...
Park Lane Getaway by Gather: Spacious 2BR w/ Ocean view Lanai & Resort Amenities
Welcome to Park Lane Getaway by Gather, an elegant two-bedroom, two-bathroom suite offering the ultimate in luxury and convenience in the heart of Honolulu. Located on the fourth floor of the prestigious Park Lane Ala Moana, this spacious 1,532-square-foot residence...
Spectacular 2bd ocean front with open layout
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...
Honua Kai Konea | 2 Free Rental Cars | KBM Resorts | Easy Pool Access | 2 Units, 4 Bedrooms | ML-1955
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Hawaiian style 1bd near beaches and golf
Napili Ridge A15 is a cozy 1-bedroom, 1-bathroom condo with tropical views from your private lanai. It comfortably accommodates up to 4 guests, with a California King bed in the bedroom and a queen sofa sleeper in the living room. Please note, that the condo is on the...
Honua Kai Hokulani | 4 Free Rental Cars | KBM Resorts | Extra Large Lanai | 4 Units, 8 Bedrooms | ML-1287
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Relax and Unwind at Kihei Akahi D-207 Across from Beautiful Kamaole Beach II
Your Tropical Oasis Across from the Beach!Welcome to Kihei Akahi D-207, your perfect retreat in the heart of Kihei, located directly across the street from the golden sands of Kamaole Beach Park II. This charming 1-bedroom, 1-bathroom condo offers a cozy, stylish haven...
Royal Kahana Maui 402 Ocean View Studio
This bright studio offers sweeping ocean vistas and easy access to Maui’s beautiful beaches—perfect for couples. Unit 402 Ocean View Studio• 4th floor studio with balcony • Studio kitchen includes microwave, stovetop/oven, coffee maker, refrigerator, toaster, blender,...
Hale Kamaole 113 - Relax and Enjoy the Beach
Book with us and come to Maui to explore everything we have to offer!Well maintained condo conveniently located very close to world class beaches, shops, and restaurants! Fantastic location close to the pool with lots of parking on site. Relax on your lanai with the...
Studio Villa
Starting from $500 per night - request your dates nowThe Westin Ka'anapali North in Maui has just what you need for your first, or next, relaxing vacation — a beautiful one bedroom villa. This well-equipped, fully furnished property offers elegant, luxurious living...
Perched at Pearl Harbor
Nestled atop a hill, our home offers an enchanting view of Pearl Harbor. Perfect for remote professionals and families alike, our property provides the perfect blend of comfort and scenic beauty.Welcome to our inviting home, where you can savor breathtaking Pearl Harbor...
Kalama Terrace 2BR with Pool, BBQ & Walk to the Beach
Aloha from Midway Vacations, your local experts in paradise! Enjoy spotless, well-kept homes, island hospitality, and 24/7 support for a worry-free Hawaiian escape.Experience the best of Maui in this nice island-style 2-bedroom, 1-bath unit at Kalama Terrace! The main...
The Turtle House, a 5 Bedroom Oceanfront Villa!!!
The Turtle Villa is the perfect location for an unforgettable and authentic Hawaiian experience. One of the best oceanfront views on the island with the most stunning sunsets. Our home is great for family getaways or large gatherings. Create family memories that will...