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.
Kahala Beachside Estate – Premier Luxury Living on Oahu’s Gold Coast
Where timeless Hawaiian charm meets modern sophistication, Kahala Beachside Estate by Gather offers the ultimate oceanfront escape on Oʻahu’s prestigious south shore. Set directly along the sands of Kahala Beach, this magnificent estate spans 7,860 square feet of indoor...
Kanaloa at Kona Oceanfront 2 Bedroom
Beautiful condominium situated on 16 acres of a secluded oceanfront lava flow overlooking beautiful Keauhou Bay. Relax in tropical gardens and lush flower-filled landscapes. Golfers, families and outdoor enthusiasts will enjoy snorkeling, golf and deep-sea fishing...
The Whaler 814, Black Rock, All 5 Stars
On Kaanapali Beach with outdoor pool, next to Whalers VillageIn this beautiful remolded Kaanapali ocean view condo, clear blue ocean waves meet vibrant green surroundings to form a perfect haven.As a guest, you'll be able to indulge in a wealth of amenities that cater...
Luxury Oceanfront 3-bedroom Retreat with AC in the heart of Kihei
Nestled in Kihei, this delightful condo boasts 3 bedrooms including 2 king beds, 1 queen bed, and 1 bunk bed. With 3 bathrooms featuring a bathtub, shower, and jetted bathtub, guests will feel right at home. The additional living room space with 1 queen bed and 1 full...
Near Lahaina Town | Dining, Spa, and Pools
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...
Making The Best Memories Along The Way! Outdoor Pools, City View!
The excitement of Waikiki Beach is at your doorstep at this Honolulu property!This listing is for a room within a hotel.✦ Your room is 390 sq. ft, equipped with complimentary toiletries, high definition 46-inch TV, available with Premium cable.✦ Cleaning services...
Studio City View Kitchenette, A/C and WiFi - Bamboo Waikīkī Hotel #305
Castle Bamboo Waikīkī Hotel #305 - Just a short walk from the sands of Waikīkī beach sits this cozy third-floor 310 square-foot gem with all the modern conveniences to make your stay comfortable and rested. Start your day on the furnished lanai with morning coffee or...
Kauai 2 Bedroom Villa Sleeps 8
Please Send An Inquiry Before Requesting To Book By Clicking The Contact Host Tab.The resort is beautifully landscaped with waterfalls and lagoons, lush tropical plants, and the sandy shores of Poipu Beach just steps away. While the beach is perfect for children, the...
waking up to the scent of tropical flowers drifting through the air. and enjoy your morning with a fresh cup of coffee. Spend your day exploring nearby beaches, hiking lush trails, or simply relaxing by the beach. A peaceful, tropical escape awaits.
Relaxing 5bd/3ba Kailua Home Just Steps from Kailua Beach with Wifi and A/C
Just four homes away from the Kailua Beach pristine white sands, this spacious retreat combines a stunning 4-bedroom home with a separate private studio cottage. Your perfect Hawaiian getaway awaits with a thoughtful blend of comfort and island living. Sleep in...
Experience oceanfront luxury at Napili Point A23
Step into the relaxed elegance of Napili Point A23, a beautifully updated 1-bedroom, 1-bathroom ground-floor condo that brings you as close to the ocean as you can get—without getting wet. Nestled just above the vibrant waters of Honokeana Bay, this oceanfront escape...
Halii Kai 8APlease scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom: 2 Full BedsAmenities:Beach Equipment: All of our vacation rentals include beach towels for the maximum occupancy, four beach chairs, two boogie boards,...
Maui Resort Rentals is proud to present this premier three-bedroom villa at Luana Garden Villas, newly launched on February 20, 2025, and now accepting bookings for stays beginning April 18, 2026!This luxurious 3BR/3BA residence is conveniently set within Enclave Two of...
3-bedroom Papakea resort in enchanting Lahaina adjacent to Kaanapali with AC
With ocean & mountain views, this spacious two-bedroom, two-bathroom + loft retreat offers a truly memorable vacation experience. Immerse yourself in the beauty of the Maui Kaanapali area, soak in vibrant rainbows, and create lasting memories with family and friends,...
Charming 1-bedroom house in tranquil Kaneohe with AC
Make yourself at home in this gorgeous 1-bedroom Kaneohe retreat. This perfect house features a cozy king bed and a child bed, ensuring a tremendous stay for guests. With amenities like AC and a hair dryer, this charming property offers everything you need for a...
Resort Living in beautiful Ko Olina Hillside Villas!
Discover the beauty of Kapolei from this 3-bedroom townhome. This gorgeous property features 2 queen beds and 1 sofa bed, perfect for a group of guests. With amenities like WiFi, a washing machine, and AC, your stay will be brilliant. Enjoy all that Kapolei has to offer...
2 Beachfront Rooms with Scenic Views and Outdoor Pool
Step into paradise: Explore Kanaha Beach Park & indulge at Queen Kaahumanu Center, right from our welcoming Kahului Bay doorstep.This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.✦ Each room is 540 sq. ft, equipped...
4 Star Beachfront Resort. AC. Lanai. Restaurant. Pool. Gym. Spa.
Welcome to the beautiful Outrigger Kauai Beach Resort & Spa — a tropical oceanfront retreat on Kauai’s scenic East Shore.Set on 25 lush acres along one of Kauai’s longest beaches, this Hawaiian style resort offers the perfect blend of relaxation, convenience, and island...
Hilton Maui Bay Villa 3-Bedroom Premier Penthouse with Ocean View
This three-bedroom, three-bathroom ocean view suite offers a forward-facing ocean view balcony with seating for six, and furniture, textiles and finishes that are unique to the suite. The primary bedroom features a king-size bed, 55-inch TV and lounge chair and the...
3 BR Haena Beachfront Home on Kauai's North Shore
Unwind in Haena, Kauai's North Shore, boosting direct beachfront access spectacular views, immersed in tropical splendor. With three spacious bedrooms featuring king beds and a cozy twin, plus an additional waterfall suite and game room, that includes another king and...
2 Separate Entry Studio Condos-Next to Each Other-Fabulous Views- 2 Free Parking
Two separate studio condos next to each other with separate entrances. Condo 2402 has a full kitchen and a washer and dryer within the unit. Condo 2401 has a Kitchenette. Both units have king beds with memory foam mattresses and desks. Each unit has a covered designated...
Oceanview Condo - Pools, Hot Tub, Spa & Beach
Welcome to Ka'anapali Shores, a perfect retreat for your Maui escape! Unwind with stunning views of the Pacific Ocean, while Maui’s top activities, dining, and adventures are just minutes away.Highlights:-Two large sparkling pools with cabanas and a waterfall jet...
Hilton's Lagoon Tower 1-Bd Plus Ocean View: A Paradise with Endless Fun
Elevate your vacation to new heights at the Hilton Grand Vacations Lagoon Tower, where stunning ocean views meet family-friendly comfort and a vibrant island atmosphere. Nestled in the heart of the Hilton Hawaiian Village® in Waikiki, this spacious 1-bedroom plus ocean...
🌊 Ocean Views & Island Vibes – Your O'ahu Escape! 🌺
Welcome to our "Kaimana" estate located on oceanside in Hau'ula. Hau‘ula is a small, scenic coastal community on the northeastern (windward) side of O‘ahu, about an hour’s drive from Honolulu. Known for its laid-back, rural atmosphere and strong sense of community,...
37th Floor Corner Unit with Stunning Ocean & Diamond Head Views – Waikiki
At the beginning of Waikiki, the tourist center of Honolulu. Our charming studio in Waikiki is a breezy unit in Hawaiian Monarch building.Enjoy breathtaking Ocean & Mountain views. Hotel quality sheets, pillows, and air conditioning await you.Excellent location right...
Kaanapali Alii 1162 Bedrooms | 2 Bathrooms | Sleeps 8 | Ocean Front--------------------------------------------------Welcome to Kaanapali Alii 116, a stunning ground-floor two-bedroom oceanfront residence at Maui’s exclusive Kaanapali Alii Resort. Just steps from the...
Waikiki Shore 710 Ocean View 1 Bedroom
Wake up to stunning ocean views in this inviting one bedroom condo, set in the only condo on world-famous Waikiki Beach. With lots of space and everything you need to unwind, it’s the perfect place to experience island living.Unit 710 Ocean View 1 Bedroom 1 Bathroom•...
Beautiful home with ocean views, lanai, private gazebo, firepit -great location
Pualani Island Getaway - Main House- 30-night minimumOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome to your hidden gem in Kailua-Kona, HI, where stunning sunset views of...
Konishiki Beachhouse: Luxury 6BR Oceanfront Home with Private Pool & Beach Access
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 Konishiki Beachhouse Estate by...
Royal Kahana Maui 819 Ocean View Studio
Experience Maui’s beauty from this serene studio with ocean vistas, close to dining, shopping, and beaches. Great for couples or solo travelers. Unit 819 Ocean View Studio• 8th floor studio with balcony overlooking the ocean • Studio kitchen includes microwave,...
Ocean View Waikiki Hawaiian Monarch
Large wide angle high floor, can better view the scenery out of the window. This unit about 260sqft, 24 hours security measures, can better protect the safety of residents. Downstairs have convenience stores, restaurants, car rental services, ext. can quickly solve the...
Honua Kai Luana Garden Villa 4D 3 Bedroom 3 Bath
Unit #4D Luana Garden Villa 3 Bedroom 3 Bath Garden Villa- Open kitchen concept – Bosch appliances to include induction cooktop, wall oven, counter-depth French Door refrigerator with two freezer drawers, quartz countertops with full height ceramic tile backsplash,...
World Famous Makaha Beach Oceanfront Condo!
Available 30 days or more regardless of VRBO calendar setting. Relax on the lanai watching the waves rolling in on the beach below, or take a good book down to the pool and enjoy the shade. Away from the crowds at Waikiki in a boutique condo building, so peaceful! If a...
Tranquil Stay at Wailea Ekahi Oceanfront Complex-2 Beds-Balcony
Relax in our renovated 1BR/1BA condo at Wailea Ekahi Village, perfect for up to 4 guests. This bright and comfortable upstairs second-floor condo in Building 36 features a California King bed, a Queen Murphy bed, a fully stocked kitchen, and modern amenities including...
Spacious Suite with Ocean Views + Pools & Dining
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...
Oceanview Air-Conditioned Kona Estate w/ Infinity Pool & Sunset Views
Set within the gated enclave of Keauhou Estates, Hale Nai'a is a striking oceanview retreat where architecture, art, and horizon-wide vistas take center stage. From its dramatic entry to the infinity-edge pool overlooking Keauhou Bay, this private home delivers a...
Great View &Waikiki Famliy Retreat
About this spaceEscape to our cozy family Space on the 21st floor, where modern comfort meets charm. Enjoy breathtaking tropical views, abundant natural light, and a peaceful atmosphere—perfect for creating cherished memories with loved ones. Book now for a serene...
Modern, Comfortable with Great Amenities! Washer/Dryer, Parking, WIFI included!
New to our inventory and remodeled in 2024, this unit is a true gem, offering modern style and all the comforts of home. The living area features a cozy sofa sleeper and a large flat-screen TV with streaming capabilities. It seamlessly connects to a dining area with...
Tranquil 3-bedroom house in Waikoloa Village with fitness room, tennis & pool
Experience Waikoloa Village like a local in this 3-bedroom house. The bedrooms feature a king bed, queen bed, and bunk bed, ensuring a comfortable stay for all guests. With 3 bathrooms equipped with a bathtub and hair dryer, relaxation is just a step away. Experience...
Marriott Maui Ocean Club | Three Studio Villas
Summary:Located on the shores of Ka'anapali Beach, Marriott Ocean Club is surrounded by Hawaii's beautiful scenery! The resort is the perfect family getaway with something for everyone to enjoy - beautiful pools, golf, on-site dining, spa services, and sports courts....
Ho'omaluhia - Luxury Coastal Residence | Ideal for Families & Groups
~NEW LISTING~Peaceful North Shore living on the Ritz-Carlton Turtle Bay groundsWelcome to Ho'omaluhia - a luxury coastal residence, a tranquil 2-bedroom, 2-bath retreat nestled on the Ritz-Carlton Turtle Bay hotel grounds and golf course on Oahu’s iconic North Shore....
Maui Wailea Spacious 4 Bedroom Sleeps 10
Please Send An Inquiry Before Requesting To Book By Clicking The Contact Host Tab.Contemporary Oceanview Retreat in Wailea Perched on a gently sloping lot in an exclusive Wailea enclave, this stunning contemporary masterpiece blends artful design with effortless coastal...
Kolea 2E - Newly furnished in 2024 3 Bedroom Condo
As you enter through the large double doors you will be struck by the spaciousness as well as the new furnishings of Kolea 2E.The great room has a wrap around couch that faces a wall mounted big screen television. Adjacent to the living room is the dining room that...
Kahana Villa 32 Direct Oceanfront Views Remodeled 2BD w AC
Kahana Village 32 NEW LISTING Experience Maui with Direct Oceanfront Views, Incredible Sunsets, and Beach Walks just Steps from your Door! FREE daily activities included with your stay value up to $1035! Complimentary admission, every day of your stay*: Lu'au, Golf,...
Perch - Kihei Ali'i Kai Front Row Penthouse | Walk to Beach & Food
Experience your Maui getaway at Kihei Ali'i Kai B402, a beautifully updated penthouse front-row condo with a fresh, modern ocean vibe. Located in one of the best view spots in the complex, this end unit boasts a spacious lanai with over 200° panoramic views—stretching...
Monkeypod Canopy with Shared Bath and Common House
Escape to the enchanting Monkeypod Canopy, a glamping-style retreat. This unique accommodation offers the perfect blend of rustic charm and modern comforts, making it an ideal choice for those seeking a tranquil yet luxurious getaway.The Monkeypod Canopy features a...
WAILEA POINT Sweet 2 Bedroom/3 Bath Oceanview Condominium
Please call or email us about the dates for your visit. Free Car promotion! Want a mini-Cooper or similar ride while you're here on Maui - Ask us! New media posted! Check out the new photos and video. Make yourself home at Wailea Point Village 3003. A first-floor...
2 Ko Olina Beachfront Resort & Spa, Hot Tub, Pools
Marriott Ko Olina Beach Club is located on the stunning western shore of Oahu, offering a tropical paradise experience with breathtaking views and luxurious amenities. Upon arrival, guests are greeted by beautiful waterfalls and fountains, setting the tone for the...
🏖️2BDRM + Loft | Sleeps 6 | Ocean & Golf Views | vrKCV
vrKCV - Country Club Villas 304, Professionally Managed by Kona Coast Vacations Country Club Villas 304 is a top-floor retreat offering breathtaking ocean and golf course views. This spacious 2-bedroom plus loft, 2.5-bathroom condo comfortably accommodates up to six...
Hilton Grand Vacation Club, All Towers, Honolulu!
Discover Oahu's incredible attractions just minutes from your Hilton Grand Vacations Club residence. Experience Hawaii's breathtaking landscapes from above with Island Seaplane Service tours - the only aerial excursions available in Hawaii - or explore vibrant...