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.
Elegant Oceanfront w/ Pool & Hot Tub in Maui Sunset
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.Maui Sunset offers a bright and breezy, fully renovated 5th-floor ocean-view 2BR/2BA retreat perfectly...
Spacious Design Studio 3 mins from the beach
This spacious studio is located in the heart of Waikiki, within 5 minutes walk to Waikiki Beach. The space is completely remodelled with high end furnishings.Features:- a fully equipped kitchen- two double beds - perfect for families and groups!- a luxurious bathroom...
Cozy Studio at WorldMark Kihei – Maui Getaway for Two
Enjoy a simple and comfortable Maui escape in this studio suite at WorldMark Kihei. Perfect for couples or solo travelers, this suite offers everything you need for a relaxing stay in paradise.Inside the studio, you’ll find a queen Murphy bed that tucks away for extra...
Elegant Oceanfront 2BR Home with Vast Panoramic Views, Steps from Kehena Beach
The Jewel Box is your private oceanfront retreat perched above Kehena’s ancient lava cliffs. From the lanai, sweeping ocean views unfold—sunrise, sea spray, and the pulse of island life. Dolphins and whales pass by too. This fully stocked home is a short walk to Kehena...
Maui Sunset Vacation Rentals B305
Watch the life of Maui unfold from the morning till evening from your private 114 sq foot private view deck. Premium condo suite located near the pool area. Third floor middle of the building views of tropical gardens and the ocean beyond. Quiet location features large...
𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢’𝐬 Beachfront Fun at KoOlina Club Resort+Amenities.2BR
𝐕𝐢𝐬𝐢𝐭 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 to enjoy 𝐄𝐱𝐜𝐥𝐮𝐬𝐢𝐯𝐞 𝐒𝐚𝐯𝐢𝐧𝐠𝐬 on this elegant, 𝐬𝐩𝐚𝐜𝐢𝐨𝐮𝐬 𝟐-𝐁𝐞𝐝𝐫𝐨𝐨𝐦 𝐕𝐢𝐥𝐥𝐚 at one of Oʻahu’s most sought-after 𝐁𝐞𝐚𝐜𝐡𝐟𝐫𝐨𝐧𝐭 𝐑𝐞𝐬𝐨𝐫𝐭𝐬 — 𝐌𝐚𝐫𝐫𝐢𝐨𝐭𝐭’𝐬 𝐊𝐨 𝐎𝐥𝐢𝐧𝐚 𝐁𝐞𝐚𝐜𝐡 𝐂𝐥𝐮𝐛.Unlock 𝐌𝐞𝐢𝐥𝐢 𝐌𝐞𝐦𝐛𝐞𝐫-𝐎𝐧𝐥𝐲 𝐑𝐚𝐭𝐞𝐬 & 𝐔𝐩𝐠𝐫𝐚𝐝𝐞𝐬:𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 𝐄𝐱𝐜𝐥𝐮𝐬𝐢𝐯𝐞 𝐒𝐚𝐯𝐢𝐧𝐠𝐬 ($500–$1000 𝐎𝐅𝐅...
Westin Princeville Villas
Essence of HawaiiThis refreshing resort lies along a lush cliff on the north shore of Kaua'i and blends into the inspiring beauty surrounding it. Resting two hundred feet above the Pacific Ocean, The Westin Princeville boasts plunge pools provide quiet relaxation while...
Royal Kahana Maui 904 Ocean View Studio
Enjoy your stay in this bright and airy studio featuring panoramic ocean views, just steps from the beach. Perfect for couples or solo travelers. Unit 904 Ocean View Studio• 9th floor studio with balcony overlooking the ocean • Studio kitchen includes microwave,...
FALL BLOWOUT-Avail dates on Sale - Ko Olina Vacation | TCP-1174-2
Indulge in the epitome of Hawaiian luxury with our exquisite three-bedroom, three-bathroom, two-story townhome nestled within the prestigious Coconut Plantation in the renowned Ko Olina Resort. Impeccably maintained inside and out, this opulent retreat boasts newly...
Kahala Beachside Estate: Luxury Estate w/Pool, Jacuzzi, AC & Spacious Yard
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
- Spacious oceanfront condos located on 1st floor- Kitchen features stovetop, oven, refrigerator, microwave, dishwasher, coffeemaker, blender, disposal, cookware and tableware- Private balcony with wet bar- Master bedroom with 1 king bed or 1 queen bed and private...
Cliffside Comfort – Studio Premium Villa on Kaua‘i’s North Shore
Perched atop Kaua‘i’s stunning North Shore cliffs, the Studio Premium Villa at The Westin Princeville Ocean Resort Villas offers a relaxing retreat that blends resort amenities with the comforts of home. Measuring about 510 square feet, this villa accommodates up to...
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...
Cozy Kihei Getaway | Steps to Beach & Ocean Views
Summary:Walk to Charley Young Beach Just 3 blocks away Ocean Views Enjoy coffee on the private lanai King-Size Bed Luxury linens for restful sleep Fast WiFi Smart TV Work stream seamlessly Beach Gear Included Chairs towels umbrellas Pool BBQs Relax grill under the Maui...
Life on the Water Hawaii with WiFi & AC & Washer/Dryer
This delightful cottage in Honolulu is the perfect escape for guests. With a cozy studio unit featuring a queen bed and a sofa bed, this property offers a brilliant space for relaxation. Enjoy the convenience of amenities like WiFi, AC, and a washing machine during your...
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...
Aloha Getaway
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...
Napili Point A23 1BD with Unbeatable Sunset Views
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...
Ocean Views! 8A Halii Kai
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: Luana Garden Villas 7D – Modern 3BR Villa at Kaanapali’s Newest Luxury Residences!
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,...
Hilton Point At Poipu Relaxing 2-bedroom resort with AC in awesome Koloa
This 2-bedroom resort is perfect for your escape to Koloa. Featuring a spacious king bed and two bathrooms, guests can enjoy both a relaxing bathtub soak and a refreshing shower. The space stays comfortable with air conditioning, and thoughtful touches like an iron and...
4 Star Beachfront Resort. AC. Lanai. Restaurant. Pool. Gym. Spa.
Kauai Beach Resort is a hidden gem situated on the sandy shore of one of Kauai's most exclusive east-side oceanfront properties, offering a blend of luxury, convenience, and affordability, and providing a serene retreat. Surrounded by natural beauty, this haven invites...
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...
Your Beach Adventure Awaits! 3 Serene Units, Short Drive to Lahaina Harbor!
Your oceanfront tropical oasis awaits on beautiful Maui!This listing is for 3 separate rooms within a hotel. The price shown in the listing covers all 3 rooms.✦ Each room is 1050 sq. ft, equipped with complimentary toiletries, TV.✦ Rooms are not adjoining and possibly...
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...
Island Comfort: 2BR at Wyndham Kona Coast Resort
Enjoy your Hawaii retreat in this spacious two-bedroom suite at Wyndham Kona Coast Resort, designed to accommodate up to six guests. The villa includes two separate bedrooms, a full kitchen with modern appliances, two bathrooms (one with a whirlpool tub in many suites),...
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,...
Kaanapali Alii Residence 116
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...
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 Estate: Luxury 6BR Oceanfront Home w/ Private Pool, Beach A
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,...
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,...
Wailea Ekahi Village Gem- Oceanfront Complex-2 Beds-Bldg 36-Walk to beach!
Relax in our 1BR/1BA condo at Wailea Ekahi Village, perfect for up to 4 guests. This renovated upstairs unit features a California King bed, Queen Murphy bed, a fully stocked kitchen, and modern amenities like WiFi, AC, and a bidet-equipped bathroom. Enjoy a private...
Escape to Paradise! 2 Attractive Units, Waikiki View, Rooftop Pool, Game Room!
Come for the beaches, stay for the adventure! With comfortable amenities and convenience to local attractions, you’ll have everything you need for a relaxing getaway or exciting family vacation. Take a dip in the rooftop pool with views of Waikiki. Enjoy a meal at the...
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...
Beautiful 2b2bth Wailea Grand Champions - Maui Condo- Special Rates!
Our beautifully appointed condo is perfect for a family (6 maximum), a couple or two couples (as there are 2 primary bedroom suites, each with a king size bed, private bath and flatscreen ). The condo features a spacious living and dining area and a fully equipped...
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....
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...
KHV 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 Bedrooms + Loft | Sleeps 6 | Ocean & Golf Views | Lanai
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...