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.
Recently Renovated - Oceanfront in Wailea
Expansive unobstructed views of blue Pacific waters and gentle waves will greet you each time you step out onto the lanai and soak in all the beauty that Wailea Elua 1604 offers. Evenings offer gorgeous sunsets framed by swaying coconut palms, perfect for a relaxing...
Recently Renovated & Professionally Managed Ocean View Villa
Welcome to Villa G302, your luxurious Hawaiian escape where relaxation meets elegance. This stunning ocean view villa features two walls of retractable sliding doors that seamlessly blend the open living area with a spacious corner lanai, complete with a built-in Viking...
Voted Top 10 Resort in Hawaii - Wailea Beach Villas F201
Welcome to Villa F201, an expansive vacation retreat that embodies upscale relaxation. Spanning a generous 3,676 square feet, this luxurious 3-bedroom, 3.5-bath villa is perfect for families or couples seeking a serene getaway. Villa F201 is a decorator\'s dream,...
Conde Nast Award Winning Property - Wailea Beach Villas E202
Warm breezes and lush tropical gardens greet guests of Wailea Beach Villas E202 as the spacious and comfortably appointed interior blends seamlessly onto the private outdoor lanai. Contemporary neutral and earth-toned furnishings are complimented by splashes of color...
Recently Renovated | Wrap-Around Ocean Views | Wailea Beach Villas D302
Welcome to Wailea Beach Villas D302! Recently renovated, this residence features a custom gourmet kitchen and dining area, offering a luxurious and spacious retreat in one of Maui\'s premier locations. Spanning over 2,900 square feet of indoor and outdoor living, it...
Beachfront Condo with Postcard Views
Experience the ultimate Hawaiian getaway when vacationing at Wailea Elua 1301. This beautifully designed vacation rental featuring an open floor plan showcases spectacular ocean views from the living room, dining area, and kitchen. The great room is perfect for...
Prime Location | Snorkeling | Wailea Beach Path
Wailea Elua 1203 is a stunning one-bedroom, one-bathroom oceanfront vacation rental located on the ground floor of the prestigious Wailea Elua Village community. This condo offers direct access to Ulua Beach, where guests can enjoy swimming and snorkeling in the gentle...
Recently Renovated - Walk to the Beach - Elua 1102
This ocean view one-bedroom Wailea Elua Village condo is a great home base for experiencing the joys and beauty of south Maui. Easily walk down to the white-sand Ulua Beach that fronts this property. Be one of the first in the ocean in the morning to snorkel the...
Stunning Ocean Views - Professionally Managed - Elua 107
Located just steps from the beach in the heart of Wailea, Elua Village 107 is a beautifully appointed two-bedroom, two-bathroom ground-floor residence that offers the perfect blend of comfort and island elegance. With a spacious layout and tasteful décor, this vacation...
Spacious Wailea Condo - Professionally Managed - Ekolu 1607
Wailea Ekolu 1607 is a stunning one-bedroom, two-bathroom vacation rental that offers an exceptional escape in beautiful Wailea. This beautifully appointed condo features calming views of the lush landscapes of the Wailea Blue Golf Course, providing a serene backdrop...
Ocean Views | Tropical Decor | Professionally Managed
Wailea Ekolu 1107 is a charming ground-floor vacation rental that offers the perfect blend of convenience and stunning views of the ocean, mountains, and the island of Lana\'i. Guests can enjoy the soothing sounds of tropical birds without the disturbance of street...
Ocean Views | Close to Wailea Golf & Beaches
Experience the beauty of Maui at Wailea Ekolu 1007, a stunning two-bedroom, two-bathroom ocean view condo designed for relaxation and comfort. Located along the picturesque Wailea Blue Golf Course, this ground floor vacation rental offers breathtaking views of the lush...
Walk to Waves, Pool, Snorkeling - Ekahi 7B
Wailea Ekahi 7B is a beautifully appointed vacation rental located within the serene Wailea Ekahi Village. This spacious one-bedroom, two-bathroom condo offers a perfect blend of comfort and luxury. The interior of Wailea Ekahi 7B features a contemporary design with...
2nd Floor Ocean Views | Whale Watch From Home
Wailea Ekahi 54D is a stunning second-floor vacation rental offering breathtaking views of the ocean and West Maui mountains. This one-bedroom, two-bathroom condo boasts panoramic vistas from multiple vantage points, including the living room, kitchen, and primary...
Stylish Beach Studio - Professional Managed
Wailea Ekahi 4D is a charming studio vacation rental perfect for the couple or solo traveler. This second-floor unit offers an elevated retreat with a bird\'s eye view of the surrounding tropical landscaping and peek-a-boo ocean views. The 600-square-foot condo is more...
Enhanced Design & Comfort - Ekahi 42C
This 1,090 square foot one-bedroom, two bathroom vacation rental sleeps four comfortably. Wailea Ekahi Village 42C is conveniently located close to the pool, but offers a quiet sanctuary surrounded by lush greenery. Featuring contemporary, yet comfortable décor â...
Spacious Condo on Favorite Local Beach
Wailea Ekahi 3E is a charming one-bedroom vacation rental located in the picturesque Wailea Ekahi Village. Situated on the second floor, this condo offers elevated views over the tropical grounds lush with colorful island landscaping. The vaulted ceilings and oversized...
Garden Retreat Close to Top Beach
If youâre seeking privacy and relaxation, Wailea Ekahi Village 39A offers a secluded Maui retreat nestled behind a lush row of towering tropical plants. This hidden gem provides a tranquil oasis perfect for unwinding after a full day exploring Maui\'s scenic...
Spacious Ocean View Condo - Perfect For Families
Nestled in the heart of Wailea, Wailea Ekahi 38F is an exquisite vacation rental that offers a luxurious and serene Maui escape. This stunning two-bedroom, two-bathroom condo takes full advantage of its second floor positioning and boasts panoramic ocean views. Take...
Sunset Ocean Views | Whale Watching | Wailea Ekahi 38B
Enjoy a relaxing indoor/outdoor tropical vacation experience from this ground floor ocean view vacation rental. Start your morning on the lanai with a freshly brewed cup of coffee and walk out on the sprawling grass lawn to feel the soft grass beneath your toes. Take in...
Recently Renovated Ocean View - Platinum Rated
Make your Maui dreams come true at Wailea Ekahi 35D! This vacation rental is perched on the top floor with a private entrance surrounded by manicured grass lawns, colorful bougainvillea, and fragrant plumeria trees. This modern remodeled one-bedroom one-bathroom condo...
Spacious Condo on Favorite Local Beach
Wailea Ekahi 35C is a stunning vacation rental located in the desirable Wailea community. This beautifully appointed one-bedroom, one-bathroom condo offers an ideal blend of comfort and luxury. Make use of the ground floor location to really live an indoor/outdoor...
Elevated Ocean Views | Walk to the Beach
Wailea Ekahi Village 12E is a delight to the senses. A vibrant row of Bougainvillea and the sweet smell of plumeria welcome you to this picture-perfect Maui vacation rental in the heart of Wailea. Once inside Wailea Ekahi 12E, you will be immediately drawn to the...
Sunset & Ocean Views | Platinum Rated
Nestled in the prestigious Wailea Ekahi Village, condo 30D is an exquisitely decorated island-inspired vacation rental that offers a perfect blend of luxury and comfort with breathtaking ocean views. The lanai provides an idyllic setting for outdoor dining or morning...
Meticulously Designed | Platinum Rated | Ocean View
This Wailea Ekahi Village residence completed a beautiful renovation in 2022. From colorful artwork to comfortable and sleek furnishings, you will instantly recognize why this Wailea vacation rental earned our highest internal ranking of \'\'platinum\'\' status. This...
Recently Renovated - Walk to the Beach
Welcome to Wailea Ekahi Village 23C. This residence was fully renovated in the fall of 2024 and features beautiful furnishings and decor to offer you a relaxing, island-inspired retreat. Nestled within 34 acres of lush tropical landscaping, 23C is a ground-floor...
Wailea Ocean Views | Great for Families
Wailea Ekahi Village 19B is a two-story, two-bedroom, two-and-a-half-bath townhome that comfortably accommodates up to four guests. This beautifully designed residence features island-inspired decor, creating a cozy and inviting atmosphere perfect for families or...
Wailea Ekahi Village 12C - 1 Bedroom Ocea View Condo
Wailea Ekahi 12C is a beautiful vacation rental nestled within the landscaped 32 acres that make up Wailea Ekahi Village. This upgraded condo offers a perfect blend of comfort and tropical elegance, making it an ideal retreat for those looking to escape the hustle and...
Wailea Ekahi 11C | Snorkeling & Waves Out Front
Wailea Ekahi 11C is an ideal Hawaiian retreat for friends or families traveling together. Each of the two bedrooms in this spacious condo feature a private lanai and en suite bathroom. Many guests return to this condo year after year for its close proximity to the pool...
Walk to the Beach - Wailea Ekahi 10F
Wailea Ekahi Village 10F is a premier vacation rental located in the heart of Wailea, Maui. This one-bedroom, two-bathroom condo is part of the Wailea Ekahi Village, a low-density community set across 34 acres of meticulously landscaped tropical gardens. The condo...
Elevated 8th Floor Ocean Views | Polo Beach 801
Perched on the top floor, this vacation home offers breathtaking views and a touch of sophistication. The spacious kitchen, featuring a central island, provides ample room for culinary creativity while allowing you to enjoy the company of guests in the open living area....
Walk to Waves, Snorkeling, Dining | Polo Beach 409
Polo Beach Club 409 is a luxurious oceanfront vacation rental located in the world-renowned beach vacation destination of Wailea. This two-bedroom, two-bathroom condo offers a premium beachfront experience with direct access to Polo Beach out front and stunning ocean...
Oceanfront Polo Beach 407 - Professionally Managed
Polo Beach Club 407 is a premier oceanfront vacation rental located in the upscale resort area of Wailea. This two-bedroom, two-bathroom condo offers guests a luxurious and comfortable stay with sweeping ocean views and direct beach access out front. If looking for the...
Wrap-Around Beach & Ocean Views | Polo Beach 301
Welcome to Polo Beach Club 301, a stunning third-floor corner residence that offers breathtaking views of Polo Beach. This spacious unit exemplifies the indoor-outdoor lifestyle that Hawaii is famous for, making it perfect for both entertaining and relaxing with friends...
Beachfront Condo with Postcard Views - Makena Surf F306
Experience effortless mingling and entertaining in Makena Surf F306, where the open living area seamlessly connects to a spacious lanai. Enjoy the refreshing ocean breezes beneath the cathedral ceilings while taking in the stunning ocean views. This residence boasts...
2nd Floor Ocean Views | Epic Sunsets | Makena Surf F208
Welcome to Makena Surf F208, a luxurious oceanfront vacation residence that offers an unparalleled Hawaiian retreat. Situated on the second floor, this 1,313 square foot residence is designed to provide the ultimate in comfort and relaxation, featuring elegant touches...
Beachfront Condo – Hear the Waves Crash | Makena Surf C207
Welcome to Makena Surf C207, a vacation rental nestled in paradise. This spacious suite offers a serene escape, featuring two large lanais surrounded by the sweet scent of Plumeria. Unwind after a day at the beach by relaxing with friends and family, engage in a...
Walk to Beach in Seconds - Makena Surf B106
Welcome to Makena Surf B106, a stunning two-bedroom beachfront suite just steps away from the golden sands and the ocean\'s edge. This beautifully appointed residence combines luxury and comfort, featuring elegant tray ceilings, exquisite wood cabinetry, and...
New Luxury Listing: Where Sweeping Ocean and Coastal Views Meet Elevated Island Living
Limited Time Introductory Rates! Property Highlights • Luxury one-bedroom, two-bath townhouse, fully remodeled with refined finishes • Expansive ocean, coastal, sunrise, and golf course views from both levels • Enjoy two spacious lanais complete with outdoor dining and...
Sugar Mill Shore, 2 Kitchens, A/C, Modern Finishes
This charming North Shore property offers a versatile layout perfect for multi-family vacations or groups of friends. The main house, private mother-in-law unit, and a separate bunkhouse with four twin beds offers the perfect balance for multi-family or group stays. The...
New Listing! Cozy condo with partial ocean views!
Aloha and welcome to your slice of paradise at Kaanapali Shores 309! This beautifully appointed 1-bedroom, 1-bath condo is perched on the 3rd floor of the sought-after Kaanapali Shores Resort, nestled right on the golden coastline of West Maui. Perfect for couples or...
Kona Reef A1: Ocean-view 2BR condo in Kailua-Kona, perfect for 4-6 guests.
Newly renovated 2-bedroom, 2-bath ocean / beachfront condo, AC throughout home. Short walk to Kona town bars & restaurants. Snorkel, swim, or surf right in front of the condo. Enjoy the parade of activities in the ocean and on shore from the comfort of the lanai couch....
Aloha and welcome to our family friendly home of 50 years!
Located a 5-minute walk from Kamaole Beach III; our 1200 square foot condo can accommodate up to 6 people comfortably and is our little piece of paradise.The open concept living space includes a kitchen equipped with all the amenities; a dining table for all six guests...
Laule‘a #14 by Gather – Mauna Lani Villa w/ Golf & Mountain Views & Private Pool
Welcome to Laule‘a at the Mauna Lani Resort #14, a 4-bedroom, 4.5-bath luxury villa on Hawaii’s Kohala Coast where golf course views and Mauna Kea’s sweeping silhouette frame your private escape. With a pool and spa surrounded by tropical landscaping, spacious...
Waikoloa Colony Villas 1404 Townhome, Central AC & Resort Amenities!
Discover the charm of Waikoloa Colony Villas, one of the Kohala Coast’s best-kept secrets for its live-ability, privacy, and exceptional value.This two-story 2-bedroom, 2.5-bath townhome offers 1,446 sq. ft. of interior living space, soaring 18’+ ceilings, and an open...
New Listing! Akahi C613 – Ocean View Top Floor Condo, Newly Updated, Sleeps 4
Welcome to Kihei Akahi C613, a beautifully refreshed top-floor condo with ocean and sunset views. Newly updated in October 2025 with modern furnishings, fresh paint, refinished tile floors, and a brand-new ductless AC system, this stylish retreat offers comfort and...
Waikiki Stay 1 BR w/Kitchen, 2 blocks from the beach
Perfect for families or groups, this unit sleeps up to 5 with a queen bed, sofa bed & a rollaway. Enjoy a full kitchen, open living area, and unbeatable location—just a short walk to Waikiki Beach, shopping & dining.- Flexible Sleeping Arrangements – The space includes...
** 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...
Bali Hai Resort 1 Bedroom w/ HOT TUB & POOL
Perched atop the cliff terrain of Princeville, adjacent to the renowned Makai golf course, seamlessly integrates natural beauty with carefully crafted amenities. Surrounded by the lush, tropical mountains of the north shore, the resort offers a harmonious blend of...
Stay Beachfront, Explore Maui’s Outdoors 629 LS
Experience the beauty of Maui from this sixth-floor oceanfront studio at Lahaina Shores, where sweeping views of the Pacific and unforgettable sunsets are yours to enjoy right from your private lanai. Elevated above the shoreline, this studio offers a unique vantage...