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.
Aqua Aloha Surf Waikiki 613 Moderate Studio with Partial City Views
Aqua Aloha Surf Waikiki 613 Moderate Studio with Partial City Views located just 2 Blocks to Waikiki Beach, (1) Queen bed, Sleeps 2, 223 Sq FtAqua Aloha Surf Waikiki brimming with island personality offers a range of accommodations that are perfect for couples and solo...
Hilton Vacation Club Kaanapali Beach Club
Lahaina is waiting for you at this 1-bedroom resort. Step into a charming space featuring a king bed and a cozy living room with another king bed, perfect for relaxing after a day of adventure. The bathroom offers both a shower and a bathtub, making it easy to unwind....
ESCAPE TO YOUR DREAM; Nature, Comfort & Tranquility Await!
Discover this charming 3-bedroom countryside retreat in Kahalu’u. This serene haven features a king bed, a queen bed, and a full bed, ensuring restful nights for all. Equipped with air conditioning, WiFi, and a cozy living room with a sofa bed, this home offers modern...
Kapalua Bay Villas | 3 Free Rental Cars | KBM Resorts | Whale Watchng! | 3 Units, 4 Bedrooms | ML-2080
** 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...
Colony Surf 208 - Studio
Nestled on the Outrigger Canoe Club Beach, this charming, fully furnished studio in Colony Surf is just steps away from the ocean. The unit boasts a complete kitchen and offers wifi & cable for your convenience. Colony surf is located next to the Outrigger Canoe Club,...
Charming 2-bedroom condo with Ocean views!
🌴🏠 Welcome to Your Slice of Paradise in Waikiki! 🏠🌴Available from September 15 - December 31Escape to your dream condo nestled in the heart of Waikiki, where breathtaking ocean and harbor views await you at every turn. This cozy yet luxurious retreat offers the perfect...
Maui Resort Rentals: Honua Kai – 8BR Groundfloor Residence, Over 5300 Combined Sq. Ft., Massive Lawn Areas, Steps to Pools/Beach/B.B.Q.s!
This package combines four neighboring ground-floor residences at the luxurious Honua Kai Resort to create an eight-bedroom masterpiece that can accommodate up to 24 guests! Large families and groups are treated to the space of a luxury home with all the advantages of...
Aqua Aloha Surf Waikiki 302 Moderate Studio with Partial City Views Sleeps 2
Aqua Aloha Surf Waikiki #302 Moderate Studio with Partial City Views located just 2 Blocks to Waikiki Beach, (2) Twin beds, Sleeps 2, 226 Sq FtAqua Aloha Surf Waikiki is located just a block from the International Marketplace and two blocks to the beachfront of Waikiki....
Royal Kahana Maui 1006 Ocean View 1 Bedroom
This bright and airy one-bedroom offers stunning ocean scenery and modern comforts near to many beaches. Great for couples, small groups, or families. Unit 1006 Ocean View 1 Bedroom 1 Bath• 10th floor condo with views of the ocean and the island of Molokai • Kitchen...
Oceanfront 2BR Villa at Westin Nanea – Maui Luxury by the Sea
Step into tropical elegance with this two-bedroom, two-bathroom oceanfront villa at Westin Nanea Ocean Villas, perched on 16 acres along Ka‘anapali’s North Beach. With approximately 1,260 sq ft of interior space, this villa comfortably accommodates up to six adults,...
Ocean View 1BR Premium Villa at Westin KÄÊ»anapali North
Wake up to the beauty of Maui’s coast in this 1-Bedroom Premium Ocean View Villa at The Westin Kāʻanapali Ocean Resort Villas North. Offering 750–900 square feet, this spacious villa is ideal for couples or small families seeking a blend of comfort and luxury with...
NEWLY redecorated unit! STYLISH Waikoloa getaway! ~7 min to Hilton
NEW! Entire UNIT! Stylish island decorRelax in a freshly styled Waikoloa retreat with island-inspired mural art by award winning local artist, HUGE wrap-around lanai with peek-a-boo-OCEAN views & SUNSET along with Kohala coast overlooking the golf course.Walk to Hilton...
New Listing Lahaina Shores Mountain View Studio
Lahaina Shores 504 – West Maui Mountain ViewsLahaina Shores is a charming boutique resort located directly on the oceanfront in the heart of historic Lahaina Town. Unit 504 is a 5th-floor West Maui Mountain view studio offering privacy, comfort, and can accommodate 2...
Gated Tropical Retreat in Kailua Kona Hawai’i, five minutes from the ocean.
The Kona Palm Retreat is a private gated estate located 8 minutes from kailua Kona town and the Pacific Ocean. This property is newly listed on VRBO, this property is a guest favorite and has over 200 5 star reviews on another popular listing site., The Kona Palm...
Partial Ocean View Two Doubles, 3 Units, The Twin Fin Hotel
Experience a memorable and charming island getaway in Honolulu!This listing is for 3 separate rooms within a hotel. The price shown in the listing covers all 3 rooms.✦ Each room is 1248 sq. ft, equipped with complimentary toiletries, high definition TV, available with...
Kanaapali Maui- Newly Renovated Peaceful Ocean View 2B/2B Condo
Relax with the whole family at this peaceful Maui condo located in the heart of Kaanapali across the street from one of Maui’s most beautiful beaches. This newly renovated one level condo on the ground floor has epic views of the ocean, the island of Lanai and Molokai....
Pono Kai Resort Unit #G308
Pono Kai Resort – Unit G-308 | Partial Ocean View 2-BedroomEnjoy island living at Pono Kai Resort in Kapa‘a. This spacious 2-bedroom, 2-bath condo features a full kitchen, private lanai, and room for up to 4 guests. Resort amenities include a pool, spa, BBQs, tennis...
Luxurious 1-bedroom villa at WESTIN Nanea Oceanfront Resort!
Make the most of Maui by treating yourself to an elegant, lavishly appointed one-bedroom villa at the exclusive WESTIN Nanea 16-acre deluxe resort. Upon arrival, guests will check-in at the resort’s front desk using their resort confirmation # just as if they had booked...
Beautiful and timeless Kona Coast Resort - 1BR/1BA
When you stay at Wyndham Kona Coast Resort in Kailua-Kona on the Big Island's west coast, you will feel as if you are stepping back in time to a more simple, unspoiled era. Every detail has been designed to re-create the charming traditional Hawaiian island ambiance...
Sunset Point Hawaiian Beachfront: Exclusive Beach Home w/Hot Tub/Surf Break Spot
Welcome to Sunset Point Hawaiian Beachfront by Gather, a captivating three-bedroom, one-and-a-half-bathroom Hawaiian home, perfectly situated on the pristine Sunset Beach in the picturesque North Shore of Oahu. This residence, known as one of the area’s finest, directly...
Kahana Outrigger #4A2 - Vacation West Maui
Maui Paradise: Family Beachfront EscapeNestled on the sunny west coast of Maui, this private haven awaits you in Kahana, between the famed Kaanapali and Kapalua resorts. This property offers a unique escape that the whole family can enjoy, mere steps from the...
Resort living in Ko Olina's Coconut Plantation!
Enjoy resort living in Ko Olina's Coconut Plantation! This fully furnished 2-bedroom has an additional bonus room with 2 single beds, to sleep up to 6. The lanai overlooks the private hot tub, the perfect space for relaxation. 1 car garage + 1 assigned open parking...
Kaanapali Alii Residence 144
Kaanapali Alii 1442 Bedrooms | 2 Bathrooms | Sleeps 8 | Ocean View________________________________________Step into Kaanapali Alii 144, an elegantly renovated residence at Maui’s exclusive Kaanapali Alii Resort. Calming island-inspired tones and thoughtful design create...
Seahorse Beach House: Calm Oasis w/ Private Yard Just Steps from Kailua Beach
Experience relaxed coastal living at Seahorse Beach House by Gather, a serene monthly rental perched just steps from the soft white sands of Kailua Beach. Nestled along one of Kailua’s most sought-after beachside loops, this elevated 2-bedroom, 2-bath retreat blends...
Maui Kamaole H-208 – Oceanview Poolside Condo Close to Beaches and Dining
Maui Kamaole #H-208 – Partial Ocean View Comfort in South KiheiExperience the beauty of Maui from Maui Kamaole #H-208, a spacious two-bedroom, two-bathroom condo offering partial ocean views and a comfortable layout. Perfect for families or friends traveling together,...
Aqua Aloha Surf Waikiki 313 Moderate Studio with Partial City Views
Aqua Aloha Surf Waikiki #313 Moderate Studio with Partial City Views located just 2 Blocks to Waikiki Beach, (1) Queen bed, Sleeps 2, 219 Sq FtAqua Aloha Surf Waikiki offers a range of accommodations that are perfect for couples and solo travelers. On-site amenities...
Maui Resort Rentals: Honua Kai – 7 Total Bedrooms, Stunning Ocean Views, 4,465 Combined Sq Ft, Sleeps up to 22!
Perfectly suited to larger groups or families, this 7 bedroom gem combines one of our most sought after 3BR oceanfront "Ali'i" residences with a stunning neighboring 2BR oceanview suite, and a spacious 2BR partial Oceanview located directly across the hall. The generous...
The Bluffs at Mauna Kea Villa 5 Five Bedroom
Set in a gated community, this oceanfront estate has been crafted by Hawaii’s best architects and interior designers and is a true masterpiece. This residence offers a great room with sliding glass pocket doors for indoor/outdoor island living, a chefs' kitchen with...
Free parking, chocolate covered MACO nuts/waters, F/Kitchen, GYM, AC, WiFi, pool
This deluxe studio is in the Royal Kuhio building. We manage 39 units and are offering a rare experience opportunity to stay in one of our units. Each unit has a full kitchen, including a box of chocolate macadamia nuts and 4 bottles of water to WELCOME you to our...
Maui Banyan T203 Spacious Island Getaway Close to Kamaole Beaches
Welcome to your serene Maui getaway at Maui Banyan T203, a beautifully designed retreat offering the perfect blend of comfort and island style. Located in the heart of Kihei, this condo sleeps up to six guests and provides everything you need for a relaxing Maui...
Happy home Hawai’i 201
Newly updated two bedrooms one bathroom home in the heart of Honolulu. 650 sq ft living space, 1 full bath, full kitchen with large dining table, and large living room. A/C in each bedroom, Ceiling fan in each bedroom and living room too. Great location and value for a...
Wailea Beach Villas K207 Luxury 2-Bed Penthouse with Partial Ocean Views
Wailea Beach Villas has been ranked #4 in Hawaii by Condé Nast Readers. This recognition places WBV among the very best resorts in Hawaii, and the best on Maui!This property is hotel zoned, and not affected by the recent proposed legislation.Welcome to your luxurious...
WorldMark Kihei - 1 Bedroom
🌺 Island Comfort at WorldMark Kihei — One-Bedroom Beachside Escape 🌺 1 Bedroom • King Bed + Queen Murphy Bed • Sleeps 4 Escape to Maui’s sunny southern shore at WorldMark Kihei, a full-service beachfront resort just steps from the sand. Perfect for couples or small...
Feel Royal in a Royal Garden studio suite, Waikiki
Located along the Ala Wai canal, the resort boasts European-style gardens blended with the tropical appeal of Oahu. The outdoor pool, garden, media lounge, and sauna bring tranquility, while bustling Honolulu adventures abound beyond the grounds. Come find your piece of...
HGVC Point At Poipu 2 Bed 2 Bath Unit
PLEASE DO NOT RELY ON CALENDAR FOR AVAILABILITY! THIS IS A TIMESHARE RESORT AND THEREFORE DATES COME AND GO EVERY DAY. PLEASE USE "ASK OWNER A QUESTION" BUTTON FIRST TO INQUIRE ABOUT AVAILABILITY. DO NOT SEND A BOOKING REQUEST BEFORE CONFIRMING YOUR DESIRED DATES ARE...
KBM Resorts | FREE CAR | Honua Kai Hokulani | Mountain view | 1-Bedroom Condo, Breathtaking views! HKH-524
** 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...
Sands of Kahana Luxury Stay – 4BR Oceanfront, Sleeps 12 in Total.
This listing is a combination of 2 separate units close to one another.Each unit can accommodate 4 adults and 2 kids. Total of 8 adults and 4 kids. DescriptionWelcome to a rare opportunity to experience the best of oceanfront living at the Sands of Kahana. This listing...
Lodge at Kukui'ula Villa 4 - 4 Bedroom Villa - Platinum
This stunning villa provides barefoot elegance and comfortable accommodations for up to eight guests across four bedrooms. Three bedrooms are found in the primary home, with a fourth bedroom located in the detached 'ohana, providing a private oasis for guests who choose...
Paradise Awaits: Luxurious Oceanfront Hawaiian Escape - Sleeps 4
Welcome to your tropical paradise! Nestled on 26 acres of lush, oceanfront property, this 1-bedroom unit at Westin Kaanapali Ocean Resort Villas offers stunning views of the Pacific and the neighboring islands of Lana'i and Moloka'i. Ideal for couples or small families,...
Wailea Beach Villas PH205 - 3 Bedroom Garden View Penthouse
Welcome to Wailea Beach Villas Penthouse 205, an elegant retreat that showcases sophisticated furnishings, vibrant colors, and striking artwork. This family-friendly penthouse features three bedrooms and three full baths, offering ample space for families or groups to...
New Listing • Stunning Zero Edge Pool & Spa • Weekly & Monthly Discounts!!!
Summary:Experience the pinnacle of Hawaiian luxury in this stunning 3-bedroom, 3.5-bath retreat, nestled within the prestigious gated community of Kauna'oa at Mauna Kea Resort. Just a short walk to the beach, this exquisite pod-style home offers seamless indoor-outdoor...
Keauhou Punahele D-102 Ground Floor, Gorgeous Remodel, Incredibly Spacious
Keauhou Punahele D-102 – Remodeled Ground Floor Retreat in Kona’s Premier Coastal CommunityWelcome to Keauhou Punahele D-102, your perfect Hawaiian getaway nestled in the heart of Kailua Kona. This beautifully remodeled ground floor condo offers modern island living...
Cool cottage with AC in Keaau
Escape to a delightful 2-bedroom cottage in Keaau. This lovely retreat features 1 queen bed, 1 sofa bed, and a cozy office space with a crib. Guests can relax in the charming living area or unwind in the modern bathroom with a shower. With amenities like AC, heating,...
Westside Magic 3bed 2 bath house in terrific westside of oahu!
Experience the paradise of Hawaii’s West Side! Just half a block from the beach, this home offers stunning ocean views. Relax on the lanai and take in the beautiful shades of blue, turquoise, and green that only Hawaii’s waters can provide. Dolphins can be spotted...
Dlx 1-BR Oceanfront Maui Condo. South Shore/Kihei.nBeachfront! AC
Aloha: Welcome to your own 1Br oceanfront Maui condo rental, ideally located on the sunny South Shore/Kihei...just steps to the sand! Enjoy stunning ocean views from your own private lanai/balcony, while listening to the sound of the surf! Appointed in a hawaiian-...
Modern Studio in the Center of Waikiki!
Enjoy a stylish experience at this centrally-located place in the center of Waikiki! Two blocks to Waikiki Beach to enjoy unforgettable sunsets, rejuvenating Pacific Ocean swimming, and mind-numbing ocean gazing. Steps to world class or budget friendly dining. You can...
Palms at Wailea Villa 301 Garden Deluxe 1 BD 2 BA
Relax in this one-bedroom villa with tranquil garden views in the heart of Wailea’s resort community. Designed for comfort and convenience, it features a full kitchen, airy living space, and easy access to beaches, golf courses, and walking paths. Villa 301 Garden 1...
7th Fl Ilikai | AC | Pool
The SpaceExperience Waikīkī charm with a touch of island aloha in this beautifully decorated Ilikai suite. From your private balcony, enjoy sweeping lagoon and ocean views while sipping morning coffee and watching surfers at Kaiser Bowls.Condo Features• Queen bed for...
Aqua Aloha Surf Waikiki 506 Deluxe Studio with Lanai and Partial City Views
Aqua Aloha Surf Waikiki 506 Deluxe Studio with Lanai and Partial City Views located just 2 Blocks to Waikiki Beach, (1) Full/double bed, (1) Twin bed + (1) Queen Futon, Sleeps 4, 361 Sq FtAqua Aloha Surf Waikiki offers a range of accommodations that are perfect for...