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.
Island Living w/Ocean Views, Wi-Fi and Pools-G510A
Your Hawaiian dream vacation becomes a reality when staying at this tropical oasis set within walking distance to the iconic Maui shores. The Maui Banyan resort is sprawling with lush flora and top-notch amenities including two swimming pools, jacuzzis, tennis courts,...
Maui Vista 1406: Top Floor Large 2 br condo with Loft & Ocean Views Sleeps 4
Large two-bedroom condo with a loft with ocean views. This vacation rental features a queen bed in the master bedroom, two twins in the loft bedroom, and a pull-out sofa bed in the living room. This unit looks out over the pool. Relax on the lanai and enjoy paradise....
Idyllic Vacation at Ko Olina Hillside Villa 1528-4
Close to scuba diving, surfing, and more, this smoke-free condo brings it all within reach. Jump into your car and make short work of the 2-minute drive to Ko Olina Marina or the 3-minute drive to Honu Lagoon (and enjoy the property's convenient covered onsite parking...
Fabulous 7 bedrooms for 16 above famous Anini Beach!
Listing provided by "The Vacation Rental Experts". Contact directly for more options!This fabulous 7 bedrooms and 5 baths for 14 to 16 people, is situated right above famous Anini Beach, with an 8-10 minute walk down the Anini Beach trail just steps away from the...
Kilipue Retreat by Gather | Luxe 3BR Home w/ Fenced Yard Near Ko Olina
Kilipue Retreat places you at the quiet end of a Kapolei cul-de-sac, minutes from beaches and big-city conveniences yet wrapped in the calm of a residential neighborhood. Newly refreshed and fully furnished, this 3-bedroom holiday home welcomes corporate guests,...
Hale Pau Hana #707 Ocean Front, Central AC, Oceanfront Complex
Hale Pau Hana #707 is a 2 bedroom, 2 bath unit on the 7th floor with a panoramic ocean view and central A/C throughout. It provides a fully-equipped kitchen, 2 flat-screen TVs, and free WIFI. Go to sleep in your comfortable cal king bed as you enjoy the sound of the...
Gorgeous Beachfront Nanea Resort+Amenities. 3BR Suite
DISCOVER AUTHENTIC HAWAI‘I at The Nanea Ocean Villas.Aloha, Island Explorers!Enjoy an additional $500-$1000 SAVINGS with 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 on certain 7-Night stays. All reservations require a SAT-SAT OR SUN-SUN STAYSHORT STAYS:...
Hotel Room Partial Ocean View w/ WiFi and AC - Bamboo Waikīkī Hotel #1101
Castle Bamboo Waikīkī Hotel #1101 - Get the most from your magical Hawaiian experience in this cozy eleventh-floor unit located just blocks from the iconic shores of Waikīkī. With resort-style amenities and a prime location at the Bamboo Waikīkī, you’ll have...
Wailea Grand Champions | 185
This two-bedroom, two-bath villa at Wailea Grand Champions offers a perfect blend of contemporary style and tropical paradise. The open floor plan seamlessly connects the fully-equipped kitchen, dining area, and spacious living room, creating an inviting atmosphere for...
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 4 neighboring ground floor residences at the luxurious Honua Kai Resort to create an 8 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 resort...
Royal Mauian 314 – Oceanfront Paradise in the Heart of Kihei!
Royal Mauian 314 – Oceanfront Paradise in the Heart of Kihei!Welcome to Royal Mauian 314, a beautifully appointed 2-bedroom, 2-bath oceanfront condo offering sweeping ocean views, modern amenities, and an unbeatable South Maui location. Perfect for families or...
Royal Kahana Maui 1006 Ocean View 1 Bedroom
- 10th floor condo with balcony- Tile & Vinyl plank flooring throughout- Fully equipped kitchen with– fridge, stove/oven, microwave, cookware, tableware- Tiled bathroom with walk-in tiled shower with grab bar- Bedroom with 1 king bed- 777 sqft- Maximum 4 persons...
Lahaina Shores 504: West Maui Studio!
* NEW PROMO: Stay 5 or more nights from September 1st - October 31, get 1 FREE!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...
Stunning Ocean-View Retreat Overlooking Laupahoehoe Point
Welcome to your tropical escape! This stunning three-level home boasts panoramic ocean views and a tranquil setting, making it ideal for a peaceful and rejuvenating vacation.With 1,500 square feet of space, the main living areas are located on the upper level, while the...
Gated Tropical Hawaiian retreat, 5 minutes to Kailua Kona town and 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
Every vacation is enjoyable and restful, thanks to the contemporary atmosphere and convenient amenities of our hotel. Spend the day at the outdoor pool with a large sun deck and lounge chairs or catch some rays at the neighboring beach. You may also try delectable meals...
Lahaina Shores 520: Studio with West Maui Mountains View
* NEW PROMO: Stay 5 or more nights from September 1st - October 31, get 1 FREE! Lahaina Shores 520 – Studio in West MauiLahaina Shores is a charming boutique resort located directly on the oceanfront in the heart of historic Lahaina Town. Unit 520 is a 5th-floor West...
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...
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...
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,...
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...
4-bedroom condo- Tropical luxury Villa in Ko Olina
Welcome to your private oasis in paradise! Nestled within the exclusive Coconut Plantation community in Ko Olina, Oahu, this luxurious villa offers the perfect blend of opulence, tranquility, and island living. With 4 bedrooms and 3 full bathrooms, this is the largest...
Seahorse Beach House: Calm Oasis w/ Private Yard Just Steps from Kailua Beach
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.Seahorse Beach House is a hidden Hawaiian gem,...
Waikiki 5-Star Marina Stay – Ocean View 1BR
Summary:Take a stroll along Waikiki beach and enjoy the warmth on your skin and the beach sand between your toes. This cute and upgraded 17th-floor ocean view studio is in the Ilikai Marina, an ocean front building located in the quieter side of Waikiki. The property is...
Island Dream Waikiki Condo - 15F
Newly renovated studio providing a comforting and welcoming stay for your trip in Hawaii This 15th floor unit overlooks the Fort DeRussy Beach Park, located across from the Hilton Hawaiian Village. The studio is located in the central of Waikiki, which takes only 10...
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...
KBM Resorts | FREE CAR | Honua Kai Hokulani | Mountain view | 1-Bedroom Condo, Breathtaking views! HKH-524
Elegant 1-bedroom villa in Hokulani Tower with mountain views, full kitchen, spacious lanai, and access to pools, hot tubs, and Duke's restaurant-perfect for couples or families in Maui paradise.*Special Offer - Book any KBM rental home in Hawaii for 6 nights or more...
Luxury Oceanfront Living at the Sands of Kahana
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...
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,...
Hawaiian Luxury Villa – Tranquil Elegance at Mauna Kea Resort
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 1BR Beachfront Maui Condo..Kihei/South Shore. AC.nStunning Ocean Views!
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
- Ground floor unit- Kitchen includes dishwasher, stove top/oven, microwave, refrigerator, coffeemaker, blender, cookware and tableware- Spacious 473 square foot lanai- Bedroom with 1 king bed and master bathroom with shower/tub combo- Queen sofa bed in sunken living...
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...
2 Bedroom Villa at the Westin Nanea Ka'anapali
Located on 16 acres of Maui's famous North Kā'anapali Beach, The Westin Nanea Ocean Ocean Villas puts you at the center Maui’s fun filled local activities and events as well a variety of world-class amenities right outside your villa door.
Wailea Ekolu Village | 1203
Wailea Ekolu Village condo #1203 is an exquisite one-bedroom, two-bathroom ocean view retreat designed for discerning travelers seeking the best of Wailea. This sanctuary offers a seamless indoor-outdoor living experience, allowing guests to enjoy breathtaking panoramic...
Kaanapali Maui Eldorado J204 Garden View 1 BD
- 2nd floor condo with balcony - Tile throughout unit- Open kitchen layout with granite counters, stainless steel fridge, stove/oven, microwave, dishwasher, cookware and tableware- 2 queen beds- Queen sofa sleeper in living room- 1200 square feet / 112 square meters-...
Bungalow 10 at Kukui‘ula – Kauai Luxury with Spa, Golf & Organic Farm
Indulge in the opulent comfort of the two-bedroom bungalows at The Lodge at Kukui’ula on Kaua’i, offering privileged access to the esteemed amenities of The Club at Kukui’ula. This exclusive enclave along Kaua'i's southern coast boasts an 18-hole Tom Weiskopf...
Kaanapali Maui Eldorado Partial Ocean 1 Bedroom
Partial Ocean View 1 Bedroom- Full kitchen includes refridgerator, stove/oven, microwave, dishwasher, cookware, tableware- 1 king bed or 2 queen beds- Queen sofa sleeper in living room- 1200 sqft / 111 sqm- Bathroom with walk-in tile shower- Air conditioning-...
Blissful 1 Bedroom w/lanai, WiFi, and Cable-#H206
Families love the homey touches of this one-bed/two-bath air-conditioned suite located across from popular Kamaole II Beach Park. The open kitchen features a breakfast bar, refrigerator, dishwasher, stovetop, oven, microwave and coffeemaker. Also enjoy a washer/dryer,...
New Listing! Private 1bd lanai with ocean views
Welcome to Papakea C209, your serene home away from home on Maui! This charming 1-bedroom, 1-bathroom garden-view condo comfortably sleeps up to 4 guests, featuring a plush king-sized bed in the bedroom and a queen sleeper sofa in the living area—perfect for couples,...
Mauna Lani Point | E106
Mauna Lani Point #E106 will check all your boxes when it comes to staying in the perfect vacation condo on Hawaii’s Big Island. This two-bedroom residence enjoys views of both the ocean and Mauna Lani Golf Course. Lounge on your private ground floor lanai and look for...
Sheraton Kaua‘i Resort Villas | Two-Bedroom Villa
Summary:Sheraton Kauai Resort Villas is located on the beautiful garden island of Kauai. This resort welcomes you with all the comforts of home for a relaxing vacation. Spend your days enjoying the beauty of nature with hikes, boat tours, whale watching, beaches, parks,...
Serene Lanikai House Near the Beach w/Full Kitchen and Great Outdoor Space
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.ENHANCED PROTOCOLS : We have revised our protocols to include contactless check-in & check-out,...
KP13-Beachfront-AC-WD-Pool-Perfect Location -Sunsets-KP13
Unit #13 is a beautifully situated, top-floor located in Building 3 of Kiahuna Plantation Resort in Poipu. This unit offers a private retreat with ocean views, making it an ideal choice. This condo does not have AC at this time but we also own #9 with AC.Guests have...
Tradewinds Plaza Waikiki Oceanview Private Rental Sleeps 4
Escape to The Tradewinds Plaza in Waikiki TP606 - Your Ideal Vacation RetreatProperty Details:Address: 2572 Lemon Road #606, Honolulu, HI 96815Property Type: 30-day Minimum 1-Bedroom Vacation RentalEscape to The Tradewinds Plaza in Waikiki Suite 606 offers a spacious...