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.
Kanaloa at Kona Unit 1403 Partial Ocean Vw 2BD 2BA
- Kanaloa at Kona is located at 78-261 Manukai Street, Kailua-Kona, HI 96740- Beautiful condominium situated on 16 acres of a secluded oceanfront lava flow overlooking beautiful Keauhou Bay. Relax in tropical gardens and lush flower-filled landscape. - Condo located on...
🏖️Charming Kona Condo with Private Lanai, Pool, and King Bed on Alii Drive
vrKCV - Alii Villas 319 - Professionally Managed by Kona Coast VacationsWelcome to Alii Villas 319 — your ideal tropical hideaway in Kailua-Kona! Perfect for couples seeking a relaxing island escape, this comfortable one-bedroom, one-bath condo offers peaceful ocean...
Maui Kā’anapali Villas 291: 1-bedroom condo located ocean side
Maui Kā’anapali Villas 291: 1-bedroom condo located ocean side in the Emerald building, overlooking the Pool, with partial Ocean views.The space:This one-bedroom condominium is located in the popular Emerald building, renowned for stunning views of the pool, grounds,...
Witness mesmerizing Sunsets!! nOcean View 2BR @ MVC Ko Olina Beach Club 2/1-2/8
Escape to Marriott's Ko Olina Beach Club, a serene oceanfront retreat nestled within the lush, gated Ko Olina Resort & Marina on Oʻahu's west coast. Just 30 minutes from Honolulu, this tropical haven offers the perfect blend of relaxation and adventure, making it an...
Maui Resort Rentals: Honua Kai - 3 Total Bedrooms, 6th Floor Deluxe Ocean Views
This fantastic three-bedroom offering delivers stunning 6th-floor ocean views in addition to views of the majestic West Maui Mountains. This tandem pairing combines one of our best two-bedroom deluxe ocean view corner suites with a neighboring one-bedroom suite to offer...
Downtown Kailua | Steps to shops | W/D | Parking
New Listing Special!Welcome to this charming 2-bed, 1.5-bath condo in a prime downtown Kailua location, just a short stroll from world-famous Kailua Beach. This updated home features a fully equipped and stocked kitchen, 2 comfortable queen beds, and modern amenities...
The Kahala Mansion – Opulent Oceanview Estate in Honolulu’s Elite Neighborhood
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.Luxury, Privacy, and Grand-Scale Elegance at...
HGV The Grand Islander. New Year's Week, 1 Bedroom/1 Bath Villa
This one-bedroom, one-bathroom resort view suite with balcony features a primary bedroom with two double beds, 50-inch flat-panel HD TV and spa-like bathroom with a sleek shower, a deep soaking bathtub, private water closet with bidet seat and elegant vanity area. The...
Lagoon Tower! Family Friendly Resort! Beautiful Hilton Condo On Waikiki Beach!
Set along the breezy coastline of Honolulu, and with all the comforts of home. You will have access to four swimming pools, one with multiple waterslides, a saltwater recreation lagoon, daily planned family activities, Waikiki Beach access, water sports, spa...
Charming studio with AC and WiFi in pleasant Kihei
The studio is located in the Maui Banyan G Building and close to nightlife, shopping, dinning, public transport, golfing and Wailea. Enjoy surfing, swimming, boogie boarding, paddle boarding, snorkeling, golfing, and the beauty of Maui. While you dine on your balcony,...
Club Wyndham Bali Hai Villas 2 Bedroom Deluxe Lower Level
Escape to this brilliant resort in picturesque Princeville. This charming property features 2 cozy bedrooms with a king and queen bed, 2 bathrooms with all the essentials, and an additional living space with a comfy sofa bed. Guests can enjoy AC, a fitness room, a...
Kihei Bay Vista - #C204 - Maluhia Beach
A peaceful Maui gem just steps away from the ocean. 1 bedroom - 1 bathroom - & sofa sleeper condo located in South Maui.It has beautiful cathedral ceilings giving the condo a spacious feel. Tile flooring throughout, and a remodeled bathroom with granite counters and a...
Kalaekilohana Inn & Retreat - #1 Rated Hawaii Island Hotel - Dinner Nightly
Hawaii's #1 Small Hotel featuring complimentary locally sourced breakfasts daily and Chef Kenny's dinner nightly. Prices are per room per night. Looking for the perfect compliment to the luxury resorts in the north? You've found it. Enjoy luxurious rooms in an iconic...
New listing! Modern Oceanfront 2nd floor 1BR Condo - Kahana Reef in Maui!
Welcome to your peaceful Maui escape. This fully renovated 1-bedroom condo sits on the second floor of the boutique Kahana Reef complex, offering unobstructed ocean views, modern coastal design, and front-row sunsets—all just steps from the beach and reef.Enjoy coffee...
Kaanapali Alii | 455
Kaanapali Alii 455 is a breathtaking two-bedroom condo that perfectly combines luxury and comfort for your Maui escape. Adorned with expansive windows, this spacious haven offers tranquil views of the magnificent West Maui Mountains, setting a peaceful tone for your...
❤️PiH❤️Secret Tropical Hideaway★ Bikes/Beach Toys ★ Nature and Private from Lanais
Presented by Paradise in Hawaii Luxury HomesWelcome to Secret Tropical Hideaway at the Fairways in Mauna Lani!Secret Tropical Hideaway offers the ultimate backdrop for your Hawaiian getaway. Perfectly designed to accommodate up to 6 guests, it's an inviting, luxurious,...
Royal Kahana Maui 919 Ocean View Studio
- 9th 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- 1 king bed and 1 twin sofa bed- 431 sqft - Maximum 3...
Hale Nani at Kukui'ula - Luxe Family Hideaway with Poolside Living in Poipu
Summary:TA-101-738-2400-01Hale Nani at Kukuiʻula is a contemporary 5BR, 5.5BA residence offering a peaceful escape in one of Kauai’s most prestigious neighborhoods. With golf course vistas, a private heated pool, and open-air living spaces, this home invites...
KPL 10 Panoramic Ocean and Golf Course Views 2BD Walking Distance to the Beach
FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch (seasonal), Dinner Sunset Sail, Snorkel Sail, Alpaca Farm Tour, Pineapple Farm Tour, and All Day Electric Bike Rental. (W1)*One ticket per...
Renovated 2 bd condo steps to Kihei beaches
Haleakala Shores A410 is a 2-bedroom, 2-bathroom with a split air conditioning system and 2 master ensuites and can accommodate up to 6 guests. This 4th-floor haven of unparalleled luxury and comfort has been meticulously crafted to enhance your Maui getaway. Recently...
Lanikea At Waikiki condo in Waikiki with parking (30 Nights Minimum Stay)
Luxury condominium located in Waikiki! This 2 bedroom unit comes with 2 parking stalls. The amenities include a resort-style swimming pool, Jacuzzi, BBQ area, and 24 hours monitored security. Secure building perfect for couples, families and friends and anyone who wants...
Kaanapali Alii | 461
Kaanapali Alii 461 is a luxurious vacation rental located in a pristine spot along the world-famous Kaanapali Beach. This oceanfront property offers a spacious layout, encompassing approximately 1,500 square feet, making it an ideal choice when compared to the smaller...
Luxurious, Private Hilltop Retreat with Postcard View -- minutes to Kailua Beach
With views like these, you may never want to leave!This top level of a 3 story executive home has its own entry driveway and private parking areaWith no homes behind it, the property’s location gives you one of the best views in the islands — providing an ideal...
Includes Beach Gear! 332 Shores at Waikoloa
Shores at Waikoloa 332Please scroll down for detailed informationPLEASE NOTE: The tile walkway on the 2nd floor of the Bo Tree Tower will be replaced from July 14-September 15, 2025. The first two weeks of the project are expected to be the noisiest while the current...
Kahala Zen by Gather: Spacious 5BR Modern Oasis w/ Studio & Lush Garden
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 Kahala ZenNestled in the...
Panoramic Views, 2 Ocean View Units, Pool, 3 Restaurants, Spa, Near
Looking for a beachfront getaway in Waikiki? Look no further than this convenient property! Just minutes from the most popular attractions, the excitement of Waikiki is all around you! And with comfortable amenities and authentic Hawaiian hospitality, you'll have...
High-Floor 1BR in Waikiki – Diamond Head View, Free Parking, Walk to Beach & Attractions
Nestled on High Floor, this One-Bedroom unit with Free Parking included (max 6’) offers Unique Moments of Rest and Fun for an Unforgettable Stay in the Island. Total of 3 Beds: 2 Full in Bedroom and 1 Queen Sofabed in Living Room, sleeps up to 4 guests. From your own...
Tropical Escape l 2 Rooms, Beach Access, Free Bikes, Pool & Pet-Friendly Stay
Endless adventure awaits in Kailua-Kona! Whether you're staying for a day or a week, our hotel puts you close to top attractions, local dining, and must-see spots like the Amy B.H. Greenwell Ethnobotanical Garden and Pu'uhonua o Hōnaunau National Historical Park....
Waikiki Shore 1000 Oceanfront 2 BD + Bonus BD 2 BA
Wake up to panoramic oceanfront views in this spacious two bedroom, two bath condo, complete with a bonus bedroom for extra flexibility. Situated on Waikiki Beach, it’s a perfect island escape for larger families.• Waikiki Shore address is: 2161 Kalia Road,...
Bali Hai, Kauai HI, 1 bedroom sleeps 4
About this spaceNestled high in the cliffs of Princeville, this Kauai resort blends natural and man-made pleasures into magnificent harmony. Take the opportunity to enjoy a meditative retreat at the on-site spa, or use the resort as a basecamp for your many Hawaiian...
Beachfront Studio Condo Sans Souci 206
Monthly Rental.A beautifully updated and well maintained Beachfront Studio with Full kitchen on the popular (and quieter) 'Gold Coast' area of Oahu, San Souci stands out as one of the top Honolulu properties year after year.With modern stainless kitchen, hardwood...
Comfy Studio in Heart of Waikiki
Love to be in the center of it all? Near beaches, restaurants, shops, access to transportation? We are a short walk from iconic Waikiki Beach. The studio also has great city and ocean views to enjoy day and night. With a full kitchen you can enjoy eating in after busy...
Kaiana Villa: Beautiful Remodeled Home w/ AC
Your Hawaiian home-away-from-home awaits, nestled into a quiet, private cul-de-sac with fabulous mountain views, surrounded by Princeville’s stately Norfolk pines. Complete with three bedrooms and three bathrooms, this beautifully updated north shore Kauai vacation...
Enviable Honolulu Address! Beachfront, Spa, Pool, 3 Restaurants, Steps to Sand!
Looking for a beachfront getaway in Waikiki? Look no further than this convenient property! Just minutes from the most popular attractions, the excitement of Waikiki is all around you! And with comfortable amenities and authentic Hawaiian hospitality, you'll have...
Maui Resort Rentals: Honua Kai Hokulani 250/51 – Incredible 6BR Oceanfront Gem, Over 4400 combined Sq. Ft. w/ Built-in Viking B.B.Q.!
This phenomenal six-bedroom offering combines two of the absolute finest 3BR/3BA oceanfront residences on offer at Honua Kai to create a true masterpiece, perfectly suited to larger groups or families. Each stunning neighboring residence boasts spectacular panoramic...
Hokulani Waikiki, a Hilton Grand Vacations Club - 1 Bedroom Premier
*** Sanitation/Cleaning Update ***We understand that our guests’ expectations for hotel cleaning and disinfecting have changed. That’s why we’ve taken additional measures beyond our industry-leading cleaning standards by partnering with RB, maker of Lysol &...
Sea Cliff Chic – Ultra-Luxury Oceanfront Retreat in Portlock
Sea Cliff Chic is the newest residence in the collection of ultra-luxury homes designed by renowned Hawaii Architect Jim McPeak and built by San Diego-based developer Mark Gosselin. This Oahu vacation home is a modern take on Oahu’s well-known Honeyed Jade. This...
Hale Kamaole #166, VIEW, Pool, A+ Wi-Fi, King, Pool
Hale Kamaole: Upscale Hawaiian Gallery Art & beautiful furnishings. Flat surface parking to entry. Steps to pool, BBQ's, BEACH & Eddie Pu walking trails. Shady lanai w/ VIEW of blue OCEAN, green garden & colorful sunsets. Aircond in bdrm. Tempur-Pedic KING bed. 2 USB...
Soothing Oceanfront Stay Ideal for Serene Sunsets
Discover Waikiki’s charms from our doorstep—steps to Kuhio Beach and Diamond Head. Explore local cuisine, shopping, and vibrant nightlife all within reach.Wake up to mesmerizing ocean views and let the day unfold with vibrant Hawaiian adventures at our beachfront...
4 Bedroom, The Cliffs at Princeville, Hawaii, Gym
You’ll love the stylish decor of this charming place to stay. Located on the north shore of Kauai. This dream of a resort overlooks the Pacific Ocean from atop a high bluff, ensuring dramatic view property-wide. There's certainly no shortage of amenities to be found...
Westin Ka'anapali North - Beautiful Resort On The Beach! Family Friendly Resort
The Westin Kā‘anapali Ocean Resort Villas North, nestled on Maui’s famous Kā‘anapali Beach, offers a luxurious Hawaiian getaway. Spacious villa-style accommodations include kitchens, private lanais, and upscale amenities. Guests enjoy lagoon-style pools, a...
Westin Kā‘anapali Ocean Resort North - 1 BR
Summary:Explore the summit of a dormant volcano. Or hike through a rainforest to a 400-foot waterfall. There’s no better place than Maui for a once-in-a-lifetime experience. The Westin Kā‘anapali Ocean Resort Villas maintains relationships with the top tour...
NEW! Volcano Tea House Cottage 2-HotTub-FirePlace
NEW LISTING 6/2025! Welcome to The Volcano Tea House Cottage 2, located just 6 minutes from Hawaii Volcanoes National Park. The original Tea House was established in 2014, and it inspired us to build and design another Tea House in the same neighborhood. The home has...
Maui Resort Rentals: Honua Kai - 3 Total Bedrooms w/ Lush West Maui Mountain Views!
This impressive 3BR offering brings together two adjacent Mountainview residences, creating the perfect gathering place for larger groups or families—all at an excellent value.Konea 332 is a remarkable 2BR/2BA suite boasting a desirable corner location and beautiful...
Comfort and Convenience! Outdoor Pool, Beach Access, Near Honolulu Museum of Art
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...
Garden View - 3 Bedroom - Marriott's Kauai Lagoons - Full Resort Access
Enjoy a luxurious stay for a fraction of the cost. Typical savings range from 30-70% when comparing our rates to direct resort bookings. All of our units are managed and maintained by the resort. Upon arrival, guests will check-in at the resort’s front desk using...
Luxury Condo w/ Resort Pool/Spa, AC, Ocean View & Spacious Lanai: Park Lane Sky
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.Intentional InteriorsThe Park Lane Sky Resort...
𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 Oceanfront Fun at Kauai Beach Club Resort+Amenities
Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢! Reserve the Ultimate Escape to Paradise: Luxury Oceanfront Kauai Adventure at Kalapaki Beach Awaits!𝐄𝐱𝐜𝐥𝐮𝐬𝐢𝐯𝐞 𝐒𝐚𝐯𝐢𝐧𝐠𝐬 𝐰𝐢𝐭𝐡...
Maui Resort Rentals: Honua Kai - 7 Total Bedrooms, 8th Floor "Penthouse" Ocean AND West Maui Mountain Views, Deluxe Corner Floor Plan!
This premier eighth-floor offering pairs five neighboring ocean and partial ocean view residences for over 4700 sq ft of combined living interior, creating the perfect space for large groups and families to gather, reconnect, and celebrate in comfort. Boasting...
Kiahuna Plantation Resort 47 Royal Garden 1 BD
- 2nd floor end unit with cooling cross breezes- Condo walk-up, no elevators- Full size kitchen with granite countertops include stove top/oven, microwave, refrigerator, dishwasher, coffee make, blender, toaster, cookware and tableware- Master bedroom with 1 king bed-...