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.
New Listing! Villa with an island charm interior
Welcome to Kapalua Ridge Villas 2712 – a bright and breezy 1-bedroom, 2-bathroom ground-floor villa that comfortably sleeps up to 6 guests. Step inside to discover an airy, open-concept living space with A/C, and large windows to showcase serene ocean and garden views....
Kaanapali Alii 2832 Bedrooms | 2 Bathrooms | Sleeps 5 | Ocean View________________________________________Surround yourself with ocean views from this beautifully upgraded two-bedroom condo located on the eighth floor of Kaanapali Alii. This large two-bedroom plus den...
Spacious Partial Ocean View W/Lanai and A/C - Bamboo Waikīkī Hotel #1006
Castle Bamboo Waikīkī Hotel #1006 - Minimalistic and excellent use of space with pops of color featured in artwork featuring local tropical sights. The functional layout is furnished with premium furniture that allows for plenty of space for storage and...
Koloa Kauai 2 Bedroom Sleeps 6
Please Send An Inquiry Before Requesting To Book By Clicking The Contact Host Tab!Flowing waterfalls, a crystal clear Koi pond, and hundreds of tropical plants make This resort appear the stuff of dreams. Nestled in over twenty acres of lush tropical gardens overlooking...
Kona's Best: Direct Oceanfront 2BR/2BA Condo w/ AC, Pool & Sunset Lanai
A True Hawaiian Paradise: Absolute Oceanfront Luxury at Kona Bali KaiWelcome to the ultimate Big Island escape. Step into our stunning 2-bedroom, 2-bathroom sanctuary, situated directly on the water at the highly-sought-after Kona Bali Kai. This condo is your Front Row...
4BR Mokulua Seaside w/ Private Studio, Steps to the Beach
Mokulua Seaside by Gather is a refined oceanside escape that brings together luxury, space, and the beauty of Lanikai. Just one house from the sand on Kailua’s coveted Mokulua Drive, this four-bedroom, four-bathroom retreat spans 3,316 square feet of interior living and...
End unit with Ocean views from all rooms. Unit H-103, just steps from the Ocean.
Experience Mauna Lani Resort like a local in this 2-bedroom condo. The space features one king bed in Principle bedroom and two queen beds in the second bedroom, perfect for a small group or family. With three bathrooms, guests can enjoy plenty of privacy and...
Papakea L106 Ocean view 2BR condo in West Maui, perfect for families or groups of 6.
Papakéa Resort L106 Unbelievable Direct Oceanfront Lawn Location with Stunning Sunsets, Steps to the Pool & Jacuzzi Welcome to your Maui Retreat: This ground-floor, oceanfront two-bedroom, two-bath condo comfortably sleeps up to eight and is located in the coveted L...
Honua Kai | 2 Free Rental Cars | KBM Resorts | Exceptional Value | 2 Units, 3 Bedrooms | HK ML-1439
** 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...
Kapalua Bay Villa 27B2 Gold Oceanfront 2 Bedroom
- Villa closest to Oneloa Beach- Split level loft style villa with no stairs between parking and front door- Tile floors throughout- Updated kitchen with granite counters, farmhouse sink includes – fridge with ice maker, stove/oven, microwave, dishwasher, cookware,...
New Home!+Napali Views+Pool/spa+Cold plunge+Sauna
Experience the essence of modern island luxury at Napali Sunsets, a stunning new home in Princeville. Designed with sophistication and comfort in mind, this retreat offers a pool, spa, sauna and a cold plunge! Enjoy the spacious covered outdoor lounge, and sweeping...
Welcome to your dream retreat in Kailua, a sun-drenched haven where tranquility meets convenience. This charming unit is part of a thoughtfully designed duplex, offering a perfect balance of privacy and community. Whether you’re here to relax, explore, or work, this...
Fully Renovated Exquisite 2bdrm w/parking
Summary:This Lux 2BD unit, is located in the heart of Waikiki, only a few minutes walk to the beach, featuring city views. This unit was just renovated in 2023 to update the unit with beautifully designer décor and to re-furnish with modern furniture.Situated only a few...
Hilton Grand Vacation Club Resort/Spa Lagoon Tower
This 1 bedroom, 1 bath villa features a king bed in the master bedroom. The spacious living area includes a separate dining area, large television with cable and DVD player, and a queen-size sleeper sofa. Our 1-bedroom plus suite features all the comfortable features of...
Garden-View 2BR at The Point – Bright Poipu Villa with Lanai & Island Comfort
Enjoy a relaxed island retreat in this spacious two-bedroom, two-bath garden-view villa at The Point at Poipu on Kauaʻi’s sunny south shore. Designed for families or groups who want comfort and space, the villa features a master bedroom with a king-size bed and en-suite...
Kaanapali Alii 3543 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean View________________________________________Welcome to Kaanapali Alii 354, an exquisite 2-bedroom, ocean-view residence with a fully enclosed den that comfortably serves as a third bedroom.This Platinum Rated...
𝐅𝐢𝐧𝐝𝐢𝐧𝐠𝐌𝐞𝐢𝐥𝐢 Luxe Beachfront Kaanapali Residence Club+Amenities. 2BR
𝐇𝐘𝐀𝐓𝐓 𝐕𝐀𝐂𝐀𝐓𝐈𝐎𝐍 𝐂𝐋𝐔𝐁 𝐀𝐓 𝐊𝐀𝐀𝐍𝐀𝐏𝐀𝐋𝐈 𝐁𝐄𝐀𝐂𝐇 – 𝟐-𝐁𝐄𝐃𝐑𝐎𝐎𝐌 𝐎𝐂𝐄𝐀𝐍 𝐕𝐈𝐄𝐖 𝐕𝐈𝐋𝐋𝐀Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢! Immerse yourself in the stunning beauty of Kā‘anapali Beach from your exclusive 2-Bedroom Ocean View Villa. Discover luxury living on the iconic shores of West Maui, with...
Marriott Maui Ocean Club Napali Villas Beachfront Resort/Spa!
Marriottu2019s Maui Ocean Club - Napili Villas is one of the most popular timeshare resorts - and for good reason! Kids and kids-at-heart will get a kick out of the resort's 3.5-acre super pool complete with a water slide, waterfalls, and children's area. The poolside...
Marriott's Maui Ocean Club-Tower-Three 2BR suites
Summary:Nestled along the pristine shores of Maui, this tropical hideaway immerses you in serene landscape. The soft sands, turquoise waters and lush rainforests set the scene for an unforgettable Hawaii vacation. This is an ideal vacation retreat, boasting spacious...
Just minutes from Green Sands Beach and Volcano!
Nestled in Naalehu, this fantastic house offers a comfortable retreat for guests seeking a peaceful getaway. With three cozy bedrooms, including two twin beds and two queen beds, there’s plenty of space for families or friends to spread out. Two bathrooms add...
Aqua Aloha Surf Waikiki 210 Moderate Studio with Partial City Views, Sleeps 2
Aqua Aloha Surf Waikiki 210 Moderate Studio with Partial City Views located just 2 Blocks to Waikiki Beach, (2) Twin beds, Sleeps 2, 224 Sq FtAqua Aloha Surf Waikiki brimming with island personality offers a range of accommodations that are perfect for couples and solo...
4-bedroom house in tranquil Keaau ~ HPP with pool ~ Authentic Hawaiian Oasis
About this spaceAolani Hale is a high quality local property and is a self-contained vacation destination! From the moment the remotely controlled gate swings open, it’s obvious that this is a place where once in a lifetime memories of paradise are bound to happen. As...
Honua Kai Ocean View 1 Bedroom
Experience island living with panoramic ocean views from this comfortable one-bedroom condo on Maui’s Kaanapali North Beach. Perfect for relaxing after a day of exploration.Ocean View 1 Bedroom 1 Bathroom• Exclusive on-site provider with the only homes that meet the...
Kapalua Golf Villa 23T1 Gold Ocean View 1 Bedroom
- 1st floor villa with 3 stairs between parking in front of condo and front door- Carpet in living room, dining room, bedroom and tile floors in kitchen and bathrooms- Kitchen with black stainless steel appliances includes – fridge with ice maker, stove/oven, microwave,...
Pili Mai 6M by Gather: Garden-View Condo w/ Lanai & Beach Access
Tucked along the Kiahuna Golf Course in sunny Poipu, Pili Mai 6M blends resort comfort with Kauai’s signature indoor-outdoor ease. This single-level, three-bedroom, three-bath condo offers 1,478 square feet of bright, air-conditioned living space framed by golf-course...
Kaanapali Alii 1222 Bedrooms | 2 Bathrooms | Sleeps 4 | Partial Ocean View________________________________________Welcome to Kaanapali Alii 122! Enjoy partial views of the sparkling Pacific in the distance from this inviting one-bedroom residence with a fully enclosed...
New Listing, Keauhou Palena, 2 bed, AC, private lanai
Nestled in the heart of Kailua-Kona, the Big Island Keauhou Palena 1203 offers a perfect blend of comfort and relaxation for your Hawaiian getaway. This beautifully appointed two-bedroom, two-bathroom condo is designed to provide a serene retreat while being close to...
OceanFront Studio Kaanapali area perfect for a relaxing getaway!
Watch the Whales and Turtles from your balcony ! Located in Kahana next to Kaanapali , this Direct Ocean Front Studio resort offers a terrific escape for guests seeking comfort and relaxation. The space features Queen Bed with one walk in shower:) The unit is direct...
Unit 1 Waena Inn – Newly Renovated Maui Private Suite
Enjoy a cozy stay at this 324 sq ft modern Ohana studio apartment in Maui, featuring a small kitchenette and private bathroom. Large windows offer beautiful views of the West Maui Volcano and the warm Hawaiian breeze. With amenities such as A/C, Wi-Fi, smart TV, and...
** 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...
** 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...
Golf Perks | Ocean Views | Pool | Sauna - Mauna Lani Point G202
Welcome to your dream vacation getaway at Mauna Lani Point on the beautiful Big Island of Hawaii! Nestled in a serene and luxurious setting, this one-bedroom ocean view condo offers an unforgettable experience.Mauna Lani Point G202 - This is the perfect place for golf...
27F Ocean View-Free Parking&Steps away from Beach
Fully renovated in 2021, this stylish one bedroom is brand new. The 27th-floor unit with a private balcony comes with amazing ocean views and is one block away from the world-famous Waikiki Beach! Included: High-speed free wifi, Smart TV, central AC, full kitchen with...
Kaanapali Alii 41121 Bedrooms | 2 Bathrooms | Sleeps 4 | Ocean View________________________________________Welcome to Kaanapali Alii 4112, a stunning ocean view condo that captures the essence of island luxury. From this elevated perch, enjoy sweeping views of the...
** 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...
Marriott's Maui Ocean Club-Tower-3 Studio Villas
Summary:Nestled along the pristine shores of Maui, this tropical hideaway immerses you in serene landscape. The soft sands, turquoise waters and lush rainforests set the scene for an unforgettable Hawaii vacation. This is an ideal vacation retreat, boasting spacious...
Aqua Aloha Surf Waikiki 408 Deluxe Studio with Lanai and Partial City Views
Aqua Aloha Surf Waikiki 408 Deluxe Studio with Lanai and Partial City Views located just 2 Blocks to Waikiki Beach, (1) Full/double bed, (1) Twin bed + (1) Queen sofa sleeper, sleeps 4, 365 St FtAqua Aloha Surf Waikiki brimming with island personality offers a range of...
** 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...
Palms at Wailea Villa 1103 Ocean View 1 BD 2 BA
- Ground floor unit- Kitchen includes stovetop, oven, microwave, refrigerator, dishwasher, coffeemaker, toaster, cookware and tableware- Spacious private 473 square feet deck- Bedroom with 1 king- Queen sofa bed in living area- 1022 square feet / 95 square meters-...
Waipouli Beach Resort Garden View 1 BD 2 BA
Surrounded by lush tropical greenery, this inviting one-bedroom condo offers a quiet island escape. Perfect for two, it features a private lanai and all the comforts of home Garden View 1 Bedroom 2 Bathroom• Kitchen features granite countertops, Wolf cooktop and...
25th Floor Cozy studio in gorgeous Honolulu perfect for your island getaway
Escape to this 25th floor studio in picturesque Honolulu. Enjoy the great views & living area featuring a comfortable double bed & a futon, perfect for relaxing after a day of adventure. The bathroom includes a shower/tub and a hair dryer, adding a touch of convenience...
Stunning Remodel I Kamaole Sands 5-207
Welcome to your perfect getaway in South Kihei! This beautifully designed and recently remodeled condo blends modern comforts with a warm, inviting atmosphere. Perfectly situated in the vibrant heart of the neighborhood, it’s just steps away from one of Maui's most...
2 Bedrm Villa + Balcony w/ Resort View @ Westin Nanea Ocean Villas in Lahaina
Experience Lahaina like a local in this 1260sqft/113sqm two-bedroom villa. The welcoming atmosphere of this phenomenal property will make guests feel right at home. With 2 king beds and a cozy living room with a sofa bed, there's plenty of space for everyone to relax....
New Listing: Waikoloa Hills 1203 – Sleeps 6, Newly Remodeled for Your Stay
Escape to the Big Island in style at Waikoloa Hills 1203, a beautifully updated 2-bedroom, 2-bathroom condo nestled in the peaceful Waikoloa Village community. This freshly renovated space features a brand-new kitchen and bathrooms, stylish new furniture, and crisp,...
Valley Isle 507 Studio Retreat – Enjoy Panoramic Lanai Views Near Beaches
Looking for a Maui getaway where you can relax, explore, and take in the beauty of the island? This 5th-floor studio condo is the perfect place to call home during your stay. Step out onto your private lanai and enjoy breathtaking views of the Pacific Ocean—whether...
Lahaina Roads 304 - Oceanfront - NEW LISTING! "Sale" into Whale Season Discounts!
Lahaina Roads 304 - NEW LISTING Direct oceanfront with stunning views in this beautifully remodeled 1-bedroom, 1-bath spacious condo at Lahaina Roads. Newly re-opened, this oceanfront complex is the ideal vacation spot. Your lanai is perfect for whale watching in the...
HM22 Stunning 22nd Floor Ocean View Cozy Studio
At the beginning of Waikiki, the tourist center of Honolulu. Our charming studio in Waikiki is a breezy unit in Hawaiian Monarch buildingEnjoy breathtaking corner unit with Ocean View. Hotel quality sheets, pillows, and air conditioning await you.Excellent location...
Kona Hawaiian Resort 2 Bedroom w/ POOL
At Kona Hawaiian Resort in Kailua-Kona on the Big Island's west coast, you'll feel transported to a simpler, unspoiled era. Designed to evoke the charming traditional Hawaiian island ambiance of the 1930s, the resort blends nostalgic details with modern amenities and...
Ka’anapali Royal C102 - Lovely 2BR Golf Course Condo, Easy Walk to Beach
Enjoy your dream getaway in the best of paradise in Maui, Hawaii, with this exquisite 1534 sqft ground-floor condo offering the ultimate in comfort and luxury. Designed to accommodate up to 6 guests comfortably, this home boasts two well-appointed bedrooms, each with...
Royal Sea Cliff Kona Ocean View 2 Bedroom 2 Bath
Surrounded by greenery, this two-bedroom condo offers a peaceful island retreat. Perfect for families or couples traveling together, and it’s just a short drive from beaches, dining, and town. Ocean View 2 Bedroom 2 Bath• Condos located on 6th and 7th floors • Kitchen...