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.
This premier 8th-floor offering pairs one of our most sought-after two-bedroom "penthouse" suites, Hokulani 815, with three neighboring one-bedroom suites, Hokulani 814, 816, and 818, creating the perfect place for your group to gather, reconnect, and celebrate. Enjoy...
Lahaina Shores 215 Direct Beachfront Views Remodeled Studio
Lahaina Shores 215 NEW LISTING Amazing West Maui Sunsets Every Night from your Private Lanai! Steps to the Beach and Pool FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch (seasonal), Dinner...
Lahaina Shores 212 Updated Studio at Lahaina Shores Resort Near Beach & Pool
Lahaina Shores 212 Beautifully Updated Lahaina Studio with Majestic West Maui Mountain Views in Quiet Beachfront ResortWelcome to your Maui Retreat: This updated second-floor studio at Lahaina Shores Beachfront Resort offers a relaxed and comfortable place to settle in...
Kona By the Sea #302 Oceanfront 2-Bedroom Retreat with Central A/C
35-Night Minimum • Central A/C • Heated Salt-Water Pool & SpaSavor jaw-dropping, third-floor ocean vistas and nightly Kona sunsets from the private lanai, living room, and even the kitchen of this spacious 2-bedroom, 2-bath suite at coveted Kona By the Sea.Inside the...
Beautiful 2-bedroom condo at the KoOlina Resort.
Discover this 2-bedroom condo in KoOlina. The space features one king bed and one queen bed, perfect for a small group or family. With two full bathrooms, guests enjoy added convenience and privacy. The condo stays comfortable with air conditioning, and thoughtful...
1 Bedroom Oceanfront W/Lanai-Kahana Reef #216
Kahana Reef #216: Grab your phone for selfies on your private lanai that has a backdrop of spectacular ocean views! Enjoy captivating sunsets nightly and during the winter, watch whales play in the distance. Lounge at palm-tree-top levels on the lanai. Here you can...
Stunning Beachfront Condo, Sans Souci, Kitchen, WiFi, Smart TV & Free Parking
Unwind in Honolulu at this cool condo. This excellent property is on the beach & features a cozy living space with a Queen murphy bed plus sofa bed, perfect for relaxing after a day of exploring. The well lit bathroom includes a bathtub / Shower combo, hair dryer &...
4 Units Perfect for Groups! Outdoor Pool, Close to the Beach!
Our spacious suites with private lanais offer breathtaking views of the pristine shoreline, courtyard, or garden, providing the perfect backdrop for relaxation and adventure. Stay connected with high-speed internet, unwind in our unique whale-shaped outdoor swimming...
Wailea Point Contemporary 2 Bedroom+Loft/3 Bath Oceanview Condominium
Yes, you can treat yourself and stay in a vacation home at Wailea Point! A premier hospitality destination nestled between the Four Seasons Wailea Resort and the Fairmont Kealani Wailea, featuring an optimal location near beaches, golf, restaurants and entertainment....
🏖️Ocean Front | Amazing Views | Walk to Beach
vrKCV - Surf and Racquet 1205, Professionally Managed by Kona Coast VacationsExperience oceanfront living in this comfortable second-floor condo at Keauhou Kona Surf & Racquet Club #1205. Enjoy direct ocean views, beautiful sunsets from the lanai, and a relaxed island...
Come Create Memories w/ Fun-filled Adventures at this Paradise! Outdoor Pool!
Step into paradise: Explore Kanaha Beach Park & indulge at Queen Kaahumanu Center, right from our welcoming Kahului Bay doorstep.This listing is for a room within a hotel.✦ Your room is 588 sq. ft, equipped with complimentary toiletries, high definition 32-inch TV,...
Island Escape: 2BR Villa at Wyndham Kona Hawaiian Resort
Get ready for the ultimate family escape to paradise at Wyndham Kona Hawaiian Resort on the breathtaking Big Island of Hawaii! Nestled along the stunning Kona coastline, this family-friendly resort offers the perfect combination of relaxation, adventure, and Hawaiian...
Clean single room across the street from the beach. 5 min walk to Historic town
Country living in Haleiwa. Happy family pets on the property. Gaze up at the stars in our hot tub after a day of swimming, surfing, kayaking and shopping. All amenities provided. On our tranquil road..extensive hiking trails nearby.
Diamond Head Sea Pool House: Oceanfront Estate w/ Private Sea Pool
Diamond Head Sea Pool House rests above the Pacific in Diamond Head’s coveted Black Point enclave, offering rare oceanfront privacy, architectural character, and seamless access to Black Point Pool, a private gated community sea pool carved into the coastline. Elevated...
1 Bedroom Resort View - Silver
Kaanapali Alii 2522 Bedroom | 2 Bathrooms | Sleeps 4 | Partial Ocean View________________________________________Welcome to Kaanapali Alii 252, a gorgeous one-bedroom partial ocean view condo with a fully enclosed den that comfortably serves as a second bedroom. This...
** 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...
Waikiki 1BR Suite at Grand Waikikian – Full Kitchen, Balcony & Resort Luxury
Elevate your Hawaiian getaway in this spacious one-bedroom suite at Grand Waikikian, a Hilton Grand Vacations Club, located within the iconic Hilton Hawaiian Village Waikiki Beach Resort on O‘ahu’s best-known beachfront. This suite blends comfort and resort luxury. 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...
Ohana Kai – Premier Luxury Retreat in Princeville
Welcom to Ohana Kai, Princeviile.Escape to your own private island retreat in the heart of Princeville, Kauai. This stunning 4-bedroom, 3.5-bath vacation home offers the perfect blend of tropical luxury, comfort, and space—ideal for families, groups, or anyone seeking a...
Ka’anapali Studio at Westin – Resort Pools, Beach Access & Island Comfor
Enjoy relaxed Maui living in this studio villa at Westin Ka’anapali Ocean Resort Villas, set along the world-famous sands of Ka’anapali Beach. Ideal for couples or solo travelers, the studio features a plush king bed, a comfortable sitting area, and a convenient...
Experience the ultimate Hawaiian getaway in the oceanfront home of your dreams! “Tropical Oceanfront Paradise” is a newly custom-built estate located on prime oceanfront property along Oahu’s scenic and peaceful west coast. Designed for relaxation, the luxury home...
We are proud to present this jaw-dropping 10th-floor deluxe oceanview grand penthouse at the Honua Kai Resort—newly launched on 3/4/25 to start taking bookings beginning May 7, 2025!Unquestionably one of the finest residences on offer at Honua Kai, this stunning 2BR/3BA...
Ko Olina Kai 1081C: 3BR Tropical Retreat, Steps from Golf and Dining
Tucked within the Ko Olina Resort, Ko Olina Kai 1081C by Gather is a cheerful two-story villa where bamboo floors, high ceilings, and breezy indoor-outdoor flow set the tone for easy island days. With three bedrooms, three full bathrooms, and 1,625 sq. ft. of interior...
Honua Kai | 2 Free Rental Cars | KBM Resorts | Extra Large Lanai | 2 Units, 4 Bedrooms | HK ML-1466
** 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...
Salt at Kakaako Luxury Penthouse - Oceanview, pool, hot tub, parking, 3 minimall
Salt At Kakaako Luxury 2 bedroom 2 bathroom residence on the top 3 penthouse floor. Corner unit, the highest balcony in the building. Covered parking, Supermarkets, Restaurants, Bars, & Entertainment.
1 BR Suite City View, w/ AC, WiFi and Kitchen - Bamboo Waikīkī Hotel #504
Castle Bamboo Waikīkī Hotel #504 - The living area is furnished with a and a desk/workspace for all those business travelers. Enjoy watching the Flat screen TV while sitting on the new couch, which doubles as a fold-out sofa bed to accommodate additional travelers. Fall...
Luxury Waipouli Condo - Steps to Beach and Pool
Waipouli Beach Resort – Private Corner Unit Steps to Beach and PoolAbout the PropertyWelcome to your Kaua‘i escape at Waipouli Beach Resort F101 — where comfort, convenience, and coastal beauty come together. This one-bedroom, two-bath condo offers ground-floor access...
Golf Villa 5102 - Best Ocean Views | Daily Housekeeping
This spacious prime ocean-view villa enjoys the premier Golf Villas location. Situated in the heart of the resort community, this single level ground floor 3-bedroom, 3.5 bath ground floor Golf Villa features unobstructed ocean, golf course, and sunset views with quick...
Whaler | 3 Free Rental Cars | KBM Resorts | 3 Units, 4 Bedrooms | WH ML-1589
** 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...
@ Marbella Lane - Vibrant and Refreshing Studio
Summary:Welcome to this vibrant and refreshing studio located in a secured apartment building in the heart of Waikiki This unit features large windows making it bright and airy with 2Queen beds a full kitchen and access to the shared BBQ area Just blocks away from the...
"Beautiful Luxury Condo with Gorgeous Views 1BR/1BA/1PKG at SKY ALA Moana"
"MODERN LUXURY CONDO WITH BEAUTIFUL VIEWS 1BR/1BA/1PKG AT SKY ALA MOANA""WELCOME TO SKY ALA MOANA" Luxury condominium built in 2023 conveniently located in Ala Moana. Enjoy beautiful views of city, mountain and sparking ocean. 1br/1ba /1assigned parking with Full...
Kihei 2 Bedroom Condo Sleeps 6
Please Send An Inquiry Before Requesting To Book By Clicking The Contact Host Tab.Located in South Maui, nestled within five acres of lush tropical landscaping. This low-density complex features amenities such as a large swimming pool, hot tub, tennis and pickleball...
Makahuena 2305 By Parrish Kauai - Great family space with AC
Located on the southernmost point of Kauai, this unique oceanfront property is situated on the edge of a bluff providing spectacular views of the blue Pacific and the entire Poipu coastline from each unit. Incredible ocean views are the dominant feature of this resort...
NEW! Spacious 3BR Home in Old Wailuku Town | Central to All of Maui
Modern Comfort in Old Wailuku Town – 3BR Ground Floor of DuplexStay where Maui locals live, in the historic Wailuku Town—an authentic small town with coffee shops, galleries, family diners, and historic charm. This fully rebuilt ground floor duplex (completed in 2025)...
Ocean View Studio at Westin Ka’anapali North
🏖 Resort Highlights✅ Directly on Ka’anapali Beach 🌴✅ Heated pools + kids’ areas + waterslides 🏊♂️✅ Access to both North & South resort amenities ✨✅ Beach cabanas, hammocks & oceanfront path 🏖✅ On-site restaurants & poolside bar 🍹✅ Westin Heavenly Spa (on South side)...
Recently Renovated - Wailea Golf Views
Welcome to Wailea Grand Champions 102, a luxurious 2-bedroom, 2-bathroom residence nestled between the fairways of one of Maui\'s most popular championship golf courses. This spacious second-floor unit, spanning over 1,400 square feet, offers a perfect blend of privacy...
Marriott Maui Ocean Club | Three 3BR/3BA Villas
Summary:Located on the shores of Ka'anapali Beach, Marriott Ocean Club is surrounded by Hawaii's beautiful scenery! The resort is the perfect family getaway with something for everyone to enjoy - beautiful pools, golf, on-site dining, spa services, and sports courts....
Ocean-MT Views From the Luxury Sky Ala Moana Condo with Amazing Amenities
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.The Sky Ala Moana is the newest addition to the luxurious building scene in Honolulu. Consisting of two...
Kapalua Golf Villas | Large Bedrooms | KBM Resorts | 3 Units, 4 Bedrooms | ML-2294
** 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...
Paradise Resort Home in Ko Olina | TCP-1220-3
Welcome to your dream vacation home at Coconut Plantation - the most amazing destination in Ko Olina! Whether you're looking for a breathtaking sunset, a romantic getaway, a fun beach stroll, an exciting round of golf or a relaxing spa retreat, this resort has got you...
Manele Bay, Lanai Hawaii Ocean Facing Home
Spacious home on the island of Lanai. Footsteps from Four Seasons at Manele Bay Hotel and Hulopoe Beach. All the comforts of home in an island paradise. Two bedrooms, each with king-sized beds, and two and one half baths, including an outdoor shower. Ocean view and...
Unit 6 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...
Luxury Beachfront Escape! Lae Nani 411| 3BD with Ocean Views, Beach Access, Heated Pool & A/C!
Summary:Welcome to Lae Nani Kauai Starfish 411, your ocean view retreat with air conditioning and direct beach access.The Space:Experience relaxed island luxury in this beautifully renovated three bedroom, two bathroom ground floor condo. Located within the highly...
Newly Renovated 11th Floor Studio with Parking
We welcome you to be one of the first guests to enjoy our new renovation! Expertly thought out and every detail taken in to consideration in its design, with you in mind! A spa like custom tiled shower, full kitchen, and everything you could need for a comfortable short...
Steps Away from the Beach! 3 Premium Units, Private Lanai, Onsite Pool
Our spacious suites with private lanais offer breathtaking views of the pristine shoreline, courtyard, or garden, providing the perfect backdrop for relaxation and adventure. Stay connected with high-speed internet, unwind in our unique whale-shaped outdoor swimming...
33FL-Renovated Elegant Waikiki 1BR+Free Parking
Summary:Gorgeous 1BR unit situated in central Waikiki is a beautiful and cozy place to stay while enjoying your Hawaiian vacation. The unit, located on the 33rd floor, offers breathtaking and unobstructed views of the picturesque Hawaiian mountains, Ala Wai Canal, and...
Breezy, spacious 3 bedroom near beach, food land, Laie temple and BYUH. Cozy and clean. Spacious shared yard and private Laie to sit and relax. Great location in Laie. Quick walk over to Temple beach.
Kahala Lani: Balinese-Inspired Home with Private Pool
Set in the prestigious neighborhood of Kahala on O‘ahu’s sunny south shore, Kahala Lani by Gather offers a refined island retreat designed for family gatherings and relaxed luxury. Blending island-style architecture with Balinese-inspired touches, this five-bedroom,...
Ka’anapali Alii 3412 Bedrooms | 2 Bathrooms | Sleeps 4 | Ocean View________________________________________Welcome to Kaanapali Alii 341, an elegant one-bedroom ocean-view condo, with a fully enclosed den that comfortably serves as a second bedroom. Enjoy breathtaking...
🏖️Large 3BR + Loft at Kanaloa | Pools, Golf Views & Prime Keauhou Location
Kanaloa at Kona #1004 – Spacious Keauhou Condo with Resort AmenitiesWelcome to Kanaloa at Kona, an oceanfront resort community in Keauhou on the south edge of Kailua-Kona. This spacious 3-bedroom, 3-bath condo offers 1,746 sq. ft. of comfortable living space with...