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.
Modern 2BR Condo | Pool & Sauna | Ala Moana
Stay in style at this brand-new 2BR/2BA condo in upscale SKY Ala Moana. Perfectly situated in Honolulu, this modern unit accommodates six guests with two queen beds and a pull-out sofa. Enjoy luxury amenities, including a year-round outdoor pool, sauna, and free garage...
This modern Princeville gem shines in comfort, luxury, and design
This modern Princeville gem shines in comfort, luxury, and design. Artfully remodeled and curated by published designer, special features include a stylish sunken living room and open concept living area with twenty-foot beamed ceilings. Relax inside with AC and ceiling...
Ocean View Condo at Foster Tower Across from Beach w/Great 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.Foster Tower located at 2500 Kalakaua Ave on the 14th floor.Welcome to The Foster, perfectly situated in the...
High Fl Mount&CityView 1BRw/2Free Park Wsher/Dryer
Centrally located in Waikiki, this High Floor 1-Bedroom, 1-Bath unit features your your own Juliette balcony/Lanai, in-unit Washer and Dryer, and rare 2 Tandem Parking Stalls included —Free! Max height for parking is 6'2". Sleeps 4 (2adult and 2 small children) with a...
Waikoloa Village Golf Course Fairway 2-bedroom condo with Central AC-WiFi, Views
Waikoloa Fairways -From the Summit of Mauna Kea to the Kohala Coast Line, Welcome to Paradise! Central Air Conditioning! Aloha! E Komo Mai! This gorgeous condominium offers everything you need for your Big Island getaway. Located in the highly sought after community of...
Kaanapali Alii | 171
Kaanapali Alii 1712 Bedrooms | 2 Bathrooms | Sleeps 6 | Partial Ocean View________________________________________Welcome to Kaanapali Alii 171, a beautifully renovated one-bedroom partial ocean view vacation rental with a fully enclosed den that comfortably serves as a...
Perch - Maui Vista 307: Ocean Palms Oasis | Remodeled, Prime Location
Nestled just across from the ocean and surf spot, this corner unit is a paradise waiting for you! Situated in one of Maui's prime locations, it's steps away from Charley Young Beach and Kamaole Beaches, where turtles often visit. With numerous restaurants, shops, a...
Kaanapali Alii | 462
Kaanapali Alii 4621 Bedroom | 2 Bathrooms | Sleeps 4 | Ocean View________________________________________Experience the ultimate tropical escape at Kaanapali Alii 462, a luxurious one-bedroom ocean view vacation rental that perfectly blends comfort and style along...
Kaanapali Alii | 263
Kaanapali Alii 2633 Bedrooms | 2 Bathrooms | Sleeps 8 | Ocean View________________________________________Welcome to Kaanapali Alii 263, a stunning 2-bedroom, ocean-view residence with a fully enclosed den that comfortably serves as a third bedroom. Inside, step into...
KRV 1723 Remodel 3BD Kapalua Villa w Ocean View
Kapalua Ridge Villas 1723 NEW LISTING Rare 3Bedroom, 3Bathroom Remodeled Ocean View Villa in Beautiful Kapalua, Maui! FREE daily activities included with your stay value up to $1035! Complimentary admission, every day of your stay*: Lu'au, Golf, Whale Watch (seasonal),...
Oceanfront 2BD/2BA Condo with Private Lanai
Welcome to Alii Villa Unit #333, your perfect vacation rental in Kailua Kona! This exceptional corner unit boasts stunning oceanfront views, providing a breathtaking panorama of Kailua Bay and the picturesque Kona coast.Location: Situated in the heart of Kailua Kona,...
Poipu Shores 101B - Ocean Front, 1 bedroom, 1.5 baths, AC
POIPU SHORES 101B AT KOLOA KAI VACATION RENTALSEscape to Poipu Shores 101B, an oceanfront haven where stunning views and luxurious amenities await. Nestled along the breathtaking Poipu coastline, this condo offers a serene retreat with access to everything you need for...
Suite on North Shore property. Walk to beach & town!
The Ho'okipa Surf Suite is located on the rear part of a private ocean front property on the North Shore of beautiful Maui. We are less than 5 minutes from world class surf breaks, kite and wind surfing beaches. The rental contains 1 bedroom, 1 bathroom, living area &...
Sparkling 1 BR condo in central Kihei w/AC. Walk to the beach!
Located in the heart of central Kihei, Kihei Akahi C-517 is a dream. Freshly updated with custom cabinets, super quiet split AC and a king bed, this condo is your perfect home away from home. Your place comes equipped with a fully-stocked kitchen, in-unit washer and...
Coconut Crest Cottage
"Coconut Crest Cottage" is a perfect tropical getaway for families, small groups, or visitors to BYU-Hawai'i. Nestled in the heart of Oahu's North Shore within convenient proximity to the ocean and the iconic Kahuku Sugar Mill, featuring numerous food trucks. Turtle Bay...
Puako Beach Luxury Oceanfront Home- 3 Guest Suites
Say aloha to this gated oceanfront retreat! Beach access is a short 5-minute walk away, but your vacation begins as soon as you step on the grounds of this stunning property. Upon arrival, you’ll be greeted by a beautiful entryway of Balinese design. Once inside, you’ll...
❤️PiH❤️ Hale Moana★ Private Pool & Spa ★ Detached Ohana Suite ★ eBikes ★ water slide
Brought to you by Paradise in Hawaii Luxury HomesWelcome to Hale Moana!Hale Moana is a brand new exquisite 4 bedroom, 4 1/2 bath home located in Hapuna Estates within the Mauna Kea Resort. Prepare to embark on a truly remarkable escape where luxury, comfort, and natural...
EL E204 Kaanapali Condo w AC Pools Near Whalers
Eldorado E204 NEW LISTING! Kaanapali Beach Dream Vacation at Maui Eldorado 1Bedroom Condo with Central AC, Private Beach Cabana, Pools, Hot Tubs, Gym. Steps to Whalers Village Aloha from Eldorado E204! Our one-bedroom, one-bathroom condo is the ideal place to spend your...
Kona Isle B3 No Stairs, Fully Remodeled, Beautifully Decorated: True Gem!
Kona Isle, Unit#B3 is a fantastic addition to Knutson & Associates Property Management! We're proud to represent this beautiful fully remodeled, ground floor unit.Enjoy notable features to include: No Stairs, AC Unit in the Living Room, Open Floor Plan!You'll notice...
4Bed Beachfront home near Pipeline
Make yourself at home in this 4-bedroom 3.5-bathroom North Shore piece of paradise. This wonderful house boasts 1 king bed, 3 queen beds, and 1 twin bed, perfect for a tranquil getaway. With beachfront views from 3 out of the 4 bedrooms and all bedrooms with their own...
Oceanfront Living at Luxurious Mermaid Manor in Kailua-Kona, Hawaii
Mermaid Manor – Oceanfront Island Home with Tidepools & Signature Indoor/Outdoor Mermaid ShowerWelcome to Mermaid Manor, your private oceanfront retreat in the heart of Kailua-Kona. This 2,500 sq. ft. island-style home features panoramic ocean views, three ocean-facing...
Maui Resort Rentals: Honua Kai - 6 Total Bedrooms with Over 3800 Combined Sq Ft and Stunning Premier Ocean Views!
This exceptional pairing combines a stunning 3BR Premier Oceanview suite overlooking the resort's lush interior courtyard and pools with a neighboring 3BR Oceanview suite offering not only stunning views of the blue Pacific but also vistas of the majestic West Maui...
Stunning Kaikea 4Br/4Ba Estate: Luxurious and Private - 5 min from Lanikai Beach
Welcome to Kaikea - a tropical oasis nestled just a short walk away from the pristine white sand and turquoise waters of Lanikai Beach, offering an unparalleled experience of luxury and relaxation. Comprised of two separate structures- one newly built in 2018, along...
180 Degree Ocean View in Wailea! WE204
Welcome to Wailea Ekolu Village, unit 204! This is a top floor, FRONT LINE, two bed, two bath condo with a 180 degree ocean view! Overlooking the Wailea Blue Golf Course course, this unit boasts dramatic ocean views! The interior has been extensively remodeled and...
Unwind on Oahu's famous north shore! Country living, country views! AC and WiFi!
Consider this house your home away from home while you visit Hauula. This cozy retreat features 2 bedrooms with a king bed, queen bed, and bunk bed, perfect for a family or group of friends. The bathroom comes equipped with a hair dryer for your convenience. Relax in...
Papakea OceanFront Resort - Beautiful Two Bedroom Ocean View Suite
Papakea Resort Maui provides amenities like dry cleaning/laundry services and 2 hot tubs. Guests can connect to free in-room WiFi.Other perks include:• 2 outdoor pools• Free self parking• Barbecue grills and concierge servicesRoom featuresAll guestrooms are individually...
New Listing- Impressive 3 Bd+2 Bath Vacation Home at Wailea Grand Champions
Bldg. 16 - Unit #153 - A front-row, ground floor, impeccable 3 Bedroom + 2 Bathroom paradise condominium at the Wailea Grand Champion Villas. This is a prime example of what Wailea Grand Champion Golf Villas has to offer in a 3 bdrm + 2 bath category. Upgraded...
Beachfront 2 Bedroom / 2 Bathroom Condo in Kihei
Indulge in luxurious island living at this oceanfront 2-bedroom, 2-bath condo in Kihei, Hawaii! This well-appointed condo is located directly on Keawakapu Beach, so you can spend your days splashing and snorkeling under the sun. Explore the excitement of the area at top...
Maui Resort Rentals: Honua Kai Hokulani 404, Luxurious 3BR w/ Stunning Ocean & Mountain Views!
Located only one stack back from oceanfront in the closest column to the ocean at the entire resort, this luxurious 3BR/3BA residence boasts stunning ocean views that extend deep into the home’s living area, as well as vistas of the West Maui Mountains. Enjoy a...
Maui Resort Rentals: Honua Kai Konea 818 – Luxurious 2BR Corner Suite w/ Oversized 450+ sq ft Balcony & Beautiful Partial Ocean & Mountain Views!
Konea 818 is a luxurious 8th-floor two-bedroom "penthouse" corner suite and one of the few offerings at Honua Kai that afford views of both the tranquil blue Pacific and the majestic West Maui Mountains. Take in the dramatic scenery while you dine, entertain, or simply...
Penthouse Sweeping Ocean Views!
Welcome to Maui and the Hono Hideaway home located in the stunning Ka`anapali Shores Resort!See the ocean from every room of this beautiful, top-floor FOUR-story condo in the oceanfront wing of the Ka`anapali Shores resort! You`ll feel like you`re walking on water as...
KBM Resorts | FREE CAR | Maui Kaanapali Villas | Renovated Studio Near Beach Central A/C! MKV-B-247
** 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...
Tranquil Golf Course Townhome Ko Olina Kai Estates w/Great Amenities by Beach
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.Welcome to your luxurious retreat nestled within the exclusive Ko Olina Kai Golf Estates and Villas gated...
Elegant suite with a large lanai and ocean views
Step into Kaanapali Shores 401, a spacious 2-bedroom, 2-bathroom condo that offers central A/C, a private washer/dryer, and panoramic ocean views. This property has elevators. Unit 401 can comfortably accommodate up to 6 guests. The master bedroom boasts a king-sized...
Magic Sands Oceanfront! Sleeps 18, 6-bedroom house in charming Kailua-Kona!
Stay comfortably in Kailua-Kona at this delightful 6-bedroom house; across the street from one of the Big Island's top destinations-Magic Sands Beach! With 4 king beds, 1 bunk bed, 2 queen beds, and 2 sofa beds, there's plenty of space for all guests. Cool off in the...
Boho Island Paradise - Remodeled 2BR/2BA
Welcome to your tropical retreat in the heart of Waikoloa, Hawaii! Our recently renovated 2-bedroom, 2-bathroom condo blends boho-chic style with modern conveniences, providing the perfect backdrop for your dream vacation. Whether you’re in search of relaxation or...
The Treehouse at Hulili Farm - NEW
High in the podocarpus trees, the Treehouse sits, with a sweeping view of the ocean, and the beautiful sound of birdsong. Sip coffee on the lanai as you watch the sunrise over the ocean. Fall asleep gazing up at the unobscured starry night sky through the carefully...
Hip Hawaiian Oceanfront Vistas (New Condo Special)
Summary:Bright, modern, and spacious. Complete remodel in August 2024! Thoughtfully designed to elevate your experience on Maui. This one-bedroom, one-bathroom condo features luxurious touches throughout paired with beautiful ocean views. Located in the sunny and...
Spacious 2BR Best Ocean Views -Kapalua Golf Villas 11P 5-6
This is a legally permitted vacation rental according to the County of Maui ordinances.Oceanfront Bliss & Golf Course Serenity – Kapalua's Premier Escape AwaitsE komo mai (welcome) to the Hawaiian escape of your dreams, where every sunrise whispers serenity and every...
Poipu Crater 23 - Vacation in the Crater/Air Conditioning in Bedrooms
POIPU CRATER 23 AT KOLOA KAI VACATION RENTALSA Tropical Retreat in an Extinct Volcano CraterDiscover the unique charm of Poipu Crater 23, nestled amidst acres of lush tropical foliage in the heart of Poipu. This two-bedroom duplex condo offers the perfect blend of...
Poipu Crater 24 - Stay in the Crater, A/C in the Bedrooms
POIPU CRATER 24 AT KOLOA KAI VACATION RENTALSYour Tropical Oasis in the Heart of PoipuImmerse yourself in the beauty of authentic island-style living at Poipu Crater 24, a tranquil retreat located in a unique enclave of 15 duplex bungalows nestled in the crater of an...
Manualoha 303 - Ground Floor with Free Poipu Beach Athletic Club Membership
MANUALOHA 303 AT KOLOA KAI VACATION RENTALSTropical Garden Retreat Near Poipu BeachEscape to paradise at Manualoha 303, a beautifully upgraded 1-bedroom, 1-bathroom garden-view condo that combines comfort, convenience, and the lush beauty of Kauai. Located just 0.2...
Newly Renovated in 2024! E22 Waikoloa Beach Villas
Waikoloa Beach Villas E22. Newly Renovated in 2024!Please scroll down for detailed information:Bedding Configuration:Master Bedroom: King BedGuest Bedroom: King BedLiving Room: Sleeper SofaAmenities:Beach Equipment: All of our vacation rentals include beach towels for...
New Remodeled Kuaui Escape! 1/1 condo in charming Kapaʻa with WiFi, AC
Welcome to our charming one-bedroom condo by the beach in the heart of Kapaa next door to Coconut Marketplace. This newly remodeled one-bedroom offers a fully equipped kitchen,a furnished lanai,a king-size bed, and a sofa sleeper that can accommodate up to four guests....
Kehena Black Sand Beach House: 2 BR Eco-Retreat with Ocean View & Swim Spa
The ultimate Hawaii eco-retreat. Timeless design for indoor-outdoor relaxation, dining and sleeping. Experience ocean views and crashing waves from wide-open bifold doors. Walk nextdoor to Kehena black sand beach, or drive the Red Road to the state's only hot springs at...
Thoughtfully Remodeled 3 Bedroom Townhouse North Shore Hale 6B
E Komo Mai (welcome!) to "The Cozy Aloha", a lovely 3-bedroom townhome oasis in the peaceful north shore community of Hale Honu in Princeville. This newly renovated 1,148 sq ft split-level condo seamlessly blends modern comfort with tropical charm.Step inside to...
Kauai Dream Retreat: Your Gateway to Coastal Living in Poipu Kai
LOCATION LOCATION LOCATIONKauai Dream Retreat: Your Gateway to Coastal Living in Poipu KaiAloha and welcome to Kauai Dream Retreat—a haven of coastal elegance and prime location in the heart of Poipu Kai. Situated along the lush Greenbelt, this 3-bedroom retreat invites...
Relax, with breathtaking ocean views. Makaha 1-bedroom condo near Ko Olina
Nestled in the town of Makaha, our 1-bedroom condo offers a tranquil retreat for your Hawaiian getaway. As you step inside, you'll be greeted by a gorgeous ocean view! A kitchenette, complete with a stove, oven, refrigerator, and all the necessary appliances and...
☀Private Unit Like No Other ☀Serene, Tranquil, Fully Equipped ☀
☀Private Unit Like No Other ☀Serene, Tranquil, Fully Equipped ☀Your Tropical Oasis!! Please come enjoy what we believe is one of the best located units in Mauna Lani Fairways. Total privacy!! No Lanai facing yours, no building right next door. No road outside your door...
Ka'anapali Beachfront Estate – Brand New Home with Luxury Amenities
The most magnificent estate to come to the rental market in decades, perhaps ever. This massive 11,000 sq. foot, 11 bedroom estate sits directly on the world famous Kaanapali Beach, recently voted the best beach in America.Developed from the ground up over a 3 year...