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.
Kolea 5A - 3 bedroom garden view vacation rental
This large, ground level 3-bedroom, 3-full bath villa is just two buildings away from the pool and provides two king-sizedbeds, two twin beds, four wall-mounted TVs, and Sonos speakers throughout the unit. It condo offers a prime location withdirect access to a grassy...
Royal Sea Cliff Kona 108 Oceanfront 3 BD 3 BA
This direct ocean front luxury condo is the largest and only 3 bedroom 3 bathroom unit in the entire Royal Sea Cliff complex. The open concept design flows seamlessly to the ocean at your doorsteps and outdoor wet bar. The luxurious master bedroom suite and living room...
Princeville Kauai 4 Bedroom Home Sleeps 10
Please Send An Inquiry Before Requesting To Book By Clicking The Contact Host Tab.Located on a quiet cul-de-sac, this magnificent, custom home was built in 2008 by a contractor for his personal residence. Attention to detail is evident throughout, with use of the finest...
Bay Villas Gold Oceanfront 1 Bedroom at The Kapalua Villas Maui, Outdoor Pool
Nestled in lush gardens and beside pristine beaches, our secluded sanctuaries offer tranquility. Enjoy world-class golf, snorkeling, award-winning spa treatments, and farm-to-table dining. Experience luxury in our fully-equipped villas, with stunning sunsets from your...
Royal Kuhio 2303 - Spacious Upgrade Studio w/ Stunning Mountain Views in Waikiki
Heart of Waikiki - Royal Kuhio (23rd Floor)Address: 2240 Kuhio Ave., #2303, Honolulu, HI 968151 Bed | 1 Bath | Sleeps 4Beds: 2 Full-size beds + 1 Queen sofa bedSize: 436 sq ft + 80 sq ft lanaiView: Partial ocean and mountain viewsKitchen: Fully equipped with oven,...
Kaanapali Alii | 394
Kaanapali Alii 394 is a luxurious ocean-view vacation rental located on the stunning white sands of Kaanapali Beach. This spacious two-bedroom condo, situated on the 9th floor, offers breathtaking elevated panoramic views of the Pacific Ocean, making it an ideal retreat...
2 bed 2 bath Condo in family-friendly building in Waikiki! Minimum 30 days
Located in Honolulu, this awesome condo features 2 queen beds in 2 bedrooms, along with a cozy living room with a sofa bed. With amenities like a washing machine, dryer, WiFi, and AC, guests can enjoy a wonderful stay in this cool space. Our place is equipped for both...
Charming Pu'ukala Sunset - Near Hiking and Golf by RedAwning
Discover the beauty of Kailua-Kona with a stay at our charming one-bedroom,one-bath Ohana vacation rental. This cozy coastal retreat is the perfectescape for couples seeking an island getaway. Nestled in a sereneneighborhood, you'll enjoy the tranquility of the ocean...
Upscale & Luxurious Oceanview Resort Vistas
Summary:Fully remodeled in March 2024. This elegant 2-bedroom, 2-bath condo features upscale touches with magnificent ocean views. Located steps from Wailea, all of Maui is within reach. We offer a fully stocked kitchen for those who want to cook. Enjoy the resort's...
Marriott's Maui Ocean Club Napili/Lahaina 1 Bedroom - Many Dates Available!
For any reservation inquiries, please use the "Contact Host" feature under "Check Availability."Hosted by TravelscowtDiscover our exceptional ratings with hundreds of 5-star reviews on VRBO, Google, and our own Travelscowt website.Most high-demand weeks during the...
Poipu Beach Amazing studio
Ideally located on serene Po'pu Beach. Peaceful stretches of white sand beach and crystal blue pacific ocean with breathtaking sunsets. Onsite spa, resort pools, steps from many beaches and beach activities.Ideal for small families, this studio unit has 403sqft of space...
Fairway Villa at Waikoloa B4 Golf View 2 Bedroom
- Front office is located at the Kings' Shops, 69-250 Waikoloa Beach Dr., Suite B-13. Office is open daily 9 am - 5 pm. - Kitchen features cooktop and oven, refrigerator, microwave, dishwasher, coffeemaker, toaster, rice cooker, blender, cookware and tableware- Master...
Marriott Waiohai Beach Club - 2 BR - Island View - Sleeps 8 (SC)
Marriott Waiohai Beach Club - 2 BR Sleeps 8 - Oceanview**PLEASE READ ENTIRE DESCRIPTION BEFORE REQUESTING RESERVATION**Book our Amazing Condo & let The Timeshare Brokers, LLC make the booking process easy!Key Points: -You’re inquiring on a Timeshare for Rent. -Please...
3 Bed Villa Views, Beach, Hot Tub, Pools, Golf
Summary:Corner unit with sweeping golf views, just steps away from the beach. Fully stocked with everything you might desire, steps restaurants or grocery stores. End unit feels like a house, provides privacy from neighbors, while being only steps away from the gorgeous...
Fabulous Poipu 6 bedrooms for 10-12! AC!
New Listing!! The Listing is made up of two separate townhomes just steps apart!This fabulous property located in wonderful proximity to Brenneckes, Poipu, and Kiahuna Beach!Surrounded by a championship golf course, the property enjoys a prime spot on Kauai’s sunny...
2 Bed Steps to the Ocean April SALE! Best Price in Kauai East Side Free Parking!
Steps to the Beach in Kapaa Town – Perfect Location and ValueEnjoy the best of Kauai’s East Side at this newly remodeled two-bedroom getaway, just steps from the beach and within walking distance to shops, restaurants, and everything Kapaa Town has to offer. This...
Valley Isle Resort #907 - Vacation West Maui
★Free Wi-fi, Free Parking, No Resort Fees★Valley Isle Unit 907 offers a serene escape on Maui's western shore. This oceanfront condo boasts breathtaking views of the Pacific, with Molokai and Lanai in the distance. Enjoy modern amenities, including a fully equipped...
Royal Kahana Maui 1215 Ocean View 1 Bedroom
- 12th floor condo with balcony- Carpet & tile 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- Queen sofa bed in living area- Ceiling...
nWake up in paradise at Plantation Hale D6
Enjoy a private lanai with sunrise views, breezy living spaces, and all the comforts of home — steps from the beach and Coconut Marketplace. Highlights:* Bright + spacious condo with island charm* Private lanai overlooking tropical gardens* Full kitchen for easy...
1-Bedroom Within The Ilikai Hotel!
1 Bedroom Economy Lagoon View on the 8th Floor! This unit features a full kitchen, queen bed, free long distance and wifi. Enjoy this sought-after view of the lagoon and Pacific ocean from your very own, spacious lanai.Just a quick walk away, is Hilton Hawaiian Village...
High-Floor Beachfront Colony Surf Condo w/ Sunset Views, Diamond Head Gold Coast
Wake up to turquoise Kaimana Beach and fall asleep to fiery Hawaiian sunsets. Located on the 12th floor of the iconic Colony Surf, this 1-bedroom suite delivers true “live like a local” comfort with resort-level amenities.There is no air conditioning, so please...
All New Interior: Premium Beachfront Ocean View Condo on Hidden Gem Beach
Come enjoy the warm, soft sands of O’ahu at our cabana where no detail has been left unattended to. Located at one of the most underrated beaches on the island with turtle, dolphin and whale sightings often, we’ve incorporated the latest technology here for you to...
Luxury Coffee Farm -Endless Views -Pool - Now Totally Exclusive
Our entire Estate is for sale. All reservations will be honored out at least 30 nights and we will probably be able to honor reservations out to 90 days depending on circumstances. You deposit and all monies received will be entirely refundable up to 14 days of arrival....
!OceanView New Remodel Near Convention Ctr Waikiki
Remodeled private cozy studio on Niu Street with Ocean, Diamond Head, Ala Wai Canal and city view. Walking distance to Convention Center, Ala Moana, beaches, shops and eateries.Please inquire about other listings in same building!Monthly discounts available!*Guests...
Relaxing Modern Oceanfront Suite–Sleeps 4 adults.
Enjoy this beautifully appointed oceanfront home in Kalapaki Bay. Take advantage of being centrally located with one of the best beaches and bays for SUP, beginner surfing, boogie boarding and more. The home is situated between 2 of the best resorts on the island. Enjoy...
Kapalua Ridge Villas Fairway View 1 Bedroom
Ridge Villas Fairway View 1 Bedroom- The Ridge Villas are perched high above with views of Kapalua Bay Course’s fairway - Fully equipped kitchen includes stovetop/oven, microwave, refrigerator, coffeemaker, cookware, tableware- Bedroom with 1 king bed- Queen sofa bed...
Oceanfront Studio with Panoramic Views - Kapa'a Sands 07
Kapaa Sands 07 – Oceanfront Studio | Queen Bed | Pool AccessWake up to stunning ocean views at this second-floor beachfront studio on Kauai’s Royal Coconut Coast. Kapaa Sands 07 features 1 queen bed, a full kitchen, private lanai, and direct access to a peaceful...
Cozy Sunset Views w/ Lanai - Close to Beach by RedAwning
Escape the hustle and bustle of everyday life and immerse yourself in theserenity of our charming Kailua-Kona Ohana, a delightful 1-bedroom, 1-bathroomvacation rental. Located on the captivating Big Island of Hawaii, this coastalretreat offers a tranquil escape for...
The Modern Kailua Beach House
Relax in this Modern vacation retreat located right across the street from Kailua beach park. Just steps from the white sand beaches of Lanikai/Kailua and minutes from local dining, shopping, and outdoor adventures. This thoughtfully designed home blends sleek...
Waikiki Studio with beautiful view and minutes to beach.
Fully furnished studio. Queen size bed sleeps 2. Complete kitchen, minutes from beach and shopping. Brand new air conditioner. Beautiful unobstructed view from 14th floor. Pool, BBQ lounge area and pay laundry on 5th floor. Near Bus routes to everywhere. This unit is...
Kaanapali Alii | 414
Kaanapali Alii 414 is a luxurious ocean-view vacation rental located in the heart of Maui's Kaanapali Beach. This spacious condo accommodates up to six guests with a well-designed layout two bedrooms and an enclosed sleeping den. The ground floor location of this condo...
Comfortable Studio at The Palms with Pool, WiFi & A/C - Sleeps up to 4 guests.
Unwind in Honolulu at this welcoming studio. This modern space offers a cozy living room with a queen bed and sofa bed, perfect for a peaceful retreat on the quiet side of the property. Enjoy the convenience of amenities like pool, WiFi, AC, and a hair dryer during your...
1 Bedroom Suite, The Modern Resort & Spa, Honolulu
Enjoy the glamour of this stylish, upscale place. Enjoy Hawaii's capital in style at the Modern Honolulu! Guests have access to a variety of amenities, including a fitness center, gift shop, several restaurants, two swimming pools, full-service spa, concierge service,...
Historic Wailuku Inn: 10 Ensuite Bedrooms | Gourmet Chef Breakfast Included
Summary:Welcome to The Historic Wailuku Inn, a fully restored 1924 estate with 10 en-suite bedrooms surrounded by lush tropical landscaping and meandering plumeria-lined pathways. Wake to a chef-prepared farm-to-table breakfast, unwind on grand lanais, and explore Maui...
Gorgeous private home with spectacular ocean views & private pool at Kohala Ranch
Gorgeous home with spectacular views and extra privacy on 6 acres in the Kohala Ranch community. This newly upgraded dream home is perfect for couples and families looking for a spacious three bedroom home where they can relax and enjoy panoramic ocean and mountain...
Private Luxury Home, Steps from the Beach w/ AC: Ranch Beach House Estate
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.Ranch Beach Estate is a hidden Hawaiian gem,...
Cozy 1-bedroom condo in Ocean Front Complex, 2 Lanai's and WiFi in Kailua-Kona.
Unwind in Kailua-Kona at this adorable condo. Bedroom with a king and loft with a queen bed, guests can enjoy a comfortable stay. The bathroom comes equipped with a hair dryer for added convenience. Kickback, relax, and enjoy everything Kailua-Kona and our condo has to...
Walking Distance from Papaloa Beach, Outdoor Pool, Free Parking, Full Kitchen!
Step into a world of relaxation, surrounded by swaying palm trees and vibrant hibiscus blooms. Your spacious suite features a full kitchen, separate living room, and private lanai. Refresh yourself in our sparkling outdoor pools, perfect for relaxation or family fun....
Kiahuna Plantation Resort 161 Ocean View 1 Bedroom
- Second floor end unit with lanai overlooking the great lawn and out to the ocean- Walk-up, no elevators- Tropical beach décor and original artwork- Tile floors with carpet in living and bedrooms- Open kitchen includes Corian countertops and new appliances, microwave,...
North Shore Oceanfront Retreat by Gather: 5BR Spacious Home Paradise
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 North Shore Beachfront Retreat by...
REDECORATED! Like-New Oceanview 4 Bedroom 3.5 Bath Lux Montage Kapalua Grand Residence Sleeps 8!
New Offering! 5201 has just joined Private Paradise Villas as another "Your Own Private Paradise" residence to enjoy. An extensive redecoration was just completed as of July 2025. We are thrilled to welcome our first guests to this FULLY redecorated (all new!) villa...
Niu Beach Estate – Private Luxury Meets Island Sophistication
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.Aloha and welcome to your own private slice of...
Kihei Estates G105 Gorgeous Remodeled Condo Home
Book with us and come to Maui to explore everything we have to offer!Enjoy the ocean, restaurants, and shops of Maui all within a couple minutes walk from this 1 bedroom 1 bath island oasis unit in the heart of Kihei. Wander right out to the well maintained grounds and...
Oceanfront Villa on Kona Coast with breathtaking views
Your home away from home in the Mauna Lani Beach Resort with 5 bedrooms, 7 beds and 9 bathrooms. This villa offers guests a relaxing retreat with an outdoor oasis with 2 pools, 2 spas, and modern amenities like WiFi, a fitness room, and AC. The 9 bathrooms ensure...
Luxury suite overlooking Waikiki skyline with Ocean View
Allure Waikiki #2702 – 1837 Kalakaua Ave.(LEGAL 30-Night Minimum Rental in the Resort Zone! ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)NEW TO OUR INVENTORY! Experience luxury Waikiki living at its finest! This 2-bedroom, 2-bath condominium with high-end touches...
Kolea 8E - 3 Bedroom Ocean View Vacation Rental
Kolea 8E is a three bedroom, three and a half bath villa with a sweeping view of Hualalai and an impeccable ocean view of Anaeho’omalu Bay. It is one of the few front row villas that also overlook the private Kolea Beach Club, where Kolea guests are invited to enjoy...
Kona Reef F2 – Charming Oceanfront Condo for 4!
Summary:The mesmerizing gem of Kailua-Kona is something that truly has to be seen to be believed, offering an unforgettable tropical escape for visitors from around the globe.The Space:Margo and Frank first came to the big island some 10 years ago. They came to Kona...
Kapalua Ridge Villa 1222 Ocean View 1 Bedroom
- Spacious lanai with views toward mountain, golf course, and ocean- Second floor unit, two-level townhome, with multiple stairs from parking to the villa- Tile in kitchen, and bathroom. Carpet in living room and bedroom- Fully equipped kitchen with stainless steel...
𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 Beachfront Kaanapali Residence Club+Amenities, 3BR
Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢🌴🌺 Escape to Tropical Opulence at The Hyatt Residence Club on Kaanapali Beach! 🌺🌴𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 may provide an additional $500-$1000 SAVINGS for members on...
Fairways South #23
Located within the desirable South Fairways at the prestigious Mauna Kea Resort, this charming 4-bedroom home is adorned with exquisite Asia-Pacific decor. This beautiful vacation rental not only offers breathtaking ocean views but also provides a serene oasis to unwind...