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.
Spacious 3 bedroom ocean view, large balcony, King beds, Pool & Spa
Welcome to your Hawaiian getaway! For your comfort, there are portable A/C units in private bedrooms and living room.Additional cooling features: swamp coolers, ceiling fans, standing fans.Our spacious 3-bed, 3-bath townhome offers stunning ocean and golf course views,...
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...
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,...
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
Welcome to Kaanapali Alii 455, your ultimate luxury vacation rental in Maui. This stunning two-bedroom condo offers a perfect blend of comfort and elegance, making it an ideal short-term rental for families and friends seeking a serene getaway. Step inside this spacious...
Four Bedroom Oceanfront Estate at Naupaka Place at Waikoloa Beach!
Welcome to Pacific Sunset Villa, home of expansive ocean views and ultimate luxury. This award winning home with 4 bedroom with ensuite bathrooms and 3 half bathrooms sits on an oceanfront setting and offers easy access to all the amenities at Waikoloa Beach Resort.The...
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...
3rd Fl Palms Waikiki Studio Overlooking the Pool | Parking
🌺 Modern Aqua Palms Studio Overlooking the Pool | Parking⚠️ Building Notice: Spalling repair work will begin January 13 and is expected to continue for approximately 8 months. Work hours are Monday–Friday, 8:00 AM–4:30 PM (excluding weekends and holidays)....
The Modern Honolulu, Sleeps 4, 453 sq ft, Central Location + Fitness Center
The Modern Honolulu is a Hilton lodging choice for your trip to Hawaii. With numerous amenities for guests such as 24 hour front desk, and fitness center, you will wake up feeling ready to go every day for your time in Honolulu. This hotel is conveniently located near...
City View Studio in Waikīkī just Steps from Beach! - Bamboo Waikīkī Hotel #605
Castle Bamboo Waikīkī Hotel #605 - This sixth-floor high rise set within walking distance to Waikiki’s famed majestic shores offers modern conveniences to make your stay as comfortable and productive as desired. Recreate and lounge on property or take advantage of...
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
Welcome to Kaanapali Alii 461, a luxury vacation rental nestled along the stunning Kaanapali Beach. This oceanfront property offers a spacious 1,500 square feet, providing a more intimate and comfortable setting compared to typical hotel rooms. Ideal for families and...
Kahala Zen: 5BR Modern Oasis with Studio & Lush Garden
Welcome to Kahala Zen, a show-stopping 5-bedroom, 4-bath luxury retreat set within Honolulu’s prestigious Kahala enclave. Spanning 3,300 sq ft of thoughtfully designed living space—including a private studio cottage—this newly built 2024 estate blends timeless...
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.Unit 1000 Ocean View 2 Bedroom + Bonus Bedroom 2...
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...
Oceanfront Villa! Westin Ka'anapali - Beautiful Resort On The Beach! Family Friendly!
The Westin Kā‘anapali Ocean Resort Villas South, located on Maui’s renowned Kā‘anapali Beach, offers an upscale island escape. These spacious villa-style accommodations feature kitchens, private lanais, and luxurious touches. Enjoy multiple pools, a spa, fitness...
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...
Laule'a Ohana Retreat: 2 Mauna Lani Villas with Golf Views & Dual Pools
Welcome to Laule'a Ohana Retreat, two side-by-side luxury villas on Hawaii’s Kohala Coast that together create the ultimate gathering place. With 8 bedrooms, 8 full baths, and 2 half baths across nearly 6,000 square feet, these residences are ideal for multi-family...
NEW Studio with 2 Queen Beds in Waikiki
– Located on the 12th floor of Island Colony, a secure high-rise with 24/7 security– Ala Wai Canal and pool views– Elevator access for easy arrival and departure– Building amenities on the 6th floor: swimming pool, jacuzzi, sauna, laundry facilities, convenience...
Kaiana Villa: 3BR North Shore Kauai Vacation Rental Home
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...
Poipu Retreat: 3BR with Ocean & Golf Views, Lanai Sunsets, Pool & Central A/C
Welcome to Pili Mai 8C – Your Private Poipu Retreat.Perched on the edge of the scenic Kiahuna Golf Course, Pili Mai 8C is a three-bedroom, three-bath condo that captures the very best of Kaua‘i living. With sweeping views of the ocean, golf greens, and surrounding...
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...
Honua Kai | 3 Free Rental Cars | KBM Resorts | Extra Large Lanai | 3 Units, 4 Bedrooms | HK ML-1826
** 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...
Kaanapali Shores 645 - Ocean View 1 Bed/1 Bath
Located in Kaanapali Shores, large one bedroom with a king size bed, queen size sleeper sofa in the living room, fully equipped kitchen with appliances, dining table with seating for four, workspace with desk, and WIFI. The condo features central AC along with an...
Cliffs at Princeville 1208, Beautiful Ocean-bluff Resort, Full Kitchen
The Cliffs at Princeville 1208 includes 2 connected studio units, 1208-A and 1208-B.Two Spacious Garden Studios for 4 Guests, Kauai North Shore Resort.Located on 22 lush acres overlooking the Pacific Ocean, The Cliffs Resort in Princeville is the perfect spot for...
MA 411 Ocean-view in West Maui, a spacious 2-bedroom condo for 6.
Mahana 411 Enjoy Breathtaking Oceanfront Views and Watch Spectacular Sunsets from as Close to the Ocean on Maui as it Gets Welcome to your Maui Retreat: This stunning 2-bedroom, 2-bathroom corner condo at The Mahana in Kaanapali offers an unforgettable oceanfront...
Kapalua Bay Villas | 2 Free Rental Cars | KBM Resorts | Premium Bay Villa | 2 Units, 2 Bedrooms | KBV ML-1981
** 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...
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...
Hale Moana by AvantStay | Incredible Hawaii Beach Resort w/ Pool & Hot Tub!
Kick your feet up at Hale Moana, the newly-renovated villa perfect for your paradise vacation. Professionally and locally designed, this condo captivates Kapolei’s lively atmosphere and offers state-of-the-art appliances, spacious dining areas, and plush lounging...
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.This listing is for a room within a hotel.✦ Your room is 350 sq. ft, equipped with complimentary toiletries,...
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...
NEW | KBM Resorts | FREE CAR | Kapalua Golf Villas | 1-Bedroom Condo with Spacious Lanai and Golf Course Views! KGV-18T4
** 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...
Quaint 2-bedroom house in Keaau for a relaxing getaway
Located in Keaau, this charming house features 2 beautiful queen bedrooms and a nice living room with a futon. The bathroom offers a shower for guests' convenience. Relax and unwind in this cozy retreat during your stay. We hope you'll enjoy your stay at our house.
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...
perfect studio suite on Kauai HI
About this spaceEscape to a South Pacific paradise on Kauai's North Shore to discover a world of tropical pleasures and condo resort-style amenities.Overlooking Anini Bay, Ka Eo Kai offers a variety of nearby recreational options including zip lining, family fun...
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...
Kaanapali Alii 2106
Welcome to Kaanapali Alii 2106, a luxury vacation rental nestled in the heart of Lahaina, Maui. This deluxe two-bedroom, two-bathroom condo is the perfect family-friendly short-term rental, offering breathtaking views of the West Maui Mountains and Kaanapali Beach. Step...
Wailea Grand Champions 52 - 2 Bedroom Garden View Condo
Welcome to your dream vacation in Wailea, Maui! This beautiful two-bedroom residence combines comfort, style, and convenience for an unforgettable stay in paradise. Upon entering, you\'ll be welcomed by a spacious, open living area, tastefully furnished for a relaxed...
SANS SOUCI 607-⛱Gold Coast Beautiful Beachfront Villa-Sleeps 6-Monthly Rental
Sans Souci Vacation Rentals2877 Kalākaua Ave 607Honolulu, HI 96815⚠MONTHLY RENTAL⚠Disclosure: All reservations require a 30-day contract. In compliance with the Ordinances of the City & County of Honolulu, the Property will be made available to you for your use and...
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-...