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.
Sunrise House: Tranquil Oceanfront Escape in Aliomanu, Kauai with Stunning Views
Welcome to the Sunrise House, your ocean front split-level oasis in Aliomanu, Kauai! Escape to paradise and experience the ultimate retreat at our tranquil two-bedroom vacation rental. Nestled along the breathtaking shores, this peaceful haven offers everything you need...
Hoaloha Hale - Gorgeous Kihei Home Across from Beach
PLEASE READ PRIOR TO BOOKING: If you have more than 10 guests the cottage will need to be booked as Maui's rental permit law requires 2 guests per room. That includes children over the age of 2 years old. Children under the age of 2 can stay with their parents in the...
NEW LISTING - Waipouli G106 Oceanfront Ground Floor 2 Bedroom
This oceanfront ground-floor two bedroom, three-bath suite is just steps from the beach at top ranked Waipouli Beach Resort and Spa on the island of Kauai. Enjoy spectacular sunrises from the lanai while enjoying the tranquility the quiet side of the resort has to...
Fantastic Ocean View in Ka'anapali at the Whaler
** Please Note ** If this property is unavailable for your preferred dates, please try our other Whaler property at www.vrbo.com/2814974Aloha! Your spectacular vacation awaits in Unit #413 on world-famous Ka’anapali beach - one of the most beautiful beaches in the US....
Hualalai Waiulu Villa 133B ~ Updated, Spacious with Great Views!
This spacious 2 bedroom, 2 bath single-level villa is centrally located on the Resort’s popular Waiulu Street overlooking beautiful Punawai Pond, the 5th Hole of the Member’s Ke`olu Golf Course and the ocean beyond. With 1854 square feet of living space, additional...
Luxury Upcountry retreat with breathtaking views!
PermitsBBMP2019/0006 & SUP2 2019/0003GE-081-730-0480-01 & TA-081-730-0480-01This is a BnB not a STRHOwners live on property.Aloha, sorry but at this time we are not hosting to families with children younger than 12 Mahalo.This is a NO SMOKING property. Mahalo. Our...
Updated 2 Bedroom Condo Walk to the Beach & Shops.
Aloha! We would like to welcome you to our little piece of paradise on the Big Island of Hawaii on the South Kohala/Kona Coast. A 20 minute drive north from the Kona airport, the South Kohala area is upscale and close to some of the islands most beautiful white sand...
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...
Luxury Moana Lani: Oceanfront Home with Pool & Jacuzzi
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 Moana Lani, a captivating...
Newly listed luxury home - great location, views, AC + free toys
With its wrap-around lanai and amazing views, this newly remodeled 3 bedroom/3 bath home in Princeville will make you want to move to Kauai. The skylights and sliding glass doors in every room remind you of the tropical paradise just outside. The open-concept, airy...
Ocean Front With Ocean View! AC, King Bed, 2 Bath!
E Komo Mai to our remodeled oceanfront unit with stunning ocean view at the Nani Kai Hale. Feel the ocean breeze, listen to the waves, and watch the whales and sunsets from our tranquil, oceanfront condo. From our comfortable lanai seating you have view of the Islands...
4 BDRs with their own baths! Modern decor! Privacy! Best Ocean View in the Hood!
Imagine relaxing in your very own pool, listening to the quiet hum of the distant surf, watching the perfect sunset. All that and more can be enjoyed in HALE KEANI ('House of Gentle Breezes')--a gorgeous modern home in a private, gated community.Welcome to Keahou...
Great Price-Amazing Ocean View-Walk to Beach-Poipu Kapili #29
Enjoy your stay in paradise in the comfort of our spacious, ground floor contemporary, island-style 1 bedroom, 2 bath condo. Whether you’re in the living room, kitchen, dining area, or lanai, our ocean views will enchant you! Enjoy your morning breakfast or evening...
Luxury Wailea Family Condo. NEW EVERYTHING! Complete Remodel! AC and Pool.
If you are looking for a modern, luxurious retreat for families in Wailea with BRAND NEW EVERYTHING, look no further! This unit was completely renovated. Guests can enjoy:— Modern, deluxe kitchen with all new appliances. Fully stocked with everything you need to cook...
Malaekahana Beachfront Oasis Steps from Excellent Sandy-Bottom Swimming
Completely restored in 2024, this light-filled, 2,800-sq-ft, open concept home features breathtaking views of Malaekahana Bay. Enjoy the fully equipped modern kitchen, living/dining room for easy entertaining and a recreation room that has a ping-pong table, a game...
Paradise found, only 50 feet from the ocean!
On our first visit to Papakea we knew we had found our home in paradise. Papakea Resort is an oceanfront resort with a true feeling of Aloha, From our ground floor unit, in the desirable G building, you can walk out 50 feet to the ocean or the pool, recline on a lounge...
Hilo Studio Retreat with Gorgeous Park View, AC, WiFi, Pool
Welcome to your cozy getaway! This inviting studio is thoughtfully designed for comfort and convenience, making it the perfect home base for your adventures.Step inside to find a bright and airy living space, complete with a comfortable bed and stylish furnishings. The...
Lovely Family & Friends Hawaii Getaway | Two Spacious Rooms w/ Outdoor Pool
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.✦ Each room is 540 sq. ft, equipped with complimentary toiletries, high definition 32-inch TV, available with Standard cable.✦ Rooms are not adjoining and possibly...
New Listing | Beautiful 2bed/2bath Oceanfront Unit 105
This 2 bedroom, 2 bathroom condo located on the ground floor, offers majestic ocean views and is fronting a beautiful golden sandy beach. Fully finished and equipped with everything you need in your home away from home, this is the perfect spot to enjoy with your...
Ocean Tower Waikoloa Village by Hilton - 2 Bedroom Penthouse (sleeps 8)
Ocean Tower Waikoloa Village by Hilton Grand Vacations Club - 2 Bedroom Penthouse (Sleeps 8)**all photos are stock images and do not guarantee the view shown****PLEASE READ ENTIRE DESCRIPTION BEFORE REQUESTING RESERVATION**Book our Fabulous Condo & let The Vacation...
Maui Resort Rentals: Honua Kai Konea 305 – Spacious Interior Courtyard 2BR w/ Partial Ocean Views!
Konea 305 is a luxurious 3rd floor interior courtyard two-bedroom suite boasting beautiful views of the blue Pacific Ocean and the lush Konea pools and courtyard.Gather, reconnect, and celebrate this expansive 2 bedroom floor plan. Konea 305 offers a spacious 1300+ ft...
Kaunakakai Vacation Rental in Molokai Shores
Escape to paradise at this 1-bedroom, 1-bath vacation rental in Kaunakakai. Located in the highly sought-after Molokai Shores Resort, this condo offers a tranquil getaway with access to a community pool, gas and charcoal grills, a private balcony with ocean views, air...
Kahikole Villa: Hualalai Resort Remodeled Villa with Pool & Spa
*Newly Remodeled*Kahikole 4 bedroom Luxury Villa on the 8th fairway of the Nicklaus designed Hualalai Golf Course. Incredible views over the 8th and 4th greens, ocean views and sunsets.Kahikole Villa offers 3 bedrooms in the main living area with two outdoor shower...
Amazing oceanfront! Updated, convenient, quiet. Book now for your choice in 2025
Completely remodeled! Our full condo remodel was completed just a few years ago, and we would love to share all the new comforts and conveniences with you. Of course, the third floor, 180º spectacular ocean view hasn't changed. Our condo now offers 2 bedrooms with...
❤️PiH❤️ Sea to Sky ★ Newly Updated★ FREE Mauna Lani Tennis, Pickleball, Lap Pool incl
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to Sea to Sky, a part of our Hawaiian Luxury Collection. Sea to Sky, at the Mauna Lani Villages is a wonderful 3 bedroom home with luxurious high end finishes in a premier resort community. This is one of a very...
^Marriott^ Ko'Olina Beach Club 1BR 1BA MT. or OCEAN view ^1st car park for free^
Marriott's Ko Olina Beach Club - 1BR 1BA OCEAN VIEW***INSTANT BOOKING***Full access to the resort’s services and amenities are included with every reservation. This listing is for 3 night stay checking in on 9/13/2025***Instant booking!!!***Relax by the pool, surf the...
Beautiful Ocean View Remodel - Luana Kai B306
This two bedroom, two-bathroom, top floor condo at Luana Kai sleeps 6 with a sofa bed in the living room. The kitchen has been beautifully remodeled with top of the line appliances and features stunning hand-crafted wood details like a split mango wood counter, custom...
Whaler's Inn -Nautical Magical
Whalecome and Aloha!You looking for an authentic Hawaiian Nautical experience? Let the Whaler`s Inn be your perfect spot to relax, set your sails with us and put down your anchor. We are located right in Downtown Hilo just Minutes away from Shops, Restaurants and just a...
HYATT RES. CLUB KA'ANAPALI BCH, OCEAN FRT -MAY24-MAY 31 AND MAY31-JUN 7, 2025
Whether you choose to spend your days exploring the island of Maui or lazing about on the soft sand of the island’s signature beach, Hyatt Residence Club Maui, Kāʻanapali Beach Resort promises to offer the ideal home base for any Hawaiian escape. Surrounded by...
Waipouli Beach Resort Extra Large Unit! Luxurious Decor! Sleeps up to 8*
Extra Large Unit! Beautiful Luxury Decor!Exquisite Luxury Condo of Distinction located at the World Renown Waipouli Beach Resort on the Coconut Coast of Beautiful Kauai!Guest Reviews: "Aloha! Thank you for an incredible stay! We enjoyed all of the great amenities this...
Luxury Villa with Artful Decor, Stunning Views, Gourmet Kitchen & Private Patio
This property is hotel zoned, and not being affected by the recent proposed legislation.Breathtaking Views and Picturesque Sunsets!!! Ho'olei 39-3 offers spacious, upscale living in a private gated community. Escape and relax at this opulent two-story Villa.As you enter...
Best Place to Stay in Kauai - 35' from the Surf - Poipu, Hawaii
Located 35 feet from the surf, my Poipu condo is one of the best places to stay on the Island of Kauai. It has the best close up ocean views on the entire Island. Miles of beautiful coastline, crashing waves, breaching whales, sea turtles, great surfing action, and...
OCEANFRONT DUPLEX, with POOL, SAUNA and steps from BEACH
Very unique property—like staying at a private resort, this listing is for TWO units on the same property with separate entrances. Located within minutes from downtown HIlo in a very quiet neighborhood, a short walk to a surfing beach and swimming river park… it’s...
Hilton Waikoloa Pool Pass Included 2025 and Waikoloa Kings Club Golf Discounts.
This vacation rental is professionally managed by ResorticaHawaiiWaikoloa Fairway Villas H4PLEASE NOTE: Waikoloa Fairway Villas H4 is listed for sale. Guests may be asked to accommodate showings/inspections with 48 hours notice. Please reach out with any questions....
Hale Kupanaha – Mid-Century Modern Luxury in Poipu
“This house is amazing!” visitors often exclaim, in those exact words. Hence, the property’s poetic and perfectly apt Hawaiian name: Hale Kupanaha (“Amazing House”). The design team behind this extraordinarily gorgeous new villa envisioned a distinctive...
Maui Resort Rentals: Honua Kai Hokulani 248 – 2 BR w/ Fantastic Partial Ocean & Mountain Views!
Hokulani 248 is a luxurious two bedroom suite that offers guests the best of both worlds. Enjoy beautiful partial ocean views, as well as stunning views of the West Maui Mountains, right from the comfort of your spacious lanai (balcony).As the first two bedroom back...
Mana Kai 608: Oceanfront Remod- Modern Surf Vibe!
Welcome to our remodeled oceanfront condo DIRECTLY on Keawakapu beach! Mana Kai is a hotel zoned resort in an ideal location on the border of Wailea and Kihei. We have designed our condo with a modern and comfortable surf feel in mind, we strive to bring the essence of...
Greenbelt 3BR/3BA villa with pool, A/C and 10min walk to the beach
THE CONDO - VILLAS at POIPU KAI B110We recently bought this extravagant 1600 square foot villa located in an upscale private boutique resort with all the amenities. Each of the three bedrooms is very spacious and has a dedicated private bathroom, giving everyone...
REMODELED Luxury Townhouse in Mauna Lani
The Islands is a luxury townhouse community located in the Mauna Lani Resort. With mature tropical landscaping & the low density in this community, The Islands is a quiet tropical oasis. D4 is an end townhouse with only one shared wall with an adjacent unit. The two...
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...
Remarkable Oceanfront Living Awesome Location
This oceanfront, single-level townhome is located just 25 feet from the water, offering a front-row seat to stunning sunsets and surfers from the comfort of your lanai. While the Lahaina fire has impacted some parts of the community, this three-bedroom, two-bath unit...
Hapuna Beach Residence A34 at Mauna Kea Resort
This newly-constructed oceanfront masterpiece sleeps 6. It features sliding window walls that open to an unobstructed view of the ocean, a chef's kitchen with top-of-the-line appliances, and dual guest suites with luxurious baths. Additional features include a den/bonus...
Beautifully Studio Condo just steps to the Beach. Stunning Ocean Front Pool.
LOCATION, LOCATION, LOCATION- Our Studio Condo in Building 9 is just steps from the Ocean Front Pool, Pavilion and Ocean. With Sweeping Views of the Greenbelt and Partial Ocean Views. Located in the lower village just steps from the beach, on the greenbelt. Wailea Ekahi...
Make Easter Memories in Maui! "Palekaiko" at Kihei Akahi is waiting for you!
We are thrilled to present 'Palekaiko' at Kihei Akahi - our little piece of 'paradise' on Maui!A two-bedroom, two-bath condo, 'Palekaiko' is suited to families, multi-generational families and is even a great fit for couples, a guys-only golf getaway or girls-only beach...
Stunning Kaanapali Oceanfront!
Welcome to Mahana 1107! Located on the eleventh-floor, this one bedroom, one bath condo sleeps 2-4 and features stunning panoramic views of the ocean, beach and outer islands! Highlights include hardwood floors, 55` HD TV, and sectional with queen sofa bed. Kitchen has...
Hawaiian House With Ocean View
THIS PROPERTY CANNOT BE RENTED FOR LESS THAN 31 DAYSMonthly rent includes utilities (water, electric, wifi, landscaping) for rental periods of 1-3. Monthly rentals of 3 months or more are utilities included with a cap on electric. Rents under 6 months are subject to a...
Hale Huna - fully air conditioned 4 BD 4 BTH, short walk to beaches
Hale Huna (Hidden House) is a delightful beach house located on the green belt with just a short walk to Poipu's finest beaches, pool, hot tub, and tennis courts. The front courtyard is private for relaxation and features a barbecue so you can enjoy all your meals in...
Beautiful Ocean-view Kailua-Kona Condo! 5 min walk to the beach!
**Please note, effective Jan 1st. 2026, Hawaii's Transient Accommodations Tax will increase from 10.25% to 11% for all stays with an arrival in 2026 forward. We will need to collect the tax difference to secure and finalize your booking. We will contact you to confirm...
Cant get any closer to the OCEAN!
Completely Renovated 3-bedroom Oceanfront at Menehune Shores with A/C The view doesn't get any better than this!! Pack your suit...Menehune 518 has everything else you'll need to enjoy your Maui vacation! This beautifully renovated upscale unit is located in South Kihei...
Uluhala Place – 6BR Ultra Luxurious New Home at Hualalai
Welcome to your ultimate vacation retreat at the Four Seasons Hualalai Resort! Step into luxury and relaxation with this brand-new, meticulously crafted 6,000 square foot, 6-bedroom home boasting the finest finishes and unparalleled comfort. THE SPACE:As you enter,...