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.
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 H4Bedding Configuration:Master Bedroom: King BedGuest Bedroom Downstairs: One Queen BedGuest Bedroom Upstairs: Two Twin BedsHilton Pool Pass: Valid for stays through December 31,...
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 designed our condo with a modern and comfortable surf feel in mind, we strive to bring the essence of Maui...
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...
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...
Hale Anuenue | Luxury 3br Kauai Residence
Settle into a blissful sense of calm at Hale Anuenue, which means “House of the Rainbow” in Hawaiian. This three-bedroom, three-and-a-half-bath villa features beautifully appointed interiors featuring contemporary coastal décor and expansive grounds, allowing you...
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...
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!
Enjoy an amazing experience at our centrally-located place. Our ocean-view condo is a 5 minute walk to the beach and an 8 minute walk to downtown Kona, where you will find awesome restaurants, bars, shops, the farmers market, churches, a great atmosphere and...
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,...
KBM Resorts | FREE CAR | Kapalua Golf Villa | Ocean view | Luxury 2-Bedroom Villa with Panoramic views! KGV-22P2
Remodeled luxury 2-bedroom villa with panoramic ocean views, RH furniture, quartz kitchen, motorized shades, & spa-style baths. Close to 4 pools, beaches, golf, dining, & scenic Kapalua sunsets.*Special Offer- Book any KBM rental home in Hawaii for 6 nights or more with...
Villa Frangipani Tropical Beachside Retreat Kailua
About this spaceOnce inside our fully gated property you will be immersed in a lush tropical garden with palms surrounding a lagoon style pool. We are just a 2 minute barefoot stroll along a private lane to the soft white sands of Kailua Beach. Built in 1938, our home...
Romantic & Breathtaking Oceanfront Kauai Condo
240+ 5 Star ***** "Wonderful" "Amazing" "Stunning" Reviews and Counting! Please plan ahead as our instant booking calendar fills up quickly.THE AMBIENCEIf thoughts of azure oceans, romantic getaways and sunrise mornings are just some of the peaceful images that makes...
Maui Sunset Vacation Rentals B405
Watch the life of Maui unfold from the morning till evening from your private 114 sq foot private view deck. Located on the fourth-floor view of tropical gardens and the ocean beyond. Quiet location features large private view deck and renovated interior. Doesn't get...
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...
Just Steps to Kamaole III Beach!!!
AWESOME QUALITY! FABULOUS VALUE! PERFECT QUIET LOCATION! FREE PARKING! NO RESORT FEES!Our condo offers casual elegance in sunny south Kihei with a warm and inviting atmosphere, guaranteed to provide the ideal setting for fun and relaxation. The spacious private lanai...
Beautiful Marriott's Ko Olina Beach Club 2BR/2BA, Free Full Resort Access
*** Concerned about COVID-19? Vacation with Confidence at Marriott Vacation Clubs. Learn about Our Next Level of Clean at: https://clean.vacationclub.com/ ** As inventory changes constantly, please contact the owner for availability and price prior to booking. * Free...
Contemporary Ocean View Suite - In the Heart of Waikiki
Thoughtfully appointed studio with contemporary decor. Fully renovated in January 2024! Includes FREE high speed Wi-Fi, cable TV, and various TV apps for streaming services.Check in and out at your convenience with a lock box. Check in after 3pm and check out before...
Ko Olina Beach Villas O905: 3BD Luxe Villa w/ Stunning Sunset Views
Immerse yourself in the luxury and beauty of Ko Olina Beach Villas O905 by Gather, a stunning villa perched on the ninth floor of the Ocean Tower, offering breathtaking views of the pool and ocean. This beautifully furnished three-bedroom, two-and-a-half-bath villa,...
Inspired 1-BR, Magic Gardens, Stream and Waterfall
Hit the pause button and relax at our peaceful stream side retreat. Located next to the Waipio Lookout, our Hamakua Coast rain forest property is the perfect place to recharge and rejuvenate. Hear the rush of our waterfall and enjoy our private oasis. We’re a ten...
The Artists House
The Artists House, Permit # STLA 2017/0002 is a home away from home with the comfortable furnishings and great amenities. The fabulous Lana'i sunsets can be enjoyed outside on the deck where there is glass dining room table with 6 chairs and bbq to enjoy. There are two...
Maui Resort Rentals: Honua Kai - 4 Total Bedrooms, 8th Floor "Penthouse" Ocean AND West Maui Mountain Views, Deluxe Corner Floor Plan!
This premier eighth-floor offering pairs one of our most sought-after two-bedroom "penthouse" suites with two neighboring one-bedroom suites to create the perfect place for your group to gather, reconnect, and celebrate. Enjoy unparalleled views of the blue Pacific...
Luxury condo • 180° Ocean Views • Steps to Beach
Enjoy panoramic ocean, mountain, beach & sunset views year round at Hale Meli (short for "Hale Mahina Meli" or “Honeymoon House” in Hawaiian), a top floor condo with exquisite designer interiors and high-end amenities. Ideally located in Kihei, the condo is right...
Kolea 7F - 3 Bedroom Front Row Penthouse
Kolea 7F is located in one of the most popular buildings within Kolea. The location offers expansive ocean views as well as easy access to the Kolea Beach Club and the white sand beach at A'Bay. Throughout the villa you will also find nice Hawaiian artwork! The moment...
Mermaid Cove Breathtaking Ocean Views 2 bdrm 2 bath
This lovely condo RIGHT on the shoreline, overlooking the beautiful Ma'alaea bay, is stunning. The 180 degree views, sweet ocean breezes, and lullaby of the ocean will take your breath away and instantly rejuvenate you! We offer A/C as well as ceiling fans, fully...
Tree Top Suite- Beautiful walk to Hanalei Bay
Aloha, Welcome to the Tree Top Suite, your enchanting escape nestled in the greenbelt of Princeville, Kauai. This secluded rental offers a unique fusion of tropical tranquility and modern comfort. Floor-to-ceiling windows bathe the space in natural light, giving views...
Kona Sea Villas- E-1
Summary:Escape to paradise in this spacious 3-bedroom, 3-bathroom townhouse in Kailua-Kona! Enjoy stunning ocean views and sunsets from your private lanai. This fully-equipped condo in a quiet, gated community offers all the comforts of home, including a BBQ grill and...
Kona Blue at Holua Kai: Luxurious Home w/ Private Pool, Spa, AC & Stunning Views
Kona Blue Vacations Holua Kai is a refined single-level retreat tucked within the private gates of Holua Kai in Kailua-Kona, perched along the manicured fairways of Kona Country Club. Blending island warmth with resort-inspired comfort, this 3-bedroom, 2.5-bath home...
Welcome to Luana Garden Villa 3B
Situated on Maui’s pristine western coast, the Luana Garden Villa marks the exquisite culmination of the Honua Kai Resort & Spa, proudly standing on the magnificent Kaanapali Beach. Nestled within a four-unit building, this villa is a distinguished part of Honua Kai's...
EXTRAORDINARY Hale Kuikahi Oceanfront Retreat - fully airconditioned!
Step onto the grounds of our oceanfront botanical garden retreat - Hale Kuikahi! Located in the quiet Paukaa area of Hilo just above famed Honolii surf beach, Hale Kuikahi boasts a private botanical garden walk onsite. Enjoy sweeping oceanfront views from almost every...