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.
KBM Resorts | FREE CAR | Kapalua Golf Villa | Ocean view | Luxury 2-Bedroom Villa with Panoramic views! KGV-22P2
** 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...
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
Welcome to Ko Olina Beach Villas O905, a refined 3-bedroom, 2.5-bath ocean-view retreat set high on the 9th floor of the Ocean Tower in Ko Olina Resort. Spanning 1,507 sq ft of open, airy living space with room for up to 8 guests, this villa blends luxury comfort with...
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...
Kaanapali Alii | 381
Welcome to Kaanapali Alii 381, your luxury vacation rental nestled in the heart of Lahaina. This stunning 1,544 sq. ft. condo, located on the eighth floor, offers breathtaking ocean views and a serene blue-themed interior that promises a tranquil escape. Whether you're...
Hale Kamaole 176 Ground floor condo, easy access to best beach on Maui!
This Modern, Maui Vacation Rental unit #176, has it all. The owner of this condo also owns unit 174, both of which have been completely remodeled from top to bottom recently. Occupancy of these units is limited to only 2 adults. Ocean & garden views from the well...
Maui Tropical Paradise - Vacation Home In Haiku - Pool/Spa
This lovely 3 bedroom, 2 bath plantation style home is located in the heart of Haiku. It has an open floor plan, vaulted ceilings and windows all around. You will enjoy lots of light and views of the lush garden, pool and spa. With high quality beds, a fully equipped...
Wailea Ekahi 1B Recently Remodeled Ocean View 1st Floor Luxury 1BD 2BA Condo
Unit 1B is located on beautiful Keawakapu Beach in gorgeous Wailea. This totally remodeled lower village, ground floor unit has one large lanai with a beautiful ocean view and Ekahi’s 34 acre tropical landscaped gardens. It has a lanai table that seats 6. It is...
Keauhou Kona Surf & Racquet 188: Renovated Oceanfront Retreat
Welcome to Keauhou Kona Surf & Racquet 188 by Gather, a fully renovated oceanfront townhome nestled along the stunning Kona Coast of Hawai‘i. This two-bedroom, two-bathroom retreat spans 921 square feet across two levels and accommodates up to six guests. Offering...
Poipu Oasis - Poipu Vacation Home with Pool
Poipu Oasis is a beautiful custom home with ocean views, just up from Poipu Beach park. This lovely two-story home's indoor outdoor living floor plan is designed to take full advantage of Poipu's views. The private pool is surrounded by a lush yard, the perfect place to...
Palm Villas at Mauna Lani B1, Spacious 3BR condo with Private Beach Club Access
Ready to escape to paradise with comfort, style & the Aloha Spirit? Just a 15 minute walk to the beach, The Palm Villas is located within the beautifully kept grounds of the Mauna Lani Resort. This is a quiet complex with swimming pool, hot tub, and small fitness...
Maui Breeze Retreat at Ho'olei openings Jul 19-29, Aug 22-Sep 14 & Sep 25-Oct 11
Surround yourself with the lush scenery of Maui Breeze Retreat at Ho'ol!ei, a tastefully decorated two-story villa with spectacular views of the Pacific Ocean. Your exquisite island retreat in Wailea offers spacious, well-appointed living quarters embraced by manicured...
HALE KE`PUA! Princeville Tranquil Jungle Retreat!
Welcome to Hale Ke' Pua, (House of Flowers) our spacious, serene space on the beautiful North Shore of Kauai. Your private area on the bottom floor within the home has its own private entrance, bedroom, full bath, living room, kitchenette, BBQ and gorgeous lanai with...
Bright & Airy Beach House w/ Oceanfront Views
Balmy days and breezy nights await at this 2-bedroom, 2-bath vacation rental in Kailua-Kona. With the Pacific Ocean as your backyard, you won't have to travel far for some vitamin D and 'sea,' whether you'd prefer to surf and swim or snorkel and sunbathe. When hunger...
Updated Kauhale Makai unit 610 1 bedroom top floor, king bed, AC
• Oceanfront• Central A/C unit• King bed• Remolded May2023• Beach access from condo complexWelcome to our home at Kauhale Makai 610. Our home was updated in May of 2023. Our beautiful and pristine one-bedroom condo sits on the top (sixth floor) of the complex....
Hapuna Beach Residence B25 at Mauna Kea Resort
Enjoy unobstructed beachfront views in this modern, luxurious two-bedroom unit decorated with Restoration Hardware furniture throughout. Overlooking the white sandy beach, the living and master bedrooms feature floor-to-ceiling sliding glass walls that open to create an...
The "Promise Tree" - Great Family Gathering Place in Kailua Kona!
Please only book through VRBO or a reputable site!Experience the exquisite natural beauty of the Big Island. This beautiful custom home built in 2014 is located in an extremely quiet community 5 minutes from downtown Kailua-Kona. There are spectacular views of both the...
Maui Banyan G202 - King Bed, Ocean View, Across from Kamaole Beach
This unit is located in South Kihei, which is on the southwest side of Maui, an easy drive to nearly all of Maui’s landmarks and outdoor activities. Kamaole II Beach is right across the street from the Resort and offers excellent swimming, snorkeling, white sand and...
Poolside Tropical Paradise Oasis
Escape to paradise and indulge in the serene ambiance of Maui Kamaole M-101, a sparkling clean condo conveniently located right next to the pool and just steps away from the stunning Kamaole III Beach. Featuring two tranquil garden patio lanais, including a completely...
Papakea H304 2BR / 2BA Condo with Spectacular Ocean Views & Central AC
The Papakea is a Kaanapali Beach Oceanfront Resort. Unit H304 is a 2 bedroom, 2 bathroom condo with Central A/C, Ocean Views from both the Lanai and Master bedroom, sleeping 5 *** Completely Renovated - new furniture, flooring, kitchen, appliances, central air...
Kona Garden Studio Ohana, private sunset lanai & seasonal fruit from the garden!
Take a break and unwind at this peaceful oasis. Enjoy beautiful views of the Kona coast from your private lanai, with plenty of fruits and herbs in the garden for your enjoyment. Depending on the season enjoy fresh papaya, mango, citrus, pineapples, figs, ulu, and...
MINUTES TO HAMOA BEACH, BEST LOCATION IN HANA
Maui County Permit # STHA 2016/0006Tax ID TA and GE 170-361-2416-01SUPER CHARMING - Hawaiian Vintage styled Cottage..Close to beaches and natural pool. Fully upgraded with lots of amenities. All new comfy furniture to kick back and watch a movie.Free high speed wireless...
Oceanfront Condo- Gorgeous Ocean Views! Sleeps 4
Aloha and welcome to Hale Ono Loa 303! Hale ono loa means "house of good living" in the Hawaiian language, and that's exactly what you'll find in our condo! Between breathtaking views, a comfortable king sized bed, and a communal pool amongst countless other amenities,...
Crown Jewel of the Coconut Coast - Waipouli B401
Experience ultimate relaxation in this tranquil, top-floor penthouse suite at Kauai's Waipouli Beach Resort & Spa. This luxurious ocean-view haven boasts two King Size Master bedrooms, each with its own lavish 3/4 Master bath adorned with elegant Indonesian woods and...
Kamoale Sands 9-410! Favorite locale near everything and ocean views!!
Kamaole Sands 9-410 is centrally located, offering a 2 bed / 2 bathroom unit, perfect for your Maui Vacation! It's just across from a large beach park and Kam III beach, providing stunning views of the ocean and West Maui Mountains.This spacious unit features vaulted...
Bali Hai Resort 1 Bedroom w/ HOT TUB & POOL
Perched atop the cliff terrain of Princeville, adjacent to the renowned Makai golf course, seamlessly integrates natural beauty with carefully crafted amenities. Surrounded by the lush, tropical mountains of the north shore, the resort offers a harmonious blend of...
ATOMIC TIKI – live like a local at Magic Sands Beach!
Vintage Hawaiian Oceanfront ParadisePop back in time and relax in 60's mod style in this quaint vintage apartment hotel, capturing a front row center view of Magic Sands Beach since 1963.Roll out of the soft and cozy queen size bed and step right across the street to...
This building has BEST PANORAMIC OCEAN VIEWS in Complex ~ VERY NICE Renovation Inside
Aloha future guests! All properties in our ohana or family have Hawaiian names. We call this Kapalua Golf Villa, Hale O Alihilani', which means 'home where the ocean meets the sky'.JUST LIKE IN THE PICTURES, QUALITY RENOVATION, FABULOUS OCEAN VIEWS!Centrally located on...
Maui Resort Rentals: Hokulani 605 – Premier 6th-Floor Oceanview Penthouse | Closest 2BR Column to the Ocean!
Maui Resort Rentals is proud to bring you this 2BR Premier Oceanview Suite at the Honua Kai Resort, newly launched and available for bookings starting August 29th, 2025!Boasting a premier top-floor location in the closest two-bedroom column to the ocean at the resort,...
April 26-May 3rd! Sleep 10 Poipu House at Makalea A/C, Private Pool & Hot Tub!
Discover your own slice of paradise at the Poipu House at Makalea, a beautifully crafted estate home offering luxury, space, and serenity on Kauaʻi’s sunny South Shore. With 2,700 square feet of thoughtfully designed living space, this elegant four-bedroom,...
Secluded Oceanfront Cottage- in Princeville – Private large Spa & Stunning Views
For less than half the price of a standard hotel room, this private ocean bluff Cottage-Studio offers a luxurious and romantic experience—giving you more space, more privacy, and more of Kauai’s magic. Instead of a crowded resort, you’ll wake up to the sound of...
Kailua-Kona Luxury Vacation Home – Ultra Private Oceanfront Gated Estate
This oceanfront residence is a gated estate situated in a private neighborhood off of Kailua-Kona’s scenic Ali’i Drive, just 5 minutes from town. Recently remodeled, this home reflects a true sense of place with Hawaii-style architecture, expansive indoor-outdoor...
Maui Paradise: Steps to Sand & Sun. Blg#1-Ocean View, AC's, Fast Wifi, 1st Floor
Come enjoy ocean views, sunsets, and sounds of waterfalls in our one-bedroom (King Size Bed), two-bath, air-conditioned condo. Kamaole Sands is just across the street from one of Maui’s best beaches. – Kamaole Sands Resort is a heavily sought-after property - has...
Modern, Designer Owned 2BD+2BA w/ Loft @ Kuilima Estates West
Experience this spacious, clean & comfortable, newly remodeled unique 2-story townhouse with the conveniences of a home which is fully air-conditioned w/ new quiet Mitsubishi split system a/c. This is especially important for the hot and humid days. There is no unit...
Lanikea at Waikiki - Luxury 2BR Suite Ocean & Park View
This 2 bedroom unit comes with 1 California king-sized bed, 1 queen-sized bed, and 1 sofa bed, and can accommodate maximum of 6 people. The unit is equipped with a full kitchen with cookwares and utensils. A brilliant view of the ocean and park from the living room and...