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.
Steps to Beach Top-Floor Maui Vista Perch w/ Pools & Tennis - Walk to Dining
Maui Vista 2410Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located across the street from beautiful Charley Young Beach, this 2BR/2BA Maui Vista condo provides a classic, quaint...
Oceanfront Sandy Beach 6 Bedrooms 4 Baths Jacuzzi
(Registered GET/TAT: 115-985-2032-01 ) Private gated beachfront property, one half acre tropical garden oasis. Escape to the quiet west side of the island and enjoy the beautiful exquisite soft sandy beaches, crystal clear blue ocean and the Waianae mountain views. Stay...
Contemporary Waikiki Beach Condo with Rooftop Pool, Superb Shopping and Dinning
The space- Bedroom – ONE queen size bed, playpen and high chair for baby- Living room – ONE queen size bed - Living room - ONE queen pull out sofa- One bathroom- A small balcony with a pick-a-boo ocean and city views- A roof top swimming pool and jet spa in the...
Modern corner studio in Waikiki. No resort fee
Newly renovated, clean and spacious studio in Waikiki. Unit is on 10th floor of the Hawaiian Monarch Hotel/Condo building and comes with queen bed, kitchenette, full bath and amazing ocean, canal, diamond head and mountain range views.Walk to Waikiki beach, Waikiki...
Secluded Corner Condo w/Nature Views, Wrap-Around Lanai, Free WiFi, Shared Pool
Paniolo Hale C1Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Your next escapade to Maunaloa will be unforgettable thanks to this 1,000+ sq. ft., garden/ocean view condo featuring...
Casa De Emdeko | Pool A/C & More!
Summary:A small family will love this recently upgraded Kailua-Kona condominium. Maximum occupancy strictly enforced in accordance with local ordinances.The Space:Welcome to Casa De Emdeko! Built in 1969, this charming and well-loved property is full of character and...
Ocean-view hideaway with pools, hot tub, tennis & grill - beaches await
Maui Kamaole G102Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Luxury and privacy meet at this Kihei Condo, located in the condo resort known as Maui Kamaole®, and just minutes...
Hale Kamaole Condo w/Private Washer/Dryer & Shared Outdoor Pool- Small Dogs OK
Hale Kamaole 106Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Hale Kamaole is a South Maui condominium complex located across the street from Kamaole Beach Park III, one of the...
The Watermark (WM1102) Luxury 11th-floor 2 BDR, balcony, AC, remote work
This luxury 11th-floor two-bedroom apartment with balcony, parking will surely become your sweet home away from home allowing you to conveniently work from Hawaii. You will be in close proximity to Waikiki Beach and Ala Moana Center.Upon arrival, you will step into a...
Island Sands Resort Condo w/ Free WiFi, Ocean View-Near Everything
Island Sands Resort 107Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'The Island Sands Resort on Maui is located oceanfront in Maalaea, just a short four miles to Kihei and a scenic...
Spring Specials! Sweeping Ocean and Golf Course Views!
Highly discounted for the holiday months of December and January! Come rent this lovely condo.This is a wonderfully, updated condo in Waikoloa Village with sweeing ocean views! Don't miss out on staying here and enjoying quiet sunsets on the lanai overlooking the...
Outstanding Oceanfront Views - Mahana 1017
Outstanding ocean front views on North Ka'anapali beach. Located in the Lanai Tower, enjoy heavenly sunsets from your living room AND bedroom. This condo has been totally remodeled and is tastefully decorated with an island style theme. The kitchen has granite counter...
Oceanfront condo with shared pool, hot tub, beach access & private balcony
Kona Bali Kai #351Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'The Big Island is just waiting to make your next vacation one for the books here at Kona Bali Kai #351. Sitting...
Waikomo Streams 203: Luxiuous 1BR Condo w/ Pool
Waikomo Streams Villas 203 is a tropical retreat tucked into lush gardens in the heart of Poʻipū. This one-bedroom, one-bath condo combines comfort, convenience, and island charm with dual lanais, poolside access, and a location just minutes from the South Shore’s...
Ground Floor Garden Studio - Kaanapali Villas B143
Maui Kaanapali Villas #B143 on the ground floor: Convenient ground floor garden view studio condo at the beautiful Maui Kaanapali Villas on Kaanapali Beach. Located in an excellent location in the Banyan Building with no stairs and the ability to walk right out your...
Maui Vista Condo w/ Pool & Tennis Courts - Walk to Beach & Local Restaurants
Maui Vista 2116Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Discover island bliss at Maui Vista! Nestled across the street from the ocean, you can stroll to the soft sand at...
Clean studio at the heart of Waikiki!!
Clean studio at the heart of Waikiki!! Cable and high-speed internet are free! Spacious Lanai!Minutes away from Waikiki Beach. Walking distance to Kalakaua Avenue for shopping and restaurants.The kitchen has been remodeled with granite counter tops and stainless steel...
Kauhale Makai 512: Stunning views of the Pacific Ocean and Mountains
Enjoy a stunning view of the Pacific Ocean and the West Maui Mountains from this two (2) bedroom Condo. This unit has a queen bed in the master bedroom, two twin beds in the second bedroom and a pull-out sofa bed in the living room, allowing this unit to accommodate up...
Kona Bali Kai studio w/pool, spa, & WiFi - steps to Banyan Surf Beach
Kona Bali Kai #234Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'As part of the exclusive Kona Bali Kai Resort, this updated studio features a private balcony. Take a dip in the...
Gardenia Studio, unit # 5
This beautifully renovated studio is located in the heart of Hilo town and is ready to welcome guests who will appreciate its transformed space. It features a bright and well-equipped environment that is both calming and inviting. The studio includes a new queen...
Tropical Maui Garden View Condo in Ocean Front Location just North of Kaanapali
Welcome to Maui Sands #6E. Just steps from the ocean with garden views in Honokowai. This second floor condo is on the corner of the building where you can find a peek-a-boo view of the ocean. There are stairs to the entrance, but no elevators. A window air conditioning...
Ground-floor getaway w/ a furnished patio, shared pools, grills, & shuffleboard
Plantation Hale E7Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This ground-floor home is in the perfect spot for the ultimate Kapa'a vacation. Inside this comfortable condo,...
Charming home w/ wood stove - 10 minutes to Hawaii Volcanoes Nat'l Park
Kahu 'lo - Guardian HawkOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Your next volcano adventure awaits at this Big Island home, beautifully situated on a property filled with...
Two comfy Queen beds at The palms Waikiki - Pool & Lanai
Legally permitted rental - 1850 Ala Moana Blvd #321** For your health and safety, we utilize additional Sterilization procedures between reservations.A super comfortable remodeled unit, this 2x Queen bed Studio suite at The Palms is the perfect place to call home for up...
Ilikai Hotel 909 2-Bedroom Suite in Lovely Waikiki
Scenic 2-Bedroom Ilikai Hotel Suite in the Heart of WaikikiWelcome to the Ilikai Hotel 909 2-Bedroom Suite, a spacious and inviting accommodation in the heart of lovely Waikiki. This well-appointed suite features two good-sized bedrooms with en-suite bathrooms at...
Oceanview -KUL207 - West Maui - Spacious Remodeled Condo in Quiet Oceanfront
** Discounted Rates through Summer 2025!! **Unit #207 is an absolutely stunning vacation rental, adorned with luxurious features that will make any guest's stay unforgettable. As soon as you step foot into the unit, you are greeted by exquisite travertine tile, which is...
36th Floor Deluxe Ocean View Condo with Free Parking & Wifi by Koko Resort Vacation Rentals
Deluxe Ocean View Condo - 36th Floor View, Free parking & Wi-Fi The pool and all associated amenities will be closed starting April 7, 2025,for an estimated duration of 10 to 14 months to accommodate the RecreationDeck renovation project. Enjoy views of the ocean from...
Pono Kai Resort Condo w/Free WiFi, Shared Pool, Shared Grill-Close to Beaches
Pono Kai Resort J101Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Pono Kai Resort is the perfect choice for rest and rejuvenation. Well-known for its family-friendly environment...
Kihei Alii Kai D104 - Private Large 1 bedroom close to the Beach and Restaurants
Book with us and come to Maui to explore everything we have to offer!A fantastic 1 bedroom 1 bath, air conditioned ground floor unit at Kihei Alii Kai, featuring a queen bed in the bedroom. Enjoy the relaxing sunny garden area and relax in the coolness from the Air...
Queen bed plus Sofa bed Balcony Studio & Pool
Pool & BBQ area included!Offering a recent upgrades, this gem Studio suite at The Palms will have you and the family returning year after year.A very comfortable Queen size bed for you and an easy to set up Pullout Sofa bed for 2 additional guests.Fresh white cotton...
Low rise, tropical oasis, corner, spacious lanai and kitchen, AC and pool.
This charming corner townhome is located in the heart of Puamana. It features a spacious kitchen, Berber carpeting, glass block accents, an expansive kitchen garden window, and tropical decor. The home’s corner position allowed for new kitchen designs and additional...
HOL 120 Oceanfront 2BR Cabana Unit Direct Beach Access AC Poolside BBQ
Hale Ono Loa 120 West Maui Oceanfront 2 Bedroom Condo with AC and Pool FREE daily activities included with your stay value up to $570! Complimentary admission, every day of your stay*: Whale Watch (seasonal), Dinner Sunset Sail, Snorkel Sail, Alpaca Farm Tour, Pineapple...
Panoramic Ocean View! Amazing sunsets!
LAST MINUTE DISCOUNTS!! 1200+sf 2BR/2BA luxury vacation resort condo decorated with exceptional style. Steps from the beach on Maui's sunny south shore in Kihei minutes from the Wailea resorts and shops.From our lanai, we have panoramic ocean views spanning from the...
Kona Nates Ocean View Escape
Welcome to my Ocean View Escape! Located in the heart of Kona, you will have an unobstructed view of the West Hawaii sunset every night! From the kitchen you can even see the sunrise over the mountains every morning. Located in Downtown Kona, you can walk to all of the...
Shores at Waikoloa Unit 301: 1 Br condo in the Sandalwood Tower Sleeps 4
This resort features many great amenities for its guests to enjoy. There is a swimming pool and hot tub on the property where you can enjoy the cool water in the Big Island weather. The resort also has a tennis court and fitness center for those days you want to do it...
Peaceful Island Beach Escape on the North Shore of Kauai!
Relax in paradise at Pali Ke Kua, a peaceful retreat nestled in the heart of Princeville on Kauai’s lush North Shore. Enjoy sweeping views of the Hanalei mountains from your private lanai, or take the private, paved path down to the secluded Hideaways Beach—one of the...
Waikiki Penthouse with Incredible Views & Pool (Sleeps 6)
Legally Permitted Vacation Rental,444 Niu St, Penthouse 303,Honolulu, HI 96815Nestled in the Heart of Waikiki this dream condo will have you returning year after year, whether is be for a short rejuvination in the aloha sun or a month long escape from the Winter rains...
Wavecrest Resort C316
Wavecrest C316Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This is a beautiful two-bedroom, one-and-a-half-bath, ocean view condo, located on the third floor of the C complex at...
Cliffs at Princeville #1208B, Ocean-Bluff Resort, Room w/Lanai
The Cliffs Resort at Princeville Unit 1208-B, Private Room on the beautiful North Shore.The Cliffs Resort, Princeville is located on 22 lush acres of tropical gardens perched above the blue Pacific Ocean on Kauai's beautiful North Shore. Accommodates up to 2 guests,...
The "Hula’s Hideaway" just 20ft to the Bar!
Legally permitted rental ✈Waikiki Grand Hotel134 Kapahulu Ave 216⚕⚕For your health and safety⚕⚕ We utilize additional Sterilization procedures between reservations.Located at the Waikiki Grand Hotel & just 20ft from the world famous Hula's Bar & Lei Stand. Enjoy our...
Kaluako'i Resort Cottage 1A Beachfront Rental - Molokai, Hawaii
Experience spectacular sunsets, white sand beaches, and gentle breezes as you put the cares of this crazy world aside. Relax and step back into the tranquility and natural beauty of this island, rich in the history and culture of old Hawaiian moods and customs. It is...
Comfy Studio at World-Famous Ilikai! Full kitchen, free Wi-Fi, and more!
Ilikai #607 – 1777 Ala Moana Blvd.Relax in this 6th-floor City View studio at The Ilikai, the perfect launching point to explore everything that Waikiki and the rest of Oahu have to offer! You'll appreciate the full kitchen, air conditioning, free Wi-Fi, and the...
Napili Bay Steps from Ocean! Nb204 - Sullivan Properties
Napili Bay is without exception one of Maui’s favorite beaches. The crescent-shape beach is located just north of Kaanapali and about 1 mile from world renowned, Kapalua. Napili Bay is known for its golden sand, amazing colorful sunsets, snorkeling and gentle surf....
Kailani #314, Top Floor, Walk to Kapaa Town and Beach
Kauai Kailani #314, Kapaa, Hawaii. Kauai vacation rental conveniently located in Kapaa Town on Kauai’s Royal Coconut Coast. This cute boutique condo is walking distance to shops, restaurants, coffee shops and more! Accommodates up to 4 guests, including children and...
15th Floor - Heart of Waikiki with Balcony Sleeps 4
Legally permitted rental - 444 Kanekapolei St #1507** For your health and safety, we utilize additional Sterilization procedures between reservations.Our studio has a air-conditioning, kitchenette area with fridge, counter-top hotplate for cooking, microwave,...
Aloha Magic Cottage Farm Stay, Rustic Farm Cottage W/ 180° Sunrise & Ocean Views
Hamakua Sunrise Cottages offers a perfect tropical country escape, on Hamakua Coast. Set in natural surroundings Aloha Cottage sleeps 2 w/ ensuite bathroom & kitchen provides comfort & relaxation. Expansive ocean Views with Sunrise, local waterfall adventures & picking...
Ocean & Diamondhead View 1 bedroom at the Waikiki Sunset
Welcome and Aloha!This 20th floor unit of the Waikiki Sunset is fully furnished with one king size bed in the bedroom, one queen size sofa bed in the living room, and kitchen counter with four dining chairs.The full size kitchen has everything you’ll need to feel right...
Best Deal Luxury Resort in Town Sleep 4 romantic, fun and relaxed
Note: if the requested dates are not available, I also have three other rooms on the property, VRBO #579874, #666626, and #595354, vrbo#460973, #492665.The Kauai Beach Resort - a gorgeous boutique is located along three miles of secluded beach in Lihue, Hawaii. Lihue...
Great Ocean View 1 Bedroom, Full Kitchen,
** Waikiki Banyan pool deck closure. Starting April 1st and lasting about 10 months, the pool deck including swimming pool, hot tub and other pool deck amenities will be closed for a major remodel. Our nightly rates have been adjusted to reflect this closure ** One...
Sunny oceanfront condo with hot tub, pool, balcony & washer/dryer
Kona Bali Kai #319Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Feel at home even while you're visiting the island with this bright condo! Step out onto the balcony and take in the...