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.
HILO HAVEN-4Bd2Ba Entire House w A/C, BBQ, Firepit
Relax with family & friends in this comfy 4BR/2BA Hilo retreat. Enjoy island breezes with fans in every room + portable AC units, cook in the full kitchen or BBQ outdoors, gather by the firepit, and rest easy with modern comforts. Just minutes to downtown and Hilo Bay,...
Spacious Family Suite, Stunning Mountain View-1 Bd. Marriott's Ko Olina Beach
Cozy yet spacious. Intimate yet extensive. This one-bedroom features luxurious comfort for memories together and space to escape.Mountain View One Bedroom Villa, 1 King, Sofa bed, Full kitchen, Microwave, 920sqft/83sqm, Living/sitting area, Dining area, Separate...
Villa 15 at The Lodge at Kukui'ula on Kaua'i
Villa 15 at The Lodge at Kukui'ula on Kaua'i is an exquisite, luxury retreat that combines the best of tropical living with world-class amenities. Located within the prestigious Kukui'ula resort on Kaua'i's south shore, this stunning villa provides an unparalleled...
Kaanapali Alii Unit 162
Welcome to Kaanapali Alii Unit 162, a luxury vacation rental that promises an unforgettable stay. This stunning condominium features hardwood flooring, luxurious decor, and a breathtaking view of the Pacific Ocean. Whether you're watching the sun set over the sparkling...
Villa Bianca: Oceanfront Elegance w/ BBQ, Lanai, Stunning Ocean & Sunset Views
Welcome to Villa Bianca by Gather, a four-bedroom, four-bathroom hideaway set just half a mile from Waimea Bay on Oahu’s famed North Shore. With panoramic ocean views, dual-level living spaces, and an unbeatable location near Haleiwa’s shops and dining, this elegant...
Kapalua Bay Villas | 3 FREE Rental Cars | KBM Resorts | Whale Watching | 3 Units, 5 Bedrooms | KBV ML-2071
** 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...
Honeymoon Bliss: Bamboo Temple with Ocean Views at Maui Eco Retreat
**Bamboo Temple – Secluded Honeymoon Cottage with Stunning Ocean Views**Discover the perfect romantic escape at Bamboo Temple, an idyllic private cottage for honeymooners and couples seeking serenity. Wake up to breathtaking sunrises over the Pacific Ocean and fall...
Modernized 1st-floor Kihei condo with A/C
Welcome to Kihei Kai Condo #20, a delightful lower-level unit offering pool and garden views. This attractively decorated and meticulously maintained condo is the perfect haven for your Maui vacation, combining comfort and convenience in a serene setting. Step inside to...
Has It All! Kitchenette, Dine/Living Areas, AC, WiFi – Waikīkī Grand #722
Castle at Waikīkī Grand #722 - Layout and furnishings create a separate kitchen, living area, and sleeping area in this 384sf retreat with floor-to-ceiling windows. Tile floors and air conditioning keep it cool after a day of sundrenched fun. Other touches include a...
Pili Mai 8K - Spacious Comfort with Ocean & Golf Views in Poipu
PILI MAI 8K AT KOLOA KAI VACATION RENTALSSpacious Comfort with Ocean & Golf Views in PoipuExperience elevated island living at Pili Mai 8K, a beautifully appointed three-bedroom, three-bathroom condo located on the second floor of Kauai’s premier Poipu resort...
Coastal Haven: Chic Studio with Parking in Waikiki
This is the perfect Waikiki Getaway for someone wanting to stay for a a month or more. Well equipped, it comes with an in-unit washer dryer and parking! Perfect for the digital nomad, or someone who just wants to come hangout in Hawaii for a while.Come Stay with...
Palms at Wailea Garden Villas 2 Bedroom 2 Bath
Garden View 2 Bedroom 2 Bath Villa- Kitchen includes stovetop, oven, microwave, refrigerator, dishwasher, coffeemaker, toaster, cookware and tableware- Spacious private deck- Master bedroom with 1 king or 1 queen- Guest bedroom with 1 queen or 2 twins- Queen sofa bed-...
Rare Find! Two Comfy Units, Close to Attractions
He mau makana nâu kêia na kô mâkou kûpuna — These are gifts for you from our elders. Hawaii Volcanoes National Park is a refuge for native flora and fauna, many of which are endemic to the Hawaiian Islands. Enjoy walking or biking around the park, spend a day...
Bright New 1 bd at Kamaole Sands I 5-208
*This unit was recently remodeled. Professional photo's and additonal artwork/decor to be completed in January.Welcome to your perfect getaway in South Kihei! This beautiful one bedroom condo blends modern comforts with a warm, inviting atmosphere. Perfectly situated in...
Garden Views W/A/C, Lanai, Laundry–Kamaole Sands
Kamaole Sands unit #6201: Socialize while prepping meals in the modern kitchen opening to the living area. Then dine on the furnished lanai of this 818sf air-conditioned suite with homey perks. Enjoy cool tile floors, ceiling fans, AC, washer/dryer, WiFi, flat screens...
Montage Kapalua Bay | 2 Free Rental Cars | KBM Resorts | Beautiful Villa At Montage Kapalua Bay | 2 Units, 6 Bedrooms | MON ML-1231
** 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...
Beachfront Condo with Park & Ocean Views
Stay steps from Honokowai Beach Park in our family-friendly oceanfront condo! Enjoy a private balcony with sweeping ocean and park views, a full kitchen, and comfortable living space perfect for relaxing after island adventures. Snorkeling, tide pools, playgrounds, and...
Oceanview Paradise: Tropical Retreat in Wailea
Welcome to our beautiful, elegantly remodeled 2-bedroom, 2-bathroom condo in the prestigious Wailea Grand Champions Villas. Perched on the 2nd floor, this luxurious condo offers breathtaking ocean views and a spacious, open floor plan with tasteful modern finishes.Upon...
Lanikai Hillside Estate – Panoramic Luxury Above the Sea
Perched above the crystalline waters of Lanikai Beach, Lanikai Hillside Estate by Gather is a newly designed 7-bedroom, 6.5-bath luxury retreat with 6,295 sq ft of interior living plus expansive lanai spaces. Floor-to-ceiling glass, an infinity-edge pool, and panoramic...
Keauhou Palena#602 Ground Floor Unit, No Stairs, On Golf Course!
Enjoy quiet, resort-style living in this beautifully renovated Keauhou Palena condo. Located along the sixteenth hole of the Kona Country Club and just steps from the community pool, this unit will make you feel like you're on a constant staycation. Beautiful features...
PHENOMENAL VIEW OCEANFRONT A/C Kahana beach n1 bedroom, 2 Lanais, Hear the Waves
SPECTACULAR OCEANFRONT A/C Kahana bch. Near everything! Experience the beauty of Maui at the Kahana Beach. 7 night minimum stay. corner condo, newly renovated with 2 Lanais oceanfront and relax in the comfort of your A/C 1 bedroom 2 full baths & full Kitchen. This...
Cool 2-bedroom apartment with AC and POOL in Kailua-Kona
Welcome to Palani Breeze, a charming 2-bedroom, 1-bath condo perfectly located in the heart of Kailua-Kona. This inviting retreat offers comfort, convenience, and a true island feel, making it the ideal home base for your Big Island adventure.Inside, you’ll find a...
Luxe Westin Kaanapali Ocean Resort,Sleep 4, full resort access. STEEP DISCOUNT !
The Westin Kā‘anapali Ocean Resort Villas is a luxurious vacation on one of the most pristine beaches in the world, offering a multitude of ocean water sports such as snorkeling, kayaking, surfing, and scuba. Set on 26 lush acres, the resort is also near the historic...
Ke Alaula Estate: Hualalai Luxury with Lanai, Heated Pool & Golf Views
Welcome to 4BD Ke Alaula Estate, an exceptional 4-bedroom, 4.5-bath private residence set within the world-renowned Hualalai Resort. Spanning 3,725 sq ft of luxurious indoor–outdoor living, this meticulously designed home offers panoramic ocean and golf course views,...
Palms at Wailea Garden Deluxe Villas 2 BD 2 BA
Garden View Deluxe 2 Bedroom 2 Bath Villa- Kitchen includes stovetop, oven, microwave, refrigerator, dishwasher, coffeemaker, toaster, cookware and tableware- Spacious private deck- Master bedroom with 1 king bed- Guest bedroom with 1 queen bed or 2 twin beds- Queen...
Regency Waikiki Partial Ocean View 1 Bedroom
A charming one-bedroom retreat offers the comforts of home and is just a short stroll from Waikiki Beach. Ideal for up to four guests, it features a queen bed in the bedroom and a cozy sofa bed in the living room.Partial Ocean View 1 Bedroom 1 Bathroom• Kitchen...
The Point at Poipu Kauai, Hawaii-HGVC Resort & Spa
You won't want to leave this charming, one-of-a-kind place. Flowing waterfalls, a crystal clear Koi pond, and hundreds of tropical plants make The Point at Poipu appear the stuff of the dreams. Nestled in over twenty acres of lush tropical gardens overlooking the...
Island relaxation in this 1bdrm suite in Kauai, HI
About this spaceRelax is our beautiful 1 bedroom suite.Resort overlooks Anini Bay, a South Pacific paradise on Kauai’s north shore. Enjoy all the resort amenities and nearby golf, or roam the whole island for breathtaking adventure. Whatever your style, there’s...
Honua Kai | 4 Free Rental Cars | KBM Resorts | Ocean Front | 4 Units, 10 Bedrooms | HK ML-1105
** 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 Maui Eldorado Partial Ocean 2 Bedroom
Wake up to gentle ocean views and swaying palms in this two-bedroom condo overlooking Kaanapali golf course. Located near the beach, it features a full kitchen, spacious layout, and a private lanai to enjoy Maui’s coastal charm. Partial Ocean View 2 Bedroom 2 Bath•...
Sunset Villa - Resort Amenities - Short Walk to Koolina Beaches - Sleeps 8 - 30 Day Rental
**Monthly Rental**Welcome to Sunset Villa at Coconut Plantation! Located in a resort community on the West side of Oahu. The unit is composed of 4 bedrooms, 3 bathrooms, with an open-concept design, spacious upstairs and downstairs patios, two-car enclosed garage, with...
2BR+Loft Huge Patio Quiet & Spacious with Free Parking
Enjoy this spacious, high-ceiling 2BR plus loft with a rarely available large open-air balcony. Save $40 a night with one secured free parking in the building plus free wifi. Walk to the best restaurants, Chinatown, and visit the historic Iolani Palace. The building has...
20th-floor corner condo with lanai, prime location, pool & hot tub
Island Colony 2020 Thirty plus night rentalOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Spend a spectacular season in the heart of Honolulu at this newly renovated condo on the...
Sky Ala Moana Luxury Condo Offering MT Views and Top Amenities
This property requires a minimum 30-day rental. Book with confidence—professionally managed by Ali'i Beach Rentals, an award-winning property management company.The Sky Ala Moana is the newest addition to Honolulu’s luxury skyline. Consisting of two towers—The...
Honua Kai | 3 Free Rental Cars | KBM Resorts | Gorgeous Inner Courtyard | 3 Units, 6 Bedrooms | HK ML-1115
** 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 Alii | 294
Welcome to Kaanapali Alii 294, your perfect luxury vacation rental in Maui! Nestled in the heart of Lahaina, this one-bedroom mountain view condo offers a spacious and luxurious retreat for your dream getaway. Ideal for couples or small families, this 1513 sq. ft. condo...
Royal Kahana Maui 1205 Ocean View Studio
- 12th 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 twin sofabed- Ceiling fan- Cable TV-...
Golf Villa 1102–Prime Location & Ocean Views | Onsite Staff & Daily Housekeeping
This spacious prime ocean-view villa enjoys the premier Golf Villas location. Situated in the heart of the resort community, this single level ground floor 3-bedroom, 3.5 bath ground floor Golf Villa features unobstructed ocean, golf course, and sunset views with quick...
Oceanview Premium Studio Villa
Rewarding days discovering Maui's boundless beauty and activity begin and end here. While you can enjoy whale watching, snorkeling, sailing, windsurfing and scuba diving just steps away, there are plenty of activities at our Maui beachfront resort near Lahaina that will...
Experience Paradise at Hilton's Ka’anapali Beach – 1 Bedroom Deluxe Ccean View
Welcome to Hilton Vacation Club Ka'anapali Beach, where endless family fun and breathtaking views of the Pacific await. Nestled on the golden shores of Ka'anapali Beach in Maui, this resort combines the natural beauty of Hawaii with the luxury and comfort you’d expect...
Brand New Remodeled Beachfront Ground Floor Stunning Studio! Steps to the sand!
Come enjoy the beautiful island of Maui and stay in this private, modern, and comfortable unit. Kahana Beach is steps away where you can soak up some sun and swim in the warm crystal clear ocean. Condo details:~ Tastefully renovated throughout with attention to detail~...
Wailea Ekahi 6E-Gorgeous Condo, #1 Location, Serene/Private, steps to Pool/Beach
***Please note: This unit is under NEW ownership. The previous owner had a 10/10 rating with 67 reviews!LOCATION, LOCATION, LOCATION is everything at Ekahi Village! Ekahi Village is a premiere condo complex in beautiful Wailea, Maui. Unit 6E is perfectly situated within...
Colony Surf unit 1503 1504
This stunning, newly renovated beachfront condo offers breathtaking views of the ocean, Diamond Head, and Sandy Beach. Enjoy the ultimate coastal lifestyle in this spacious one-bedroom, two-bath unit.Key Features:Direct Oceanfront: Enjoy panoramic ocean views from every...
The Avocado Cottage
Your own private guest cottage on a 3 acre working avocado farm out of the heat and activity of Kona. We are at around 1,200 elevation but still only 12 minutes from all major grocery stores and restaurants.
3 Bedroom Luxury Home w/Private Pool
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 and...
Hilton Hawaiian Village Lagoon Tower Ocean Front PH, 3 Bedrooms, 2.5 B, sleeps 8
Plenty of space for everyone to relax and enjoy! Beautiful views, steps from the beach, activities galore. Master suite has a king bed, full bath with bidet. Middle bedroom has 2 twin beds and third bedroom has a king bed. Second full bath between the two rooms. Living...
Makaha Mountain Hideaway
The spacePlenty of drawers and cabinets for ample storage for all your travel items. Walk-in closet with storage. I have provided all the basic necessities to start your vacation comfortably upon arrival.Guest accessThe entire property inside and out are available to...
NEW!! Charming 1 bedroom bungalow in amazing Kailua-Kona
NEW! NEW! NEW!Welcome to our dream home! After years of anticipation, we have finally made it into this hidden gem complex in Kona. In September 2024, we completed a full remodel, bringing our vision to life. We have installed A/C. The kitchen has been completely...
Kapalua Golf Villas | 2 Free Rental Cars | KBM Resorts | Large Bedrooms | 2 Units, 2 Bedrooms | KGV ML-2108
** 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...
NEW KBM Resorts | FREE CAR | Maui Kaanapali Villas | Renovated 2 BD Near Beach Central A/C! MKV-A606
** 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...