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.
EL K102 Spacious Kaanapali Condo Relax Recharge Pool AC
Eldorado K102 1bedroom/2bath Relax, Restore and Unwind. Enjoy Resort Life at its Best! Eldorado K102 is a spacious, air-conditioned one bedroom that sleeps 6 people. The bedroom has 2 queen size beds while the living room features a sleeper sofa and two full bathrooms....
Kihei, Maui Ground Floor Tropical Getaway - Across street from beach
Ground floor condo in the heart of South Kihei on the beautiful island of Maui. We welcome you to stay at our cute, clean, well-cared for condo during your visit to the Valley Isle. Directly across the street from Kamaole Beach Park II, a beautiful golden sand beach...
Following Oahu laws a 30 minimum lease required for any rental. Please inquire about it.Right on renowned Kailua beach, our beachfront villa equipped with a pool and jacuzzi is perfect for all your vacation needs. Wake up and go watch the sunrise or a morning jog. The...
Beachside Kihei Vacation Rental w/ Stunning Views!
Book this airy corner vacation rental condo for an incredible stay in Kihei, Maui!! Nestled in Leina’ala Condominiums, this unit offers access to a shared pool and tennis courts, and is just a short stroll to the beach. Not to mention, the beach is in your front yard...
Spacious and Peaceful Corner Unit at Fairway Villas
Experience the best of island living in this spacious and modern corner villa overlooking the lush fairways and majestic mountain backdrop. With no units above or below, this private multi-level retreat offers peace, comfort, and the perfect blend of convenience and...
Maui Banyan P304 - Remodeled, Partial Ocean View, AC, Across from Kamaole Beach!
You will LOVE this 1BR/1BA Luxurious, ceiling to floor totally remodeled single level floor plan. While you dine on your balcony, enjoy the partial ocean and mountain view. This condo is located on the cooler side of the building. The Maui Banyan is a Premier Property...
2-story, spacious layout steps from pool, near beach.
Welcome to Hale 'Olu'Olu, a stunning 2-level condo nestled in the renowned Waikoloa Beach Resort, an idyllic retreat. This home has a breathtaking views of the golf course and majestic mountains, with easy access to sandy beaches, shopping, restaurants, and world-class...
4 bedroom, 2.5 bath, Sleeps 9 in beds
DUE TO BILL 41 we are only allowed to rent one time in a 30 day period so our minimum bookings will be 30 days or longer. We have been waiting to remodel this home, but first the pandemic made it difficult with not being able to travel, and now the 90 day rule, so not...
Idyllic island gem with pool, beach access, high-speed WiFi & central AC
Ilikai Hotel 838Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Get away from the mundane and let all of life's worries slip away here on the beautiful island of Honolulu. Whether...
KBM Resorts | FREE CAR | Honua Kai Konea | Ocean view | 2-Bedroom Condo with Large Villa! HKK-245
** 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...
Amazing oceanfront condo with hot tub, pool, W/D, & grill - gorgeous ocean view
Kona Reef Oceanfront Condo, D6Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Sail away to this ideally located, oceanfront Hawaiian condo! Here, you'll be just a few steps away from...
Your Kihei Kai Nani Home! Comfortable and Quiet
Enjoy South Kihei on Maui! The Kamaole beaches are pristine; the air is beautiful, and Maui will benefit from your visit.We are proud of our carefully maintained Kihei Kai Nani condo. Consider: air conditioning, new drapes, walk-in shower, firm and comfortable king-size...
Hale Tatahi, comfortable home in charming Hanalei!
Perfect for a romantic getaway or a family vacation, this comfortable, rustic home is surrounded by tropical foliage in charming Hanalei. Beautiful vaulted ceilings in the living area. 2 bedroom home with 2 bathrooms. The fully equipped kitchen will make meal...
Ocean View Condo with Pool, Extra Large Lanai, New Kitchen & Bathroom.
This Beautiful 1 bed condo has a Sunset Ocean View and is perfectly located in the heart of Kona! The kitchen is brand new, and the bathroom has a new walk in shower. You will love the short walking distance to all that Kona has to offer. Walk across the street to...
Spacious Condo, one minute walk from Kahaluu Beach Park
Enjoy the perfect balance of privacy and convenience at this cozy 2-bedroom, 2-bath condo, just a short walk from Kahalu’u Beach Park, one of Kona’s most popular snorkeling spots! With a full kitchen, private lanai, and all the comforts of home, this peaceful retreat is...
South Kona House with Spectacular Ocean View
Exceptional vacation house with ocean view. 33 miles south of Kailua-Kona on the Big Island of Hawaii. Located near the village of Milolii. From here, travel to Volcano National Park, beaches, ancient ruins, Kona plantations, and Kailua-Kona.In the evening, watch the...
Nice, Big House near Kehena/ Pohoiki Black Sand Beaches and Lava Fields.
Aloha! The 'Nice, Big House is a private 3 bedroom /1.5 bath fully furnished town house w/ 4 beds (3 beds downstairs and 1 on the 3rd floor) which is part of a larger building with two private studios attached. This 'unique' design allows us to rent it for less and...
Modern Home on Golf Course, Walk to Tennis, Golf, Shopping and Restaurants
***DISCLOSURE 8/11/25: The home has been listed for sale and guests may be required to accommodate viewings with 48 hours notice.This beautifully appointed four-bedroom home is tucked off a sleepy street in the resort community of Princeville. Featuring expansive...
Remodeled 1bd with great ocean views
Kaleialoha 415 does not have A/C, is a 1-bedroom, 1-bathroom corner condo located on the 4th floor. This condo offers unobstructed ocean views, a private washer/dryer, and more! There is an elevator for your convenience. Unit 415 can accommodate up to 4 guests. The...
Oceanfront TownHome Upgraded 2 BR, 2.5BA Fully Air Conditioned
**Due to a component malfunction, 104C's AC system is down across the property until March 2026, when a new condo-wide system will be installed.**Poipu Shores 104C is a fully-oceanfront, 2-story, 2-bedroom townhome with two lanais and complete air conditioning. A fully...
D306 is a beautiful 2 bedroom, 2 bathroom apartment with a king bed in master, two twin beds in guest room & a sofa bed in living room. D306 has pergo floor downstairs with a carpeted stairway and master bedroom in the loft. There are ceiling fans in each room. Table...
Beachfront Oasis: Kihei Beach #303, Your Retreat with Breathtaking Ocean Views!
Kihei Beach #303 – Remodeled One-Bedroom Beachfront CondoWelcome to Kihei Beach #303, a beautifully remodeled one-bedroom, one-bathroom beachfront condo offering comfort, charm, and sweeping ocean views. Located in a six-story beachfront property in North Kihei, this...
Beach Gear Incl. Just add Sun & Fun. A/C -Pool & BBQ -Free parking 🏖
It's where Beach days, Sunset swims, and Poolside BBQs are part of the daily plan.• Air Conditioning and Ceiling Fans• Walk to Charlie Young Beach• New Cleaning Crew on Deck• Your Prime Kihei Location• Private Pool, BBQ Area • Free Assigned Parking• Walk to Beach Parks...
Ocean-View Maui Penthouse w/ Balcony & Pool Access
Treat yourself to a slice of Hawaiian paradise when you book this 2-bedroom, 2-bath Lahaina condo! Along with a private balcony, ocean views inside and out, and a full kitchen, this penthouse provides access to Kahana Villa community amenities. Walk 2 minutes to Pohaku...
Newly Upgraded 1BR Unit Near Beach Max 5 Guests
Come stay in this beautifully decorated 1 BR & enjoy paradise only steps from the beach! Enjoy the Sunsets from the Lanai and relax to the Hawaiian trade winds. This 1 BR is perfect for you and your family to visit Kona. Stay across the street from the sandy beach and...
Includes Beach Gear! Vista Waikoloa D302
This vacation rental is professionally managed by ResorticaHawaii Vista Waikoloa D302Please scroll down for detailed informationBedroom Configuration:Master Bedroom: King Bed with ensuite bathroomGuest Bedroom: Queen Bed with ensuite bathroomLiving Room: Twin Fold Out...
Nice 2BR@Beach Sleeps 4+ Hear Waves! Value Comfort-Best Location! See new deals
SALE! Save $50 off per night March and April 1st to end of month. 2026. Now $239 a night. NO hidden fees or nightly hotel resort charges! Free Parking.Aloha! Welcome to Kauai's central location to beach, shopping, and fun!Simply: I invite you to spend your beach...
Top Floor, Favorite Location, Ocean Views! Palms at Wailea 2104
#2104 is a spacious and recently refreshed 2-bedroom, 2-bathroom condo in Maui with fun tropical accents and cozy comfort. It offers approximately 1500 sq. ft. of living area, including a large lanai. This unit features central air conditioning for your comfort. The...
Maui Sunset A-322 | Relax in Paradise
You’ll be near both the beach and Waipuilani Park when you book your vacation at Maui Sunset A-322. Grab your beach towel and walk right down to the beautiful sand and surf. Your Maui Sunset community also offers a large pool, hot tub, tennis courts, shuffleboard, and a...
Molokai Shores Oceanfront Condo
Aloha Molokai! It will be Humpback Whale season in the Kaholi channel of Molokai, Hawaii, December - April, an epic event to watch these giants with their babies so close up. If you are looking for the true ALOHA spirit, this charming condo offers you just that for your...
Ocean View, Ground-Floor Condo w/ Lanai & Shared Hot Tub/Pool - Walk to Beach
Ke Nani Kai 121Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'One of the loveliest condos on the property, Ke Nani Kai 121 is a ground-floor escape where you can step out onto the...
Oceanview*fully Renovated*refined Elegance 2B/2B
*Ongoing Roofing Project Fall of 2025. There could be periods of intermittent noise during the hours of 8:30am - 4:30pmExperience the perfect blend of comfort, style, and island charm in this beautifully furnished condo featuring a breezy “beachy” vibe and an open,...
❤️PiH❤️ "Once Upon a Tide" ★OceanViews★ Hilton Passes Included
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to Once Upon a Tide at KaMilo, a part of our Hawaiian Luxury Collection. Once Upon a Tide at KaMilo is a wonderful 4 bedroom home.Once Upon a Tide at KaMilo provides a perfect setting for your Hawaii getaway and...
Bright Island-Style Suite w/WiFi, Modern Kitchen, AC, Lanai–Kamaole Sands 9208
It’s the sweet life in this air-conditioned 884sf retreat with island artwork and accents. The full kitchen with stainless steel appliances lets you dine your way on the private lanai with palm tree backdrop. Enjoy WiFi, flat screens, washer/dryer and ceiling fans....
Kaha Lani 213, Beautiful Oceanfront Corner condo... wonderful sunrise views
Kaha Lani #213 is a beautiful oceanfront 2 story (2nd and 3rd floor) 2-bedroom corner condo in a quiet area surrounded by Wailua Golf Course and Lydgate Park. The condo is light and airy and decorated with Hawaiian furnishings. Upon entering you are greeted with a...
Nihilani Family Condo 3A, Townhome Style 2-car Garage, Bonus Den
Three bedrooms plus den, 2 King beds and 2 twin beds, plus sofa sleeper, 2.5 bathrooms, 2 story town home, washer and dryer in unit, multiple lanai spaces, attached two car garage, great complex amenities.This spacious 3 bedroom, 3 bath town home is a perfect place to...
Awesome one of the very best!!!! Unbeatable quiet location and great ocean view
This private 3 brm 2-1/2 bath Na Hale O Keauhou Townhome is located in a gated luxurious resort complex with breathtaking views of the ocean, beach or mountains. Within walking distance to shopping, activities, restaurants, theater and beaches, including the famed...
Lucky you! Great value, fantastic location! Immaculate Studio steps to the beach
Stay in the best location, just steps to the beach, across the street from the Hyatt, but at a fraction of the cost! In addition, you have your own full kitchen to prepare meals in, and a quiet lanai to dine on, thus adding to your cost savings. This modern cozy studio...
"Bliss on the Bay: Serene 2nd Floor Views Perfect for Whale Watching and Ocean Adventures!"
Bliss on the Bay at the Wailua Bay View- Oceanfront One Bedroom One Bath with AC in the BedroomOcean front views from this Wailua Bay condo. Your gaze will get lost on the horizon of the Pacific Ocean and swaying coconut trees. Comfy Oceanfront Hawaiian Style living is...
Hale Kamaole 236 Second floor condo, easy access to best beach on Maui!
Begin your day with the golden sunlight of the Valley Isle emerging over Haleakala and bringing the multicolored hues of Maui to life. Whether you’re in Hawaii for an action-packed island vacation or a relaxing retreat to the Paradise in the Pacific, Hale Kamaole and...
A premier offering, Villa 6C boasts one of the most sought-after locations at the entire Luana Garden Villas. With its west-facing orientation and its open view between the Hokulani and Konea Towers, Villa 6C is among the few Luana Villas to offer glimpses of the...
Direct oceanfront views, remodeled condo
Papakea L107 is a charming ground-floor 1-bedroom, 1-bathroom condo that can accommodate up to 4 guests with a split air conditioning system to keep you cool and comfortable. Upon entering this open-concept space, you'll be greeted by a serene ambiance that invites you...
🏖️Oceanfront Complex | No Stairs | AC | WIFI | vrKCV
vrKCV - Casa de Emdeko 225, Professionally Managed by Kona Coast VacationsWelcome to your tropical retreat at Casa De Emdeko #225 in Kona, Hawaii!This charming 1-bedroom, 1-bath condo offers the perfect blend of comfort and convenience, distinguishing itself as one of...
Jungle Estate - 3 Cottages, 1.5 Acres and a POOL Sleeps 9
If you are dreaming of your own private tropical getaway for up to nine guests in the verdant landscapes on the east side of Hawaii Island, you've come to the right place! Jungle Estate offers three cottages spread over a 1.5 acre parcel in Hawaiian Paradise Park, just...
Pineapple Loft - Downtown Hilo wAC
Let this inviting, Newly renovated space be your home away from home as you enjoy your stay in Hawaii! For your comfort we have AC units in the Bedrooms and Ceiling Fans in the living room and kitchen which provide a great Breeze. The location is amazing! Tucked away...
Cold Plunge and Sauna at this Modern Home with Amazing Golf Course Views!
Absolutely the best location on Kauai with stunning views of the lush mountains of Namolokama. Close proximity to Princeville Shopping Center, with shopping and eateries, Princeville Park and Library, and the Makai Golf Course. Minutes from "Hideaways Beach", Kenomene...
OCEAN VIEW - Sleeps 6 -Single Level - Family Room -No Stairs-Steps to Beach!
Needs lots of space? Want Ocean Views? Then check out this spacious (almost 1300 sq feet) 2 bedroom/ 2 bath PLUS Family Room with Queen Murphy bed! (becomes a 3rd bedroom with privacy divider) Sleeps 6 adults comfortably.Located on the 3rd floor of the prestigious...
View: Partial Ocean, Mountain, City, Canal, and Rainbow Maximum Number of Guests: 4 Minimum Length of Stay: 2 Nights Parking: No (There is condominium parking, but guests must check the availability and pay the condo directly. There is also public parking nearby.) Room...
❤️PiH❤️ CORAL REEF ★ BIG Mauna Lani Golf Discounts ★ Heated Private Pool & Spa ★
Brought to you by Paradise in Hawaii Luxury HomesWelcome to the newest home in our Hawaiian Luxury Collection. Coral Reef Villa at KaMilo is a wonderful large single-level 4 bedroom home that includes three bedrooms, each with a large master bath/ensuite in the main...
Hale Hui Kai 109 along Keawakapu Beach-Two Bedroom Two Bathroom condo with AC
Located along South Maui's gem, Keawakapu Beach, this North facing ground floor/garden view condo is only 30 steps to beach with easy access to condo common areas. This private garden condo is on the first floor of the south side of the building ...about 60 steps along...