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.
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...
🏖️Newly Renovated | Gorgeous area and condo | Concierge Included | vrKCV
vrKCV - The Shores at Waikoloa 231, Professionally Managed by Kona Coast VacationsAloha and welcome to Shores at Waikoloa Beach Resort Unit 231! This beautifully updated 1-bedroom, 1-bathroom condo offers a relaxing getaway in the heart of Waikoloa Beach Resort. Enjoy...
West Side Westy - 1985 VW Westfalia
This 1985 VW Westfalia has everything you need to explore the island your way. This classic bus seats & sleeps up to 4 adults in its 2 fold out beds. It also includes a kitchenette with sink, cooler, and two burner stove. There are direct hookups for electricity &...
North shore Maui B and B room 1.
Holomakai B and B is a vacation rental with three bedrooms for rent individually on Maui’s north shore. Each room is on a separate floor with a private bathroom, ac, tv and Wi-Fi. The rest of the house, the entrance, fully equipped kitchen, living room and spacious...
Luxury beachfront villa on a world class beach in Kailua, HI
As you enter the electric remote gate into this luxurious villa you will feel this sense of peace and calmness come over you.This luxurious Kailua Villa is located on the ocean which is hidden in the best part of Kailua. Wake up every day to the most amazing sunrises...
Ocean view studio with WiFi, balcony, onsite pool/spa/bar/grills, & beach access
Islander on the Beach 367Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Indulge in a tropical retreat at the Islander on the Beach! This beachfront complex hosts a bevy of onsite...
4 bed/4 bath Entire custom-built house 5 mins from Volcanoes National Park
Enjoy peaceful Big Island Hawaii in a Contemporary Hawaiian Craftsman Cottage style home set in a Tropical Rainforest directly outside Hawai’i Volcanoes National Park. The custom designed & built home features artisan beds with fine linens, private baths, cozy...
Kona Hillside Estate - Gated Property with Lap Pool
Welcome to our family's private gated estate located on the beautiful hillside of Hualalai mountain in Kailua-Kona. We recently renovated our 4,000 SF home and enjoy hosting guests when we have availability since 2022.Guests will appreciate soaring ceilings, open living...
Two-bedroom corner condo with spectacular views of Hanalei Bay & AC
Hanalei Bay Resort 4205 sixOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Hanalei Bay Resort 4205/6 is an air-conditioned condo, featuring two bedrooms, two bathrooms, kitchen,...
Palms at Wailea 1904! Nicely Updated and Great Wailea Location!
Welcome to Palms at Wailea 1904, a beautifully updated 2-bedroom, 2-bath vacation rental in the heart of Wailea. Perfect for families or couples traveling together, this spacious condo blends modern upgrades with relaxed island charm. Perched above the golden sands of...
Maui Kamaole G211, Picturesque Ocean Views!
Maui Kamaole G211, picturesque ocean views! This 2bed/2bath condo offers the perfect getaway for families or couples traveling together. Take in the relaxing views from your private lanai. Enjoy your morning coffee or dine al fresco with seating for four! With floor to...
Oceanfront condo in Poipu with balcony, W/D & partial AC - 10 steps to the beach
Kuhio Shores 410Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'E komo mai! Do you want on the water? This is it! You cannot get closer to the breaking surf than Kuhio Shores 410!...
Top-floor condo with amazing ocean/Bali Hai view, lanai, AC, 2 pools & tennis
Hanalei Bay Resort 8233Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Admire unobstructed views of the Pacific Ocean, the mountains, and iconic Bali Hai from Hanalei Bay Resort...
Tropical designer retreat right on the water with ocean view, pool & AC
Puu Poa 101Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Spend your vacation enjoying the salty sea air and ocean views from the spacious lanai and nearly every room inside this...
Top floor condo & loft with partial AC, W/D, outdoor pool, hot tub & grills
Hanalei Bay Resort 8233 fourOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Hanalei Bay Resort 8233/4 is located in the Plumeria Building with air-conditioning in the bedrooms....
Resort getaway with views of Hanalei Bay, pools & tennis
Hanalei Bay Resort 4204/5Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Hanalei Bay Resort 4204/5 is an air-conditioned condo, featuring two bedrooms, two bathrooms, kitchen, living...
Steps to the Beach! Ocean Front Condo! 5 Star Views! Centrally Located!
Steps To The Beach! Ocean Front Condo! 5 Star Views! Centrally Located!Aloha-We bet that because you’re reading this you’ve looked at the descriptions of many vacation rentals on Kauai. Likely all of them gave glowing descriptions of how wonderful they are – and no...
Lovely 2 bed 2 bath Maui Kamaole 2 story condo w views, tennis, pools, hot tubs
Stay in the heart of South Maui at tranquil, low-density Maui Kamaole in southern Kihei. This quiet, second-floor, two-level 2-bedroom, 2-bath condo comfortably sleeps six with two king bedrooms and a queen sofa sleeper in the living room. Enjoy three-zone split A/C in...
New! Kona Reef Resort Oceanfront 🌊 2 Bdrm, 2 Bath D-11 🏖 Right on the Ocean!
Wonderful Ocean Views Throughout your Spectacular 2 Bedroom, 2 Bath Condo! When you are dreaming about your much deserved Hawaii Oceanfront Getaway, this condo will exceed your expectations!Your ocean view lanai (balcony) is ready for you to dine, read, rest and enjoy...
Hale Kamaole 112 Romantic Beach Retreat/ King Bed/ A+ Internet
Hale Kamaole: Romantic Bright & Airy Beach Condo ACROSS THE STREET from Kamaole III Beach in South Kihei! Tasteful heritage decor, fast internet, King bed, walk-in shower, 1st floor unit. Perfect for couple's getaway, anniversaries, brides & honeymooners. Spacious lawns...
Hale Awa'puhi 1-C Oceanfront Luxury 2 BR w/ AC and Private Beach Access
Welcome to Hale Awa'puhi 1-C, an oceanfront gem among one of the most luxurious oceanfront condominiums on Kaua’i in a gated boutique 9-unit property on a private cove. Relish the panoramic ocean views and the soothing sound of surf while relaxing in this modern...
5 Bed 3 Bath Home in Poipu Kai
Hale Aouli is a beautiful newly renovated five-bedroom and three-bathroom custom home located in beautiful Lanai Villas in the Poipu Kai Resort. From the home, you will find walking paths to Poipu's finest beaches, restaurants, tennis courts, pool, and spa. Start...
Gorgeous two-level condo with resort-style pool & hot tub - close to beach
Ka Pu'uwai at Nihilani 29BOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'A lush exterior, with a gorgeous resort-style pool and hot tub, and a bright, modern interior with two...
Guest House on gorgeous tropical private 3 acre estate perfect central location.
Located on the Big Island of Hawaii, this detached studio guest house is fully furnished, very private, with vaulted ceilings on a beautifully landscaped 3 acre privately enclosed property. Property has a gated entrance with private gate code, grounds security system,...
You'll feel well-cared for and cozy in this new two-bedroom home. High-end design and luxury finishes bring art, comfort and beauty indoors; wrapping you in a jewel box of tranquility. The large open deck offers plenty of outdoor living space. The black sand beach of...
Kailua-Kona Condo w/ Resort Amenities Access!
Pack your bags for a trip to paradise at this Kailua-Kona vacation rental! This 1-bedroom, 2-bathroom penthouse unit boasts vaulted ceilings and proximity to local attractions, making it an ideal island home base. Begin your adventures by sampling Kona coffee and fresh...
Luxury Ground Floor Villa, Sunset/Ocean Views, Huge Lanai, 2 King MBR suites
We first listed Villa One on VRBO May 2022. We've had many happy guests, and many 5 star reviews. This exceptional and private condominium is the first ground floor villa at The Shores at Waikoloa Beach. Villa One has views of the Pacific Ocean peeking through Palm and...
Oceanfront Paradise! Sea Turtle Cove Napili Point
WOW! Spectacular Ocean and outer island views. Your oceanfront patio is just steps away from the beautiful Honokeana Cove (commonly called turtle cove), which lends to excellent and safe snorkeling on most days. Sip on your Mai Tai, take a deep breath, and enjoy the...
Very Comfortable Kamaole Sands Condo in Kihei
Please check out my comfortable quiet (end unit, Building #5 2nd floor) 1 bedroom condo 2 baths (818 sq ft) with views of the pool, partial ocean view, remodeled kitchen and bathrooms, recently painted, new carpets and conveniently located to everything you need, the...
You're Resort Home! Walk to Disney, Beach & Pool!
It can’t get any better than Hawaii resort living in Ko’olina! Make yourself at home in this beautiful, bright, fully equipped family home. There are plenty of comfortable work-friendly spaces & fast reliable WiFi. Soak up the sun at the pristine Ko’olina beach lagoons...
Private Cozy Studio walking distance to beaches, shops, restaurants and bars
This studio is perfect for the vacationers who wants to spend their time out and about exploring the island and still have a very nice, comfortable place to come home to. It's on the 4th floor of The Island Surf in South Kihei and within walking distance of many shops,...
Oceanfront Luxury Home in Lanikai- sleeps 8
Hale Mokulua is perfectly situated in front of the iconic Mokulua Islands. Relax as you watch the sun and moon rise over the turquoise water. Lounge next to the pool or dine in the outdoor dining area. Close to shopping and dining, this 4-bedroom, 3 bath home is perfect...
Beautiful Kukui'ula Home With Great Lanai Space
New pool just added! This home has it all, private hot-tub, brand new pool, fire pit, 2,000 sqftlanai, and enough room for the whole family with over 3,000 sqft of insideliving space! - 5,000 soft totalThis home is special with it's open indoor/outdoor main living area...
Serene Kauai South Shore Retreat, Full A/C, Walk to Beaches
The moment you step out to the private lanai and take a deep breath, the mind is instantly reset by birds chirping in the trees and the tropical foliage all around. You will appreciate the quiet and secluded vibe, yet with easy access to beaches, shops, restaurants....
Aston Maui Kaanapali Villas A101: 2 Br Premium on N. Kaanapali Beach Sleeps 6
At the heart of the Maui Ka’anapali Villas Resort, an opulent retreat awaits. This sprawling ground-floor condo boasts wide open spaces, with lofty ceilings, and walls adorned with fine Polynesian and Asian Pacific antique art. Soft creamy décor pays muted compliment to...
Beach Cozy North Shore Turtle Bay Condo - Kuilima Estates East
Summary:Welcome to our little slice of paradise on the North Shore of Oahu, Hawaii. Our beach cozy condo is nestled in a well maintained gated community at the famous Turtle Bay Resort. Whether you are looking to relax or enjoy adventurous activities, this is the...
F507 - 2 Bedroom/2 Bath - Steps from the Beach, Super Clean!
This is a legal vacation rental in a hotel zone area of Maui. F507 has been completely remodeled - everything has been professionally updated including new kitchen and baths, stainless steel appliances, granite, tile, carpet and furniture. The unit is beautifully...
Charming Guest House in Mountain View
Newly remodeled home on a two acre property will provide you a real taste of big island living. Peaceful and relaxing environment. Fresh mountain air. Magnificent native foliage. Comfortable cool climate.Explore the island by kayaking in Hilo Bay. Complimentary rental...
Spectacular views from this newly remodeled direct oceanfront 2bd/2bth unit.
The building is about 300 feet from the sand which makes it perfect for water sports or nice walks on the beach. The updated kitchen has plenty of counter and cupboard space and is open to the dining area The side view from the dining area overlooks a waterway, upscale...
Mauna Lani Terrace G102 Lagoon View Condo Beach - Restaurants, Bars Waterfront
⭕ UPSCALE LUXURY SUITE. LAGOONVIEW TERRACE #G102 ⭕ LARGE 1,150 SQ FT. WATER VIEWS OF LAGOON. COVERED LANAI ⭕ TWO MINUTE WALK TO OCEAN. 5 MINUTE WALK TO RESTAURANTS BARS ⭕ NO STAIRS! CENTRAL AIR CONDITIONING ⭕ FLOOR TO CEILING GLASS. LAGOON VIEW • Upscale furniture,...
Breathtaking Oceanfront Suite @ Kalapaki Bay
Luxury oceanfront suite in paradise!From endless deep blue of Kalapaki Bay to emerald greens of the Hokuala golf course this suite is the kind of paradise you’ve been dreaming of. Perched upon the Kalapaki Cliffs, this location provides the ultimate indoor-outdoor...
Spectacular Oceanfront Penthouse, AC, Sleeps 6
Luxury oceanfront penthouse in paradise!From endless deep blue of Kalapaki Bay to emerald greens of the Hokuala golf course this penthouse is the kind of paradise you’ve been dreaming of. Perched upon the Kalapaki Cliffs, this location provides the ultimate...
Stunning Oceanfront Home @ Kalapaki Bay, AC, Sleeps 8
Luxury oceanfront home in paradise!From endless deep blue of Kalapaki Bay to emerald greens of the Hokuala golf course this home is the kind of paradise you’ve been dreaming of. Perched upon the Kalapaki Cliffs, this location provides the ultimate indoor-outdoor island...
Kona Beach Estate: Oceanfront Home with Pool & Private Beach
This luxury oceanfront vacation rental in Kailua Kona promises an unforgettable experience, blending unparalleled comfort with the natural beauty and vibrant culture of the islands. It's a place where every moment is infused with the spirit of aloha, creating memories...
🏖️Sophisticated Oceanfront Retreat | Air-Conditioned | Walk to Beach | vrKCV
vrKCV - The Kona Hideaway at Kona Onenalo No. 11, Professionally Managed by Kona Coast VacationsThe Kona HideawayDiscover the essence of Hawaiian living at The Kona Hideaway, a private oceanfront villa nestled in the exclusive gated community of Kona Onenalo. Adjacent...
Relaxing oceanfront home overlooking Kaneohe Bay
Take in the expansive ocean views and relax in this 3 bedroom, 1 bathroom downstairs unit just steps from the ocean! The unit is fully furnished, includes a full kitchenette with a 2 burner induction cooktop, a countertop convection oven (can cook up to a 20 lb...
** 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...
(P17D) Hale Blue Hawaii 1Br with Loft, Puamana, Pool, Wifi
Welcome to Hale Blue Hawaii at Puamana 17D! Ideal for a family beach vacation, this spacious, two-story villa offers top-notch features throughout as well as plenty of on-site resort amenities located just steps from your door. Start your days with breakfasts and fresh...
Quiet get-away in Lush Tropical Setting- 5 min walk to snorkeling beach!
Experience spinner dolphins, sea turtles, hump-back whales (in winter), manta rays, amazing fish and coral reefs at pristine Kealakekua Bay, a protected marine sanctuary.Enjoy glorious sunsets through the palm fronds from the lanai or walk a few steps to the bay for...
Direct Oceanfront View! Walk on Beaches - A/C
Watch the palm trees sway and whales breach from this beautifully renovated direct oceanfront unit just steps away from the white sand beach. Unobstructed panoramic views of the ocean and outer islands. Enjoy stunning year-round sunsets all from your living area and...