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.
Stunning Beachfront - Hale Kai O Kihei 112
Welcome to your perfect escape in Kihei! This bright and beautifully updated oceanfront ground-floor one-bedroom condo is just steps away from the beach, offering breathtaking views and modern comforts. Ideal for couples or small families, this inviting retreat features...
Maui Resort Rentals: Luana Garden Villas 14C – Modern 3BR Villa at Kaanapali’s Newest Luxury Residences!
This luxurious 3BR/3BA residence is conveniently set within Enclave Three of the Luana Garden Villas. Villa 14C's north-facing orientation offers a shady respite from West Maui's legendary sun, and its designation within our "Elevated" collection offers a level of...
A/C Jacuzzi ~BBQ ~Golf Course & Mountain Views
Indulge in island-inspired artwork and luxurious elegance that awaits the discerning traveler in this exquisite home. Air conditioning seamlessly envelops the entire residence, ensuring comfort throughout. Just steps away from Hanalei Bay Resort, where open-air dining...
Newly Renovated Second Floor North Shore Princeville Condo Master Bedroom & Loft
This Air Conditioned, newly renovated, spacious 1 BdRm condo with Primary Bedroom and Full Bathroom plus Loft with half Bath is located in the Resort Community of Princeville. New Novaform Comfortgrande King Size Bed in the Primary Bedroom and Queen Size Bed with half...
Trivett Oceanfront Estate: 5BR Luxury Retreat in Kailua-Kona
STVR- 19-365146NUCR 20-1787TMK - (3) 7-5-005-096GE/TAT - 051-694-0288-01Transcend paradise with our absolute oceanfront 3 story 5 bedroom home located only blocks to Kailua-Kona town and within a guarded gate community of luxury estates. Your private oceanfront setting...
Quiet Paradise on Bay w/Aircon
A true Hawaiian-style vacation rental makes you feel welcome in this fully equipped family home. Just steps to the magical blue waters of Kealakekua Bay, you'll be able to swim, snorkel, and paddle practically in your front yard. With a peekaboo ocean view you can see...
Lae Nani 534 Fantastic view is what we have, none better on the island of Kauai
Summary:Fantastic view is what we have, none better on the island of Kauai.The Space:COMPLETELY REMODELED AND NEWLY INSTALLED SPLIT SYSTEM AC!! Come and enjoy this beautiful condo with unparalleled view of the Wailua Bay and Pacific. One our most requested condos. Very...
Panoramic Ocean View Condo
Welcome to our little slice of paradise. Our condo is located across the street from Cove Park in Kihei at the Shores of Maui. Your morning cup of coffee view will be a panoramic shot of the pacific ocean with surfers you can nearly throw rocks at. This air conditioned...
Poipu Sands 513 - Ocean Front with Awesome View of Beach
Summary:True oceanfront ground-floor retreat with unobstructed views of Shipwreck Beach and the Pacific. Poipu Sands 513 offers a private lanai, direct greenbelt access, and front-row seats for sunsets, whales in season, and crashing waves. Walk to Shipwreck, Poipu...
Hale Waima Lani - Luxury Oceanfront Estate in Puako
Modern luxury and old Hawaii charm meet and beckon from one of the largest oceanfront lots in Puako. With 350+ feet of beachfront access and ocean views from every room, this unique and meticulously maintained home is a vacation dream—the main hale with a luxury...
Steps from the Beach, Stunning View, Newly Remodeled, +AC
1 minute walk to a beautiful sandy beach. This beautifully remodeled one bedroom condo is at Kiahuna Plantation, the only beach-front condominiums on Poipu Beach, located on the sunny side of Kauai. The condo complex is situated directly on the beach among 35 acres of...
NEW Gorgeous BEACHFRONT Condo with Fabulous Ocean Views! Fully Renovated!
Waikiki Shore #702 – 2161 Kalia Rd.FULLY RENOVATED! This condo is perfect for 2 couples or up to 6 guests (STRICT MAX OCCUPANCY, using optional rollaway beds).– Contemporary beachfront condo overlooking famous Waikiki Beach with spectacular OCEAN Views!– Exquisitely...
LUXURY DIRECT OCEANFRONT! Fully Renovated! Free Parking! Sleeps 6
Waikiki Shore #700 – 2161 Kalia Rd.TRUE direct beachfront unit overlooking the sandy Waikiki shoreline with breathtaking panoramic ocean views! Gorgeously renovated from top to bottom in 2021 with FREE onsite Parking and everything you need for a luxurious Hawaiian...
*25% Off-Steps to Beach-AC in Every Room-Remodeled
🌟 COMFORT AND ELEGANCE COMBINED 🌟Step Into A World Of Contemporary Elegance With This Modern Remodeled Condo. Honus Hideaway Is Thoughtfully Designed To Provide A Comfortable And Luxurious Stay. The Condo Is 880 Square Feet. It Features Two Cozy Bedrooms With Queen Beds...
Epic Ground Floor Unit - Step onto Hapuna Beach from Large Lanai w/ Plunge Pool
A Rare opportunity to live on the beach in your very own contemporary Hawai'i home next to the Westin Hapuna Resort within the iconic Mauna Kea Resort. Enjoy unparalleled ocean, sunset and beachfront views - steps from the white sands of Hapuna Beach. This is the...
Relax in this beautiful ocean view studio condo!
Welcome to our beautiful studio unit B303 in the beautiful Papakea Resort which is located in West Maui. This condo is on the third flood in the highly desired "B" building. Our unit is steps away from the ocean, pool, cabana, and has a putting green right off of the...
Includes Hilton Waikoloa Pool Pass for stays in 2025! Includes Golf Package.Wai
This vacation rental is professionally managed by ResorticaHawaiiWaikoloa Beach Villas E23Please scroll down for detailed informationHilton Pool Pass: Valid for stays now through December 31, 2026. Maximum 6 persons per pass (children under the age of 5 are not counted...
HIGH Floor w/Canal, Mtn and Partial Ocean Views! AC, W/D, WiFi, Pool,Parking!
Fairway Villa #2418 – 2345 Ala Wai Blvd(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL.)You'll love this corner property with its amazing Ala Wai Canal, mountain and partial ocean views and its proximity to shopping, restaurants and entertainment...
Kapalua Golf Villa 23P 5&6: 2BD Spring Special!
Welcome to Kapalua Golf Villa 23P 5&6, a beautifully updated 2-bedroom, 2-bathroom retreat offering the ultimate island luxury, comfort, and convenience. Nestled in the heart of one of Maui's most prestigious resort communities, this villa boasts breathtaking views of...
Poipu Paradise Beach Condo
Welcome to the South Shore of the Garden Island of Kauai and beach town of Poipu! Your stay at our well appointed modern beach inspired condo will be a wonderful place for your Hawaii vacation. Just a short 5 min walk on the greenway to Poipu's beaches for activities...
Remodeled 1BR Kihei Condo: Ocean Views, Gourmet Kitchen, Steps to Kamaole Beach
Kihei Alii Kai 1BD/1BA Remodeled with Ocean Views - Book 5 Nights, Get the 6th night Free!Kihei Alii Kai 1BD/1BA Remodeled unit with Gorgeous Ocean Views and Maui Sunsets from the Spacious Lanai.Beautiful remodeled 1 bedroom, 1 bath fully furnished condo is ready for...
Farm House with Ocean Views! #BBPH 2021/001
Our two bedroom farm house has a very unique feel with detailed craftsmanship (built by the owner). The home is 1000 square fee. It has an open concept with a 500 sq. ft. deck and views of the ocean, mountains, and our farm. We have goats and plenty of fruit trees. We...
MAUI BEAUTY ~ Tropical Napili Bay Lahaina CONDO ~1BR King ~ Kitchen ~ AC!!!
All New Interior - New Listing! Hidden gem of the West Side of Maui, Completely remodeled condo w/ all New Furniture, full kitchen with dishwasher, beautiful bathroom w/ walk-in tile shower, brand-new AC in Living Room AND Bedroom.***Napili Ridge is just north of...
VI 206 OceanFront Studio w Ocean Views Pool
Valley Isle 206 Beautiful Studio at Convenient Location and Close to Amazing Beaches! 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...
2 bedroom 1 bathroom, walk to world famous Waikiki beach only 0.3mi
Cozy 2 bedroom condo 805 sq.ft in Waikiki with great mountain and golf cruise view. North-facing floor plan, cool in summer time. Big balcony/lanai 125sq.ft one parking lot included in garage. Access to rooftop with great view. Shared gym and laundry in the building.
Hale Laniakea ~ 4 BR Modern Island Escape w AC
Hale Laniakea ~Princeville at Hanalei 4 Bedroom Modern Retreat Our home - Hale Laniakea, (Immeasurable Heaven) is located a private cul-de-sac in the best part of the beautiful Princeville resort. You will love being able to walk to Queen's Bath, Hideaways Beach &...
Hale Mele Polynesian Pod Style with Pool/Hot Tub, Gazebo, Golf Cart & Ebikes
Welcome to Hale Mele — A Premier Hawaiian Retreat on the Big Island’s South Kohala CoastEscape to Hale Mele, an extraordinary luxury residence situated within the exclusive, gated community of Champion Ridge on the radiant South Kohala Gold Coast. Recognized by Condé...
Sands of Kahana 243 was $560/nt, now $425/nt
Rent with confidence. Our condo is in a resort property that is zoned Hotel and is exempt from the new Short Term Rental prohibition. We offer a very friendly cancellation policy.BEAUTIFULLY REMODELED HOME AT THE SANDS OF KAHANA! THE REMODEL INCLUDES ZONED AIR...
Recently Fully Renovated-Oceanfront, Top floor, Million Dollar View, Sleeps - 2
Our newly renovated condo #310, is on the top floor. Enjoy the 3rd floor with NO noise above you, directly over beautiful Wailua beach. "Fall asleep to the sounds of the crashing waves" The condo is located on the quieter end of the building, away from Main Street. From...
Hale Nalu: Tropical Cottage in Poipu-Walk to Beach
Scenically situated on the Green Belt pedestrian pathway, this enchanting island-style home combines the casually elegant charm of a country-plantation retreat with an ideally convenient location. Not only is it close to everything—an easy stroll to beaches and...
Private Villa on 3 acres with Pool and Spa TVNC-4195
This spacious home is Located in the Seacliff gated community, adjacent to the Kilauea Point National Wildlife Refuge and the Kilauea Lighthouse.You will enjoy large panoramic windows throughout the home with extensive mountain and bay views. This well maintained three...
Oceanfront Home w/ Incredible Lanai, Great Ocean View, WiFi, Washer/Dryer
Hale AikalaniOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'The open waters of the Pacific Ocean are right in your backyard at this modern and comfortable home just outside Pahoa,...
Princeville Mountain View Private Home
Private home within walking/biking distance of Sea Lodge Beach, Golfing, Tennis and Princeville Center. Distant ocean views from upstairs office. Enjoy wonderful mountain and waterfall views as you sip your coffee or cocktails from the back deck. Downstairs bedrooms are...
Wailea Beach Villas E-302 on Wailea Beach
Modern living, in one of the best locations at Wailea Beach Villas, with outer island and sunset views that are unmatched. Centrally located in the complex, and only steps away to both pools on property as well as the white sand beach and Wailea Beach path, leading you...
JJs Hāna Hale - Farm House
Aloha!Welcome to Beautiful Hana! JJ’s Hana Hale is a air conditioned 1 bedroom cottage, conveniently located near idyllic Hana town near the tiny Hana Airport in a historic district Hawaiian’s call: Ka’eleku, we’re on 6 verdant acres (turn left near the 31 mile marker...
Waikīkī Shore 404 - Studio Waikīkī Beach View
Castle Waikīkī Shore Unit 404 offers all the comforts of home on your Hawaii vacation: a fully equipped kitchen, air conditioning, WiFi, mounted flat screen television, washer/dryer, and private lanai. The unit is tastefully furnished with beautiful koa wood furniture...
Family-Friendly Condo w/Balconies, Shared Pool, Hot Tub, Garden View, Central AC
Nihilani 25BOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Enjoy the close proximity and easy access to the beautiful walkways of Princeville that offers this incredibly...
Luxurious Kolea Penthouse with direct access to Anaehoʻomalu Beach.
Located in the acclaimed Kolea community, one of the most sought-after oceanfront developments on the island, Hale Mermaid penthouse is a spacious 2 bedroom, 2 bath luxury penthouse with partial views of Anaeho’omalu Bay. It is an 'end-unit' which allows light and...
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...
Exceptionally Remodeled Oceanfront, Sunsets, A/C, King bed Hale Kai O Kihei
• Oceanfront• Split A/C units• King bed• Remolded Oct 2021• Beach access from condo complexFully remodeled in September 2021, this bright, beautiful one bedroom, one bathroom oceanfront property in Hale Kai O Kihei 210 welcomes you! This second floor condo is luxurious...
KBM Resorts | FREE CAR | Honua Kai Konea | 1-Bedroom Condo, Steps to Beach! HKK-236
** 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...
Poipu Kapili 46 - Fabulous Ocean Views - Whole Unit AC - Walk to BEACH/ Shopping
Poipu Kapili is a luxury, boutique oceanfront resort located in one of the most desirable locations on Kaua'i: Poipu. Walking in the door to Poipu Kapili 46, you will be drawn to the lanai overlooking the lush green grass, deep blue pool, and the spectacular Pacific...
Newly Remodeled Modern Condo + Free Parking Waikiki
Welcome to our spacious, modern one bedroom condo located on the 6th floor above the swimming pool/jacuzzi. Renovations on the condo were completed in January 2021. Along with 24 hr. security, amenities include free secured parking (hotels charge up to $50 a day), with...
City-View Waikiki Beach Condo - Free Parking!
Who needs an ocean view when you can have majestic green mountains, blue skies, and lively street views from the 17th floor of Ilikai condo? Plus, you might even catch a rainbow or two! This cozy 500 sq. foot condo may not have a wall separating the bedroom from the...
Kilauea Lakeside Estate - Secluded Luxury Retreat on Private 4-Acre Peninsula
This totally private resort has been described as the best private Kauai retreat in the Hawaiian islands. Located in a wildlife refuge on its own private lake on the island of Kauai, Kilauea Lakeside Estate is a beautifully secluded Hawaiian retreat, simply perfect for...
Close to Kahala Beach/Air Conditioning/Heated Pool/Clean/Quiet Neighborhood
Ask owner about available dates/rates. Elegantly remodeled in 2018, this one level, very clean, 4 bedroom & 3 bath home, has 2 master suites, a gourmet kitchen, air conditioning in every bedroom & high end finishes throughout this private oasis. Please inquire about...
Recently Remodeled, Modern, Nice Condo in a Great Location
One bedroom, one bath condo with a great walk in shower. Nice kitchen to save money and prepare your meals. Large tv, fast wireless internet, full size in unit washer and dryer, and a free parking stall. Nice lanai to enjoy your morning coffee, and ac in the unit....
Ali'i Point #12: Oceanfront Getaway w/ Hot Tub, AC, Lanai & Shared Pool
Set along the lava rock shoreline of Kailua-Kona’s Aliʻi Drive, Aliʻi Point #12 is a private oceanfront sanctuary within an exclusive gated enclave of just 16 homes. With 3,199 square feet of interior space and a sprawling 1,500-square-foot lanai overlooking tide pools...
Modern and Luxurious Beachfront Property at Polo Beach
Maui beachfront elegance Polo Beach Club is conveniently situated at the beginning of Makena and the Wailea oceanfront pathway that connects the luxurious Makena and Wailea Resorts. The interior is open, light and bright, fully furnished with creative flair and luxury....
Lani Oasis - Princeville Vacation Home with Saltwater Pool
Lani Oasis welcomes you with its serene ambiance and tropical charm, perfectly situated in beautiful Princeville, Hawaii. This luxurious villa is designed for both relaxation and recreation, featuring a private saltwater pool surrounded by lush gardens and inviting...