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.
Puamana Maluhia - Princeville Two Bedroom / Two Bathroom
Come and relax in our newly renovated, two bed, two bath condominium on Kauai's famous North Shore. Adventures abound so rest assured our place will be your spot to rejuvenate. Surrounded by cool coastal towns like Kilauea and Hanalei, Puamana is centrally located...
Ekahi 8F, Oceanview Studio, extremely close to Beach and Main Pool! 2nd Floor
Escape to paradise with stunning ocean and green belt views from the lanai of this 2nd floor studio. 8F is a fully-furnished studio featuring cathedral ceilings, a comfortable living area, a California King bed, and a fully-equipped kitchen. The layout and décor of our...
Private Paia Studio in a Tropical Sanctuary, a short walk to Paia town & beach.
This Private air conditioned studio is located on a newly remodeled ocean view estate, within walking distance to some of Maui's best restaurants and shops in the historic plantation town of Pa'ia. The property offers stunning views of both the ocean and Haleakala....
"Paradise Found" at Hale Awapuhi! Incredible Views at this 2 Bedroom | 2 Bathroom Ocean Front.
Welcome to Paradise Found, a luxurious oceanfront escape at Hale Awapuhi along Kauai's breathtaking Coconut Coast. Located in an exclusive, gated community with only nine private units, this stunning two-bedroom, two-bath condo offers sweeping ocean views, island...
KaMilo at Mauna Lani Condo w/ Resort Pool Access!
Experience the perfect blend of oceanfront adventure and tranquil relaxation when you stay at this 4-bedroom, 3.5-bath vacation rental in KaMilo at Mauna Lani. Complete with several private lanais, a large chef's kitchen, and unbelievable views of the golf course and...
Lucky you! 2 Bedrooms, Large Lanai, Stunning Mountain Views, Pool, Parking, W / D
Whether you are coming to Waikiki on business or just to escape the stress of business with a vacation, you will find this 2 bedroom condo in a very desirable building your perfect tropical oasis. Designer -inspired décor echoes the peaceful colors seen in the...
May on Sale! Book now and SAVE BIG! Walk to the Beach from Your Private Lanai!
Located on the sandy beaches of Kahana just north of Lahaina, Valley Isle Resort is the perfect spot for your oceanfront getaway. You can enjoy unobstructed ocean views and spectacular sunsets from the lanai or relax on the beach just steps away.Spacious and updated,...
Steps to Keauhou Bay! Great Water Access! Pool! Foosball table!
Beautiful home 120 steps from the warm waters of Keauhou Bay. House has 4 bedrooms, 2 1/2 baths and will comfortably sleep 8 in beds and up to 10 including futon couches. Fully equipped to give all the comforts of home while on holiday. Close to shopping, snorkeling...
❤️PiH❤️TROPICAL BREEZES★ Hilton Passes ★ Closest KaMilo to beach ★
Brought to you by Paradise in Hawaii Luxury Homes.Welcome to the wonderful Tropical Breezes Villa, a part of our Hawaiian Luxury Collection. Tropical Breezes Villa at KaMilo is a wonderful 3 bedroom single level home with exquisite finishes and golf course views....
Gorgeous Ocean View Villa with Heated Pool/Spa, Mauna Kea Club Member
Aloha! Welcome to Hapuna Beach Villa, our home overlooking the Hapuna Golf Course in the beautiful Waiulaula development with panoramic 180 degree views of the ocean and Kohala mountains. We also have partial views of the 14th green.Our home is a 3 bedroom, 3.5...
** Summer Special ** Gorgeous Golf Course and Ocean Views ** Luxury Living ** Private Pool and Spa ** Mauna Lani Resort** Includes 6 person Golf Cart
Enjoy the splendor of this Luxury 2 story townhome, at the exclusive Residences of Laule'a located within the world class Mauna Lani Resort.This Luxury residence is designed for comfort and serenity. The main level of this property offers a spacious Great Room that...
Monthly Discovery Bay 3717 Mountain/City Views 2 Bd 1Ba 2 Queen Beds
PANORAMIC MOUNTAIN VIEWS, 5 Minute Walk to Beach, High Floor, Remodeled, Furnished and Fully Appointed. No smoking condo. Parking, Pool, Utilities, WIFI, BBQ, Gym, Sauna, Security, Washer/Dryer Included. Monthly.Sweeping Views from High Rise, Tasteful and Clean. Monthly...
2 Bedroom Condo On Hawaiian Beach - Family Friendly - 7 nights
Treat your family to the tropical vacation of a lifetime at this luxurious Marriott beachfront resort on the island of Oahu. Nestled along the sparkling Pacific Ocean and surrounded by palm-lined lagoons, this premium retreat offers the perfect mix of adventure,...
Maalaea Kai 307 Maui Prime Oceanfront nKing Beds w/ ensuitenDedicated Workspace
Welcome to our nicely remodeled 3rd floor unit featuring gorgeous views throughout the unit of Maalaea Bay, the grand volcano Haleakala and the sparkling Kihei lights at night. The unit is tastefully decorated with the spirit of Aloha and has a large split air...
𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 Beach Fun at Waiohai Club +Resort Amenities. 2-Bedroom
𝐕𝐢𝐬𝐢𝐭 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 to enjoy 𝐄𝐱𝐜𝐥𝐮𝐬𝐢𝐯𝐞 𝐒𝐚𝐯𝐢𝐧𝐠𝐬 on this elegant, 𝐬𝐩𝐚𝐜𝐢𝐨𝐮𝐬 𝟐-𝐁𝐞𝐝𝐫𝐨𝐨𝐦 𝐕𝐢𝐥𝐥𝐚 at one of Poʻipū...
*Milowai 410* Prime Oceanfront Maui Condo, A/C!
Enjoy breathtaking ocean views from this 4th/top floor unit. One of the largest lanais at the complex! The bedroom has a new comfy king bed, beautifully remodeled tiled walk-in shower, 40" Roku smart TV and a split system a/c unit to keep you cool. The living room also...
Peaceful North Shore Beach Oasis
Our beautiful 2 bedroom 3 bathroom house has direct access to one of the most beautiful beaches on the North Shore. The house is the last house on the beach so you have unobstructed views of a beautiful cove with warm, calm waters and a large horse ranch on one side....
Hale Cassia: New Listing! Home w/ Lanai, Outdoor Dining, Near Shops, Restaurants
Hale Cassia welcomes you to the heart of Princeville, a lush corner of Kauai where mountain peaks meet tropical gardens. This detached, single-level residence blends modern comfort with island ease, offering three bedrooms and two bathrooms across 1,700 square feet....
Napili Point A16-A Piece of Paradise-Turtles Just a Few Steps Away!
Do you enjoy beautiful sunsets, walking on the beach, smelling tropical flowers, looking at breathtaking scenery, being one with nature? Want to enjoy paradise? Make memories as beautiful as the sunsets? If so, you will want to book this fully equipped one bedroom...
Kaanapali Alii #193. 3 Bedroom
This property was remodeled in 2020 and was just added to our rental pool! We are still working on finalizing furniture then professional photos will be taken. **THE TOTAL AMOUNT LISTED IN THE "RATE CALCULATOR" REPRESENTS ROOM AND TAX ONLY. ADDITIONAL FEES APPLY. See...
***SPRING SPECIAL*** Fairway Villas : Golf View-AC- 2br - Golf Discount
Aloha and welcome to our Hale Okakopa, Fairway Villas A22 in the Waikoloa Beach Resort. Each room features its own treasures: from intuitive Sapele built-ins like the kitchen desk and entry bench, to the tropical elegance of the primary suite—complete with a...
Rainbow Deluxe - 2 BR/2 BA Cottage - Simply Wonderful!
'RAINBOW DELUXE' is a 700 square foot standout 2 bedroom / 2 bath fully licensed vacation home conveniently located in Maui Meadows, along the south shore of Maui, Hawaii. Our luxury Polynesian pole cottage sits on its own quarter acre, ideally nestled in a peaceful...
Tropical Paradise Awaits: Stunning Hawaii Condo with Ocean Views!n
STVR-19-345056Kai Indigo Condo is luxury and elegance on a budget! This quiet third floor unit is surrounded by a beautiful forest and has fantastic views of the ocean. Our unit offers air-conditioning in the living room and overlooks beautifully manicured grounds with...
130K Hawaiian Reno on Wailea Blue Golf *Ocean View
BRAND NEW 130K Renovation+BRAND NEW Hawaiian Styled Contemporary Decor. Located right on Wailea Blue Golf course in the Grand Champions at Wailea with incredible ocean views from the patio.We are perfectly located just down from Money Pod+up from The Shops of...
5-STAR KONA COAST RESORT 2 bedr/2 bath Top Floor, AC, GORGEOUS Unit#10-301!
Kona Coast Resort #10-301 is one of the best ocean view 2 bedroom, 2 bath condos, with all of the amazing amenities of a 5-Star Resort! Enjoy two Swimming Pools, one “family” pool with an on-site Restaurant/bar, and nightly live music plus one quiet pool, three...
Oceanfront Remodeled Luxury Penthouse / Cooling Trades & A/C / LIGHT & BRIGHT
Discounted Summer Rates & additional discount for stays of 7 days or more.Why Reserve this Condo? Spectacular Ocean Views from this Condo! Light, Bright and Airy! Comfortable Newer Furniture! Modern Hawaiian Decor! Well Maintained & Constantly Upgraded! In Direct Path...
The Pool House: 6 BR Kailua Home with Pool, Walking Distance to Kailua and Lanikai
The Pool House in Kailua offers 3,200 sq ft with 6 bedrooms, 4 baths and one amazing pool. Located in a peaceful and lush neighborhood with views of the Ko’olau Mountain range, it is an easy walk to Kailua Beach, Lanikai Beach and Buzz's Steakhouse. The home offers a...
K L V R presents the Beautiful Ground floor Villa LUANA 6B Honua Kai
Kaanapali Luxury Vacation Rentals welcomes you to our beautiful garden level Luana Villa at the Honua Kai Resort.This luxurious villa is located within a private garden enclave at the spectacular, beach front, Honua Kai resort. This villa boasts 2047 sq. ft. of...
The Home of the Hula Moon – Puako Beachfront Estate
Stately and serene, THE HOME OF THE HULA MOON is one of the most beautiful contemporary oceanfront properties in PUAKO. Each bedroom has a perfect ocean view. Located near the end of the road, you will enjoy year-round sunsets and privacy. Puako probably has the best...
Ekahi Ocean Studio: Couples Retreat, Just 300 Feet To Keawakapu Beach
Ekahi Ocean Studio is a studio perfectly located in the lower village of Wailea Ekahi (#8C), a lush-landscaped paradise, just steps from the oceanfront pool and to world-renowned Keawakapu beach. This studio is perfect for couples seeking a peaceful, romantic retreat....
3 Bedroom / 3 Bath Family Friendly Groundfloor Beach Villa!
Your Paradise Awaits . . . Aloha and Welcome to Oahu's newest beachfront condominium community! The Beach Villas at Ko Olina offers exceptional resort living at its finest with its earthly warmth and sophisticated island inspired architecture. This family friendly...
Featured on A&E's Vacation Rental Potential! Luxury Family Condo! AC and Pool!
**JUST OPENED CALENDAR FOR WINTER 2026**Modern Luxury! Featured on A&E home show Vacation Rental Potential. This luxurious, modern retreat at The Palms at Wailea was recently completely renovated from the studs out! NEW AC SYSTEM! Unit #706 is very quiet and does NOT...
3 Bedroom Private Home at Waikoloa Beach with Pool
This home has been well furnished and is great for families looking to enjoy a quiet, private vacation yet be near all the amenities of Waikoloa Beach Resort.The house has been nicely furnished and offers a spacious great room. The living room has two couches facing a...
Westin Ka’anapali Ocean Villas North, OCEAN FRONT 2 bedroom lock off - 2025!
Welcome to the beautiful, family friendly, Westin Ka’anapali Ocean Resort Villas, North. We have both Nanea and an OCEAN FRONT 2 bedroom lock off available. Best availability occurs when inquiry is at least 8 months in advance as the resort and type of unit is very...
Marriott's Kauai Beach Club Studio - Parlor - Many Dates Available!
The Kauai Beach Club resort features an array of amazing on-site amenities such as a 26,000 square-foot pool rimmed with colonnades and waterfalls, a children's pool, spa, fitness center, and two 18-hole championship golf courses designed by Jack Nicklaus. The resort...
Luxurious golfside condo with ocean and golf course views
Emmalani Court at Princeville #321Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Experience luxury and relaxation at this stunning condo located in Princeville, Hawaii, overlooking...
Beachfront Paradise! Updated, Fresh and Ready for your tropical getaway.
Need more Info? Not sure of Dates? Got Questions? Click "Ask Owner a Question" link on the right. We are here to help!***This property is guaranteed Maui-approved (zoned) for short-term rental and is NOT subject to the ongoing controversy of attempts to limit short term...
Luxury Mauna Lani Home w/Fairway Views, Private Pool, Jacuzzi & AC - Kamilo 333
Located in the premiere gated community of KaMilo in the Mauna Lani Resort, this exquisite four bedroom property offers 3,100+ sq. ft. of living space including a detached guest house. Our rental home is brand new and the furnishings and decor are of impeccable quality....
Ultimate Luxury Oceanfront 2 bedroom 2 bath @ The Kaanapali Alii Resort
*note: if you are booking a short stay for 7 or less days, please inquire first before doing a reservation request, unless your arrival date is less than 30 days away, in which case you're welcome to proceed with the reservation request*The views from this 8th floor...
PRIVATE HOME-NEWLY REMODELED-AC-HOT TUB-METICULOUS CLEANING
Book With Confidence, This Gorgeous, Newly Remodeled, 4 Bedroom, 2.5 Bathroom Private Home, With Modern Finishes, Located In A Residential Neighborhood In Central Kihei That Has Been Permitted For Short Term Vacation Rentals (STRH Permit #STKM2018/0005). This Home Is...
Kamaole Sands 1 BR/2 BA Oceanview w/Large Lanai (Unit 2-303)
Kamaole Sands has acres of luxuriant tropical gardens and private spots for picnics by the fountain pond. Stroll along golden sand beaches and enjoy an ocean full of water sports including snorkeling! Shopping and restaurants are just minutes walking distance away....
Spectacular Ocean Views! 5 Star Reviews! ʻIke Kai at Wailea Ekolu Village
Aloha!Start your day with coffee and beautiful ocean views from the lanai, and finish the day watching amazing sunsets!Welcome to our Our Maui Condo! ʻIKE KAI, which means "OCEAN VIEWS," offers a one-bedroom, two-bath, ground floor retreat that will delight even the...
Remodeled Condo W/Ocean Views-Kamaole Sands 10301
Kamaole Sands unit #10301 on the third-floor: Plush new furnishings enhance the living room, with a brand new flat screen TV and a pull-out sofa couch for additional comfort. Sliding glass doors open from the living room to a fully furnished lanai, where you can enjoy...
Tracy's Tropical Treasures earned "Best in Kihei" four times and “#1 in Maui”
Aloha from Maui…Thank you for your interest in Tracy’s Tropical Treasures for your upcoming Maui vacation. I would be honored to assist you.~ Welcome to Tracy's Tropical Treasure #2 (Unit 222): the Corner Penthouse. This condo is a fully loaded, award winning, legal...
Ko Olina Kai Estate #20: Elegant Fairway Retreat with Luxe Amenities
This property is offered as a monthly rental. Although full-month occupancy is not required, the monthly rate remains fixed and applies in full, regardless of the number of nights stayed, as prorated rates are not available.Imagine yourself living the life of luxury in...
Island Chic w/Loft! AC, Lanai, Kitchen, WiFi, Flat Screens+Laundry–Kamaole Sands 9411
Toast epic sunsets on the lanai of this modern 1,200sf suite with Pacific view. Tropical style rolls out with a spiral staircase to loft and master bedrooms, modern kitchen flowing into the open living area, laundry, ceiling fans, AC, WiFi, flat screens and DVD. Sleeps...
#1 Kaanapali Beach Modern Condo C101 Maui Eldorado
Situated in the Kaanapali Beach Resort area, enjoy this spacious ground floor studio at #1 Kaanapali Beach, Maui Eldorado Resort C101, located in the heart of Kaanapali. Relax in this spacious and tropical suite condo, fully furnished with a full kitchen, washer/dryer...
Kapalua Bay Villa 18G3 Gold Oceanfront 1 Bedroom
- Villa closest to Oneloa Beach- 22 stairs between the driveway and front door - Tile floors throughout this 2-story condo - Updated kitchen with granite counters includes stovetop/oven, microwave, refrigerator with ice maker, coffeemaker, cookware, tableware- Bedroom...
Westin Kaanapali Ocean Resort - Luxury 2 Bedroom Villas
Perched on twenty-six lush acres with breathtaking views of the Pacific Ocean and the islands of Lana'i and Moloka'i, Westin Kaanapali Ocean Resort Villas (commonly referred to as WKORV) provides the ultimate in pampering and relaxation. Enjoy an afternoon unwinding...
Royal Mauian #307: Beachfront Bliss with Stunning Views & Resort Amenities
Royal Mauian #307 – Oceanfront Views in the Heart of KiheiRoyal Mauian #307 is a two-bedroom, two-bathroom condo offering breathtaking views of the Pacific Ocean and Maui’s stunning coastline. Perfectly located along the oceanfront in South Kihei, this unit combines...