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.
VOK29 Hawaiiana 3br 3ba Villa of Kamalii, AC, Pool
Professional photos coming soon. Located in the resort community of Princeville are the Villas of Kamalii, a gated complex located across from the Makai Golf Club. Enjoy lush garden, mountain and waterfall views from Villa #29, an end unit, split-level townhouse with...
Noiulu One – Brand New Estate | Onsite Staff & Daily Housekeeping
Located in the exclusive Noi‘ulu Estates neighborhood, this brand new 6 bedroom, 6.5 bathroom custom gated estate home offers an expansive luxury residential experience highlighted by majestic ocean views. Abundant natural light accentuates modern, natural finishes...
crater rim cabin garden view
Crater Rim Cabin is located on the boundary of Hawaii Volcanoes National Park in the edge of the ohia-fern forest of Kilauea. The cabin is nestled among ohia and koa trees in botanical-garden-like surroundings. At an elevation of just over 4000 feet we have a cool...
Spectacular Ocean Front Views and A/C in Every Room - Princeville/Hanalei
A beautiful, unobstructed view of the deep blue Pacific Ocean and coral reef from every room! Our condo is located on an ocean bluff having the luxury of a 180 degree view of blue water from every room. Along with magical waves, you will see outrigger paddlers and sea...
Ideal Family Retreat! - Beach Pass Included - Great Location - Beautiful Sunsets
Fairways at Mauna Lani 1001 -- One of the best locations within the complex -- INCLUDES COMPLIMENTARY ACCESS to the parking at the Beach Club (calm water beach with a great snorkeling and restaurant: 5 minutes driving from us) -- Renovated with attention to details in...
PUN 202 Oceanfront Condo w Stunning Ocean Views
Punahoa 202 NEW LISTING! Refreshed OceanFront Condo with Spectacular Ocean Views for a Peaceful and Relaxing Hawaiian Vacation FREE daily activities included with your stay value up to $554! Complimentary admission, every day of your stay*: Whale Watching (seasonal),...
Spacious luxury 2-floor villa with breathtaking ocean, golf, and mountain views.
Welcome to our spacious luxury villa, where you can enjoy breathtaking ocean views, golf courses, and mountains.This exceptional two-floor, 2-bedroom, 3-bathroom unit beckons you into a bright and open layout, encompassing an impressive 1756 square feet of interior...
Beach Studio with private yard in Lanikai - 30 day Minimum Stay
Escape to your beachside retreat with this beautifully renovated studio located just a block from the pristine sands of Lanikai Beach on the east side of the island. Designed as your ultimate home away from home, this property offers a unique blend of seclusion and...
Fairway Villas Waikoloa G31-Top Floor Villa w/loft and 2025 Hilton Pool Pass!
Aloha and Welcome to our 2 Bedroom 2 Bath with a loft villa located at the Fairway Villas Waikoloa. We are located in the Waikoloa Beach Resort on the Island of Hawaii. You can explore our Island of Hawaii, beaches, waterfalls, coffee farms, Mauna Kea snow-capped...
Cozy Kona condo walking distance to the beach, shops and restaurants.
Beautiful, clean, cozy, recently updated Kona condo, your home away from home. Beaches, coffee shops, restaurants and boutique stores are all in walking distance. Includes all the essentials to make your stay comfortable and worry-free. In home amenities include:•...
ALOHA-WAIKIKI 2 Blocks 2 Shoreline of BEACH and Upgraded!!!
Located just two short blocks from the shoreline, this unit features a comfy queen sized bed, free wifi, a kitchenette, private bathroom and a private covered balcony from which you are able to enjoy mountain views and tropical breezes.Within our CLEAN PRIVATE unit, my...
Hokulani 749 Luxury Penthouse Panoramic Ocean Views - 2BD/2BA
🌴 West Maui is Open – and Honua Kai is Resort-Zoned. 🌴Book with confidence knowing you’re safe from the recent legislation impacting other short-term rentals.🌊 Welcome to Hokulani 749 at the award-winning Honua Kai Resort – a stunning penthouse offering one of the most...
Private Beachfront Condo in Haleiwa
Your Private Beachfront Retreat in Haleiwa – 30-Day Minimum Stay Escape to your own slice of paradise at Haleiwa Beach on Oahu’s legendary North Shore. This charming one-bedroom, two-bath condo offers the perfect blend of comfort and island charm, with breathtaking...
Poipu Kai Hale, Poipu's Hidden Gem
Welcome Poipu's Hidden Gem! This amazing home offers 3 bedrooms and 3 bathrooms on the ocean with incredible views of Poipu! Imagine your vacation experience in this gorgeous location with unparalleled and unobstructed 200°+ views. This spacious home consists of a...
Modern, Designer Owned 2BD+2BA w/ Loft @ Turtle Bay, AC in every room
Experience this spacious, clean & comfortable, newly remodeled unique 2-story townhouse with the conveniences of a home which is fully air-conditioned w/ new quiet Mitsubishi split system a/c. This is especially important for the hot and humid days. There is no unit...
Prime Location for Oceanfront Lovers
Situated in Maalaea, just a short drive from the airport, Island Sands 110 is the perfect base to enjoy all that Maui has to offer. The condo is steps away from the daily bustle of Maalaea Harbor, where you can indulge in a variety of ocean activities, including snorkel...
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...
Downtown Luxury Penthouse, Free Parking, Washer/Dryer
Welcome to your stunning getaway in the heart of downtown Honolulu! This spacious, High-Ceiling two story Penthouse is perfect for families, large groups, or anyone looking to experience the best of the city with comfort and style. With 8 beds distributed across 3...
Pacific Palm Villas at Hali’I Kai 5H! 3 bedroom, Luxury Location With A/C
Welcome to your dream vacation home at Pacific Palm Villas, Hali'i Kai, located in the heart of the exquisite Waikoloa Beach Resort. This opulent 3-bedroom, 2-bathroom villa offers a seamless blend of elegance and comfort, featuring breathtaking views of the lush golf...
Breathtaking Ocean Views from Quiet Beachfront Condo! Free Parking & Wi-Fi!
Colony Surf #1005 – 2895 Kalakaua Ave(30-Night Minimum. ALL MONTHLY RESERVATIONS ARE SUBJECT TO APPROVAL. Preference given to calendar month bookings.)Stunning ocean and Diamond Head views! This spacious (853 sq. ft.) open floor plan suite is the perfect spot to enjoy...
Renovated beachfront with gorgeous ocean views! Luxurious and family friendly!
(See Video Below) Upgraded, with ocean and garden views, direct beach access, patio and luxury amenities to make this your most memorable vacation! Minutes from Shops at Wailea! Family friendly and serene! Just bring your swimsuit and flip flops because we have you...
Kona Sea Ridge#X1: Beautiful 2 level Spacious 3 bedroom with Ac & Ocean Views
Kona Sea Ridge#X-1 is an excellent beautifully furnished option for your Vacation. This VERY spacious, 2 story 3 bedroom, 3 bath unit has fantastic features that many guests enjoy. A perfect option for up to 6 people! ~Largest Floor Plan in Kona Sea Ridge. Living Area,...
Maui Resort Rentals: Honua Kai Hokulani 341 - Upgraded 2BR Ocean View Suite w/ Deluxe Corner Floor Plan!
Hokulani 341 delivers a tranquil interior courtyard location with stunning views of the Pacific Ocean. Gather, reconnect, and celebrate in this spacious 2 bedroom/2 bathroom deluxe floor plan which offers an abundance of interior living space and a 340 sq. Ft....
Bright & Cozy Stay Near Waikiki Beach + Parking
Aloha from Midway Vacations! Our team of local hospitality experts is dedicated to turning your Hawaiian getaway into a reality. When you stay at one of our properties, you can count on a professionally cleaned and meticulously maintained experience. We're even...
Maui Kaanapali Villas #A102: At the heart of the Maui Ka’anapali Villas Resort,
Maui Kaanapali Villas #A102: At the heart of the Maui Ka’anapali Villas Resort, a tropical retreat awaits. This ground-floor condo has two bedrooms with en-suites and a half bathroom. The primary bedroom is just off the living area and features a king bed. The second...
Kihei Beach Retreat: Ocean Views and Sandy Feet!
Experience Maui's charm in our 2-bed, 2-bath condo, directly managed by us for a personal touch. Just steps from top beaches and snorkeling, with stunning ocean and West Maui Mountain views. Enjoy our resort-style amenities including a pool, hot tubs, game room, and...
Perfect location in Kihei! 5 minutes to the beach!
If you want to be close to it all - best beaches, best snorkeling, only surf spot in Kihei, SUP, kayaking, snorkel tours, dinner cruises, shopping, restaurants, nightlife - our recently updated, owner-managed (no dealing with unresponsive property managers) condo is the...
A+ Location Steps to Kamaole Beach #1 Great Rate! Updated MV2107 AC King BD
Welcome to your ultimate Maui getaway at Honu Kihei -- Maui Vista 2107! Building 2 Minimal Road Noise✅ Fully air-conditioned for your comfort (mini-split/living room and air conditioner/bedroom)✅ King Bed ✅ Free Fast WiFi and Flat-screen TV for streaming and limited...
Dramatic New Kukui'ula Estate: Dazzling Style + Seaviews + Unique Pool & Spa
Jaw-dropping, breathtaking, spectacular: sometimes even the highest superlatives can seem like low-key understatement. Pali Nui—this uniquely gorgeous new Kukui'ula villa—is distinctively designed and stylishly curated, with artful décor, tropical allure, and delightful...
Garden oasis, spacious lanai & open concept living
Welcome to Maui Kamaole K104, a tranquil oasis nestled within the heart of paradise. This ground floor unit, boasting 1 bedroom and 2 bathrooms, offers a haven of comfort for up to 4 guests, surrounded by lush garden views that inspire serenity and relaxation. From the...
NEW! "Aloha Kai": Oceanfront at Lae Nani's Newest Renovation + AC + Free Laundry
Welcome to "Aloha Kai" -- the newest-renovated condo in Lae Nani. Here, modern design meets jaw-dropping, unobstructed ocean views. Inside: AC; a fully-equipped kitchen; stone countertops; all-new, comfortable bedding and furniture; and a spa-like standing shower await....
4Br 4.5 Ba Punahele House with Ocean and Mountain Views, Beach Gear, Near Queens Pond
Welcome to the Punahele bluff! The treehouse style upstairs vibe of this house with oversized deck, entertainment kitchen, and extremely large spaces makes you feel like you are part of the Hanalei mountain range. It's so close you can touch it! You have ocean views,...
Bright & Modern 2BR on the 6th Floor with Stunning Ocean & Pool Views!
Set in the serenity of the Hokulani Tower interior, Hokulani 645 boasts impressive ocean views from its prime 6th-floor location high above the palm trees that often obstruct the view of lower floors. The suite's expansive 200+ sq ft lanai also overlooks the lush...
🏖️Concierge Included| No Stairs | Fantastic Ocean View | Spacious Lanai
vrKCV - Country Club Villas 230, Professionally Managed by Kona Coast VacationsDiscover the essence of island living at Unit 230 of the Country Club Villas in Kona, Hawaii. This charming 2-bedroom, 2-bathroom retreat offers an idyllic getaway in the desirable Keauhou...
Ultra Luxurious New Home in Four Seasons Hualalai
Welcome to your ultimate vacation retreat at the Four Seasons Hualalai Resort! Step into luxury and relaxation with this brand-new, meticulously crafted 6,000 square foot, 6-bedroom home boasting the finest finishes and unparalleled comfort. THE SPACE:As you enter,...
𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢’𝐬 Beachfront Fun at KoOlina Club Resort+Amenities.2BR
𝐕𝐢𝐬𝐢𝐭 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 to enjoy 𝐄𝐱𝐜𝐥𝐮𝐬𝐢𝐯𝐞 𝐒𝐚𝐯𝐢𝐧𝐠𝐬 on this elegant, 𝐬𝐩𝐚𝐜𝐢𝐨𝐮𝐬 𝟐-𝐁𝐞𝐝𝐫𝐨𝐨𝐦 𝐕𝐢𝐥𝐥𝐚 at one of Oʻahu’s most sought-after 𝐁𝐞𝐚𝐜𝐡𝐟𝐫𝐨𝐧𝐭 𝐑𝐞𝐬𝐨𝐫𝐭𝐬 — 𝐌𝐚𝐫𝐫𝐢𝐨𝐭𝐭’𝐬 𝐊𝐨 𝐎𝐥𝐢𝐧𝐚 𝐁𝐞𝐚𝐜𝐡 𝐂𝐥𝐮𝐛.Unlock 𝐌𝐞𝐢𝐥𝐢 𝐌𝐞𝐦𝐛𝐞𝐫-𝐎𝐧𝐥𝐲 𝐑𝐚𝐭𝐞𝐬 & 𝐔𝐩𝐠𝐫𝐚𝐝𝐞𝐬:𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 𝐄𝐱𝐜𝐥𝐮𝐬𝐢𝐯𝐞 𝐒𝐚𝐯𝐢𝐧𝐠𝐬 ($500–$1000 𝐎𝐅𝐅...
Royal Kahana 210
Welcome to Royal Kahana 210. This 1400 sqft, 2 bedroom, 2.5 bath condo features a massive wrap around lanai with unobstructed oceanfront views of the encompassing islands of Molokai & Lanai. Admire seasonal whale watching, sailboats, sea turtles, and sunsets from this...
❤️PiH❤️ONE OCEAN OHANA★ Expansive Views★Oceanfront Grotto pool plus private pool & spa
Welcome to One Ocean Ohana!This spacious home is set in the One Ocean private luxury community. It features a private back yard overlooking the ocean, Kohala Mountain, Mauna Lani South golf course and Maui in the distance. The home features a private pool and spa but...
Puna Rainforest Hot Spring Retreat - Green Bamboo Cottage
Studio with oceanview, full kitchen and bathroom, queen size bed, plus small couch for one child or small adult. Perfect for couples. The property offers 1 mile private rainforest trail, pool, steam vents, two steam vent hot springs and private retreat setting...
Includes Mauna Lani Beach Club Pass. 1702 Kulalani
Kulalani 1702. Includes Mauna Lani Beach Club Pass This vacation rental is professionally managed by ResorticaHawaiiPlease scroll down for detailed informationBedding Configuration:Master Bedroom: King BedGuest Bedroom: King BedGuest Bedroom: Queen BedMauna Lani Beach...
KP212-Beach-AC-Pool-Gym-Oceanview-Two lanais, Spectacular View w/ W/D and AC
Relax! Condo on Kiahuna Beach! Updated Stone Countertops, cabinets, and open concept! This amazing oceanview Kiahuna condo with AC overlooking the garden/lagoon on the most beautiful resort grounds on the south shore has plenty of space for the whole family! The pool...
Hilton Pool Pass included - Lux Penthouse w/ Views
Experience the ultimate Hawaii getaway in our beautiful condo, meticulously designed to provide unparalleled comfort and luxury. Step into the welcoming open-concept living area that blends modern amenities with gorgeous furnishings, bathed in natural light that...
Cozy jungle boat hideaway with stunning ocean view TA-154-746-2656-01
The Jungle Queen is a perfect getaway for 2 or a rejuvenating hideaway for the independent traveler. You’re staying on a landlocked boat in the middle of a jungle with coqui frogs singing you to sleep each night. Relax on the deck and treat yourself to ocean views just...
Rainbow Shack :: Kauai
NEW ~ Beautiful condo nestled in the heart of Princeville. Private garage fits one mid-size car. Located on a magnificent bluff between the mountains & the sea. A 10-minute drive to world-famous Hanalei Bay, & a 10-minute walk to Hideaways beach. The condo has all the...
🏖️Complete Remodel | Stunning Ocean Views | Discount of Golf
vrKCV - Halii Kai 11D, Professionally Managed by Kona Coast VacationsWelcome to Your Island Retreat at Hali'i Kai 11DDiscover the perfect combination of modern elegance and Hawaiian charm at Hali'i Kai 11D. Nestled in an unbeatable location overlooking the Kings Golf...
Nani Kai Hale 209
Welcome to Nani Kai Hale 209. This is a completely remodeled oceanfront 1 bedroom, 2 bathroom condo stunner. Enjoy ocean views throughout this unit and from your private lanai. Feel right at home with split AC, a fully equipped kitchen, and beach gear & luxury bath...
Aloha Waikiki Condo 2Beds, 2Baths, Free Parking.
Aloha, thanks for checking in our listing. A Newly remodeled penthouse 2 bedrooms and 2 full baths. There are 4 queen beds and 1 single beds, full kitchen with kitchenette. It's spacious 1,000 sq. ft. with 2 patio and 3 Air-Con. It’s on 17 top floor with beautiful view,...
Fairway Villas @ Waikoloa Beach Resort Ground Floor Central A/C Golf Course View
You’ve landed in the most desirable location on the island. Fairway Villas is the best complex within Waikoloa Beach Resort due to its amazing views and perfect location near everything you'll want or need!Only an 18 min walk to one of the best white-SAND beaches on the...
Beautiful Hawaii!nPanoramic Ocean View, a Private Pool!
30 Days Rental!**Rates are subject to change during peak seasons, holiday and summers. Please communicate with Host for renting!Panoramic Ocean & Mountain View from Entire House.Located in central area that is close to everywhere, 5 to 10 minutes to World famous Waikiki...
Manta Suite w/ ocean view and sleeping 6 --TA-154-746-2656-01
Our newly renovated 2-story Manta Suite occupies two upper floors in a unique 3-story building that used to be a processing site for a macadamia nut farm, now converted into fun, spacious living quarters. A large shared outdoor kitchen and barbecue are just steps away....