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.
Charming Studio In Waikiki - Minutes to the Beach!
Construction Notice 5/30/25: Spall repairs are currently underway on the mountain-side units. Please be aware that construction noise may occur between 8 AM and 4 PM. Access to the lanai will be restricted from late August to early October. The project is expected to be...
Stylish Studio w/ Great Ocean Views & Near Beach!
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...
Exquisite condo situated on Kaanapali Beach
Welcome to Kaanapali Shores 223, a 2-bedroom, 2-bathroom condo that offers central A/C, a private washer/dryer, and high-speed Wi-Fi. This property has elevators. Unit 223 can accommodate up to 6 guests. The master bedroom is a tranquil retreat, offering a king-sized...
Oceanview, Renovated and Gated, Private Lanai
Beautiful ocean views greet you upon entering this 3rd floor unit at Lae Nani. Recently renovated with a fresh and light decor and new laminate floors in May 2025! This 1 bedroom, 1.5 bath unit with comfy King Sized Bed has a lanai out front to enjoy that oceanview...
Hale Hui Kai 102 on Keawakapu Beach
This private garden condo is on the first floor of the south side of the building ...about 60 steps along the pathway leads to the gem of south Maui, Keawakapu Beach!Keawakapu Beach, located on the south shore of Maui, Hawaii, is known for its stunning natural beauty...
Legal Short Term on North Shore Oahu, Upper Floor - Kuilima Estates
We welcome short term rentals Welcome to this nicely updated two bedroom condo located on the peaceful East side of Kuilima Estates at Turtle Bay. The condo features brand new tile flooring in the living room and kitchen along with new kitchen cabinetry!This unit has a...
Emmalani Court 523 By Parrish Kauai - Great views & Princeville Location
Enjoy this luxurious Kauai condo next to the Makai Golf Course at Princeville Resort. This small resort features only 42 units, pool, spa and outdoor barbecue area. Conveniently located near our North Shore office at the Princeville Resort Center. Stop by and meet our...
Kauai 2 BR/2 BA Condominium Oceanfront - Pono Kai Resort!
Enjoy beautiful sunrises and all the luxuries that accompany beach side living. This two-bedroom ground floor condominium in Pono Kai is steps from a mile-long, sandy beach. This beautiful condominium has been privately owned, cared for, and enjoyed by us for many...
Ali'i Point Spacious and Private Oceanfont Villa with A/C.
Ali'i Point #5 is located at Ali'i Point, a private and gated community of 16 seaside homes with community pool and tennis court.Central A/C throughout. Main floor has living room, dining room, kitchen, half bath, and master king bedroom with en suite bathroom.Large...
Top floor-quiet, 3 min walk to beach, Espresso machine, pool/ fitness, HBO
Feel like living in a treehouse…Quiet, top flor location, lots of special features *** Pls note that from Jan1st, 2024, for stays the end cleaning fee for each unit 1 BR is $ 268.00 plus Tax. For stays of 10 nights or more, an additional mid-stay replenishment fee per...
KONA MAGIC SANDS#309 TOP FLOOR DIRECT BEACHFRONT, AIR CONDITIONING!!
*LOOK NO FURTHER! YOU HAVE FOUND AN INCREDIBLE PROPERTY!**Kona Magic Sands#309 is a DIRECT oceanfront, Top floor condo that is meticulously maintained, beautifully furnished, and has absolutely anything any guest could dream of. Air Conditioning, Wifi, beach gear,...
BEAUTIFUL.... Keauhou Ocean View Condo
Capture the essence of Hawaii with ever present ocean view, trade winds, palm trees , birds, and lovely flowers. All things Hawaii. The condo is filled with natural light and always present ocean breezes eliminate the need for air conditioning! This ”bridge unit” is...
White Sands Village #120
Summary:Say aloha to your Big Island vacation rental! White Sands Village is an oceanfront condo complex in the gorgeous town of Kailua-Kona. Maximum occupancy strictly enforced in accordance with local ordinances.The Space:Guests will find themselves in the perfect...
Honu Cottage: Quiet, Oceanfront Comfort + EPIC VIEWS!
WE ARE LITERALLY ON THE WATER! E Komo Mai (Welcome) to Paradise!one rental per 30 day period as required by city & county law Honu Hale is a charming island-style cottage that sleeps 3 adults or 2 adults and 2 children. A cozy loft bedroom has a comfortable king size...
Second floor, Great Ocean view #260
Great second floor unit , with Ocean views, and views of the garden This is are little peace of paradise, pool and spa tiki bar This studio has newqueen bed , mini fridge, BBQs , full bathroom, microwave , coffee maker, dishes for four complete BBQs set , This condo is...
Oceanfront ground-floor condo with amazing views, pool, & full kitchen -walkable
Kapa'a Sands 12Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This boutique establishment is right on the ocean, enveloped in lush tropical gardens with everything you need for your...
Poipu Makai Villas C1 - Amazing Views, Ocean Front, AC
POIPU MAKAI C1 AT KOLOA KAI VACATION RENTALSYour Oceanfront Oasis on Kauai’s South ShoreDiscover unparalleled tranquility and breathtaking ocean views at Poipu Makai C1, an exclusive oceanfront condo perched on a bluff overlooking the vibrant blue Pacific. With only...
INCREDIBLE OCEAN VIEW! A/C, Wi-Fi, Pool, FREE Valet Parking, Steps to Beach!
Waikiki Beach Tower #1904 – 2470 Kalakaua Ave.If you'd like to be directly across the street from the best swimming and surfing beach in Waikiki, then this two-bedroom, two-bath Waikiki Beach Tower condo with 1092 sf interior living space and a large (171 sf)...
Kaha Lani Resort #114, Ocean View, Steps to Beach, Sunrise, Pool/Wi-fi
Kaha Lani Resort #114, Beachfront Resort, Wailua, Kauai. Ocean view, ground floor end unit on a beachfront resort. Surrounded by parks, a golf course and the ocean. Beach towels, beach chairs, beach umbrella and a small cooler are provided for your use during your stay....
Updated 1-bed, 1.5-bath with mountain views near beaches and dining
Be our guest at The Shores, on the sunny Waikoloa Resort coast. This one-bedroom one-and-a-half-bath, newly updated condo features a fully stocked kitchen, sweeping mountain views, and close proximity to numerous white sand beaches. Enjoy a multitude of dining options,...
Perch - Kamaole Beach Club: Oceanview upgraded one bedroom, walk to beach
Walk across the street to the best beach in Maui! This ocean view ground floor condo is the best location in the complex. Nicely updated in 2022, this one bedroom unit features travertine floors, crown molding, granite kitchen counters in the kitchen, stainless steel...
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...
Fantastic Beach Front Villa
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...
Spacious and Peaceful Corner Unit at Fairway Villas
Please note, effective Jan 1st. 2026, Hawaii's Transient Accommodations Tax will increase from 10.25% to 11% for all stays with an arrival in 2026 forward. We may need to collect the tax difference to secure and finalize your booking. We will contact you to confirm the...
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...
Kiahuna 106 - Ocean View, Close to World-Class Beach, Poipu Beach Club Included
KIAHUNA PLANTATION 106 AT KOLOA KAI VACATION RENTALSOcean-View Condo in the Heart of Poipu’s Tropical ParadiseNestled on 35 acres of lush lawns and tropical gardens, Kiahuna Plantation 106 offers the perfect combination of history, charm, and modern comforts. This...
Maui Resort Rentals: Honua Kai Konea 1022 - Top-Floor 1BR w/ Partial Ocean AND West Maui Mountain Views
Konea 1022 is a luxurious 10th-floor "penthouse" one-bedroom suite that offers partial ocean views along with expansive vistas of The West Maui Mountains. The suite is ideally suited for small families and couples who are looking for luxurious and spacious...
Nihi Kai 510 - Garden w/ Ocean Peek View/AC/Walk to Beaches
NIHI KAI 510 AT KOLOA KAI VACATION RENTALSYour Garden View Escape in the Heart of PoipuWelcome to Nihi Kai 509, a beautifully updated 2-bedroom, 2-bathroom condo in the heart of Poipu. Located within walking distance to Brennecke’s Beach and Poipu Beach, this charming...
Oceanfront 2BD/2BA Sugar Beach Tranquility at Koa Lagoon
For the sun worshiper South Maui is the driest, hottest, and most popular coastline on the island. One glance at the 180 degree view from this beautiful, tranquil spot with its spacious 2 bedroom/2 bath condo at Koa Lagoon and you know you have the perfect spot for your...
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, offering an idyllic retreat for families and groups. This home has a breathtaking views of the golf course and majestic mountains, with easy access to sandy beaches,...
Ground floor condo w/ lanai, shared pools, & hot tub - near beaches & golf
Honua Kai - Hokulani 110Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Welcome home to this nicely updated, bright, and spacious condo located in the heart of Ka'anapali. Enjoy your...
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
This 2-bedroom, 2-bath villa in the Konea Building offers stunning ocean views, a spacious lanai, and modern comforts. Enjoy a gourmet kitchen, relaxing living space, and access to resort amenities.** Limited Time Special Offer: Reserve any KBM Resorts property in...
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
Please note, effective Jan 1st. 2026, Hawaii's Transient Accommodations Tax will increase from 10.25% to 11% for all stays with an arrival in 2026 forward. We may need to collect the tax difference to secure and finalize your booking. We will contact you to confirm the...
Private Banana Tree Cottage with Ocean Views
Aloha and welcome to our private banana tree house. Experience a peaceful, unique cottage with spectacular ocean & lush tropical valley views. The cottage floats above and overlooks an operating organic banana orchard. Gated in a 20 acre estate, with majestic royal...
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...
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...
Kihei Akahi A102: Maui Ocean Front Town House - Location, Location, Location!!!
Oceanfront Townhouse in Kihei on the beautiful island of Maui – Totally Renovated Aloha: We are the owners of Kihei Akahi A-102, a beautiful upscale Townhouse, steps from Kamaole Beach II in the wonderful and affordable Kihei Akahi development in South Maui, the...
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...
Poipu Ohana Vista - Spacious Home Near Beaches, Community Pool Access
POIPU OHANA VISTA AT KOLOA KAI VACATION RENTALSExperience the essence of Kauai’s beauty and relaxation at Poipu Ohana Vista, a spacious and versatile home ideally located between Poipu Beach and Shipwreck Beach. With breathtaking views of sunrises and sunsets just...
Oceanfront TownHome Upgraded 2 BR, 2.5BA Fully Air Conditioned
Poipu Shores 104C is a fully-oceanfront, 2-story, 2-bedroom townhome with two lanais and complete air conditioning. A fully oceanfront townhome is a rarity on the south shore of Kauai, doubly so for an air conditioned one! It is an exquisite choice for an unforgettable...
Luana Kai Resort D306
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. ...
Waikiki Sunset City & Mountain View w/ 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...
Beachfront Oasis: Kihei Beach #303, Your Retreat with Breathtaking Ocean Views!
A Note from the Owners: As true Maui lovers, we've created a space in Unit #303 that feels like home. The newly remodeled kitchen is fully equipped for our personal use, and we've updated the living room and bathroom for added comfort. You'll find a beautiful underwater...
Beach Gear Incl. Just add Sun & Fun. nA/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...
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...