Best Vacation Homes in Wailuku
Condo
10.0(195 Reviews)
2 Bedrooms
2 Baths
4 Guests
980 ft²
Oceanfront
Hot Tub
Pool
Ocean View
US $399/Night
7 Nights - US $2,790
Apartment
10.0(23 Reviews)
2 Bedrooms
2 Baths
5 Guests
979.52 ft²
- Oceanfront
Fireplace/Heating- Pool
- Ocean View
US $817/Night
7 Nights - US $5,716
Bed & Breakfast
10.0(56 Reviews)
1 Bedroom
1 Bath
Balcony/Terrace
Breakfast
Kitchen
Parking
US $275/Night
7 Nights - US $1,925
Condo
10.0(180 Reviews)
2 Bedrooms
2 Baths
4 Guests
950 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $481/Night
7 Nights - US $3,365
Apartment
10.0(3 Reviews)
2 Bedrooms
2 Baths
6 Guests
882.64 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $349/Night
7 Nights - US $2,443
Condo
10.0(178 Reviews)
2 Bedrooms
2 Baths
6 Guests
878 ft²
Private Pool- Oceanfront
- Pool
- Ocean View
US $523/Night
7 Nights - US $3,661
Condo
10.0(156 Reviews)
1 Bedroom
1 Bath
2 Guests
565 ft²
- Pool
- Ocean View
- Balcony/Terrace
View
US $361/Night
7 Nights - US $2,524
Condo
10.0(151 Reviews)
2 Bedrooms
2 Baths
4 Guests
1000 ft²
- Pool
- Ocean View
- Balcony/Terrace
- View
US $475/Night
7 Nights - US $3,324
Wailuku Luxury Rentals
House
10 Bedrooms
10 Baths
20 Guests
6500 ft²
- Balcony/Terrace
- Breakfast
- Kitchen
- Parking
US $4,939/Night
7 Nights - US $34,572
Condo
1 Bedroom
1 Bath
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $1,566/Night
7 Nights - US $10,963
Condo
10.0(4 Reviews)
3 Bedrooms
2 Baths
8 Guests
1700 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $1,510/Night
7 Nights - US $10,572
House
3 Bedrooms
2 Baths
8 Guests
1248.61 ft²
- Oceanfront
- Pool
- Ocean View
- View
US $1,295/Night
7 Nights - US $9,065
House
10.0(1 Review)
4 Bedrooms
3 Baths
8 Guests
3000 ft²
- Balcony/Terrace
- Kitchen
Air Conditioner
Internet
US $1,289/Night
7 Nights - US $9,026
Condo
4 Bedrooms
3 Baths
10 Guests
2950 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $1,223/Night
7 Nights - US $8,562
House
3 Bedrooms
2 Baths
8 Guests
1216.32 ft²
- Pool
- Parking
- Air Conditioner
- Internet
US $1,136/Night
7 Nights - US $7,952
House
9.2(36 Reviews)
4 Bedrooms
3 Baths
8 Guests
2000 ft²
- Oceanfront
- Ocean View
- View
- Kitchen
US $1,134/Night
7 Nights - US $7,940
Wailuku Pet Friendly Vacation Rentals
Apartment
10.0(3 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $401/Night
7 Nights - US $2,805
House
6.9(87 Reviews)
6 Bedrooms
6 Baths
12 Guests
95.08 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $118/Night
7 Nights - US $828
Apartment
1 Bedroom
1 Bath
4 Guests
- Pool
Pet Friendly- Kitchen
- Parking
US $297/Night
7 Nights - US $2,077
Condo
2 Bedrooms
2 Baths
4 Guests
884 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $165/Night
7 Nights - US $1,158
Wailuku Large Vacation Homes
House
10.0(3 Reviews)
5 Bedrooms
5 Baths
2 Guests
275 ft²
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $416/Night
7 Nights - US $2,909
House
10.0(1 Review)
3 Bedrooms
4 Baths
12 Guests
785.77 ft²
- Oceanfront
- Hot Tub
- Ocean View
- View
US $523/Night
7 Nights - US $3,661
Villa
8.8(3 Reviews)
3 Bedrooms
1 Bath
5 Guests
1360 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $412/Night
7 Nights - US $2,881
House
8.5(68 Reviews)
11 Bedrooms
20 Baths
40 Guests
686.93 ft²
- Balcony/Terrace
- View
- Parking
- Air Conditioner
US $555/Night
7 Nights - US $3,884
Villa
2 Bedrooms
1 Bath
4 Guests
870 ft²
- Oceanfront
Spa- Ocean View
- Balcony/Terrace
US $552/Night
7 Nights - US $3,866
House
2 Bedrooms
5 Baths
12 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $1,714/Night
7 Nights - US $11,997
House
5 Bedrooms
4 Baths
12 Guests
- Hot Tub
- Fireplace/Heating
- Kitchen
- Parking
US $1,955/Night
7 Nights - US $13,684
House
4 Bedrooms
6 Baths
15 Guests
- Breakfast
- Air Conditioner
- Internet
Child Friendly
US $2,697/Night
7 Nights - US $18,881
Why Choose Rent By Owner for your Wailuku Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Popular Areas for Wailuku Vacation Rentals
Where are the best neighborhoods to stay in Wailuku?
When exploring the charming town of Wailuku, Hawaii, choosing the right neighborhood to stay in can greatly enhance your vacation experience. The area offers a variety of neighborhoods, each with its own unique character and convenience, whether you're seeking close proximity to local markets or a peaceful retreat away from bustling streets. Staying in a well-selected neighborhood ensures easy access to Wailuku’s rich cultural heritage and natural beauty, making your visit both comfortable and memorable. Trustworthy vacation rentals in Wailuku provide a seamless booking process, helping you find the ideal location to enjoy everything this historic town has to offer.
Wailuku Heights
Perched in a scenic part of the region, this neighborhood offers tranquil surroundings and easy access to the natural beauty characteristic of the area. Here, you can find vacation rentals that provide a peaceful retreat while still being close to local attractions.
View 117+ Rentals in Wailuku HeightsUkumehame Ahupuaa
Located along the coast, this community presents an ideal setting for relaxing by the water and exploring the nearby landscapes. The vacation rentals available here serve as a convenient base for experiencing the authentic charm of the region.
View 383+ Rentals in Ukumehame AhupuaaBest Times to Visit Wailuku
When should you plan your Vacation Rentals stay?
Choosing the right time to vacation in Wailuku, Hawaii, can enhance your experience by aligning with the region’s mild climate and local festivities, making it ideal for a memorable stay in this inviting destination.
Peak Season Highlights
December to April
This is the most popular time to visit the area, with warm days and inviting evenings perfect for exploring outdoor activities and enjoying the scenic beauty. During these months, you can expect higher demand for vacation rentals.
Average Temperature Daytime: around 80°F - Nighttime: approximately 65°F
June to August
Summer here attracts travelers seeking sunny weather and optimal conditions for outdoor adventures. The region's vibrant atmosphere peaks during these months, making it an ideal period for securing desirable accommodations.
Average Temperature Daytime: about 85°F - Nighttime: roughly 70°F
Off-Season Highlights
April to June
Before the summer rush, this timeframe offers a quieter experience with pleasant weather, providing excellent opportunities for relaxing stays at your chosen vacation rentals without the crowds.
Average Temperature Daytime: around 78°F - Nighttime: about 63°F
September to November
Post-summer, the region sees fewer tourists, offering a more peaceful environment while still enjoying mild temperatures. It’s a great time to find deals on vacation rentals and explore at a leisurely pace.
Average Temperature Daytime: roughly 80°F - Nighttime: approximately 67°F
Weekly Weather Forecast for Wailuku
How to Book Your Wailuku Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Wailuku
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor dining area for meals with scenic views of the surrounding landscape.
- Take advantage of well-maintained barbecue grills perfect for outdoor cooking during your stay.
- Relax by a sparkling swimming pool, ideal for cooling off in the warm Hawaiian climate.
- Make use of lush, landscaped gardens that provide tranquil outdoor spaces to unwind.
- Benefit from shaded sitting areas or patios to enjoy the fresh air and island breezes.
- Utilize dedicated outdoor recreational facilities such as tennis courts or volleyball areas.
- Experience the beauty of nearby outdoor trails and walking paths accessible directly from the property.
Top Attractions Around Wailuku
What attractions are nearby?
Within this charming region, you can explore a variety of outdoor activities, cultural sites, and local attractions that showcase the unique beauty and heritage of Wailuku, Hawaii, ensuring your stay here is filled with memorable experiences.
Family Activities
- Hale Ho’ikeike: Discover this cultural center where your family can learn about Hawaiian history and traditions through engaging exhibits and demonstrations.
- Wailuku Old Courthouse: Explore the historic courthouse to appreciate the region’s architectural heritage and enjoy a family-friendly walk around its charming surroundings.
- Iao Valley State Park: Hike through lush scenery to see the iconic Iao Needle, offering an accessible adventure that promises memorable nature experiences for all ages.
- Kahului Harbor Tours: Embark on boat excursions from the harbor to enjoy scenic views of the coastline, perfect for creating lasting family memories in the area.
Adult Activities
- Exploring Iao Valley State Park: Discover lush landscapes and scenic hiking trails in this iconic park, offering a serene escape into the natural beauty of the region.
- Visiting Maui Historical Society Museum: Immerse yourself in the area's rich history through engaging exhibits that showcase local culture and heritage.
- Enjoying Local Cuisine at Wailuku Town: Savor authentic flavors at charming eateries and food spots that highlight the culinary diversity of this destination.
- Participating in Cultural Festivals: Experience vibrant celebrations and community events that offer insight into the traditions and spirit of the area.
Other Places to Stay in Wailuku, HI
Turnbull Studios & Sculpture Garden
Kahakuloa Beach
Kahakuloa
Nakalele Blow Hole
Maui Ocean Center
Ohai Viewpoint
Maalaea Harbor
Kahili Golf Course
Maalaea
Wailuku Heights
Waihee-Waiehu
Central Maui
Wailuku Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Markets: Visit nearby markets to experience authentic flavors and find unique souvenirs that reflect the region's vibrant culture.
- Enjoy Outdoor Activities: Take advantage of the area's scenic parks and trails for outdoor adventures that showcase the natural beauty here.
- Discover Hidden Gems: Ask locals or your vacation rental host about lesser-known spots to get an off-the-beaten-path perspective of this destination.
- Plan Your Day Strategically: Use the area’s quiet mornings to visit popular attractions with fewer crowds, ensuring a more relaxed experience during your stay.
Transportation Options
- Rental Car Services: You can easily explore the area and its surrounding attractions with rental cars available from local providers, offering flexibility during your stay.
- Public Transit: The regional bus system provides a budget-friendly and convenient way to get around this destination without the need for a car.
- Taxi and Ride-Sharing: Taxis and ride-sharing options are readily available here, making short trips within the region quick and hassle-free.
- Bike Rentals: For a scenic and environmentally friendly experience, bike rentals offer an enjoyable way to navigate the local streets and trails.
Local Customs Options
- Respect for the Aloha Spirit: Embrace the local culture by practicing kindness, hospitality, and respect, which are core to the welcoming atmosphere here.
- Observing Hawaiian Traditions: Participate in or observe local customs such as the traditional Luau to gain a deeper understanding of the region’s rich cultural heritage.
- Environmental Respect: Follow eco-friendly practices by respecting natural sites and minimizing your impact on the environment during your visit to this destination.
- Honor Native Practices: Show reverence for native Hawaiian customs, including appropriate etiquette when engaging with local community members and cultural sites.
Wailuku Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Wailuku?
There are a lot of options in Wailuku. If you plan on staying in the Wailuku area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Wailuku:
- Amazing Oceanfront Condo, Tropical Luxury, Great Value, 2 BR, 2 Bath
- Super Luxury, Direct Oceanfront, 20 yards From Ocean, Whale Watchers Paradise
- Ma'alaea Kai 110 - Spectacular Oceanfront PLUS Mountain View/Quiet Setting
- BEAUTIFUL OCEANFRONT CONDO* EXCELLENT VIEW* PERFECT LOCATION & A/C
- Beautifully Upgraded, Beachfront, Ground Floor.Dream Vacation! #118
- Perfect getaway for couples for honeymoon or anniversary.
- Relaxing Ocean Front Views on Maui! Island Sands Condominium
- Spectacular Wall of Glass!
- Five Star Inspired JULY/AUGUST SPECIAL
- OCEANFRONT Create Forever Memories, Panoramic Views; 2 bdrm, 2 bath, Central A/C
2. How many vacation rentals have private pools in Wailuku?
There are 36 vacation rentals with private pools near Wailuku. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Wailuku are best for families?
If you are looking for a family-friendly vacation home in Wailuku, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Wailuku:
4. How many Rentbyowner vacation rentals are available in Wailuku?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 625 in the Wailuku area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Wailuku.
5. What is the cancellation policy for vacation rentals in Wailuku, Hawaii?
Cancellation policies vary by property rental. You should review the specific listing details or contact the property owner directly to understand the terms and any associated fees before booking.
6. Are there any additional fees when booking a vacation rental in Wailuku?
Additional fees such as cleaning fees, service charges, or taxes are typically outlined in the listing details. It's important to carefully review these charges during the booking process or reach out to the host for clarification.
7. How do I ensure my reservation for a vacation rental in Wailuku is secure?
Your reservation security depends on following the platform's booking procedures. Confirm your payment through the secure checkout, and communicate with the property owner through verified channels to safeguard your booking.
8. Can I modify or cancel my reservation if my plans change?
Modification or cancellation options depend on the individual property's policies. Make sure to check the specific listing’s terms or contact the host directly for guidance before confirming your reservation.
9. What amenities should I expect in vacation rentals here?
Amenities can vary, but typical features include a fully equipped kitchen, Wi-Fi, and outdoor spaces. Review the property listing thoroughly to ensure it meets your needs, or contact the owner for additional details.
Wailuku Top Rated Vacation Rentals
Condo
10.0(136 Reviews)
1 Bedroom
1 Bath
4 Guests
- Pool
- Ocean View
- Balcony/Terrace
- View
US $371/Night
7 Nights - US $2,599
Condo
10.0(135 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Pool
- Ocean View
- Balcony/Terrace
- View
US $558/Night
7 Nights - US $3,906
Condo
10.0(131 Reviews)
2 Bedrooms
2 Baths
4 Guests
1200 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $338/Night
7 Nights - US $2,364
Condo
10.0(120 Reviews)
2 Bedrooms
2 Baths
4 Guests
1088 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $560/Night
7 Nights - US $3,923
Condo
10.0(114 Reviews)
2 Bedrooms
1 Bath
3 Guests
600 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
US $284/Night
7 Nights - US $1,986
Condo
10.0(109 Reviews)
1 Bedroom
1 Bath
4 Guests
591 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $329/Night
7 Nights - US $2,302
Condo
10.0(104 Reviews)
2 Bedrooms
2 Baths
6 Guests
979 ft²
- Pool
- Ocean View
- Balcony/Terrace
- View
US $338/Night
7 Nights - US $2,368
Condo
10.0(102 Reviews)
1 Bedroom
1 Bath
4 Guests
570 ft²
- Private Pool
- Hot Tub
- Pool
- Ocean View
US $352/Night
7 Nights - US $2,463
