Wailea, Wailea-Makena vacation rentals
Book unique homes, vacation rentals, and more on Airbnb
Top-rated vacation rentals in Wailea, Wailea-Makena
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Wailea, Wailea-Makena vacation rentals
Stay near Wailea, Wailea-Makena's top sights
Other great vacation rentals in Wailea, Wailea-Makena
Condo in Kihei
4.95 out of 5 average rating, 130 reviewsRenovated! Just 3 Min Walk to Toes in the Sand
Apartment in Kihei
4.9 out of 5 average rating, 157 reviewsClassic Beachfront Studio
Condo in Kihei
4.99 out of 5 average rating, 147 reviewsMana Kai 608: Oceanfront Remod- Modern Surf Vibe!
Condo in Kihei
4.95 out of 5 average rating, 144 reviewsNewly Renovated Beach Condo
Condo in Kihei
4.94 out of 5 average rating, 198 reviewsMana Kai Maui - Oceanfront Condo in Kihei
Condo in Kihei
4.99 out of 5 average rating, 131 reviewsMaui Dream Place at Maui Kamaole G-209, Ocean View
Condo in Kihei
4.96 out of 5 average rating, 226 reviewsBeautiful Modern Decor in a Light-Filled Condo
Condo in Kihei
4.9 out of 5 average rating, 298 reviewsEverything you need to enjoy true paradise!
Wailea, Wailea-Makena home rentals
Home in Kihei
4.98 out of 5 average rating, 102 reviewsMana Hale Vacation Rental
Home in Kihei
4.97 out of 5 average rating, 133 reviews12 Minute Walk to Kam Beach II-Quiet Private Easy
Home in Kihei
4.96 out of 5 average rating, 209 reviewsSouth Maui Guesthouse
Home in Kihei
4.87 out of 5 average rating, 132 reviewsCajudoy's Hale - STKM 2O13-OO18/TA-081-709-8752-01
Home in Kihei
4.94 out of 5 average rating, 203 reviewsThe Maui Beach Ohana• Prime Location• Maui Vibes
Home in Paia
4.91 out of 5 average rating, 178 reviewsPaia cottage walk to town and beach
Home in Wailuku
4.92 out of 5 average rating, 134 reviewsGratitude Bed and Breakfast BBWK2022/0001
Home in Lahaina
4.91 out of 5 average rating, 127 reviewsKaanapali Cottage ICC 29 Indoor/Outdoor Living
Wailea, Wailea-Makena cottage rentals
Cottage in Kula
4.96 out of 5 average rating, 332 reviewsHALEKALANI - Paradise in Upcountry
Cottage in Wailuku
4.97 out of 5 average rating, 161 reviewsNewly Renovated Modern Cottage; Walk into Town!
Cottage in Haiku-Pauwela
4.94 out of 5 average rating, 205 reviewsGreat Location, 1 BR Beachy, VERY CLEAN Cottage
Cottage in Kihei
4.96 out of 5 average rating, 25 reviewsPrivate 2 bedroom cottage with pool
Cottage in Kihei
4.98 out of 5 average rating, 48 reviewsMaui Meadows Ocean View Cottage
Cottage in Kihei
4.83 out of 5 average rating, 69 reviewsTropical Getaway: Maui's Best - Honeymoon Suite
Cottage in Haiku-Pauwela
4.99 out of 5 average rating, 75 reviewsLeilani's "Leimomi" Cottage - County Licensed
Cottage in Haiku-Pauwela
4.99 out of 5 average rating, 75 reviewsHo'okipa Rose - Peace and Serenity
Quick stats about vacation rentals in Wailea, Wailea-Makena
Total rentals
1.9K properties
Rentals with dedicated workspaces
960 properties have a dedicated workspace
Rentals with a pool
1.7K properties have a pool
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
1.1K properties are a good fit for families
Total number of reviews
43K reviews
Destinations to explore
- Condo rentals Wailea
- Rentals with a sauna Wailea
- Fitness-friendly rentals Wailea
- Villa rentals Wailea
- Waterfront rentals Wailea
- Kid-friendly rentals Wailea
- Serviced apartment rentals Wailea
- Rentals with pools Wailea
- House rentals Wailea
- Monthly Rentals Wailea
- Wheelchair accessible rentals Wailea
- Rentals with an EV charger Wailea
- Beachfront rentals Wailea
- Rentals with a hot tub Wailea
- Apartment rentals Wailea
- Rentals with a patio Wailea
- Townhouse rentals Wailea
- Beach house rentals Wailea
- Family-friendly rentals Wailea
- Hotel rentals Wailea
- Rentals with a washer and dryer Wailea
- Cottage rentals Wailea
- Rentals with beach access Wailea
- Rentals with outdoor seating Wailea
- Beach condo rentals Wailea
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes