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
4.99 out of 5 average rating, 143 reviewsMana Kai 608: Oceanfront Remod- Modern Surf Vibe!
Sep 2 – 9
Condo in Kihei
4.85 out of 5 average rating, 308 reviews1 minute to Beach & Downtown! Remodeled XL Apt!
Oct 6 – 13
Condo in Lahaina
4.96 out of 5 average rating, 140 reviews❤️Best Views on Maui! Perfect for Honeymooners!!❤️
Aug 9 – 16
Condo in Kihei
4.99 out of 5 average rating, 130 reviewsLuxury condo • 180° Ocean Views • Steps to Beach
Feb 2 – 9
Condo in Kihei
5.0 out of 5 average rating, 163 reviewsCozy Beach Condo Ocean & Mountain View’s
Jan 1 – 8
Condo in Kihei
4.94 out of 5 average rating, 198 reviewsMana Kai Maui - Oceanfront Condo in Kihei
Mar 6 – 13
Condo in Wailuku
4.94 out of 5 average rating, 162 reviewsRare Beachfront Ground floor Oceanview from Lanai!
Sep 1 – 8
Condo in Kihei
4.86 out of 5 average rating, 432 reviewsAmazing views at Oceanfront Studio
Oct 12 – 19
Wailea, Wailea-Makena home rentals
Home in Kihei
4.98 out of 5 average rating, 102 reviewsMana Hale Vacation Rental
Sep 7 – 14
Home in Kihei
4.97 out of 5 average rating, 132 reviews12 Minute Walk to Kam Beach II-Quiet Private Easy
Jan 8 – 15
Home in Kihei
4.87 out of 5 average rating, 130 reviewsCajudoy's Hale - STKM 2O13-OO18/TA-081-709-8752-01
Apr 19 – 26
Home in Kihei
4.96 out of 5 average rating, 207 reviewsSouth Maui Guesthouse
Jan 20 – 27
Home in Haiku-Pauwela
4.99 out of 5 average rating, 116 reviewsCharming Hoku Pauwela Breathtaking ocean views!
Jul 20 – 27
Home in Kihei
4.93 out of 5 average rating, 199 reviewsThe Maui Beach Ohana• Prime Location• Maui Vibes
Mar 4 – 11
Home in Paia
4.91 out of 5 average rating, 176 reviewsPaia cottage walk to town and beach
Nov 11 – 18
Home in Haiku-Pauwela
4.96 out of 5 average rating, 198 reviewsHaiku Hale Aloha
Sep 25 – Oct 2
Wailea, Wailea-Makena condominium rentals
Condo in Kihei
4.95 out of 5 average rating, 120 reviewsLuxury Vacationing Modern Condo May Specials $249
May 4 – 11
Condo in Kihei
4.92 out of 5 average rating, 189 reviewsBeautiful & clean condo w/ excellent location
Sep 25 – Oct 2
Condo in Kihei
4.95 out of 5 average rating, 129 reviewsModern Condo. Just 3 Min Walk to Toes in the Sand
Oct 13 – 20
Condo in Kihei
4.82 out of 5 average rating, 118 reviews*UPDATED* Wailea Condo in Oceanfront Complex!!
Jul 3 – 10
Condo in Kihei
4.99 out of 5 average rating, 130 reviewsMaui Dream Place at Maui Kamaole G-209, Ocean View
Jan 23 – 30
Condo in Kihei
4.91 out of 5 average rating, 211 reviewsGorgeous Getaway on the Beach
Apr 9 – 16
Condo in Wailea
4.93 out of 5 average rating, 144 reviewsStunning ocean view! 2/2 in the heart of Wailea
Nov 10 – 17
Condo in Kihei
4.88 out of 5 average rating, 110 reviewsMaui Vista Air-Conditioned Condo Across from Beach
May 23 – 30
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
- Townhouse rentals Wailea
- Condo rentals Wailea
- Monthly Rentals Wailea
- Beach house rentals Wailea
- Fitness-friendly rentals Wailea
- Rentals with an EV charger Wailea
- Rentals with outdoor seating Wailea
- House rentals Wailea
- Rentals with a washer and dryer Wailea
- Rentals with pools Wailea
- Kid-friendly rentals Wailea
- Hotel rentals Wailea
- Villa rentals Wailea
- Rentals with a hot tub Wailea
- Waterfront rentals Wailea
- Rentals with a patio Wailea
- Pet-friendly rentals Wailea
- Serviced apartment rentals Wailea
- Wheelchair accessible rentals Wailea
- Beachfront rentals Wailea
- Cottage rentals Wailea
- Family-friendly rentals Wailea
- Rentals with beach access Wailea
- Apartment rentals Wailea
- Beach condo rentals Wailea
- 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