Airbnb, Vacation Rentals in Kaupo, HI
Compare 9,678 available, short term oceanfront holiday vacation home properties, starts from $30
Navigate forward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.
Navigate backward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.
Find the best vacation rental
Save Up To 81%
Airbnb, Vacation rentals and hotel deals in Kaupo, HI
9.6 (244 reviews)
Four Seasons Resort Maui at Wailea
Resort · 2 Guests · 1 Bedroom
$1,580 /night
Gardenia Room on Tropical Lush Farm in Haiku, Maui
Farmhouse · 2 Guests · 1 Bedroom
$350 /night
10 (2 reviews)
Wailea Beach Villas PH211
Condo · 2 Guests · 1 Bedroom
$1,402 /night*
10 (1 review)
The Villas at Fairmont Kea Lani
Villa · 2 Guests · 1 Bedroom
$3,302 /night
9.4 (52 reviews)
Partial Oceanview #107 at Hana Kai Maui - 1 Bedroom (corner unit)
Condo · 2 Guests · 1 Bedroom
$450 /night*
9.4 (92 reviews)
Hotel Wailea, Relais & Chateaux - Adults Only
Resort · 2 Guests · 1 Bedroom
$999 /night
Luxurious Home in Wailea
Holiday home · 2 Guests · 1 Bedroom
$1,100 /night
Grand Champion Villa Getaway - Wailea Beaches
Apartment · 2 Guests · 1 Bedroom
$418 /night
9.0 (712 reviews)
Wailea Beach Resort - Marriott, Maui
Resort · 2 Guests · 1 Bedroom
$754 /night
8.8 (22 reviews)
AC Hotel by Marriott Maui Wailea
Hotel · 2 Guests · 1 Bedroom
$879 /night
10 (11 reviews)
Wailea Beach Villas F201 - Newly Renovated!
Condo · 2 Guests · 1 Bedroom
$2,422 /night*
9.8 (18 reviews)
Oceanfront #2 at Hana Kai Maui - Romantic Studio 100' from Water!
Condo · 2 Guests · 1 Bedroom
$485 /night*
10 (3 reviews)
Wailea Beach Villas PH306
Condo · 2 Guests · 1 Bedroom
$1,657 /night*
9.6 (19 reviews)
Oceanfront #4 at Hana Kai Maui - 1 Bedroom Upper Floor Corner 100ʻ from Water!
Condo · 2 Guests · 1 Bedroom
$525 /night*
10 (65 reviews)
Panoramic Ocean Views! - * Luxury Villa! * - Owner Direct!
Villa · 2 Guests · 1 Bedroom
$2,225 /night*
9.8 (55 reviews)
Oceanfront #5 at Hana Kai Maui - 2 BR/2 BA Upper Floor Corner 100ʻ from Water!
Condo · 2 Guests · 1 Bedroom
$765 /night*
10 (50 reviews)
Kula Luxury Retreat With Stunning Ocean & Mountain Views!
Holiday home · 2 Guests · 1 Bedroom
$1,300 /night*
Wailea Beach Villas F202
Condo · 2 Guests · 1 Bedroom
$2,422 /night*
9.0 (455 reviews)
Wailea Ekahi Village, a Destination by Hyatt Residence
Resort · 2 Guests · 1 Bedroom
$549 /night
9.6 (29 reviews)
Ocean Views & Privacy! Best Value! Modern Ekolu Remodeled Home
Condo · 2 Guests · 1 Bedroom
$338 /night*
How Does The Amenity Info Looks Like at Kaupo, HI?
Trending Vacation Rental Amenities in Kaupo, HI
+
Which Price Range Is Considered As A Good Deal in Kaupo, HI Area?
Vacation Condo & House Rental Price Information in Kaupo, HI
+
Which Accommodations Should I Pick in Kaupo, HI?
Rental Property Types in Kaupo, HI
+
How Many Accommodations Are Not Pets Friendly in Kaupo, HI?
Percentage of Pet Friendly Rental Properties in Kaupo, HI
+
What Are The Must-Visit Places in Kaupo, HI?
Tourist Attractions In Kaupo, HI
+
How Many Airports in Kaupo, HI?
Airports Options in Kaupo, HI
+
Airbnb, Holiday Oceanfront Condo with Pool, and Other Rental Options in Kaupo, HI
Pool
10 (11 reviews)
Wailea Beach Villas F201 - Newly Renovated!
Condo · 2 Guests · 1 Bedroom
$2,422 /night*
Pool
10 (8 reviews)
Wailea Beach Villas PH209
Condo · 2 Guests · 1 Bedroom
$1,742 /night*
Pool
9.6 (29 reviews)
Ocean Views & Privacy! Best Value! Modern Ekolu Remodeled Home
Condo · 2 Guests · 1 Bedroom
$338 /night*
Airbnb, Vacation House with Full Kitchen, and Other Rental Options in Kaupo, HI
Full Kitchen
9.6 (102 reviews)
Hana's Luxurious 'Ohana Cottage for Peace, Quiet, and Nature
Cottage · 2 Guests · 1 Bedroom
$355 /night*
Full Kitchen
9.8 (153 reviews)
IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'
Holiday home · 2 Guests · 1 Bedroom
$350 /night*
Full Kitchen
10 (50 reviews)
Kula Luxury Retreat With Stunning Ocean & Mountain Views!
Holiday home · 2 Guests · 1 Bedroom
$1,300 /night*
* The displayed nightly rate may be estimated based on a future travel date. Narrow down your search with checkin and checkout dates to see the exact price.