Help on Feeds

Vacation Rentals in Wailea, Hawaii

$114 $182 5
about Wailea

Wailea, Hawaii Vacation Rentals and Tourism

Unless you’re planning to book one of the Wailea vacation rentals found here, be prepared to cash in all your savings for a trip to South Maui. This beautiful part of Hawaii is a favorite spot for beachgoers and golfers, because the weather simply couldn’t be better here – but that also means plenty of fancy restaurants and upscale resorts are eager for you to spend money on them. If you want to enjoy all that Wailea has to offer and still stay within budget, turn to Wailea beach rentals!

Just south of Wailea is Makena Beach, which is ideal for swimming! The Wailea Beach Walk is also a must-see and must-do; take a stroll along this mile-and-a-half long stretch of land and catch glimpses of boogie boarders, swimmers, boaters, and maybe even whales! In addition to the amazing beaches, a Wailea vacation rental comes in handy because of the area’s equally amazing golf courses. Since the championship courses are so expensive, it’s a good idea to save money with a vacation rental in Wailea, HI. Enjoy the same convenience and wonderful location of a resort hotel, without spending all your dough! Don't forget that your Wailea beach vacation rental will likely feature a full kitchen, so there's no reason to waste money in restaurant after restaurant. Wailea vacation rentals have made it easier than ever for regular Joes to visit South Maui; in the past, when hotels ruled, only the wealthiest could vacation here.

But just because you’re saving money, doesn’t mean you have to deny yourself luxury. It’s not hard to find a great Wailea luxury beach condo for your family getaway or romantic honeymoon!

No matter what you’re looking for – monthly vacation house rentals in Wailea, Maui, or pet-friendly beachfront condos, or cheap, casual villas, better look here, before you look anywhere else. A great deal and a great vacation await you in Wailea!

Wailea Vacation Rental Deals

If you're lucky enough to be coming to Wailea for you next vacation, you are in for a huge savings on your Wailea rental home. Stay in an affordable Wailea vacation condo, villa, or beach house that is not only spacious but budget-friendly. Wailea vacation rentals accommodate any size group, so bring the whole family or just come get away with that special someone. No matter who you're with, we don't want you worrying about money, so that's why you can get a good deal even last minute on Wailea vacation rentals. Every vacation will cost, but staying in Wailea vacation rentals won't cost as much!

more destinations

Check out more areas which feature homes, villas, cabins, cottages, or condos.

rental results

filter by:

filter rates by: Weekly rates based on 7 nights; Monthly rates based on 28 nights

Min $0, Max $4000

$0
$2,000
$4,000+

Bedrooms: Min 0, Max 5

0
5+

Bathrooms: Min 0.5, Max 5

0.5
5+





Property Type:


legend

savings
freebies
has photos
has calendar
has swimming pool
has hot tub
pets allowed

* Nightly rates and average rates per bedroom are based on actual rates in this area. Learn More .

DEAL!! Gorgeous Private Corner End Unit, Magnificent Views!
Wailea Condo Rental Picture
  • Condo Rental Deals and Discounts $70 off = $125 per night
  • bedrooms 2
  • sleeps 6
  • community Grand Champions
  • baths 2
  • rental type Condo
  • rates (USD) $195 - $290 /nt
 
 
 
 
 
DEAL!! Polo Beach Club on the sand in Wailea
Wailea Condo Rental Picture
  • Condo Rental Deals and Discounts free night valued at USD $357
  • bedrooms 2
  • sleeps 6
  • community Polo Beach Club
  • baths 2
  • rental type Condo
  • rates (USD) $2,100 - $7,900 /wk
 
 
 
 
 
DEAL!! Wailea Ekahi 7G Ocean View Luxury (Ocean Front Complex)
Wailea Condo Rental Picture
  • Condo Rental Deals and Discounts $25 off = $290 per night
  • bedrooms 1
  • sleeps 4
  • community Wailea Ekahi AOAO
  • baths 2
  • rental type Condo
  • rates (USD) $315 - $375 /nt
    $2,200 - $2,650 /wk
 
 
 
 
 
DEAL!! Grand Champions Poolside Condo
Wailea Condo Rental Picture
  • Condo Rental Deals and Discounts 10% off = $1,125 per week
  • bedrooms 1
  • sleeps 4
  • community Grand Champions
  • baths 2
  • rental type Condo
  • rates (USD) $1,250 - $1,450 /wk
 
 
 
 
 
DEAL!! Charming Private Studio condo
Wailea Studio Rental Picture
  • Studio Rental Deals and Discounts $16 off = $99 per night
  • bedrooms 0
  • sleeps 2
  • community Grand Champions
  • baths 1
  • rental type Studio
  • rates (USD) $99 - $135 /nt
    $99 - $120 /mth
 
 
 
 
 
Actually In Wailea Ocean View-Ekahi Oceanfront Village Condo
Wailea Condo Rental Picture
  • bedrooms 1
  • sleeps 4
  • community Wailea Ekahi AOAO
  • baths 2
  • rental type Condo
  • rates (USD) $1,100 - $1,250 /wk
 
 
 
 
 
Wailea Ekahi Beautiful Ocean/Garden View Vacation Condo
Wailea Condo Rental Picture
  • bedrooms 1
  • sleeps 4
  • community Wailea Ekahi AOAO
  • baths 2
  • rental type Condo
  • rates (USD) $800 - $1,000 /wk
 
 
 
 
 
Amazing Wailea Ekahi 11E Big Ocean View Lower Village
Wailea Condo Rental Picture
  • bedrooms 1
  • sleeps 4
  • community AOAO Wailea Ekahi
  • baths 2
  • rental type Condo
  • rates (USD) $305 - $405 /nt
    $2,135 - $2,500 /wk
 
 
 
 
 
Wailea Ekahi Village Oceanfront Condo 20E
Wailea Condo Rental Picture
  • bedrooms 1
  • sleeps 6
  • community Wailea Ekahi Village
  • baths 2
  • rental type Condo
  • rates (USD) $240 - $290 /nt
    $1,700 - $2,100 /wk
 
 
 
 
 
Ekahi #6A - As close to the beachfront pool as you can get!
Wailea Condo Rental Picture
  • bedrooms 1
  • sleeps 4
  • community Ekahi Village
  • baths 2
  • rental type Condo
  • rates (USD) $1,550 - $2,250 /wk
 
 
 
 
 
Ekahi 6B - A short, flat walk to the beach!
Wailea Condo Rental Picture
  • bedrooms 1
  • sleeps 4
  • community Wailea Ekahi Village
  • baths 2
  • rental type Condo
  • rates (USD) $250 - $350 /nt
    $1,750 - $2,150 /wk
 
 
 
 
 
Fall in LOVE with Wailea Ekolu's Ocean View from YOUR Lanai!
Wailea Condo Rental Picture
  • bedrooms 1
  • sleeps 4
  • community Wailea Ekolu
  • baths 2
  • rental type Condo
  • rates (USD) $175 - $275 /nt
    $1,225 - $1,925 /wk
    $5,000 - $6,000 /mth
 
 
 
 
 
Mana Kai Maui, Spectacular Top Floor View.
Wailea Condo Rental Picture
  • bedrooms 2
  • sleeps 4
  • community Mana Kai Maui Resort
  • baths 2
  • rental type Condo
  • rates (USD) $850 - $2,600 /wk
 
 
 
 
 
Discounts! Wailea Ekahi 2 bedroom beautiful ocean views 32C
Wailea Condo Rental Picture
  • bedrooms 2
  • sleeps 6
  • community Wailea
  • baths 2
  • rental type Condo
  • rates (USD) $2,700 - $3,100 /wk
 
 
 
 
 
Luxury Cottage at entrance to Wailea, "Under the Maui Sun"
Wailea Villa Rental Picture
  • bedrooms 2
  • sleeps 4
  • community
  • baths 2
  • rental type Villa
  • rates (USD) $290 - $360 /nt
    $2,050 - $2,550 /wk
 
 
 
 
 
Wailea Ekahi 2 Bedroom Spectacular Ocean Views, 2A
Wailea Condo Rental Picture
  • bedrooms 2
  • sleeps 6
  • community Wailea Ekahi Village
  • baths 2
  • rental type Condo
  • rates (USD) $405 - $485 /nt
    $2,835 - $3,395 /wk
 
 
 
 
 
Sweeping Ocean Views at The Palms at Wailea #1202
Wailea Condo Rental Picture
  • bedrooms 2
  • sleeps 6
  • community Palms at Wailea
  • baths 2
  • rental type Condo
  • rates (USD) $2,650 - $2,950 /wk
 
 
 
 
 
Grand Champion on Wailea Blue Course, FREE WIFI.....
Wailea Condo Rental Picture
  • bedrooms 2
  • sleeps 6
  • community Wailea
  • baths 2
  • rental type Condo
  • rates (USD) $175 - $295 /nt
    $1,050 - $2,100 /wk
 
 
 
 
 
Palms at Wailea Garden View Deluxe unit
Wailea Condo Rental Picture
  • bedrooms 2
  • sleeps 7
  • community Palms at Wailea
  • baths 2
  • rental type Condo
  • rates (USD) $1,200 - $2,350 /wk
 
 
 
 
 
Wailea Beach Villa - Stunning 2.5 Bedroom Paradise
Wailea Condo Rental Picture
  • bedrooms 2
  • sleeps 6
  • community Wailea Beach Villas
  • baths 2
  • rental type Condo
  • rates (USD) $650 - $2,000 /nt
    $4,500 - $14,000 /wk
 
 
 
 
 
Polo Beach Club
Wailea Condo Rental Picture
  • bedrooms 2
  • sleeps 6
  • community Polo Beach Club
  • baths 2
  • rental type Condo
  • rates (USD) $400 - $695 /nt
 
 
 
 
 
Ekahi 20A Steps from the Beach Remodeled Ground Floor Condo
Wailea Condo Rental Picture
  • bedrooms 2
  • sleeps 6
  • community AOAO Wailea Ekahi
  • baths 2
  • rental type Condo
  • rates (USD) $405 - $550 /nt
 
 
 
 
 
Palms at Wailea Polynesian Villa
Wailea Condo Rental Picture
  • bedrooms 2
  • sleeps 6
  • community Wailea Resort
  • baths
  • rental type Condo
  • rates (USD) $295 - $325 /nt
 
 
 
 
 
Awesome Ocean View - Beautiful 2 BR/2.5 BA Wailea Condo
Wailea Condo Rental Picture
  • bedrooms 2
  • sleeps 6
  • community Weilea Ekahi Village
  • baths
  • rental type Condo
  • rates (USD) $375 - $425 /nt
    $2,625 - $2,975 /wk
 
 
 
 
 
Hale Mana Kai
Wailea House Rental Picture
  • bedrooms 3
  • sleeps 6
  • community
  • baths 2
  • rental type House
  • rates (USD) $250 - $350 /nt
    $1,750 - $2,450 /wk
    $7,000 - $9,800 /mth
 
 
 
 
 
Exquisite Aloha Kai Suite at Wailea Beach Villas
Wailea Villa Rental Picture
  • bedrooms 3
  • sleeps 8
  • community Wailea
  • baths 3
  • rental type Villa
  • rates (USD) $895 - $1,995 /nt
    $6,265 - $13,975 /wk
 
 
 
 
 
Ocean Front Luxury Villa at Wailea Beach
Wailea Villa Rental Picture
  • bedrooms 3
  • sleeps 8
  • community Wailea Beach Villas
  • baths
  • rental type Villa
  • rates (USD) $15,000 - $36,000 /wk
 
 
 
 
 
Ho'olei
Wailea Townhome Rental Picture
  • bedrooms 3
  • sleeps 8
  • community Wailea
  • baths
  • rental type Townhome
  • rates (USD) $5,000 - $6,500 /wk
 
 
 
 
 
Trip Advisor says Wailea Beach Villa L409 is perfect
Wailea Villa Rental Picture
  • bedrooms 4
  • sleeps 10
  • community Wailea Beach VIlla
  • baths 3
  • rental type Villa
  • rates (USD) $895 - $2,300 /nt
    $7,165 - $16,100 /wk
    $25,000 - $32,000 /mth
 
 
 
 
 
RedsMauiHouse - The Best Panoramic View of Wailea Shoreline!
Wailea House Rental Picture
  • bedrooms 4
  • sleeps 11
  • community
  • baths 3
  • rental type House
  • rates (USD) $430 - $625 /nt
    $3,010 - $4,375 /wk