Villa rentals in Wailea - HomeToGo base64Hash Villa rentals in Wailea - HomeToGo

Villa rentals in Wailea

Anytime
1 guest
Anytime
1 guest

  • Price per night

    • Up to $100
    • $100 - $199
    • From $200

  • Accommodation types

    • Condo
    • House
    • Apartment

  • Rating

    • 4.5+
    • 4+

  • Bedrooms

    • Any
    • 1 bedroom
    • 2+ bedrooms

  • Booking Options

    • Instant Booking

  • Services

    • Pool
    • Air conditioning
    • Kitchen
    • Parking
    • Balcony/patio
    • WiFi
    • Washing machine
    • TV
    • Microwave
    • Dishwasher
    • Yard
    • Hot tub
    • Crib
    • Sauna
    • Fireplace
    Show more

  • Accommodation type

    • No smoking
    • No pets
    • Pet-friendly
    • Wheelchair access

  • Activities

    • Grill
    • Fishing

Villa rentals in Wailea: Recommended rentals

Villa rentals in Wailea: find your perfect rental from just $267 per night!

Villa Wailea
-35%
Jan 24 - Jan 31
Villa ∙ 6 guests ∙ 3 bedrooms

Villa with Pool, Garden & Grill | Nature View

Wailea, Wailea-Makena, Hawaii, United States
$1,630$966
per night
Outstanding(84 ratings)
$1,630$966
per night
View deal
Villa Wailea
May 24 - May 31
Villa ∙ 9 guests ∙ 4 bedrooms

Villa with Patio, Barbecue & Yard

Wailea, Wailea-Makena, Hawaii, United States
$1,891
per night
Outstanding(105 ratings)
$1,891
per night
View deal
Villa Wailea
Feb 24 - Mar 3
Villa ∙ 8 guests ∙ 3 bedrooms

Villa with Terrace, Barbeque & Heated Pool | Nature View

Wailea, Wailea-Makena, Hawaii, United States
$3,784
per night
Outstanding(18 ratings)
$3,784
per night
View deal
Villa Wailea
Nov 8 - Nov 15
Villa ∙ 5 guests ∙ 2 bedrooms

Fully Equipped Villa with Grill, Terrace & Pool

Wailea, Wailea-Makena, Hawaii, United States
$414
per night
Outstanding(151 ratings)
$414
per night
View deal
Villa Wailea
-50%
Nov 8 - Nov 15
Villa ∙ 4 guests ∙ 2 bedrooms

Villa with Patio, Barbecue & Pool

Wailea, Wailea-Makena, Hawaii, United States
$485$343
per night
Outstanding(144 ratings)
$485$343
per night
View deal
Villa Wailea
May 24 - May 31
Villa ∙ 4 guests ∙ 2 bedrooms

Villa with Pool, Barbeque & Jacuzzi

Wailea, Wailea-Makena, Hawaii, United States
$267
per night
Excellent(73 ratings)
$267
per night
View deal
Villa Wailea
Apr 19 - Apr 26
Villa ∙ 8 guests ∙ 3 bedrooms

Child-Friendly Lovely Villa with Yard, Private Pool & Grill | Close to the Beach

Wailea, Wailea-Makena, Hawaii, United States
$3,320
per night
Outstanding(23 ratings)
$3,320
per night
View deal
Villa Wailea
Feb 27 - Mar 6
Villa ∙ 7 guests ∙ 3 bedrooms

Fully Equipped Beautiful Villa with Barbeque & Heated Pool | Beach Nearby

Wailea, Wailea-Makena, Hawaii, United States
$1,211
per night
Outstanding(95 ratings)
$1,211
per night
View deal
Villa Wailea
Jan 25 - Feb 1
Villa ∙ 6 guests ∙ 3 bedrooms

Fully Equipped Villa with Heated Pool, BBQ & Terrace | Nature View | Beach Nearby

Wailea, Wailea-Makena, Hawaii, United States
$2,123
per night
Outstanding(22 ratings)
$2,123
per night
View deal
Villa Wailea
Jan 24 - Jan 31
Villa ∙ 8 guests ∙ 4 bedrooms

Villa with Pool, Terrace & Grill | Suitable for Remote Work

Wailea, Wailea-Makena, Hawaii, United States
$1,393
per night
Outstanding(16 ratings)
$1,393
per night
View deal
Villa Wailea
-71%
Mar 11 - Mar 18
Villa ∙ 10 guests ∙ 4 bedrooms

Family-Oriented Villa with Pool, Barbeque & Sauna | Good for Workation

Wailea, Wailea-Makena, Hawaii, United States
$3,747$1,112
per night
Outstanding(157 ratings)
$3,747$1,112
per night
View deal
Villa Wailea
-19%
May 10 - May 17
Free cancellation
Villa ∙ 10 guests ∙ 3 bedrooms

Children-Friendly Nice Villa with Pool, BBQ & Hot Tub | Close to the Beach

Wailea, Wailea-Makena, Hawaii, United States
$1,534$1,239
per night
Outstanding(117 ratings)
$1,534$1,239
per night
View deal
Villa Wailea
-56%
Apr 6 - Apr 13
Villa ∙ 8 guests ∙ 3 bedrooms

Villa with Barbeque, Jacuzzi & Fast Internet | Garden View

Wailea, Wailea-Makena, Hawaii, United States
$2,348$1,126
per night
$2,348$1,126
per night
View deal
Villa Wailea
-32%
Feb 24 - Mar 3
Villa ∙ 6 guests ∙ 3 bedrooms

Villa with Terrace, Heated Pool & Grill

Wailea, Wailea-Makena, Hawaii, United States
$2,708$1,744
per night
Outstanding(24 ratings)
$2,708$1,744
per night
View deal
Villa Wailea
Dec 21 - Dec 28
Villa ∙ 4 guests ∙ 1 bedroom

Children-Friendly Villa with Terrace, Private Pool & Barbeque | Mountain View

Wailea, Wailea-Makena, Hawaii, United States
$390
per night
Outstanding(64 ratings)
$390
per night
View deal
Show all 196 properties

Popular amenities for Villa rentals in Wailea

Find the perfect home for your stay

Villas with pools

Villas with air conditioning

Villas with kitchen

Villas with parking

Top-rated villas in Wailea

Browse our top rated villas offers

Villa Wailea
Sep 19 - Sep 26
-31%
$1,656
$1,341
per night
Villa ∙ 6 guests ∙ 3 bedrooms

Fully Equipped Villa with Pool, Sauna & BBQ | Next to the Beach

5.0
Outstanding(38 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
House Wailea
Apr 26 - May 3
-67%
$1,941
$984
per night
House ∙ 6 guests ∙ 2 bedrooms

Fully Equipped House with Pool, Yard & Hot Tub | Garden View | Next to the Beach

5.0
Outstanding(1 rating)
Wailea, Wailea-Makena, Hawaii, United States
Free cancellation
View deal
House Wailea
Mar 29 - Apr 5
-48%
$3,042
$2,115
per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation Home with Pool, Yard & Grill | Sea View

5.0
Outstanding(1 rating)
Wailea, Wailea-Makena, Hawaii, United States
Free cancellation
View deal

Best Deals and Discounts on Villas

Save up to 48%

Villa Wailea
Apr 27 - May 4
-23%
$2,138
$1,647
per night
Villa ∙ 8 guests ∙ 3 bedrooms

Fully Equipped Lovely Villa with Patio, Barbecue & Pool | Beach Nearby

5.0
Outstanding(51 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Villa Wailea
Jan 19 - Jan 26
-48%
$4,471
$3,246
per night
Villa ∙ 8 guests ∙ 3 bedrooms

Villa with Heated Pool, Terrace & Garden | Nature View

5.0
Outstanding(2 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Villa Wailea
Jun 11 - Jun 18
-46%
$1,390
$610
per night
Villa ∙ 4 guests ∙ 2 bedrooms

Fully Equipped Villa with Heated Pool, Yard & BBQ | City View | Close to the Beach

5.0
Outstanding(148 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal

Budget-friendly villas in Wailea

Our top value vacation rentals for villas

Villa Wailea
Jan 7 - Jan 14
$2,896
per night
Villa ∙ 6 guests ∙ 3 bedrooms

Family-Oriented Charming Villa with Heated Pool, Terrace & BBQ | Nature View | Next to the Beach

4.9
Outstanding(12 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Villa Wailea
Apr 11 - Apr 18
$359
per night
Villa ∙ 4 guests ∙ 1 bedroom

Villa with Yard, Pool & Patio | Perfect for Remote Work

5.0
Outstanding(102 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal
Villa Wailea
Feb 25 - Mar 4
$1,874
per night
Villa ∙ 6 guests ∙ 3 bedrooms

Family-Friendly Big Villa with Heated Pool, Patio & Barbeque | Beach Nearby

4.9
Outstanding(23 ratings)
Wailea, Wailea-Makena, Hawaii, United States
View deal

Stay Cool: Villas with Air Conditioning

Villa Wailea
Apr 30 - May 7
-65%
$3,802
$1,449
per night
Villa ∙ 8 guests ∙ 3 bedrooms

Villa with Hot Tub, Fast Internet & Grill | Water View | Perfect for Remote Work

Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
View deal
Villa Wailea
Sep 27 - Oct 4
-61%
$2,414
$953
per night
Villa ∙ 7 guests ∙ 2 bedrooms

Villa with Terrace, Hot Tub & Barbecue | Water View

Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
View deal
Villa Wailea
Nov 30 - Dec 7
-69%
$3,139
$1,150
per night
Villa ∙ 6 guests ∙ 3 bedrooms

Child-Friendly Spacious Villa with Barbecue, Jacuzzi & Yard | Garden View | Close to the Beach

Wailea, Wailea-Makena, Hawaii, United States
Air conditioning
View deal
See all offers

Soak Up the Sun: Villas with Patios

House Wailea
Dec 1 - Dec 8
-67%
$3,220
$1,317
per night
House ∙ 8 guests ∙ 3 bedrooms

Fully Equipped Charming Vacation Home with Yard, Hot Tub & BBQ | Sea View

Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
Villa Wailea
Nov 30 - Dec 7
-69%
$2,670
$1,308
per night
Villa ∙ 6 guests ∙ 2 bedrooms

Villa with Fast Internet, Hot Tub & Terrace | Water View | Perfect for Remote Work

Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
Villa Wailea
Dec 13 - Dec 20
-64%
$2,507
$1,106
per night
Villa ∙ 8 guests ∙ 3 bedrooms

Villa with Garden, Pool & Jacuzzi

Wailea, Wailea-Makena, Hawaii, United States
Balcony/Patio
View deal
See all offers

Villas with Hot Tubs

Rentals Featuring Jacuzzis and Whirlpools

Villa Wailea
Dec 11 - Dec 18
-68%
$3,661
$1,458
per night
Villa ∙ 7 guests ∙ 3 bedrooms

Children-Friendly Villa with Barbeque, Hot Tub & Terrace | Water View | Beach Nearby | Perfect for Remote Work

Wailea, Wailea-Makena, Hawaii, United States
View deal
House Wailea
Nov 30 - Dec 7
-63%
$3,001
$1,852
per night
House ∙ 8 guests ∙ 3 bedrooms

Vacation Home with Jacuzzi, Pool & Garden | Garden View

Wailea, Wailea-Makena, Hawaii, United States
View deal
House Wailea
Apr 30 - May 7
-65%
$3,747
$1,442
per night
House ∙ 8 guests ∙ 3 bedrooms

Fully Equipped Big Vacation Home with Pool, Hot Tub & BBQ | Close to the Beach

Wailea, Wailea-Makena, Hawaii, United States
Free cancellation
View deal

Villas in Wailea for Any Type of Traveler

Need a place to stay with a group of eight or more people in Wailea?

HomeToGo features numerous Villas in Wailea with eight or more bedrooms and eight or more bathrooms. Find luxurious Villas for big groups in Wailea, complete with private pool, large kitchen, and lots of space to relax. September is the most affortable time to stay in Wailea with a big group, when nightly prices for Villas will range from $1,617 to $4,132 per night. Begin searching our top cabins for 8+ people and plan the perfect trip!

Planning a private getaway in Wailea with your partner?

Reserve amazing Villas in Wailea for a private retreat, complete with hot tub, sauna, and a amazing view of Wailea's surrounding scenery. There are tons of exciting activities to try with your partner on your couples trip, including hiking, swimming, biking, and many other outdoor activities. The cheapest month to book is September with prices starting at $267 per night. Search HomeToGo's best offers for romantic getaways in Wailea now!

Information about Villa rentals in Wailea

🏡 Villas available 196 rentals
💳 Possible discounts up to 66%
🌙 Nightly prices starting at $267
⭐ Popular amenities Internet, TV and Pool
🐾 Pet friendly homes 14 homes
🏊 Villas with pools 127 homes

Villa rentals in Wailea: frequently asked questions

Villa rentals in Wailea: What is the price per night for a stay?

HomeToGo has great vacation rentals, with prices as low as $267 per night.

Villa rentals in Wailea: are there many vacation rentals available for a group?

Villa in Wailea can fit 7 people.

Other Popular Destinations for Villas

Villa rentals in Wailea Inspiration

Show more

Searching for something else?

Find more interesting places to stay in Wailea

House

Apartment

Hotel

Bed and breakfast

image-tag