133+ Vacation Rentals Near Wailea Beach |
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Sonoma Villas - Vacation Rentals in Wailea Beach

I.P.M PRESENTS: HOOLEI 69-2: GREAT LOCATION + STUNNING NEW REMODEL! WOW! From US $1,585
         

10.0 (43 Reviews)
Villa
I.P.M PRESENTS: HOOLEI 69-2: GREAT LOCATION + STUNNING NEW REMODEL! WOW!
  • Air Conditioner
  • Parking
  • Pool

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Wailea Beach Villa H202 by Coldwell Banker Island Vacations From US $1,372
         

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10.0 (1 Review)
Villa
Wailea Beach Villa H202 by Coldwell Banker Island Vacations
  • Air Conditioner
  • Parking
  • Pool

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Spectacular 3rd Row Villa at Ho'olei with Ocean Views From US $1,420
         

10.0 (58 Reviews)
Villa
Spectacular 3rd Row Villa at Ho'olei with Ocean Views
  • Air Conditioner
  • Parking
  • Pool

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Ho'olei Unit 12-2, Close to Pool, Walk to Beach From US $995
         

10.0 (1 Review)
Villa
Ho'olei Unit 12-2, Close to Pool, Walk to Beach
  • Parking
  • Security/Safety
  • Wellness Facilities

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5 Star Ocean View, Beach House Chic, Click the Video tour below! From US $457
         

10.0 (95 Reviews)
Villa
5 Star Ocean View, Beach House Chic, Click the Video tour below!
  • Air Conditioner
  • Parking
  • Pool

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Grand Champions Golf Villas 94 From US $744
         

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10.0 (1 Review)
House
Grand Champions Golf Villas 94
  • Air Conditioner
  • View
  • Ocean View

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OCEAN VIEWS AT THE EXQUISITE SEA BREEZE J405 WAILEA BEACH VILLAS From US $1,866
         

10.0 (16 Reviews)
Villa
OCEAN VIEWS AT THE EXQUISITE SEA BREEZE J405 WAILEA BEACH VILLAS
  • Air Conditioner
  • Parking
  • Pool

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OCEANVIEWS, FRESH UPGRADES AT THE LUXURIOUS GRAND SEASCAPE K407! From US $1,730
         

9.8 (12 Reviews)
Villa
OCEANVIEWS, FRESH UPGRADES AT THE LUXURIOUS GRAND SEASCAPE K407!
  • Air Conditioner
  • Parking
  • Pool

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WAILEA'S SUPER CHIC - SUPER LUXE W/OCEAN VIEWS! EXPERIENCE WAILEA SEASHORE K507! From US $1,753
         

9.6 (15 Reviews)
Villa
WAILEA'S SUPER CHIC - SUPER LUXE W/OCEAN VIEWS! EXPERIENCE WAILEA SEASHORE K507!
  • Air Conditioner
  • Parking
  • Pool

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I.P.M PRESENTS: HOOLEI 99-2 BRAND NEW REMODEL - WOW! FLEXIBLE CANCELATION POLICY From US $1,518
         

9.4 (20 Reviews)
Villa
I.P.M PRESENTS: HOOLEI 99-2 BRAND NEW REMODEL - WOW! FLEXIBLE CANCELATION POLICY
  • Air Conditioner
  • Parking
  • Pool

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XXL 4 BEDROOM MER ET SOLEIL K408 VILLA PANORAMIC OCEAN VIEWS CONTEMPORARY INTERIOR, FRESHLY UPDATED! From US $2,507
         

9.8 (8 Reviews)
Villa
XXL 4 BEDROOM MER ET SOLEIL K408 VILLA PANORAMIC OCEAN VIEWS CONTEMPORARY INTERIOR, FRESHLY UPDATED!
  • Air Conditioner
  • Parking
  • Pool

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Escape to Ho'olei – Ocean Views & Luxe Comfort From US $1,329
         

9.6 (76 Reviews)
Villa
Escape to Ho'olei – Ocean Views & Luxe Comfort
  • Air Conditioner
  • Parking
  • Pool

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~ BOOK WITH WITH US AND WITH CONFIDENCE THOUGH 2031 ~ From US $406
         

10.0 (139 Reviews)
Villa
~ BOOK WITH WITH US AND WITH CONFIDENCE THOUGH 2031 ~
  • Air Conditioner
  • Parking
  • Pool

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Hula On In to Beach House Chic Style, Click the Video tour below! From US $541
         

10.0 (137 Reviews)
Villa
Hula On In to Beach House Chic Style, Click the Video tour below!
  • Air Conditioner
  • Parking
  • Pool

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Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere From US $1,513
         

10.0 (93 Reviews)
Villa
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere
  • Air Conditioner
  • Parking
  • Pool

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Panoramic Ocean Views at Wailea Beach Villas I503 From US $1,960
         

10.0 (78 Reviews)
Villa
Panoramic Ocean Views at Wailea Beach Villas I503
  • Air Conditioner
  • Parking
  • Pool

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Gated 2-story beach house with big yard From US $904
         

10.0 (74 Reviews)
Villa
Gated 2-story beach house with big yard
  • Air Conditioner
  • Parking
  • Pet Friendly

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Panoramic Ocean Views! - Luxury Villa! - Owner Direct! From US $2,848
         

10.0 (71 Reviews)
Villa
Panoramic Ocean Views! - Luxury Villa! - Owner Direct!
  • Air Conditioner
  • Parking
  • Pool

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Exquisite Oceanview Villa with Resort Amenities in Gated Community From US $1,853
         

10.0 (70 Reviews)
Villa
Exquisite Oceanview Villa with Resort Amenities in Gated Community
  • Air Conditioner
  • Parking
  • Pool

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Bright and Luxurous Wailea Beach Villas I204 From US $1,521
         

10.0 (66 Reviews)
Villa
Bright and Luxurous Wailea Beach Villas I204
  • Air Conditioner
  • Parking
  • Pool

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Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei From US $1,390
         

10.0 (59 Reviews)
Villa
Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei
  • Air Conditioner
  • Parking
  • Pool

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Luxury Villa Steps from Wailea Beach with Resort Amenities and Stunning Upgrades From US $1,447
         

10.0 (58 Reviews)
Villa
Luxury Villa Steps from Wailea Beach with Resort Amenities and Stunning Upgrades
  • Air Conditioner
  • Parking
  • Pool

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I.P.M PRESENTS: HOOLEI 81-4: AMAZING NEW REMODEL! FLEXIBLE CANCELATION POLICY From US $1,410
         

10.0 (42 Reviews)
Villa
I.P.M PRESENTS: HOOLEI 81-4: AMAZING NEW REMODEL! FLEXIBLE CANCELATION POLICY
  • Air Conditioner
  • Parking
  • Pool

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Maui escape with ocean views, lanai dining, poolside jacuzzis & gated community From US $1,833
         

10.0 (32 Reviews)
Villa
Maui escape with ocean views, lanai dining, poolside jacuzzis & gated community
  • Air Conditioner
  • Parking
  • Pool

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★ Pro Tip: Sonomavillas makes it easy to compare the best listings on Sonomavillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Sonomavillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Wailea Beach.

Weather in Wailea Beach

View the weather forecast for Wailea Beach before booking your Wailea Beach Vacation Rentals to confirm your best time to go.

December - February
High 82°F       Low 63°F
March - May
High 86°F       Low 66°F
June - August
High 90°F       Low 71°F
September - November
High 90°F       Low 66°F

Top Attractions Around Wailea Beach, HI

Sonomavillas offers a large selection of top attractions around Wailea Beach. Research things to do on your vacation before you visit Wailea Beach.


Haleakala National Park Maui Ocean Center Molokini Maalaea Harbor Kamaole Beach Park 3 Makena State Park Beach Keawakapu Beach Maui Tropical Plantation Kihei Town Center Shopping Center Kamaole Beach Park Kihei Regional Park Kamaole Beach Park 2 Maluaka Beach Kalama Beach Park Little Beach Hawaiian Islands Humpback Whale Sanctuary Visitor Center Maui Nui Golf Club Polo Beach Maalaea Beach Maui Fish Pipe

Wailea Beach Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Wailea Beach?

There are a lot of options in Wailea Beach. If you plan on staying in the Wailea Beach area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Wailea Beach:

How many vacation rentals are available in Wailea Beach?

Currently, the total number of properties listed in 2026 is over 133 in the Wailea Beach area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Wailea Beach.