7977+ Vacation Rentals Near Kihei |
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Madison Vacation Rental - Vacation Rentals in Kihei

Breathtaking Oceanfront Boutique From US $405
         

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8.5 (2 Reviews)
House
Breathtaking Oceanfront Boutique
  • Air Conditioner
  • Parking
  • Pool

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Polo Beach Club Vacation Rentals - APlus Resorts From US $1,895
         

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10.0 (2 Reviews)
Condo
Polo Beach Club Vacation Rentals - APlus Resorts
  • Air Conditioner
  • Pool
  • TV

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Ocean Front Penthouse Best View Most Amenities Fully Stocked Feels like home From US $555
         

10.0 (220 Reviews)
Condo
Ocean Front Penthouse Best View Most Amenities Fully Stocked Feels like home
  • Air Conditioner
  • Parking
  • Pool

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Beautiful Maui Beachfront Townhouse! Great Views! 200+ Five Star Reviews ! From US $1,083
         

10.0 (171 Reviews)
House
Beautiful Maui Beachfront Townhouse! Great Views! 200+ Five Star Reviews !
  • Air Conditioner
  • Parking
  • Pool

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Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted From US $695
         

10.0 (155 Reviews)
Cottage
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted
  • Air Conditioner
  • Parking
  • Pool

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LOW JUNE RATES NOW ! RESERVE SOON ! From US $605
         

10.0 (149 Reviews)
Apartment
LOW JUNE RATES NOW ! RESERVE SOON !
  • Air Conditioner
  • Parking
  • Pool

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🌺Lush Oceanfront Penthouse with Pool, Hot Tub, Mountain Sunrises, Ocean Sunsets From US $454
         

10.0 (143 Reviews)
Condo
🌺Lush Oceanfront Penthouse with Pool, Hot Tub, Mountain Sunrises, Ocean Sunsets
  • Air Conditioner
  • Parking
  • Pool

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🤙 June-July-August SPECIALS PLUS VRBO discounts 🏝️ at the LIVE ALOHA SUITE From US $603
         

10.0 (141 Reviews)
Condo
🤙 June-July-August SPECIALS PLUS VRBO discounts 🏝️ at the LIVE ALOHA SUITE
  • Air Conditioner
  • Parking
  • Pool

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Luxury Places to Stay in Kihei

Over 7968+ Luxury Places to Stay in or Near Kihei
10.0 (1 Review)
House
Luxurious Oceanfront Sandy Beach Estate on Makena Beach-6BR/7.5BA 8,030 Sq Ft
  • Air Conditioner
  • Parking
  • Pet Friendly

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Maui Vista 1106 · MV 1106 Updated 1BD Condo Steps from Beach Poo From US $9,723
         

9.5 (2 Reviews)
House
Maui Vista 1106 · MV 1106 Updated 1BD Condo Steps from Beach Poo
  • Parking
  • Pool
  • Security/Safety

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Wailea Beach Villas Penthouse Panoramic Ocean Views 2 Units 6 Bedrooms and Complimentary Rental Car w 6 Nights WBV ML-3485 by KBM Resorts From US $7,187
         

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New
Apartment
Wailea Beach Villas Penthouse Panoramic Ocean Views 2 Units 6 Bedrooms and Complimentary Rental Car w 6 Nights WBV ML-3485 by KBM Resorts
  • Air Conditioner
  • View
  • Balcony/Terrace

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KBM Resorts FREE CAR Polo Beach Ground Floor 2-Bedroom Condo Steps to the Sand Sunset views POL-109 From US $6,190
         

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1.0 (1 Review)
Apartment
KBM Resorts FREE CAR Polo Beach Ground Floor 2-Bedroom Condo Steps to the Sand Sunset views POL-109
  • Air Conditioner
  • Parking
  • Pool

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Wailea Beach Villas | Penthouse Panoramic Ocean Views 2 Units, 6 Bedrooms and Complimentary Rental Car w/6+ Nights | WBV ML-3485 by KBM Resorts From US $5,479
         

New
Condo
Wailea Beach Villas | Penthouse Panoramic Ocean Views 2 Units, 6 Bedrooms and Complimentary Rental Car w/6+ Nights | WBV ML-3485 by KBM Resorts
  • Balcony/Terrace
  • Security/Safety
  • Child Friendly

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Fairmont Kea Lani Maui Villa Experience From US $5,399
         

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9.8 (6 Reviews)
Resort
Fairmont Kea Lani Maui Villa Experience
  • Air Conditioner
  • Parking
  • Pool

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NEW AND MODERN PANORAMIC OCEANVIEW 4 BEDROOM VILLA WITH HEATED PLUNGE POOL AND LUX INTERIOR From US $4,819
         

New
House
NEW AND MODERN PANORAMIC OCEANVIEW 4 BEDROOM VILLA WITH HEATED PLUNGE POOL AND LUX INTERIOR
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  • Parking
  • Pool

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Ultimate Oceanfront Luxury-Private penthouse in South Maui-Perfect for families From US $4,725
         

10.0 (45 Reviews)
Condo
Ultimate Oceanfront Luxury-Private penthouse in South Maui-Perfect for families
  • Air Conditioner
  • Parking
  • Pool

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Find More Kihei Villas, Resorts, & Rentals on BedroomVillas

Top-Rated Vacation Rentals with a Pool in Kihei

Over 6938+ Top-Rated Vacation Rentals with a Pool in or Near Kihei
10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles! From US $412
         

10.0 (310 Reviews)
Condo
10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!
  • Air Conditioner
  • Parking
  • Pool

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Dazzling Ocean View, Modern, Whole house AC. Upgraded Glass for a quiet setting From US $473
         

10.0 (286 Reviews)
Condo
Dazzling Ocean View, Modern, Whole house AC. Upgraded Glass for a quiet setting
  • Air Conditioner
  • Parking
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Breathtaking ocean views! Steps to the beach! Recently remodeled! From US $422
         

10.0 (283 Reviews)
Condo
Breathtaking ocean views! Steps to the beach! Recently remodeled!
  • Air Conditioner
  • Parking
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5-Star Reviews! All Remodeled! Split Air! Quiet Building 5! Ocean/Garden View! From US $322
         

10.0 (243 Reviews)
Condo
5-Star Reviews! All Remodeled! Split Air! Quiet Building 5! Ocean/Garden View!
  • Air Conditioner
  • Parking
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Maui Paradise – BEACH FRONT condo w/AC, Stunning Ocean & Sunset Views! From US $608
         

10.0 (224 Reviews)
Condo
Maui Paradise – BEACH FRONT condo w/AC, Stunning Ocean & Sunset Views!
  • Air Conditioner
  • Parking
  • Pool

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200+ 5 Star Reviews, Premier Front-Row Sunset Views,1 Of Largest Spacious Condos From US $574
         

10.0 (217 Reviews)
Condo
200+ 5 Star Reviews, Premier Front-Row Sunset Views,1 Of Largest Spacious Condos
  • Air Conditioner
  • Parking
  • Pool

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Romantic, Luxury, Sensual Retreat - Couples Only From US $568
         

10.0 (207 Reviews)
Condo
Romantic, Luxury, Sensual Retreat - Couples Only
  • Air Conditioner
  • Parking
  • Pool

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Oceanfront, Exceptionally Remodeled, Split A/C, King bed, OH the sunsets From US $477
         

10.0 (201 Reviews)
Condo
Oceanfront, Exceptionally Remodeled, Split A/C, King bed, OH the sunsets
  • Air Conditioner
  • Parking
  • Pool

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Pet-Friendly Vacation Rentals in Kihei

Over 52+ Pet-Friendly Vacation Rentals in or Near Kihei
Maui What a Wonderful World Bed & Breakfast From US $339
         

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9.4 (82 Reviews)
Bed & Breakfast
Maui What a Wonderful World Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly

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

10.0 (79 Reviews)
Villa
Gated 2-story beach house with big yard
  • Air Conditioner
  • Parking
  • Pet Friendly

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The Ocean View Residence From US $577
         

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10.0 (1 Review)
Apartment
The Ocean View Residence
  • Air Conditioner
  • Parking
  • Pet Friendly

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Luxury, 20 steps from the ocean, pool, jacuzzi! Newly remodeled, best location! From US $369
         

10.0 (1 Review)
Condo
Luxury, 20 steps from the ocean, pool, jacuzzi! Newly remodeled, best location!
  • Air Conditioner
  • Pet Friendly
  • Pool

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Maui Sunset Oasis- Top Unit w/AC, watch whales from from Lanai (Dec-Apr) From US $483
         

9.8 (10 Reviews)
Condo
Maui Sunset Oasis- Top Unit w/AC, watch whales from from Lanai (Dec-Apr)
  • Air Conditioner
  • Parking
  • Pet Friendly

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Oceanfront Kihei Condo Stunning Sunsets Beach Access Maui Getaway From US $370
         

9.0 (2 Reviews)
Condo
Oceanfront Kihei Condo Stunning Sunsets Beach Access Maui Getaway
  • Parking
  • Pet Friendly
  • Pool

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Hale Kamaole Condo w/Private Washer/Dryer & Shared Outdoor Pool- Small Dogs OK From US $270
         

8.4 (19 Reviews)
Condo
Hale Kamaole Condo w/Private Washer/Dryer & Shared Outdoor Pool- Small Dogs OK
  • Air Conditioner
  • Parking
  • Pet Friendly

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Comfortable condo with private lanai in sunny South Kihei From US $417
         

6.0 (1 Review)
Condo
Comfortable condo with private lanai in sunny South Kihei
  • Air Conditioner
  • Parking
  • Pet Friendly

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Large Vacation Homes & Villas in Kihei

Over 282+ Large Vacation Homes & Villas in or Near Kihei
Villa Moana Maui From US $1,892
         

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New
Villa
Villa Moana Maui
  • Air Conditioner
  • Parking
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I.P.M PRESENTS: HOOLEI 69-2: GREAT LOCATION + STUNNING NEW REMODEL! WOW! From US $1,456
         

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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Spectacular 3rd Row Villa at Ho'olei with Ocean Views From US $1,383
         

10.0 (62 Reviews)
Villa
Spectacular 3rd Row Villa at Ho'olei with Ocean Views
  • Air Conditioner
  • Parking
  • Pool

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5 Star Ocean View, Beach House Chic, Click the Video tour below! From US $485
         

10.0 (100 Reviews)
Villa
5 Star Ocean View, Beach House Chic, Click the Video tour below!
  • Air Conditioner
  • Parking
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OCEAN VIEWS AT THE EXQUISITE SEA BREEZE J405 WAILEA BEACH VILLAS From US $1,789
         

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 $1,891
         

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

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Specials - Sep-Dec, Tropical Oceanfront Estate, Pool, Gated, Privacy, Ocean view From US $2,532
         

9.6 (220 Reviews)
House
Specials - Sep-Dec, Tropical Oceanfront Estate, Pool, Gated, Privacy, Ocean view
  • Air Conditioner
  • Parking
  • Pool

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WAILEA'S SUPER CHIC - SUPER LUXE W/OCEAN VIEWS! EXPERIENCE WAILEA SEASHORE K507! From US $1,717
         

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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Wheelchair Accessible Vacation Homes in Kihei

Over 2799+ Wheelchair Accessible Vacation Homes in or Near Kihei
Hale Hui Kai #112 From US $420
         

10.0 (1 Review)
House
Hale Hui Kai #112
  • Pool
  • View
  • Wheelchair Accessible

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Direct Oceanfront/Beachfront Luxury! Recently Remodeled From US $823
         

10.0 (111 Reviews)
Condo
Direct Oceanfront/Beachfront Luxury! Recently Remodeled
  • Air Conditioner
  • Parking
  • Pool

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Kihei Surfside - Maui Condo & Home From US $343
         

8.6 (69 Reviews)
Condo
Kihei Surfside - Maui Condo & Home
  • Pool
  • Designated Smoking Area
  • TV

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Great Rates JULY-DEC, AC, 1st fl, Remodeled Kihei Oceanfront property BBQ & Pool From US $342
         

9.8 (174 Reviews)
Condo
Great Rates JULY-DEC, AC, 1st fl, Remodeled Kihei Oceanfront property BBQ & Pool
  • Air Conditioner
  • Parking
  • Pool

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PARADISE IS CALLING-Oceanview Family Size-Resort Zoned-King Beds-No Cleaning Fee From US $349
         

9.6 (108 Reviews)
Condo
PARADISE IS CALLING-Oceanview Family Size-Resort Zoned-King Beds-No Cleaning Fee
  • Air Conditioner
  • Parking
  • Pool

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Faces Kamaole Beach Park 3, Ground Floor, Large Lanai, partial Ocean View From US $357
         

9.6 (94 Reviews)
Condo
Faces Kamaole Beach Park 3, Ground Floor, Large Lanai, partial Ocean View
  • Air Conditioner
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Newly Renovated Kihei Condo with Sunset Views – Steps From a Beautiful Beach! From US $333
         

9.8 (143 Reviews)
Condo
Newly Renovated Kihei Condo with Sunset Views – Steps From a Beautiful Beach!
  • Air Conditioner
  • Parking
  • Pool

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BEAUTIFULLY REMODELED WITH GREAT OCEAN VIEW! From US $261
         

9.8 (131 Reviews)
Condo
BEAUTIFULLY REMODELED WITH GREAT OCEAN VIEW!
  • Air Conditioner
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Kihei Vacation Rentals and Airbnb Places to Stay Under $200

Over 242+ Kihei Vacation Rentals and Airbnb Places to Stay Under $200
Maui Vista 1207 From US $197
         

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7.8 (16 Reviews)
Apartment
Maui Vista 1207
  • Air Conditioner
  • Parking
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Private Cozy Studio walking distance to beaches, shops, restaurants and bars From US $138
         

10.0 (146 Reviews)
Apartment
Private Cozy Studio walking distance to beaches, shops, restaurants and bars
  • Air Conditioner
  • Parking
  • Pool

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Kamaole Sands One Bedrooms by Coldwell Banker Island Vacations From US $88
         

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10.0 (2 Reviews)
Condo
Kamaole Sands One Bedrooms by Coldwell Banker Island Vacations
  • Parking
  • Pool
  • Security/Safety

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Elevated Island Vacation on Wheels From US $165
         

10.0 (2 Reviews)
House
Elevated Island Vacation on Wheels
  • Air Conditioner
  • Parking
  • Balcony/Terrace

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Paradise Jays Maui Island Breeze From US $126
         

10.0 (2 Reviews)
House
Paradise Jays Maui Island Breeze
  • Air Conditioner
  • Parking
  • Security/Safety

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Cozy Maui 'Treehouse' with lovely views and amenities From US $179
         

9.8 (98 Reviews)
Cottage
Cozy Maui 'Treehouse' with lovely views and amenities
  • Air Conditioner
  • Parking
  • Pool

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South Maui, Condo in Kihei, Great Location - Top Floor, Quiet And Private! From US $196
         

9.8 (44 Reviews)
Condo
South Maui, Condo in Kihei, Great Location - Top Floor, Quiet And Private!
  • Air Conditioner
  • Parking
  • Pool

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Your Kihei Kai Nani Home! Comfortable and Quiet From US $198
         

9.4 (74 Reviews)
Condo
Your Kihei Kai Nani Home! Comfortable and Quiet
  • Air Conditioner
  • Parking
  • Pool

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Instantly Bookable Vacation Homes in Kihei

Over 5181+ Instantly Bookable Vacation Homes in or Near Kihei
Amazing view, Close to the beach, Wailea Ekahi Unit 20i From US $575
         

10.0 (136 Reviews)
Condo
Amazing view, Close to the beach, Wailea Ekahi Unit 20i
  • Air Conditioner
  • Parking
  • Pool

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Oceanfront, Million-Dollar-View, Newly renovated! B421 From US $725
         

10.0 (178 Reviews)
Condo
Oceanfront, Million-Dollar-View, Newly renovated! B421
  • Air Conditioner
  • Parking
  • Pool

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Beachfront Condo B303 From US $1,088
         

10.0 (99 Reviews)
Condo
Beachfront Condo B303
  • Air Conditioner
  • Parking
  • Pool

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2BR/1BA BEACHFRONT GREAT LOCATION EXCEPTIONAL REVIEWS From US $495
         

10.0 (54 Reviews)
Apartment
2BR/1BA BEACHFRONT GREAT LOCATION EXCEPTIONAL REVIEWS
  • Air Conditioner
  • Parking
  • TV

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NEWLY RENOVATED, PRIVATE BEACHFRONT HIDEAWAY ^MOANA^ SLEEPS 8! From US $3,991
         

10.0 (25 Reviews)
House
NEWLY RENOVATED, PRIVATE BEACHFRONT HIDEAWAY ^MOANA^ SLEEPS 8!
  • Air Conditioner
  • Parking
  • Pool

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Largest Two Bedroom/Two Bath in the Village, Sleeps Eight & Close to the Beach From US $870
         

9.8 (197 Reviews)
Condo
Largest Two Bedroom/Two Bath in the Village, Sleeps Eight & Close to the Beach
  • Air Conditioner
  • Parking
  • Pool

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Soooooo Close to the Beach & Completely Remodeled! Relax to the Sound of Waves From US $469
         

9.8 (165 Reviews)
Condo
Soooooo Close to the Beach & Completely Remodeled! Relax to the Sound of Waves
  • Air Conditioner
  • Parking
  • Pool

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Vacation in Paradise at our charming condo by the best of everything Maui offers From US $406
         

9.8 (106 Reviews)
Condo
Vacation in Paradise at our charming condo by the best of everything Maui offers
  • Air Conditioner
  • Parking
  • Pool

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About Kihei Vacation Rentals

With more than 7977 Kihei vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Madisonvacationrental and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Kihei.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Madisonvacationrental Kihei, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Kihei. Places to stay near Kihei are 787.66 ft² on average, with prices averaging US $564 a night.

Madisonvacationrental makes it easy and safe to find and compare vacation rentals in Kihei with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Kihei

Type Count
Holiday Apartments 1401
Vacation Homes 759
Resorts 137
Villas 127
Hotels 62
Cottages 15
B&B 8
Cabin Rentals 1
Others 1

Use these Quick Filters to Find a Vacation Rental in Kihei

★ Pro Tip: Madisonvacationrental makes it easy to compare the best listings on Madisonvacationrental homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Madisonvacationrental 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 Kihei.

Weather in Kihei

View the weather forecast for Kihei before booking your Kihei 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 Kihei, HI

Madisonvacationrental offers a large selection of top attractions around Kihei. Research things to do on your vacation before you visit Kihei.


Wailea Beach Kamaole Beach Park 3 Makena State Park Beach Keawakapu Beach 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 Shops at Wailea Po'olenalena Beach Makena Beaches Ulua Beach Park

Other Places to Stay Near Kihei, HI


Cove Park 6,672 Properties Kamaole Beach Park 6,653 Properties Maui Fish Pipe 6,428 Properties Kalama Beach Park 6,290 Properties Kamaole Beach Park 2 6,259 Properties Halama Street 6,082 Properties South Maui 6,063 Properties Kamaole Beach Park 3 5,949 Properties Kihei Town Center Shopping Center 5,796 Properties Coast Guard Beach 5,765 Properties Makena 1,312 Properties Wailea 1,312 Properties

Complexes around Kihei, HI


Sugar Beach Resort Kihei 557 Properties Grand Champions 30 Properties Makena Surf 29 Properties Maui Parkshore 23 Properties Polo Beach Club 7 Properties Koa Lagoon 6 Properties Leinaala 6 Properties Aloha Aku Bamboo 4 Properties Aloha Aku Cocopalm 4 Properties Aloha Aku Honu 4 Properties Aloha Aku Ohana 4 Properties Kamaole Sands Ground 4 Properties Maalaea Surf 4 Properties Maui Br Ocean 4 Properties Residence Inn 3 Properties
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Kihei Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Kihei?

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

How many vacation rentals are available in Kihei?

Currently, the total number of properties listed in 2026 is over 7977 in the Kihei area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Kihei.