3373+ Vacation Rentals Near Haleakala Crater |
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Vacation Rentals Fort Myers - Vacation Rentals in Haleakala Crater

Hawaiian Cottage and Personal Paradise/BBKM 2013/0004 in Kihei From US $1,139
         

10.0 (208 Reviews)
Cottage
Hawaiian Cottage and Personal Paradise/BBKM 2013/0004
  • Air Conditioner
  • Parking
  • Pool

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Keawakapu by Coldwell Banker Island Vacations in Wailea From US $518
         

New
House
Keawakapu by Coldwell Banker Island Vacations
  • Parking
  • Wheelchair Accessible
  • Child Friendly

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Papaya Suite in Kihei From US $347
         

|
10.0 (10 Reviews)
Bed & Breakfast
Papaya Suite
  • Air Conditioner
  • Parking
  • TV

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Wailea Custom Home, Pool, Panoramic Ocean View, Waterfalls - Maui Ocean Palms in Kihei From US $742
         

10.0 (186 Reviews)
House
Wailea Custom Home, Pool, Panoramic Ocean View, Waterfalls - Maui Ocean Palms
  • Air Conditioner
  • Parking
  • Pool

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South Maui 1 BR Guest Suite - Kamaole Beach Area in Wailea From US $250
         

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10.0 (8 Reviews)
Apartment
South Maui 1 BR Guest Suite - Kamaole Beach Area
  • Air Conditioner
  • Parking
  • View

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Luxurious Wailea Ocean Vistas in Kihei From US $1,151
         

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10.0 (8 Reviews)
Condo
Luxurious Wailea Ocean Vistas
  • Air Conditioner
  • Parking
  • Pool

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NEW KITCHEN REMODEL! Amazing View! in Wailea From US $492
         

10.0 (159 Reviews)
Condo
NEW KITCHEN REMODEL! Amazing View!
  • Air Conditioner
  • Parking
  • Pool

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Kihei Akahi C210 in Wailea From US $223
         

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10.0 (6 Reviews)
House
Kihei Akahi C210
  • Parking
  • Pool
  • View

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

10.0 (156 Reviews)
Cottage
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted
  • Air Conditioner
  • Parking
  • Pool

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Amazing view, Close to the beach, Wailea Ekahi Unit 20i in Wailea From US $541
         

10.0 (138 Reviews)
Condo
Amazing view, Close to the beach, Wailea Ekahi Unit 20i
  • Air Conditioner
  • Parking
  • Pool

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Amazing Front-Row Ocean View, Retractable Lanai Awning. Walk to Beaches & Shops in Kihei From US $406
         

10.0 (73 Reviews)
Condo
Amazing Front-Row Ocean View, Retractable Lanai Awning. Walk to Beaches & Shops
  • Air Conditioner
  • Parking
  • Pool

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Maui Family Owned & Managed - Wailea Grand Champions Villa in Kihei From US $529
         

10.0 (60 Reviews)
Condo
Maui Family Owned & Managed - Wailea Grand Champions Villa
  • Air Conditioner
  • Parking
  • Pool

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Largest Two Bedroom/Two Bath in the Village, Sleeps Eight & Close to the Beach in Wailea From US $966
         

9.8 (199 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 in Kihei From US $434
         

9.8 (167 Reviews)
Condo
Soooooo Close to the Beach & Completely Remodeled! Relax to the Sound of Waves
  • Air Conditioner
  • Parking
  • Pool

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Wailea Ekahi 51F Oceanview - Walk to Beach in Kihei From US $405
         

9.8 (109 Reviews)
Condo
Wailea Ekahi 51F Oceanview - Walk to Beach
  • Air Conditioner
  • Parking
  • Pool

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PARADISE IS CALLING-Oceanview Family Size-Resort Zoned-King Beds-No Cleaning Fee in Kihei From US $331
         

9.6 (109 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 in Kihei From US $300
         

9.6 (97 Reviews)
Condo
Faces Kamaole Beach Park 3, Ground Floor, Large Lanai, partial Ocean View
  • Air Conditioner
  • Parking
  • Pool

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Wailea Ekahi 14F - Best Views - 3 Minutes Walk to Beach in Wailea-Makena From US $836
         

10.0 (86 Reviews)
Condo
Wailea Ekahi 14F - Best Views - 3 Minutes Walk to Beach
  • Air Conditioner
  • Parking
  • Pool

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Maui Dream Place at Maui Kamaole G-209, Direct Ocean View, 2 Story Modern Condo in Kihei From US $644
         

10.0 (38 Reviews)
Condo
Maui Dream Place at Maui Kamaole G-209, Direct Ocean View, 2 Story Modern Condo
  • Air Conditioner
  • Parking
  • Pool

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Newly Renovated Kihei Condo with Sunset Views – Steps From a Beautiful Beach! in Kihei From US $350
         

9.8 (144 Reviews)
Condo
Newly Renovated Kihei Condo with Sunset Views – Steps From a Beautiful Beach!
  • Air Conditioner
  • Parking
  • Pool

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Kamaole Sands BUILDING ONE Ocean View- 2BR/2BA- Large Lanai & A/C THRU-OUT in Kihei From US $579
         

9.8 (112 Reviews)
Condo
Kamaole Sands BUILDING ONE Ocean View- 2BR/2BA- Large Lanai & A/C THRU-OUT
  • Air Conditioner
  • Parking
  • Pool

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Kam Sands -Innercourt- Ocean views- large lanai & very private third floor end in Kihei From US $355
         

9.8 (61 Reviews)
Condo
Kam Sands -Innercourt- Ocean views- large lanai & very private third floor end
  • Air Conditioner
  • Parking
  • Pool

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Beautiful Wailea Retreat with Pool, Lanai & Beach Access in Wailea From US $611
         

9.6 (43 Reviews)
Condo
Beautiful Wailea Retreat with Pool, Lanai & Beach Access
  • Air Conditioner
  • Parking
  • Pool

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Ocean View Ground Floor Condo | Maui Kamaole I-103 in Kihei From US $383
         

10.0 (82 Reviews)
Condo
Ocean View Ground Floor Condo | Maui Kamaole I-103
  • Air Conditioner
  • Parking
  • Pool

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

Weather in Haleakala Crater

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

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Haleakala Crater, HI

Vacationrentalsfortmyers offers a large selection of top attractions around Haleakala Crater. Research things to do on your vacation before you visit Haleakala Crater.


Haleakala National Park Shops at Wailea Hanawi Falls Hana Forest Reserve Kahikinui Forest Reserve Maui Garden Of Eden - Botanical Gardens & Arboretum Maui Spa Retreat Wailea Emerald Golf Course Ho'omana Spa Maui Wailea Blue Golf Course Pua'a Ka'a State Park Maui's Winery Lani Kai Snorkeling Garden of Eden Arboretum Hosmer Grove Kalaloa Point Makaluapuna Point Wailea Gold Golf Course Kalahaku Overlook Maui Agricultural Research Center

Haleakala Crater Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Haleakala Crater?

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

How many vacation rentals are available in Haleakala Crater?

Currently, the total number of properties listed in 2026 is over 3373 in the Haleakala Crater area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Haleakala Crater.