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Holiday Lettings
> North America
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> Maui
> Villas and condos in Wailea

Villas in Wailea and Condos - Holiday Lettings - Holiday Rentals Wailea

Price per night

£1 £750 -

Bedrooms

Property rating (out of 5)
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  • 4 and above
  • 3 and above
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Filtered properties are rated either by Tripadvisor Vacation Rentals users, or by Vrbo users. Both rating systems are separate, and are depicted differently as shown in the key above. Tripadvisor performs checks on its reviews. Holiday Lettings and companies under Tripadvisor Group do not check Vrbo reviews.
Property type
  • Studio (3)
  • Apartment (48)
  • Villa (6)
  • Cottage (2)
  • House (21)
  • Penthouse (1)
  • Condo (105)
  • Hotel apartment (9)

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3 Holiday homes

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Studio
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Great rentals within 20 miles that match your search

Holiday studio in Lahaina

Lahaina studio

  • Studio
  • 1 bathroom
  • sleeps 4

from £420 / night

£2,283 / week

1 / 16

Great rentals within 20 miles that match your search

Holiday studio with shared pool, golf nearby in Ka'anapali

Ka'anapali studio

  • Studio
  • 1 bathroom
  • sleeps 4

from £240 / night

£1,677 - £2,445 / week

1 / 30

Great rentals within 20 miles that match your search

Holiday studio rental

Napili-Honokowai studio

  • Studio
  • 1 bathroom
  • sleeps 2

from £182 / night

£1,274 / week

1 / 9

Great rentals within 20 miles that match your search

These homes match some but not all of your filters.

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Lahaina holiday condo rental

Lahaina condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Property type

from £275 / night

£1,920 / week

1 / 8

Great rentals within 20 miles that match your search

Condo rental in Wailea with shared pool, golf nearby

Wailea condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Property type

22 reviews

from £316 / night

£2,208 / week

1 / 17

Great rentals within 20 miles that match your search

Holiday apartment with shared pool in Maalaea

Maalaea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Property type

6 reviews

from £302 / night

£2,112 / week

1 / 23

Great rentals within 20 miles that match your search

Villa rental in Ka'anapali with golf nearby

Ka'anapali villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Property type

1 review

from £653 / night

£4,571 / week

1 / 12

Great rentals within 20 miles that match your search

Kihei holiday condo rental

Kihei condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Property type

65 reviews

from £206 / night

£1,440 / week

1 / 45

Great rentals within 20 miles that match your search

Holiday home with swimming pool in Haiku

Haiku house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Property type

102 reviews

from £823 / night

£5,760 / week

1 / 26

Great rentals within 20 miles that match your search

Holiday home in Paia

Paia house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Property type

1 review

from £484 / night

£3,386 / week

1 / 37

Great rentals within 20 miles that match your search

Holiday condo with shared pool in Kihei

Kihei condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Property type

from £183 / night

£1,280 / week

1 / 19

Great rentals within 20 miles that match your search

Kihei holiday condo rental

Kihei condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Property type

from £274 / night

£1,914 / week

1 / 27

Great rentals within 20 miles that match your search

Condo rental in Kihei

Kihei condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Property type

from £174 / night

£1,216 / week

1 / 23

Great rentals within 20 miles that match your search

Holiday condo rental

Lahaina condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Property type

from £457 / night

£3,194 / week

1 / 9

Great rentals within 20 miles that match your search

Holiday apartment in Kihei

Kihei apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Property type

9 reviews

from £182 / night

£1,274 / week

1 / 30

Great rentals within 20 miles that match your search

Holiday apartment in Kihei

Kihei apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Property type

15 reviews

from £219 / night

£1,530 / week

1 / 12

Great rentals within 20 miles that match your search

Napili-Honokowai holiday apartment rental

Napili-Honokowai apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Property type

31 reviews

from £453 / night

£3,168 / week

1 / 51

Great rentals within 20 miles that match your search

Holiday apartment in Kihei

Kihei apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Property type

3 reviews

from £237 / night

£1,658 / week

1 / 34

Great rentals within 20 miles that match your search

Kihei ski home to rent.

Kihei house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Property type

44 reviews

from £823 / night

£5,760 / week

1 / 50

Great rentals within 20 miles that match your search

Holiday apartment with shared pool in Ka'anapali

Ka'anapali apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Property type

15 reviews

from £169 / night

£1,096 - £1,224 / week

1 / 22

Great rentals within 20 miles that match your search

Kihei holiday apartment let

Kihei apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Property type

from £274 / night

£1,914 / week

1 / 62

Great rentals within 20 miles that match your search

Holiday apartment in Kihei

Kihei apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Property type

4 reviews

from £270 / night

£1,619 / week

1 / 33

Great rentals within 20 miles that match your search

Lahaina holiday apartment rental

Lahaina apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Property type

28 reviews

from £822 / night

£5,754 / week

1 / 31

Great rentals within 20 miles that match your search

Cottage rental in Paia

Paia cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Property type

26 reviews

from £293 / night

£2,048 / week

1 / 60

Great rentals within 20 miles that match your search

Holiday apartment with shared pool in Kihei

Kihei apartment

  • 1 bathroom
  • sleeps 2

1 filter does not match: Property type

62 reviews

from £283 / night

£1,978 / week

1 / 89

Great rentals within 20 miles that match your search

Holiday apartment in Napili-Honokowai

Napili-Honokowai apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Property type

from £226 / night

£1,581 - £3,245 / week

1 / 21

Great rentals within 20 miles that match your search

Holiday apartment in Kihei

Kihei apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Property type

24 reviews

from £639 / night

£4,474 / week

1 / 30

Great rentals within 20 miles that match your search

Maalaea holiday apartment rental

Maalaea apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Property type

40 reviews

from £192 / night

£1,342 / week

1 / 17

Great rentals within 20 miles that match your search

Ka'anapali holiday apartment rental

Ka'anapali apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Property type

59 reviews

from £338 / night

£2,362 / week

1 / 54

Great rentals within 20 miles that match your search

Holiday apartment with golf nearby in Maalaea

Maalaea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Property type

74 reviews

from £247 / night

£1,152 / week

1 / 42

Great rentals within 20 miles that match your search

Holiday apartment in Maalaea

Maalaea apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Property type

71 reviews

from £183 / night

£1,280 / week

1 / 18

Great rentals within 20 miles that match your search

Lahaina holiday hotel apartment rental

Lahaina hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Property type

55 reviews

from £200 / night

£1,398 / week

1 / 30

Great rentals within 20 miles that match your search

Kihei holiday condo rental

Kihei condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 filter does not match: Property type

7 reviews

from £362 / night

£2,528 / week

1 / 47

Great rentals within 20 miles that match your search

Lahaina holiday condo rental

Lahaina condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Property type

18 reviews

from £343 / night

£2,400 / week

1 / 48

Great rentals within 20 miles that match your search

Holiday apartment with shared pool in Wailea

Wailea apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Property type

1 review

from £202 / night

£1,338 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday cottage in Kihei

Kihei cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Property type

8 reviews

from £595 / night

£4,160 / week

1 / 40

Great rentals within 20 miles that match your search

Holiday villa rental

Lahaina villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Property type

1 review

from £952 / night

£6,658 / week

1 / 33

Great rentals within 20 miles that match your search

Kihei holiday condo rental

Kihei condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Property type

from £178 / night

£1,242 - £1,888 / week

1 / 16

Great rentals within 20 miles that match your search

Holiday condo in Kapalua

Kapalua condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Property type

1 review

from £823 / night

£5,760 / week

1 / 44

Great rentals within 20 miles that match your search

Holiday villa with golf nearby in Ka'anapali

Ka'anapali villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

1 filter does not match: Property type

from £343 / night

£3,429 / week

1 / 7

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