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United States
Hawaii
Wailea
Maui

Wailea

570 properties available

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Long-term leases

✓487+ vacation rentals available in Wailea

✓Beachfront condos, homes, and villas

✓Flexible nightly and monthly stays

✓Professionally managed with transparent pricing

Properties in Wailea

Condo in Kihei · ★4.79 · 1 bedroom · 2 beds · 1 private bath - Image 1

Condo in Kihei · ★4.79 · 1 bedroom · 2 beds · 1 private bath - Image 2

Condo in Kihei · ★4.79 · 1 bedroom · 2 beds · 1 private bath - Image 3

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Condo in Kihei · ★4.79 · 1 bedroom · 2 beds · 1 private bath - Image 38

Condo in Kihei · ★4.79 · 1 bedroom · 2 beds · 1 private bath

1 bedroom · 2 beds

Managed by FantasticStay

Condo in Kihei · ★4.61 · 2 bedrooms · 4 beds · 2 shared baths - Image 1

Condo in Kihei · ★4.61 · 2 bedrooms · 4 beds · 2 shared baths - Image 2

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Condo in Kihei · ★4.61 · 2 bedrooms · 4 beds · 2 shared baths - Image 34

Condo in Kihei · ★4.61 · 2 bedrooms · 4 beds · 2 shared baths

2 bedrooms · 4 beds

Managed by FantasticStay

Condo in Kihei · ★4.93 · 1 bedroom · 1 bed · 2 private baths - Image 1

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Condo in Kihei · ★4.93 · 1 bedroom · 1 bed · 2 private baths - Image 24

Condo in Kihei · ★4.93 · 1 bedroom · 1 bed · 2 private baths

1 bedroom · 1 bed

Managed by FantasticStay

Condo in Kihei · ★4.89 · 1 bedroom · 2 beds · 2 shared baths - Image 1

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Condo in Kihei · ★4.89 · 1 bedroom · 2 beds · 2 shared baths - Image 33

Condo in Kihei · ★4.89 · 1 bedroom · 2 beds · 2 shared baths

1 bedroom · 2 beds

Managed by FantasticStay

Condo in Kihei · ★4.86 · 2 bedrooms · 4 beds · 3 private baths - Image 1

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Condo in Kihei · ★4.86 · 2 bedrooms · 4 beds · 3 private baths

2 bedrooms · 4 beds

Managed by FantasticStay

Condo in Kihei · ★4.83 · 2 bedrooms · 4 beds · 2 private baths - Image 1

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Condo in Kihei · ★4.83 · 2 bedrooms · 4 beds · 2 private baths

2 bedrooms · 4 beds

Managed by FantasticStay

Condo in Kihei · ★4.94 · 3 bedrooms · 6 beds · 3.5 private baths - Image 1

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Condo in Kihei · ★4.94 · 3 bedrooms · 6 beds · 3.5 private baths - Image 59

Condo in Kihei · ★4.94 · 3 bedrooms · 6 beds · 3.5 private baths

3 bedrooms · 6 beds

Managed by FantasticStay

Condo in Kihei · ★4.8 · 2 bedrooms · 4 beds · 2 private baths - Image 1

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Condo in Kihei · ★4.8 · 2 bedrooms · 4 beds · 2 private baths - Image 46

Condo in Kihei · ★4.8 · 2 bedrooms · 4 beds · 2 private baths

2 bedrooms · 4 beds

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Condo in Wailea · ★4.73 · Studio · 2 beds · 1 private bath - Image 1

Condo in Wailea · ★4.73 · Studio · 2 beds · 1 private bath - Image 2

Condo in Wailea · ★4.73 · Studio · 2 beds · 1 private bath - Image 3

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Condo in Wailea · ★4.73 · Studio · 2 beds · 1 private bath - Image 20

Condo in Wailea · ★4.73 · Studio · 2 beds · 1 private bath

Studio · 2 beds

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Condo in Kihei · ★5.0 · 2 bedrooms · 3 beds · 2 private baths - Image 1

Condo in Kihei · ★5.0 · 2 bedrooms · 3 beds · 2 private baths - Image 2

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Condo in Kihei · ★5.0 · 2 bedrooms · 3 beds · 2 private baths - Image 50

Condo in Kihei · ★5.0 · 2 bedrooms · 3 beds · 2 private baths

2 bedrooms · 3 beds

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OCEAN FRONT modern 2BR 2BA, king bed, beach, pool! - Image 1

OCEAN FRONT modern 2BR 2BA, king bed, beach, pool! - Image 2

OCEAN FRONT modern 2BR 2BA, king bed, beach, pool! - Image 3

OCEAN FRONT modern 2BR 2BA, king bed, beach, pool! - Image 4

OCEAN FRONT modern 2BR 2BA, king bed, beach, pool! - Image 5

OCEAN FRONT modern 2BR 2BA, king bed, beach, pool! - Image 6

OCEAN FRONT modern 2BR 2BA, king bed, beach, pool! - Image 7

OCEAN FRONT modern 2BR 2BA, king bed, beach, pool! - Image 8

OCEAN FRONT modern 2BR 2BA, king bed, beach, pool! - Image 9

OCEAN FRONT modern 2BR 2BA, king bed, beach, pool! - Image 10

OCEAN FRONT modern 2BR 2BA, king bed, beach, pool! - Image 11

OCEAN FRONT modern 2BR 2BA, king bed, beach, pool! - Image 12

OCEAN FRONT modern 2BR 2BA, king bed, beach, pool! - Image 13

OCEAN FRONT modern 2BR 2BA, king bed, beach, pool! - Image 14

OCEAN FRONT modern 2BR 2BA, king bed, beach, pool! - Image 15

OCEAN FRONT modern 2BR 2BA, king bed, beach, pool! - Image 16

OCEAN FRONT modern 2BR 2BA, king bed, beach, pool! - Image 17

OCEAN FRONT modern 2BR 2BA, king bed, beach, pool! - Image 18

OCEAN FRONT modern 2BR 2BA, king bed, beach, pool! - Image 19

OCEAN FRONT modern 2BR 2BA, king bed, beach, pool! - Image 20

OCEAN FRONT modern 2BR 2BA, king bed, beach, pool! - Image 21

OCEAN FRONT modern 2BR 2BA, king bed, beach, pool! - Image 22

OCEAN FRONT modern 2BR 2BA, king bed, beach, pool! - Image 23

OCEAN FRONT modern 2BR 2BA, king bed, beach, pool! - Image 24

OCEAN FRONT modern 2BR 2BA, king bed, beach, pool! - Image 25

OCEAN FRONT modern 2BR 2BA, king bed, beach, pool! - Image 26

OCEAN FRONT modern 2BR 2BA, king bed, beach, pool!

2 bedrooms · 4 beds

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Condo in Kihei · ★4.85 · 3 bedrooms · 5 beds · 3.5 private baths - Image 1

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Condo in Kihei · ★4.85 · 3 bedrooms · 5 beds · 3.5 private baths - Image 50

Condo in Kihei · ★4.85 · 3 bedrooms · 5 beds · 3.5 private baths

3 bedrooms · 5 beds

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Condo in Kihei · ★5.0 · 2 bedrooms · 3 beds · 2 private baths - Image 1

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Condo in Kihei · ★5.0 · 2 bedrooms · 3 beds · 2 private baths - Image 91

Condo in Kihei · ★5.0 · 2 bedrooms · 3 beds · 2 private baths

2 bedrooms · 3 beds

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Condo in Kihei · ★4.81 · 1 bedroom · 2 beds · 2 private baths - Image 1

Condo in Kihei · ★4.81 · 1 bedroom · 2 beds · 2 private baths - Image 2

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Condo in Kihei · ★4.81 · 1 bedroom · 2 beds · 2 private baths - Image 61

Condo in Kihei · ★4.81 · 1 bedroom · 2 beds · 2 private baths

1 bedroom · 2 beds

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Condo in Wailea · ★4.96 · 2 bedrooms · 4 beds · 2 shared baths - Image 1

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Condo in Wailea · ★4.96 · 2 bedrooms · 4 beds · 2 shared baths - Image 47

Condo in Wailea · ★4.96 · 2 bedrooms · 4 beds · 2 shared baths

2 bedrooms · 4 beds

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Condo in Kihei · ★4.87 · 1 bedroom · 2 beds · 1 shared bath - Image 1

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Condo in Kihei · ★4.87 · 1 bedroom · 2 beds · 1 shared bath - Image 65

Condo in Kihei · ★4.87 · 1 bedroom · 2 beds · 1 shared bath

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Condo in Kihei · ★4.93 · Studio · 1 bed · 1 private bath - Image 1

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Condo in Kihei · ★4.93 · Studio · 1 bed · 1 private bath - Image 36

Condo in Kihei · ★4.93 · Studio · 1 bed · 1 private bath

Studio · 1 bed

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Home in Kihei · ★4.89 · 4 bedrooms · 8 beds · 6 private baths - Image 1

Home in Kihei · ★4.89 · 4 bedrooms · 8 beds · 6 private baths - Image 2

Home in Kihei · ★4.89 · 4 bedrooms · 8 beds · 6 private baths - Image 3

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Home in Kihei · ★4.89 · 4 bedrooms · 8 beds · 6 private baths - Image 41

Home in Kihei · ★4.89 · 4 bedrooms · 8 beds · 6 private baths - Image 42

Home in Kihei · ★4.89 · 4 bedrooms · 8 beds · 6 private baths - Image 43

Home in Kihei · ★4.89 · 4 bedrooms · 8 beds · 6 private baths

4 bedrooms · 8 beds

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Condo in Kihei · ★5.0 · Studio · 1 bed · 1 private bath - Image 1

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Condo in Kihei · ★5.0 · Studio · 1 bed · 1 private bath - Image 31

Condo in Kihei · ★5.0 · Studio · 1 bed · 1 private bath

Studio · 1 bed

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Condo in Kihei · ★4.79 · 2 bedrooms · 6 beds · 2 shared baths - Image 1

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Condo in Kihei · ★4.79 · 2 bedrooms · 6 beds · 2 shared baths - Image 12

Condo in Kihei · ★4.79 · 2 bedrooms · 6 beds · 2 shared baths

2 bedrooms · 6 beds

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Condo in Kihei · ★4.97 · 2 bedrooms · 4 beds · 2 private baths - Image 1

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Condo in Kihei · ★4.97 · 2 bedrooms · 4 beds · 2 private baths - Image 21

Condo in Kihei · ★4.97 · 2 bedrooms · 4 beds · 2 private baths

2 bedrooms · 4 beds

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Condo in Kihei · ★4.85 · 1 bedroom · 2 beds · 2 private baths - Image 1

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Condo in Kihei · ★4.85 · 1 bedroom · 2 beds · 2 private baths - Image 6

Condo in Kihei · ★4.85 · 1 bedroom · 2 beds · 2 private baths - Image 7

Condo in Kihei · ★4.85 · 1 bedroom · 2 beds · 2 private baths - Image 8

Condo in Kihei · ★4.85 · 1 bedroom · 2 beds · 2 private baths - Image 9

Condo in Kihei · ★4.85 · 1 bedroom · 2 beds · 2 private baths - Image 10

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Condo in Kihei · ★4.85 · 1 bedroom · 2 beds · 2 private baths - Image 14

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Condo in Kihei · ★4.85 · 1 bedroom · 2 beds · 2 private baths - Image 22

Condo in Kihei · ★4.85 · 1 bedroom · 2 beds · 2 private baths - Image 23

Condo in Kihei · ★4.85 · 1 bedroom · 2 beds · 2 private baths

1 bedroom · 2 beds

Managed by FantasticStay

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Spring Special / One Bedroom- Closest to beach!

1 bedroom · 1 bed

Managed by FantasticStay

Condo in Wailea · ★4.95 · 2 bedrooms · 3 beds · 2 private baths - Image 1

Condo in Wailea · ★4.95 · 2 bedrooms · 3 beds · 2 private baths - Image 2

Condo in Wailea · ★4.95 · 2 bedrooms · 3 beds · 2 private baths - Image 3

Condo in Wailea · ★4.95 · 2 bedrooms · 3 beds · 2 private baths - Image 4

Condo in Wailea · ★4.95 · 2 bedrooms · 3 beds · 2 private baths - Image 5

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Condo in Wailea · ★4.95 · 2 bedrooms · 3 beds · 2 private baths - Image 25

Condo in Wailea · ★4.95 · 2 bedrooms · 3 beds · 2 private baths - Image 26

Condo in Wailea · ★4.95 · 2 bedrooms · 3 beds · 2 private baths

2 bedrooms · 3 beds

Managed by FantasticStay

What it's like in Wailea

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