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Olowalu Vacation Packages

Build your package with 2 more options

Olowalu Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Maui Beach Vacation Club

Maui Beach Vacation Club

2.5 out of 5
Save 100% on your flight
Price was $2,348, price is now $1,505 per person
$1,505
per person
Nov 13 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Book a stay at this beach aparthotel in Kihei. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Wailea Beach and Hawaiian Islands Humpback Whale National Marine Sanctuary Headquarters are located nearby.

Maui Banyan - Maui Condo & Home

Maui Banyan - Maui Condo & Home

3 out of 5
Save 100% on your flight
Price was $2,578, price is now $1,802 per person
$1,802
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Kahului (OGG)
Stay at this condo in Kihei. Enjoy free WiFi, 2 outdoor pools, and a picnic area. Popular attractions Wailea Beach and Kamaole Beach Park 2 are located nearby.

Hotel Wailea Maui

Hotel Wailea Maui

5 out of 5
Price was $7,179, price is now $5,087 per person
$5,087
per person
Dec 16 - Dec 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Book a stay at this luxury resort in Kihei. Enjoy 3 restaurants, 3 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Wailea Beach and Wailea Blue Golf Course are located nearby.

Maui Schooner Resort

Maui Schooner Resort

3.5 out of 5
Price was $3,646, price is now $2,613 per person
$2,613
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Book a stay at this beach aparthotel in Kihei. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Wailea Beach and Waipuilani Park are located nearby.
Everything is perfect, I’ll stay agin.

Reviewed on Oct 9, 2026

The Residences at Kamaole Sands Resort

The Residences at Kamaole Sands Resort

4.5 out of 5
Save 100% on your flight
Price was $2,794, price is now $2,032 per person
$2,032
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Kahului (OGG)
Book a stay at this luxury aparthotel in Kihei. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Wailea Beach and Kamaole Beach Park 3 are located nearby.
Bonus was there were beach chairs, towels and an umbrella. We only used two chairs as our family were busy snorkeling or boarding away while 1-2 sat out and rested. Clean, right down from beach park 3...stocked pantry got some add-ons and pots and pans enough to allow us making most of our meals. Great times and great communication from host. Thanks! Lucas

Reviewed on Aug 30, 2026

Palms at Wailea Maui

Palms at Wailea Maui

3.5 out of 5
Save 100% on your flight
Price was $2,770, price is now $2,042 per person
$2,042
per person
Nov 13 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Kahului (OGG)
Book a stay at this golf aparthotel in Kihei. Enjoy free WiFi, free parking, and a garden. Our guests praise the property condition in our reviews. Popular attractions Wailea Beach and Keawakapu Beach South are located nearby.

The Ocean View Residence

The Ocean View Residence

3 out of 5
Price was $3,872, price is now $2,864 per person
$2,864
per person
Dec 27 - Jan 4
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Book a stay at this beach apartment in Kihei. Enjoy free WiFi, free parking, and in-room massages. Popular attractions Wailea Beach and Charley Young Beach are located nearby.
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Reviewed on Sep 28, 2026

Maui Kamaole - Maui Condo & Home

Maui Kamaole - Maui Condo & Home

3 out of 5
Price was $3,797, price is now $2,866 per person
$2,866
per person
Dec 24 - Dec 31
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Kahului (OGG)
Stay at this condo in Kihei. Enjoy free WiFi, 2 outdoor pools, and a garden. Popular attractions Wailea Beach and Kihei Boat Ramp are located nearby.

Olowalu Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Maui Beach Vacation Club

Maui Beach Vacation Club

2.5 out of 5
North Kihei
Price was $1,210, price is now $857 per person
$857
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Kahului (OGG)
Hotel Wailea Maui

Hotel Wailea Maui

5 out of 5
Wailea
Save 100% on your flight
Price was $2,851, price is now $1,935 per person
$1,935
per person
Dec 21 - Dec 24
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Maui Banyan Vacation Club

Maui Banyan Vacation Club

3 out of 5
South Kihei
Price was $1,230, price is now $903 per person
$903
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Kahului (OGG)
The Ocean View Residence

The Ocean View Residence

3 out of 5
South Kihei
Save 100% on your flight
Price was $1,758, price is now $1,294 per person
$1,294
per person
Jan 3 - Jan 7
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)

Olowalu Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Maui Beach Vacation Club

Maui Beach Vacation Club

2.5 out of 5
North Kihei
Save 100% on your flight
Price was $2,348, price is now $1,505 per person
$1,505
per person
Nov 13 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Maui Banyan - Maui Condo & Home

Maui Banyan - Maui Condo & Home

3 out of 5
South Kihei
Save 100% on your flight
Price was $2,578, price is now $1,802 per person
$1,802
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Kahului (OGG)
Hotel Wailea Maui

Hotel Wailea Maui

5 out of 5
Wailea
Price was $7,179, price is now $5,087 per person
$5,087
per person
Dec 16 - Dec 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Maui Schooner Resort

Maui Schooner Resort

3.5 out of 5
Central Kihei
Price was $3,646, price is now $2,613 per person
$2,613
per person
Dec 24 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Alaska Airlines
Thu, Nov 5 - Thu, Nov 5
HNL
Daniel K. Inouye Intl.
OGG
Kahului
$133 Roundtrip, found 4 hours ago
$133
Roundtrip
found 4 hours ago
Select Alaska Airlines flight, departing Thu, Nov 5 from Daniel K. Inouye Intl. to Kahului, returning Thu, Nov 5, priced at $133 found 4 hours ago
Bargain Flight
Tue, Jan 5 - Tue, Jan 12
SFO
San Francisco Intl.
OGG
Kahului
$280 Roundtrip, found 1 day ago
$280
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Tue, Jan 5 from San Francisco Intl. to Kahului, returning Tue, Jan 12, priced at $280 found 1 day ago
Bargain Flight
Wed, Jan 6 - Tue, Jan 19
OAK
Oakland Intl.
OGG
Kahului
$284 Roundtrip, found 3 days ago
$284
Roundtrip
found 3 days ago
Select Bargain Flight flight, departing Wed, Jan 6 from Oakland Intl. to Kahului, returning Tue, Jan 19, priced at $284 found 3 days ago
Bargain Flight
Mon, Oct 26 - Mon, Nov 16
LAX
Los Angeles Intl.
OGG
Kahului
$358 Roundtrip, found 4 days ago
$358
Roundtrip
found 4 days ago
Select Bargain Flight flight, departing Mon, Oct 26 from Los Angeles Intl. to Kahului, returning Mon, Nov 16, priced at $358 found 4 days ago