Kahoolawe Romantic Vacations

Book a Romantic Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Top Romantic vacation packages in Kahoolawe

Price found within the past 48 hours. Click for updated prices.
Courtyard Maui Kahului Airport

Courtyard Maui Kahului Airport

Save 100% on your flight
$1,423
per person
Sep 24 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
9.2/10 Wonderful! (1,000 reviews)
Wailea Beach Villas

Wailea Beach Villas

Wailea
Save 100% on your flight
$1,929
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
9.8/10 Exceptional! (199 reviews)
Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

Wailea
Save 100% on your flight
$2,697
per person
Oct 25 - Oct 29
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
9.4/10 Exceptional! (1,000 reviews)
The Residences at Kamaole Sands Resort

The Residences at Kamaole Sands Resort

South Kihei
Save 100% on your flight
$1,988
per person
Nov 11 - Nov 18
found 23 hours ago
Roundtrip non-stop flight included
Portland (PDX) to Kahului (OGG)
10/10 Exceptional! (3 reviews)
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

Wailea
Save 100% on your flight
$1,992
per person
Oct 25 - Oct 29
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
9.4/10 Exceptional! (1,006 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Kahoolawe
View all trips

5* Romantic vacations in Kahoolawe

Price found within the past 48 hours. Click for updated prices.
Royal Lahaina Bungalows & Spa

Royal Lahaina Bungalows & Spa

$1,021
per person
Oct 25 - Oct 29
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
8.2/10 Very Good! (24 reviews)
**ONE OF THE WORST HOTEL MANAGEMENT EXPERIENCES WE'VE HAD** We gave Royal Lahaina every opportunity to address our experience privately and even escalated it to their management company, with no response. We stayed for a week in June 2026 with two rooms. Three days before check-in, the hotel couldn't locate our confirmed reservation. After more than TWO HOURS on the phone, manager Gretchen told me they couldn't accommodate our requests, suggested we "book a better hotel like the Montage or the Ritz," said she was canceling our reservations, and hung up. I had to repeatedly call back to ensure our family still had rooms. Management later told me Gretchen received disciplinary action. We tried contacting Hotel Manager Yvette three times during our stay and left two voicemails. She never contacted us until two days after we left. A brief call with my wife was later characterized as accepting their "final resolution": a $75 beach-chair credit. Even after I emailed a detailed complaint, Yvette never personally responded. The resort itself fell short: housekeeping every other day despite a $45/night resort fee; two beach chairs cost another $75/day and were collected at 5 PM sharp; rude beach staff; and large gaps around our renovated room door that let in light, noise and bugs. After spending thousands on two rooms, fees, food and services, management's lack of ownership was the worst part. Ironically, their original advice was best: **Next time, we'll stay somewhere better.

Reviewed on Aug 21, 2026

Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

Wailea
Save 100% on your flight
$2,697
per person
Oct 25 - Oct 29
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
9.4/10 Exceptional! (1,000 reviews)
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

Wailea
Save 100% on your flight
$1,992
per person
Oct 25 - Oct 29
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
9.4/10 Exceptional! (1,006 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Kahoolawe
View all trips

3 Night Romantic vacations in Kahoolawe

Price found within the past 48 hours. Click for updated prices.
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

Wailea
Save 100% on your flight
$1,606
per person
Oct 23 - Oct 26
found 10 hours ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
9.4/10 Exceptional! (1,006 reviews)
Wailea Beach Villas

Wailea Beach Villas

Wailea
Save 100% on your flight
$1,747
per person
Nov 2 - Nov 5
found 20 hours ago
Roundtrip non-stop flight included
Seattle (SEA) to Kahului (OGG)
9.8/10 Exceptional! (199 reviews)
Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

Wailea
Save 100% on your flight
$1,981
per person
Oct 25 - Oct 28
found 12 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Kahului (OGG)
9.4/10 Exceptional! (1,000 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Kahoolawe
View all trips

4 Night Romantic vacations in Kahoolawe

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

Maui Beach Vacation Club

North Kihei
Save 100% on your flight
$921
per person
Oct 25 - Oct 29
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
8.4/10 Very Good! (926 reviews)
Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

Wailea
Save 100% on your flight
$2,697
per person
Oct 25 - Oct 29
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
9.4/10 Exceptional! (1,000 reviews)
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

Wailea
Save 100% on your flight
$1,992
per person
Oct 25 - Oct 29
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
9.4/10 Exceptional! (1,006 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Kahoolawe
View all trips

How to find a romantic Kahoolawe vacation

How can I find the best Kahoolawe vacation packages for couples?

To win over the love of your life, first choose where and when you want to bring the romance. Now flirt with the filters to add ocean views, spa, pools, and anything else that gets your heart racing.

How can I find cheap Kahoolawe romantic packages for two?

For dollar-friendly delights, sort your search results by price or deals. You can also filter by budget to find romantic retreats at prices you’ll love. For an affordable and alluring adventure, try self-catering and visiting outside busy months of .

How can I plan a great romantic trip to Kahoolawe?

Find what fills you with joy and dive right in, whether you thrill in a little adventure or lust for long lazy days by the pool, handcrafted cocktails in hand. Fire cupid’s arrow at our filters and build your dream trip for two.

How much is a trip for two to Kahoolawe?

Put a price on love with stunning deals for duos starting at just $921. Stay during the quiet season, in , for breaks to make your bank balance smile. Prices and availability are subject to change. Additional terms may apply.

Can I book Kahoolawe spa packages for couples?

Check the filter box for a seductive stay at a spa. Sort your results by price, deals, rating, and more to guarantee the perfect match.

What’s the best time of year for a romantic vacation in Kahoolawe?

Book your romantic getaway during the quieter months of when you can have the place to yourself, pretty much. To show your partner off to the world, provide a more abundant audience.

How can I book romantic weekend getaway packages in Kahoolawe?

To book a loved-up break in Kahoolawe, enter your travel dates and sort by price, deals, rating—whatever matters most to you and your partner. Now, you can add some adult-only amenities, like a hot tub or full-service spa for total R, R, & R (that’s romance, rest, and recuperation).

Can I book a romantic trip to Kahoolawe with free cancellation and/or flexible dates?

The course of true love should always run smooth, but we get that there are hiccups. So, filter by payment option to search for romantic stays with free cancellation and buy now, pay later options.

Why should I book my Kahoolawe romantic holiday with Expedia?

If you’ve only got eyes for excellent escapes, book your loved-up break with Expedia. Fling the filters to find accommodation you’ll adore. And what’s more attractive than ATOL protection?

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.