Kahoolawe Romantic Vacations

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Top Romantic vacation packages in Kahoolawe

Price found within the past 48 hours. Click for updated prices.
Maui Vista – Maui Condo & Home

Maui Vista – Maui Condo & Home

South Kihei
$1,192
per person
Nov 10 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
8.6/10 Excellent! (54 reviews)
Everything was great

Reviewed on Feb 1, 2026

Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

Wailea
Save 100% on your flight
$2,776
per person
Nov 24 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
9.4/10 Exceptional! (1,000 reviews)
My husband and I had an incredible honeymoon stay. We couldn't recommend Hotel Wailea enough!! The team are all so lovely and attentive and all went out their way to give us the best experience. Shannon was an absolute star organising an itinerary prior to arrival so everything was so smooth and easy. Would definitely recommend the in-room Lomi Lomi couples massage and hiring e-bikes with Bear. Shoutout to Sunny also for her help on the front desk and assistance with our postcards! Our hotel room was spacious, comfortable and had a breathtaking ocean view and sofa balcony loungers. We were also very grateful to the valet team for all their assistance chauffeuring us around Wailea and the beaches. The food was utterly divine, in particular the Bird Cage was a highlight, superb menu and sake. The breakfasts also were so fresh! Not to mention the moreish cocktail menu and bites by the pool! The ariel and flow yoga with Andrea and outrigger canoe experience were also fantastic. We couldn't fault it and was the most perfect honeymoon. Thank you all so so much again. We look forward to returning one day X

Reviewed on Sep 6, 2026

Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

Wailea
Save 100% on your flight
$11,946
per person
Nov 22 - Nov 27
found 24 hours ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
8.6/10 Excellent! (1,008 reviews)
Royal Lahaina Bungalows & Spa

Royal Lahaina Bungalows & Spa

Save 100% on your flight
$1,433
per person
Nov 10 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
8/10 Very Good! (26 reviews)
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

Wailea
Save 100% on your flight
$3,701
per person
Nov 10 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
9.6/10 Exceptional! (1,003 reviews)
N/A

Reviewed on Sep 9, 2026

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5* Romantic vacations in Kahoolawe

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

Royal Lahaina Bungalows & Spa

Save 100% on your flight
$1,433
per person
Nov 10 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
8/10 Very Good! (26 reviews)
Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

Wailea
Save 100% on your flight
$2,776
per person
Nov 24 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
9.4/10 Exceptional! (1,000 reviews)
My husband and I had an incredible honeymoon stay. We couldn't recommend Hotel Wailea enough!! The team are all so lovely and attentive and all went out their way to give us the best experience. Shannon was an absolute star organising an itinerary prior to arrival so everything was so smooth and easy. Would definitely recommend the in-room Lomi Lomi couples massage and hiring e-bikes with Bear. Shoutout to Sunny also for her help on the front desk and assistance with our postcards! Our hotel room was spacious, comfortable and had a breathtaking ocean view and sofa balcony loungers. We were also very grateful to the valet team for all their assistance chauffeuring us around Wailea and the beaches. The food was utterly divine, in particular the Bird Cage was a highlight, superb menu and sake. The breakfasts also were so fresh! Not to mention the moreish cocktail menu and bites by the pool! The ariel and flow yoga with Andrea and outrigger canoe experience were also fantastic. We couldn't fault it and was the most perfect honeymoon. Thank you all so so much again. We look forward to returning one day X

Reviewed on Sep 6, 2026

Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

Wailea
Save 100% on your flight
$11,946
per person
Nov 22 - Nov 27
found 24 hours ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
8.6/10 Excellent! (1,008 reviews)
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3 Night Romantic vacations in Kahoolawe

Price found within the past 48 hours. Click for updated prices.
The Residences at Kamaole Sands Resort

The Residences at Kamaole Sands Resort

South Kihei
$1,299
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) to Kahului (OGG)
10/10 Exceptional! (5 reviews)
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

Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

Wailea
Save 100% on your flight
$1,473
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (QLA) to Kahului (OGG)
9.4/10 Exceptional! (1,000 reviews)
My husband and I had an incredible honeymoon stay. We couldn't recommend Hotel Wailea enough!! The team are all so lovely and attentive and all went out their way to give us the best experience. Shannon was an absolute star organising an itinerary prior to arrival so everything was so smooth and easy. Would definitely recommend the in-room Lomi Lomi couples massage and hiring e-bikes with Bear. Shoutout to Sunny also for her help on the front desk and assistance with our postcards! Our hotel room was spacious, comfortable and had a breathtaking ocean view and sofa balcony loungers. We were also very grateful to the valet team for all their assistance chauffeuring us around Wailea and the beaches. The food was utterly divine, in particular the Bird Cage was a highlight, superb menu and sake. The breakfasts also were so fresh! Not to mention the moreish cocktail menu and bites by the pool! The ariel and flow yoga with Andrea and outrigger canoe experience were also fantastic. We couldn't fault it and was the most perfect honeymoon. Thank you all so so much again. We look forward to returning one day X

Reviewed on Sep 6, 2026

Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

Wailea
$1,393
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
9.2/10 Wonderful! (1,008 reviews)
I brought my fiancée to Wailea Beach Resort in Maui for her birthday and proposal.

Reviewed on Sep 9, 2026

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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
$745
per person
Dec 4 - Dec 8
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
8.4/10 Very Good! (937 reviews)
Amazing location right across from the water. Gorgeous pool and spa. Room was bigger than expected and very clean. Brandi in the front office was amazing at check in and when I had more questions. Room had laundry and full kitchen, everything was so comfy. Would definitely stay here again. Only con about this place was the woman with the barking dog and her attitude towards kids. She thought it was appropriate to play piano to “punish” the children for playing in the pool and making her dog bark. Piano playing was decent and I don’t think she punished anyone. It was wonderful background music and kids still played. It’s better to bring everyone together instead of being spiteful. Aloha!

Reviewed on Sep 9, 2026

Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

Wailea
Save 100% on your flight
$1,913
per person
Nov 11 - Nov 15
found 9 hours ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
9.4/10 Exceptional! (1,000 reviews)
My husband and I had an incredible honeymoon stay. We couldn't recommend Hotel Wailea enough!! The team are all so lovely and attentive and all went out their way to give us the best experience. Shannon was an absolute star organising an itinerary prior to arrival so everything was so smooth and easy. Would definitely recommend the in-room Lomi Lomi couples massage and hiring e-bikes with Bear. Shoutout to Sunny also for her help on the front desk and assistance with our postcards! Our hotel room was spacious, comfortable and had a breathtaking ocean view and sofa balcony loungers. We were also very grateful to the valet team for all their assistance chauffeuring us around Wailea and the beaches. The food was utterly divine, in particular the Bird Cage was a highlight, superb menu and sake. The breakfasts also were so fresh! Not to mention the moreish cocktail menu and bites by the pool! The ariel and flow yoga with Andrea and outrigger canoe experience were also fantastic. We couldn't fault it and was the most perfect honeymoon. Thank you all so so much again. We look forward to returning one day X

Reviewed on Sep 6, 2026

Maui Banyan Vacation Club

Maui Banyan Vacation Club

South Kihei
Save 100% on your flight
$876
per person
Dec 4 - Dec 8
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
8/10 Very Good! (388 reviews)
Very nice room. Amazing stay!

Reviewed on Sep 9, 2026

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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 $745. 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.