Cayman Islands Romantic Vacations 2026

Photo by Cayman Islands Department of Tourism

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 Cayman Islands

Price found within the past 48 hours. Click for updated prices.

Shangri-La Boutique Bed & Breakfast

$910

per person

Dec 2 - Dec 6

found 1 hour ago

Roundtrip non-stop flight included

Memphis (MEM) to George Town (GCM)

9.8/10 Exceptional! (221 reviews)

I love everything

Reviewed on Sep 23, 2026

The Sunshine Hotel and Suites

$1,740

per person

Dec 2 - Dec 6

found 1 hour ago

Roundtrip non-stop flight included

Memphis (MEM) to George Town (GCM)

9/10 Wonderful! (1,005 reviews)

Kimpton Seafire Resort + Spa by IHG

$5,148

per person

Dec 2 - Dec 6

found 1 hour ago

Roundtrip non-stop flight included

Memphis (MEM) to George Town (GCM)

9.8/10 Exceptional! (1,007 reviews)

We loved our stay!

Reviewed on Oct 1, 2026

Grand Cayman Marriott Beach Resort

$1,654

per person

Dec 2 - Dec 6

found 1 hour ago

Roundtrip non-stop flight included

Memphis (MEM) to George Town (GCM)

9/10 Wonderful! (1,003 reviews)

The Ritz-Carlton, Grand Cayman

$1,773

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip flight included

New York (JFK) to George Town (GCM)

9.6/10 Exceptional! (1,004 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Cayman Islands

View all trips

5* Romantic vacations in Cayman Islands

Price found within the past 48 hours. Click for updated prices.

The Ritz-Carlton, Grand Cayman

$1,773

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip flight included

New York (JFK) to George Town (GCM)

9.6/10 Exceptional! (1,004 reviews)

Kimpton Seafire Resort + Spa by IHG

$5,148

per person

Dec 2 - Dec 6

found 1 hour ago

Roundtrip non-stop flight included

Memphis (MEM) to George Town (GCM)

9.8/10 Exceptional! (1,007 reviews)

We loved our stay!

Reviewed on Oct 1, 2026

Don't see what you're looking for?

See all available trips from Columbus to Cayman Islands

View all trips

3 Night Romantic vacations in Cayman Islands

Price found within the past 48 hours. Click for updated prices.

Shangri-La Boutique Bed & Breakfast

$700

per person

Nov 5 - Nov 8

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to George Town (GCM)

9.8/10 Exceptional! (221 reviews)

I love everything

Reviewed on Sep 23, 2026

The Sunshine Hotel and Suites

$816

per person

Nov 5 - Nov 8

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to George Town (GCM)

9/10 Wonderful! (1,005 reviews)

Kimpton Seafire Resort + Spa by IHG

Save 100% on your flight

$3,806

per person

Dec 3 - Dec 6

found 13 hours ago

Roundtrip non-stop flight included

Detroit (DTW) to George Town (GCM)

9.8/10 Exceptional! (1,007 reviews)

We loved our stay!

Reviewed on Oct 1, 2026

Don't see what you're looking for?

See all available trips from Columbus to Cayman Islands

View all trips

4 Night Romantic vacations in Cayman Islands

Price found within the past 48 hours. Click for updated prices.

Shangri-La Boutique Bed & Breakfast

$910

per person

Dec 2 - Dec 6

found 1 hour ago

Roundtrip non-stop flight included

Memphis (MEM) to George Town (GCM)

9.8/10 Exceptional! (221 reviews)

I love everything

Reviewed on Sep 23, 2026

The Reef Beach Resort, East End, Grand Cayman

$961

per person

Dec 2 - Dec 6

found 7 hours ago

Roundtrip non-stop flight included

New York (NYC) to George Town (GCM)

8.4/10 Very Good! (1,098 reviews)

Clean room, beach view excellent staff

Reviewed on Sep 27, 2026

The Sunshine Hotel and Suites

$1,740

per person

Dec 2 - Dec 6

found 1 hour ago

Roundtrip non-stop flight included

Memphis (MEM) to George Town (GCM)

9/10 Wonderful! (1,005 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Cayman Islands

View all trips

How can I find the best Cayman Islands 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 Cayman Islands 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 Cayman Islands?

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 Cayman Islands?

Put a price on love with stunning deals for duos starting at just $700. 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 Cayman Islands 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 Cayman Islands?

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 Cayman Islands?

To book a loved-up break in Cayman Islands, 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 Cayman Islands 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 Cayman Islands 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?

Top Romantic Cayman Islands Hotels

Kimpton Seafire Resort + Spa by IHG

60 Tanager Way Seven Mile Beach Grand Cayman

24 min drive from Grand Cayman Beaches

$677 nightly

$756 total

Oct 5 - Oct 6

Total with taxes and fees

Fall in love again at this upscale hotel. You and your special someone are sure to love the hot tub, spa, and poolside dining. You'll also appreciate the beach ...

9.8/10 Exceptional! (1,003 reviews)

Couples like: full-service spa, couples spa treatments, poolside dining, hot tub

Travelers say...

"We loved our stay!"

Reviewed on Oct 1, 2026

The Reef Beach Resort, East End, Grand Cayman

2221 Queens Highway East End Grand Cayman

20 min drive from Grand Cayman Beaches

A spa, ocean-view dining, and a garden await couples visiting this romantic aparthotel. The property also offers luxury bedding, a terrace, and a waterfront ...

8.4/10 Very Good! (1,098 reviews)

Couples like: full-service spa, couples spa treatments, restaurant with ocean view, on the beach

Travelers say...

"Clean room, beach view excellent staff"

Reviewed on Sep 27, 2026

Get rates

The Ritz-Carlton, Grand Cayman

West Bay Road Seven Mile Beach Grand Cayman

23 min drive from Grand Cayman Beaches

$760 nightly

$859 total

Oct 3 - Oct 4

Total with taxes and fees

A spa, al fresco dining, and a garden await couples looking for a romantic getaway at this upscale resort. The property also offers soaking tubs, a hot tub, ...

See all 1,562 properties in Cayman Islands

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.