Cayman Islands Romantic Vacations 2026

Photo by Cayman Islands Department of Tourism

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Top Romantic vacation packages in Cayman Islands

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

Grand Cayman Marriott Beach Resort.

$516

per person

Oct 16 - Oct 18

found 1 day ago

Roundtrip flight included

Miami (MIA) to George Town (GCM)

9/10 Wonderful! (1,003 reviews)

Kimpton Seafire Resort + Spa by IHG

Save 100% on your flight

$755

per person

Oct 16 - Oct 18

found 1 day ago

Roundtrip flight included

Miami (MIA) to George Town (GCM)

9.8/10 Exceptional! (1,005 reviews)

Friendly staff, clean rooms, great resort overall

Reviewed on Sep 15, 2026

The Westin Grand Cayman Seven Mile Beach Resort & Spa

Save 100% on your flight

$1,614

per person

Nov 16 - Nov 20

found 18 hours ago

Roundtrip non-stop flight included

Boston (BOS) to George Town (GCM)

9.2/10 Wonderful! (1,009 reviews)

Shangri-La Boutique Bed & Breakfast

$754

per person

Nov 16 - Nov 20

found 18 hours ago

Roundtrip non-stop flight included

Boston (BOS) to George Town (GCM)

9.8/10 Exceptional! (220 reviews)

The Sunshine Hotel and Suites

$976

per person

Nov 16 - Nov 20

found 18 hours ago

Roundtrip non-stop flight included

Boston (BOS) to George Town (GCM)

9/10 Wonderful! (1,007 reviews)

The hotel was great. Brand new, clean, comfortable beds. The restaurant was delicious and in walking distance to so many great places. The Westin is across the street and you have access to everything there. There is a bus stop at the corner which was also very helpful. Highly recommend.

Reviewed on Sep 14, 2026

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5* Romantic vacations in Cayman Islands

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

Kimpton Seafire Resort + Spa by IHG

Save 100% on your flight

$755

per person

Oct 16 - Oct 18

found 1 day ago

Roundtrip flight included

Miami (MIA) to George Town (GCM)

9.8/10 Exceptional! (1,005 reviews)

Friendly staff, clean rooms, great resort overall

Reviewed on Sep 15, 2026

The Ritz-Carlton, Grand Cayman

$1,846

per person

Nov 16 - Nov 20

found 18 hours ago

Roundtrip non-stop flight included

Boston (BOS) to George Town (GCM)

9.6/10 Exceptional! (1,000 reviews)

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See all available trips from Columbus to Cayman Islands

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3 Night Romantic vacations in Cayman Islands

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

Shangri-La Boutique Bed & Breakfast

$622

per person

Oct 16 - Oct 19

found 16 hours ago

Roundtrip flight included

Boston (BOS) to George Town (GCM)

9.8/10 Exceptional! (220 reviews)

Kimpton Seafire Resort + Spa by IHG

$1,079

per person

Oct 16 - Oct 19

found 16 hours ago

Roundtrip flight included

Boston (BOS) to George Town (GCM)

9.8/10 Exceptional! (1,005 reviews)

Friendly staff, clean rooms, great resort overall

Reviewed on Sep 15, 2026

The Sunshine Hotel and Suites

$1,084

per person

Nov 19 - Nov 22

found 20 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to George Town (GCM)

9/10 Wonderful! (1,007 reviews)

Reviewed on Sep 14, 2026

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4 Night Romantic vacations in Cayman Islands

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

Shangri-La Boutique Bed & Breakfast

$754

per person

Nov 16 - Nov 20

found 18 hours ago

Roundtrip non-stop flight included

Boston (BOS) to George Town (GCM)

9.8/10 Exceptional! (220 reviews)

The Reef Beach Resort, East End, Grand Cayman

$898

per person

Oct 17 - Oct 21

found 13 hours ago

Roundtrip non-stop flight included

New York (JFK) to George Town (GCM)

8.4/10 Very Good! (1,091 reviews)

The Westin Grand Cayman Seven Mile Beach Resort & Spa

$1,222

per person

Oct 17 - Oct 21

found 13 hours ago

Roundtrip non-stop flight included

New York (JFK) to George Town (GCM)

9.2/10 Wonderful! (1,009 reviews)

Don't see what you're looking for?

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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.

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 $516. 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.

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

5 min walk from Seven Mile Beach

$632 nightly

$706 total

Sep 21 - Sep 22

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! (1,000 reviews)

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

Travelers say...

"Friendly staff, clean rooms, great resort overall"

Reviewed on Sep 15, 2026

The Reef Beach Resort, East End, Grand Cayman

2221 Queens Highway East End Grand Cayman

43 min drive from Seven Mile Beach

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 ...

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

Get rates

The Ritz-Carlton, Grand Cayman

West Bay Road Seven Mile Beach Grand Cayman

17 min walk from Seven Mile Beach

$760 nightly

$859 total

Sep 17 - Sep 18

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 1,566 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.