Cayman Islands Romantic Vacations

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Top Romantic vacation packages in Cayman Islands

Price found within the past 48 hours. Click for updated prices.
Shangri-La Boutique Bed & Breakfast

Shangri-La Boutique Bed & Breakfast

$788
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to George Town (GCM)
9.8/10 Exceptional! (219 reviews)
What a wonderful and relaxing stay! It was the perfect place to unwind after 7 days at a timeshare resort. The rooms are spacious and beautiful. The staff , especially Rose is amazing! Rose was very friendly and full of local recommendations! The pool and hot tub are a hidden oasis which we really enjoyed after a day of playing tourist. The common area was also very relaxing and the availability of a kitchen was exceptional. Nothing beat the morning coffee and enjoying it outside in the swing! We highly recommend Shangri La!

Reviewed on Aug 3, 2026

Kimpton Seafire Resort + Spa by IHG

Kimpton Seafire Resort + Spa by IHG

$855
per person
Oct 16 - Oct 18
found 9 hours ago
Roundtrip non-stop flight included
New York (NYC) to George Town (GCM)
9.8/10 Exceptional! (1,005 reviews)
Excellent stay!! We loved our stay at this hotel. Hotel is beautiful, very clean. Beautiful lobby , great pool , on the beach. Excellent staff: very professional, warm and accommodating.. upon arrival , one of the members greeted us with Prosecco and punch for the children and showed us around the hotel. we arrived early and gave us an upgrade! The lobby is modern and updated - very tall ceilings throughout . decorated beautifully with paintings from a studio that is housed in the lower level. They offer a complimentary coffee bar for guests in the morning and a wine happy hour and live music in the evening - and include juice boxes for families with children. The ocean front room we had was very spacious, immaculate, tall ceilings .Beds were very comfortable .. I didn’t get to use the spa but it looked really nice . They had several restaurants on property that were very good, and also a gourmet market in the lobby that offered coffee, baked goods and amazing pastries and drinks. Our turn down service included individually wrapped freshly baked shortbread cookies that were delicious ! The valet staff brought our car up with cold waters each time. We had a great stay and I would HIGHLY RECOMMEND this hotel for a wonderful stay while in Grand Cayman.

Reviewed on Aug 14, 2026

The Westin Grand Cayman Seven Mile Beach Resort & Spa

The Westin Grand Cayman Seven Mile Beach Resort & Spa

$1,162
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to George Town (GCM)
9.2/10 Wonderful! (1,008 reviews)
Grand Cayman Marriott Resort

Grand Cayman Marriott Resort

$1,076
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to George Town (GCM)
9/10 Wonderful! (1,004 reviews)
Clean room, polite stuff.

Reviewed on Aug 15, 2026

The Sunshine Hotel and Suites

The Sunshine Hotel and Suites

$871
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to George Town (GCM)
9/10 Wonderful! (1,007 reviews)
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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

Kimpton Seafire Resort + Spa by IHG

$855
per person
Oct 16 - Oct 18
found 9 hours ago
Roundtrip non-stop flight included
New York (NYC) to George Town (GCM)
9.8/10 Exceptional! (1,005 reviews)
Excellent stay!! We loved our stay at this hotel. Hotel is beautiful, very clean. Beautiful lobby , great pool , on the beach. Excellent staff: very professional, warm and accommodating.. upon arrival , one of the members greeted us with Prosecco and punch for the children and showed us around the hotel. we arrived early and gave us an upgrade! The lobby is modern and updated - very tall ceilings throughout . decorated beautifully with paintings from a studio that is housed in the lower level. They offer a complimentary coffee bar for guests in the morning and a wine happy hour and live music in the evening - and include juice boxes for families with children. The ocean front room we had was very spacious, immaculate, tall ceilings .Beds were very comfortable .. I didn’t get to use the spa but it looked really nice . They had several restaurants on property that were very good, and also a gourmet market in the lobby that offered coffee, baked goods and amazing pastries and drinks. Our turn down service included individually wrapped freshly baked shortbread cookies that were delicious ! The valet staff brought our car up with cold waters each time. We had a great stay and I would HIGHLY RECOMMEND this hotel for a wonderful stay while in Grand Cayman.

Reviewed on Aug 14, 2026

The Ritz-Carlton, Grand Cayman

The Ritz-Carlton, Grand Cayman

$892
per person
Oct 16 - Oct 18
found 9 hours ago
Roundtrip non-stop flight included
New York (NYC) to George Town (GCM)
9.6/10 Exceptional! (1,005 reviews)
We had a great time at The Ritz-Carlton, Grand Cayman. It’s an amazing resort for families with kids! The staff was lovely, welcoming, and attentive throughout our stay. The property is beautiful. We truly enjoyed our time there and would definitely come back!

Reviewed on Aug 12, 2026

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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

Shangri-La Boutique Bed & Breakfast

$588
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to George Town (GCM)
9.8/10 Exceptional! (219 reviews)
What a wonderful and relaxing stay! It was the perfect place to unwind after 7 days at a timeshare resort. The rooms are spacious and beautiful. The staff , especially Rose is amazing! Rose was very friendly and full of local recommendations! The pool and hot tub are a hidden oasis which we really enjoyed after a day of playing tourist. The common area was also very relaxing and the availability of a kitchen was exceptional. Nothing beat the morning coffee and enjoying it outside in the swing! We highly recommend Shangri La!

Reviewed on Aug 3, 2026

Kimpton Seafire Resort + Spa by IHG

Kimpton Seafire Resort + Spa by IHG

Save 100% on your flight
$922
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to George Town (GCM)
9.8/10 Exceptional! (1,005 reviews)
Excellent stay!! We loved our stay at this hotel. Hotel is beautiful, very clean. Beautiful lobby , great pool , on the beach. Excellent staff: very professional, warm and accommodating.. upon arrival , one of the members greeted us with Prosecco and punch for the children and showed us around the hotel. we arrived early and gave us an upgrade! The lobby is modern and updated - very tall ceilings throughout . decorated beautifully with paintings from a studio that is housed in the lower level. They offer a complimentary coffee bar for guests in the morning and a wine happy hour and live music in the evening - and include juice boxes for families with children. The ocean front room we had was very spacious, immaculate, tall ceilings .Beds were very comfortable .. I didn’t get to use the spa but it looked really nice . They had several restaurants on property that were very good, and also a gourmet market in the lobby that offered coffee, baked goods and amazing pastries and drinks. Our turn down service included individually wrapped freshly baked shortbread cookies that were delicious ! The valet staff brought our car up with cold waters each time. We had a great stay and I would HIGHLY RECOMMEND this hotel for a wonderful stay while in Grand Cayman.

Reviewed on Aug 14, 2026

Grand Cayman Marriott Resort

Grand Cayman Marriott Resort

$792
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to George Town (GCM)
9/10 Wonderful! (1,004 reviews)
Clean room, polite stuff.

Reviewed on Aug 15, 2026

Don't see what you're looking for?
See all available trips from Columbus to Cayman Islands
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4 Night Romantic vacations in Cayman Islands

Price found within the past 48 hours. Click for updated prices.
The Reef Beach Resort, East End, Grand Cayman

The Reef Beach Resort, East End, Grand Cayman

Save 100% on your flight
$817
per person
Sep 19 - Sep 23
found 24 hours ago
Roundtrip non-stop flight included
New York (NYC) to George Town (GCM)
8.4/10 Very Good! (1,084 reviews)
I was very disappointed that I looked forward to having a room with direct access to the beach. The beach was unbearable to enjoy during my stay due to the putrid rotten egg smell the massive piles of seaweed caused. The water was a murky dirty color. I had booked this hotel to be able to enjoy swimming/snorkeling in the ocean. I could not even enjoy walking along the beach due to the horrible smell. Also my room was not cleaned at all during my stay though I hung out the maid service sign requesting service. The only bright spot to this hotel was how good the food was both off the menu and on the special buffet nights. The all inclusive price however was too high for what was offered. The hotel is very interested in providing tours to sell timeshares/condos. Not what my vacation was about.

Reviewed on Aug 15, 2026

Kimpton Seafire Resort + Spa by IHG

Kimpton Seafire Resort + Spa by IHG

$1,365
per person
Oct 17 - Oct 21
found 2 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to George Town (GCM)
9.8/10 Exceptional! (1,005 reviews)
Excellent stay!! We loved our stay at this hotel. Hotel is beautiful, very clean. Beautiful lobby , great pool , on the beach. Excellent staff: very professional, warm and accommodating.. upon arrival , one of the members greeted us with Prosecco and punch for the children and showed us around the hotel. we arrived early and gave us an upgrade! The lobby is modern and updated - very tall ceilings throughout . decorated beautifully with paintings from a studio that is housed in the lower level. They offer a complimentary coffee bar for guests in the morning and a wine happy hour and live music in the evening - and include juice boxes for families with children. The ocean front room we had was very spacious, immaculate, tall ceilings .Beds were very comfortable .. I didn’t get to use the spa but it looked really nice . They had several restaurants on property that were very good, and also a gourmet market in the lobby that offered coffee, baked goods and amazing pastries and drinks. Our turn down service included individually wrapped freshly baked shortbread cookies that were delicious ! The valet staff brought our car up with cold waters each time. We had a great stay and I would HIGHLY RECOMMEND this hotel for a wonderful stay while in Grand Cayman.

Reviewed on Aug 14, 2026

The Westin Grand Cayman Seven Mile Beach Resort & Spa

The Westin Grand Cayman Seven Mile Beach Resort & Spa

$1,162
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to George Town (GCM)
9.2/10 Wonderful! (1,008 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Cayman Islands
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How to find a romantic Cayman Islands vacation

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 $588. 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

Kimpton Seafire Resort + Spa by IHG

60 Tanager Way Seven Mile Beach Grand Cayman
  • 24 min drive from Grand Cayman Beaches
$665 nightly
$744 total
Aug 27 - Aug 28
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! (1,002 reviews)

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

Travelers say...
"Excellent stay!! We loved our stay at this hotel. Hotel is beautiful, very clean. Beautiful lobby , great pool , on the beach. Excellent staff: very professional, warm and accommodating.. upon arrival , one of the members greeted us with Prosecco and punch for the children and showed us around the ..."

Reviewed on Aug 14, 2026

Kimpton Seafire Resort + Spa by IHG
The Reef Beach Resort, East End, Grand Cayman

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! (1,087 reviews)

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

Travelers say...
"I was very disappointed that I looked forward to having a room with direct access to the beach. The beach was unbearable to enjoy during my stay due to the putrid rotten egg smell the massive piles of seaweed caused. The water was a murky dirty color. I had booked this hotel to be able to enjoy swimming/snorkeling ..."

Reviewed on Aug 15, 2026

Get rates
The Reef Beach Resort, East End, Grand Cayman
The Ritz-Carlton, Grand Cayman

The Ritz-Carlton, Grand Cayman

West Bay Road Seven Mile Beach Grand Cayman
  • 23 min drive from Grand Cayman Beaches
$767 nightly
$859 total
Aug 27 - Aug 28
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, ...
9.6/10 Exceptional! (1,002 reviews)

Couples like: full-service spa, beachfront dining, hot tub, on the beach

Travelers say...
"We had a great time at The Ritz-Carlton, Grand Cayman. It’s an amazing resort for families with kids! The staff was lovely, welcoming, and attentive throughout our stay. The property is beautiful. We truly enjoyed our time there and would definitely come back!"

Reviewed on Aug 12, 2026

The Ritz-Carlton, Grand Cayman
See all 1,543 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.

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.