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
Price was $616, price is now $484 per person
$484
per person
Aug 14 - Aug 17
found 1 day ago
Roundtrip flight included
Miami (MIA) to George Town (GCM)
9.8/10 Exceptional! (215 reviews)
The Shangri La is an absolute gem of a B&B. We selected it because we were looking for a quiet place far from the large hotels . What we actually found was a welcoming home, not just a functional accommodation. The facilities are great (hammock, pool, hot tub, beach towels etc). The rooms are very clean and comfortable, yet also private. The fully equipped kitchen is accessible at all hours, and breakfast on the deck is in a very peaceful setting. All these are important considerations in a relaxing place to stay . But what made the Shangri La truly memorable is the folks who run it. We have rarely had stays where we felt so genuinely welcome. Rose, who manages the operation, is especially accommodating. Our flight arrival was well before check in time, and we stopped by just in case our room was ready. It wasn’t, but we waited in the comfortable lounge and they made up the room very quickly. We would have been fine to just leave our bags and return later, but this way we were able to settle in and unpack. Throughout our stay, nothing was too much trouble for Rose, and we recommend the Shangri La very highly.
Reviewed on May 5, 2026
Kimpton Seafire Resort + Spa by IHG
Save 100% on your flight
Price was $1,603, price is now $1,180 per person
$1,180
per person
Aug 14 - Aug 17
found 1 day ago
Roundtrip flight included
Miami (MIA) to George Town (GCM)
9.8/10 Exceptional! (1,002 reviews)
Kimpton Seafire did not disappoint. It’s been 5+ years since our last visit and I was thrilled to see the quality (facilities, staff, cleanliness, etc) maintained the same high standard.
Reviewed on Jun 5, 2026
The Sunshine Hotel and Suites
Price was $647, price is now $505 per person
$505
per person
Aug 14 - Aug 17
found 1 day ago
Roundtrip flight included
Miami (MIA) to George Town (GCM)
9/10 Wonderful! (1,002 reviews)
I thoroughly enjoyed my stay at Sunshine suites. All of the staff were helpful in answering questions and given recommendations on where to go, calling for a cab or any other needs. I also appreciated that we had full access to the amenities at the Westin Hotel right across the street that definitely helped to make our stay more enjoyable and affordable.
Reviewed on Jun 7, 2026
Grand Cayman Marriott Resort
Price was $914, price is now $800 per person
$800
per person
Aug 14 - Aug 17
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to George Town (GCM)
9/10 Wonderful! (1,004 reviews)
They are building a wall to prevent beach erosion so the beach outside the hotel is inaccessible and you have to walk quite a distance to get beach stuff
Reviewed on Jun 11, 2026
The Westin Grand Cayman Seven Mile Beach Resort & Spa
Price was $882, price is now $882 per person
$882
per person
Aug 14 - Aug 17
found 1 day ago
Roundtrip flight included
Miami (MIA) to George Town (GCM)
9.2/10 Wonderful! (1,000 reviews)
I’m comparing it to the Palm Heights and the Ritz Carlton, so it may not be fair. It was a louder place with loud people. Bands playing in the lobby at night. Bar filled with people. Lots of families.
Not my usual stay so I wasn’t impressed.
Reviewed on Jun 12, 2026
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See all available trips from Columbus to Cayman Islands
View all trips5* Romantic vacations in Cayman Islands
Price found within the past 48 hours. Click for updated prices.
The Ritz-Carlton, Grand Cayman
Price was $1,167, price is now $1,167 per person
$1,167
per person
Aug 14 - Aug 17
found 1 day ago
Roundtrip flight included
Miami (MIA) to George Town (GCM)
9.6/10 Exceptional! (1,001 reviews)
Awesome place. We’ve been there several times. Family friendly but still great for us, an older couple. You won’t regret staying here. The entire staff is very friendly and accommodating. We’ll be back again.
Reviewed on May 31, 2026
Kimpton Seafire Resort + Spa by IHG
Save 100% on your flight
Price was $1,603, price is now $1,180 per person
$1,180
per person
Aug 14 - Aug 17
found 1 day ago
Roundtrip flight included
Miami (MIA) to George Town (GCM)
9.8/10 Exceptional! (1,002 reviews)
Kimpton Seafire did not disappoint. It’s been 5+ years since our last visit and I was thrilled to see the quality (facilities, staff, cleanliness, etc) maintained the same high standard.
Reviewed on Jun 5, 2026
Don't see what you're looking for?
See all available trips from Columbus to Cayman Islands
View all trips3 Night Romantic vacations in Cayman Islands
Price found within the past 48 hours. Click for updated prices.
Shangri-La Boutique Bed & Breakfast
Price was $616, price is now $484 per person
$484
per person
Aug 14 - Aug 17
found 1 day ago
Roundtrip flight included
Miami (MIA) to George Town (GCM)
9.8/10 Exceptional! (215 reviews)
The Shangri La is an absolute gem of a B&B. We selected it because we were looking for a quiet place far from the large hotels . What we actually found was a welcoming home, not just a functional accommodation. The facilities are great (hammock, pool, hot tub, beach towels etc). The rooms are very clean and comfortable, yet also private. The fully equipped kitchen is accessible at all hours, and breakfast on the deck is in a very peaceful setting. All these are important considerations in a relaxing place to stay . But what made the Shangri La truly memorable is the folks who run it. We have rarely had stays where we felt so genuinely welcome. Rose, who manages the operation, is especially accommodating. Our flight arrival was well before check in time, and we stopped by just in case our room was ready. It wasn’t, but we waited in the comfortable lounge and they made up the room very quickly. We would have been fine to just leave our bags and return later, but this way we were able to settle in and unpack. Throughout our stay, nothing was too much trouble for Rose, and we recommend the Shangri La very highly.
Reviewed on May 5, 2026
Kimpton Seafire Resort + Spa by IHG
Save 100% on your flight
Price was $1,603, price is now $1,180 per person
$1,180
per person
Aug 14 - Aug 17
found 1 day ago
Roundtrip flight included
Miami (MIA) to George Town (GCM)
9.8/10 Exceptional! (1,002 reviews)
Kimpton Seafire did not disappoint. It’s been 5+ years since our last visit and I was thrilled to see the quality (facilities, staff, cleanliness, etc) maintained the same high standard.
Reviewed on Jun 5, 2026
The Sunshine Hotel and Suites
Price was $647, price is now $505 per person
$505
per person
Aug 14 - Aug 17
found 1 day ago
Roundtrip flight included
Miami (MIA) to George Town (GCM)
9/10 Wonderful! (1,002 reviews)
I thoroughly enjoyed my stay at Sunshine suites. All of the staff were helpful in answering questions and given recommendations on where to go, calling for a cab or any other needs. I also appreciated that we had full access to the amenities at the Westin Hotel right across the street that definitely helped to make our stay more enjoyable and affordable.
Reviewed on Jun 7, 2026
Don't see what you're looking for?
See all available trips from Columbus to Cayman Islands
View all trips4 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
Price was $1,155, price is now $655 per person
$655
per person
Aug 14 - Aug 18
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to George Town (GCM)
8.4/10 Very Good! (1,075 reviews)
It’s right on the ocean and I really enjoyed that.
Reviewed on May 25, 2026
Morritts Tortuga Club
Price was $1,368, price is now $1,018 per person
$1,018
per person
Aug 14 - Aug 18
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to George Town (GCM)
8.2/10 Very Good! (365 reviews)
My hubby and I stayed at Morritts Tortuga for our anniversary and we had an amazing time. They hotel was clean and the staff was super friendly and helpful. The pools were fun and the food at the restaurants were great. Everything we had was good and the drinks were very reasonable too. Loved playing pool, darts and ping pong at The Cavern. We hope to make this our annual tradition to stay here.
Reviewed on May 14, 2026
The Westin Grand Cayman Seven Mile Beach Resort & Spa
Price was $1,474, price is now $1,108 per person
$1,108
per person
Aug 14 - Aug 18
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to George Town (GCM)
9.2/10 Wonderful! (1,000 reviews)
I’m comparing it to the Palm Heights and the Ritz Carlton, so it may not be fair. It was a louder place with loud people. Bands playing in the lobby at night. Bar filled with people. Lots of families.
Not my usual stay so I wasn’t impressed.
Reviewed on Jun 12, 2026
Don't see what you're looking for?
See all available trips from Columbus to Cayman Islands
View all tripsHow 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 $484. 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
$945 nightly
The price is $1,056 total per night from Jul 15 to Jul 16
$1,056 total
Jul 15 - Jul 16
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...
"Kimpton Seafire did not disappoint. It’s been 5+ years since our last visit and I was thrilled to see the quality (facilities, staff, cleanliness, etc) maintained the same high standard."
Reviewed on Jun 5, 2026
The Reef Beach Resort, East End, Grand Cayman
2221 Queens Highway East End Grand Cayman
A spa, ocean-view dining, and luxury bedding await couples visiting this romantic aparthotel. The property also offers a terrace, 2 outdoor pools, and a waterfront ...
8.4/10 Very Good! (1,075 reviews)
Couples like: full-service spa, couples spa treatments, restaurant with ocean view, on the beach
Travelers say...
"Property was rebranded before we arrived and yes we knew of change but this would have been 2nd stay was good enough that we decided to come back with our daughter for her graduation present unfortunately it was nowhere near what we expected and our daughter was also disappointed. So we where left ..."
Reviewed on Jun 7, 2026
The Ritz-Carlton, Grand Cayman
West Bay Road Seven Mile Beach Grand Cayman
$1,086 nightly
The price is $1,216 total per night from Jul 11 to Jul 12
$1,216 total
Jul 11 - Jul 12
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! (1,003 reviews)
Couples like: full-service spa, beachfront dining, hot tub, on the beach
Travelers say...
"Awesome place. We’ve been there several times. Family friendly but still great for us, an older couple. You won’t regret staying here. The entire staff is very friendly and accommodating. We’ll be back again."
Reviewed on May 31, 2026
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.
