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 $833, price is now $721 per person
$721
per person
Jul 9 - Jul 11
found 1 day ago
Roundtrip flight included
Denver (DEN) to George Town (GCM)
9.8/10 Exceptional! (213 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
The Westin Grand Cayman Seven Mile Beach Resort & Spa
Price was $1,724, price is now $1,555 per person
$1,555
per person
Jun 7 - Jun 9
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to George Town (GCM)
9.2/10 Wonderful! (1,005 reviews)
Very accommodating to my needs
Reviewed on May 4, 2026
The Sunshine Hotel and Suites
Price was $921, price is now $827 per person
$827
per person
Jul 9 - Jul 11
found 1 day ago
Roundtrip flight included
Denver (DEN) to George Town (GCM)
9/10 Wonderful! (1,004 reviews)
Beautiful clean rooms. Comfy bed. Immaculate bathrooms. Friendly and helpful staff.
Reviewed on Apr 17, 2026
Grand Cayman Marriott Resort
Price was $968, price is now $909 per person
$909
per person
Jul 9 - Jul 11
found 1 day ago
Roundtrip flight included
Denver (DEN) to George Town (GCM)
9/10 Wonderful! (1,008 reviews)
Beautiful location. Very cool lobby bar that turns into a great breakfast spot in the morning. Lively atmosphere with people always around.
Reviewed on May 3, 2026
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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 $1,257, price is now $1,257 per person
$1,257
per person
Jul 9 - Jul 11
found 1 day ago
Roundtrip flight included
Denver (DEN) to George Town (GCM)
9.6/10 Exceptional! (1,002 reviews)
The staff was very welcoming and helpful throughout our stay. The property is stunning with a lovely beach area.
Reviewed on May 2, 2026
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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 $1,104, price is now $944 per person
$944
per person
Jun 7 - Jun 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to George Town (GCM)
9.8/10 Exceptional! (213 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
Grand Cayman Marriott Resort
Price was $1,431, price is now $1,342 per person
$1,342
per person
Jun 7 - Jun 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to George Town (GCM)
9/10 Wonderful! (1,008 reviews)
Beautiful location. Very cool lobby bar that turns into a great breakfast spot in the morning. Lively atmosphere with people always around.
Reviewed on May 3, 2026
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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.
Shangri-La Boutique Bed & Breakfast
Price was $880, price is now $666 per person
$666
per person
Jun 7 - Jun 11
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to George Town (GCM)
9.8/10 Exceptional! (213 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
The Reef Beach Resort, East End, Grand Cayman
Save 100% on your flight
Price was $1,165, price is now $710 per person
$710
per person
Jun 7 - Jun 11
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to George Town (GCM)
8.4/10 Very Good! (1,059 reviews)
We had a great time at this resort, where all rooms have an amazing ocean view that is hard to beat. We had a studio, which was very nice and spacious, with a generously sized balcony, which we unfortunately had to share with the room next door. We later found out that this was because this is a time-share resort, where each studio room is attached to a 1-BR unit that is often used by the timeshare owners, who also have the option to close the separating door and rent out the adjacent unit. Nonetheless, it was a very nice stay, the pool was great, with a nice hot tub and plenty of beach chairs at the pool, as well as up and down the extensive beach. We only at at the resort a few times, but the food we had was good and worth the money. The location of the resort is thankfully remote and quite, with a few good restaurants located near by, which we visited frequently; however, it is also such a small island that driving to the Boden Town, Georgetown, or even 7-mile Beach was no problem, where we enjoyed many good restaurants and eateries. Overall, I would stay here again.
Reviewed on May 8, 2026
Morritts Tortuga Club
Price was $997, price is now $796 per person
$796
per person
Jun 7 - Jun 11
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to George Town (GCM)
8.2/10 Very Good! (360 reviews)
Great property located in Grand Cayman's tranquil east end. There's quite a bit of noisy construction ongoing, but otherwise a wonderful place to practice a bit of needed escapism.
Reviewed on Apr 13, 2026
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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 $666. 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
$1,080 nightly
The price is $1,206 total per night from May 9 to May 10
$1,206 total
May 9 - May 10
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...
Beautiful property with amazing staff!
Reviewed on May 3, 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! (1,063 reviews)
Couples like: full-service spa, couples spa treatments, restaurant with ocean view, on the beach
Travelers say...
We had a great time at this resort, where all rooms have an amazing ocean view that is hard to beat. We had a studio, which was very nice and spacious, with a generously sized balcony, which we unfortunately had to share with the room next door. We later found out that this was because this is a ...
Reviewed on May 8, 2026
The Ritz-Carlton, Grand Cayman
West Bay Road Seven Mile Beach Grand Cayman
$1,251 nightly
The price is $1,400 total per night from May 9 to May 10
$1,400 total
May 9 - May 10
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...
The staff was very welcoming and helpful throughout our stay. The property is stunning with a lovely beach area.
Reviewed on May 2, 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.
