Trusted Short Term Vacation Marketing & Rental Management Since 1989
Cayman Vacation has grown into the Cayman Islands’ most trusted vacation rental management company, managing over 300 luxury properties across prime locations.
Our Legacy of Excellence

Expert Market Knowledge
An experienced trusted leader in Cayman Vacation rentals with over 30 years of local marketing and management.

Financial Management & Reporting
Including transparent and trust accounting, payment processing, tax compliance & detailed reporting.

100% Turn Key Solutions
Full-service management, including guest bookings, inquiries, check-ins & property management.

Guest Service & Experience
Delivering exceptional guest experiences and 5-star property reviews from every rental guest.

Travel & Damage Insurance
Partnered with Rental Guardian to ensure your property is covered.

Integrated Systems & Technology
Cutting edge platforms integrated across online travel agencies.

Maximizing Profits
Creative digital marketing strategies & dynamic pricing tools for optimized owner returns.
Why Choose Us?
Cayman Vacation offers 30+ years of property management excellence and above industry occupancy rates and average daily rates. We offer advice you can trust with proven results that speak volumes.

Integrated Systems & Technology
- Digital marketing and social media promotion strategies
- Multi-platform presence (VRBO, Airbnb, Booking.com, Homes and Villas by Marriott, and more)
- Beyond Pricing and LMPM to deliver real-time data and dynamic pricing strategies
- Responsive web design and real time bookings
- Extensive SEO, SEM, Social Media, and Pay Per Click (PPC) campaigns (Google, Perplexity, Bing, YouTube)
100% Turn-Key Solutions
- Local expertise and recommendations
- Full service management, including guest bookings, inquiries, check-ins, and property management
- Marketing strategies designed to target high-value guests and drive repeat bookings
- 24/7 guest support


Complete Booking & Accounting Management
- Real time performance tracking
- Monthly detailed financial reports
- Direct bank deposits
- Trust accounting
- Tax compliance management
Need On-Island Property Management
- Emergency response systems
- Connect with Cayman Islands Department of Tourism-registered property manageers
- Professional on-island property management services
- Quality cleaning services and concierge services available
- Preventive maintenance


Property Owner Benefits
- Comprehensive property damage protection through Rental Guardian and Insure Stays
- Professional revenue management
- Dynamic pricing strategy
- Technology-enabled owner dashboards for real time performance monitoring
- Detailed monthly reporting and tax compliance support

Next Steps of Your Journey
- Reach out with any questions or for clarification.
- Schedule a follow-up call to finalize details and address any remaining concerns.
- Once you’re ready, let us know, and we’ll prepare everything to get your property listed and bookings underway!

Contact Us Today
Onboarding FAQ’S
Once you talk with our team, we’ll start the process of walking you through our management fees, the listing process, and the awesome technology we use to price your home.
If you decide caymanvacation.com is the best option for you, then we’ll sign an agreement. This agreement includes everything we’ll need to manage the property.
Then we will send you a questionnaire to get more details about your property. There are a few more things we’ll take care of to get your home ready for booking.
And after that’s all settled, you can sit back and relax. caymanvacation.com handles all the little details that will make your home a profitable, streamlined investment.
We provide hands-on listing management for all the best vacation rental booking platforms. After your home is listed, everything is streamlined from check-in to check out.
– Advanced technology and dynamic pricing software to get you the best booking prices for every holiday – any season, all year round
– 1-on-1 support online, on the phone, and in person for your guests
-Premier cleaning and upkeep by our local teams or your own
– Thorough post-checkout inspections
You name it, we’ve thought about it. If you have any questions about how we will help you get the best income from your home, we’re here for you.
caymanvacation.com is backed by years of industry expertise, driven by a team with diverse professional backgrounds—including financial services, marketing, advertising, and experience with corporate hotels and banking. As pioneers of online booking in Cayman, we bring a deep understanding of numbers, strategy, and what travelers truly value. While we’re not physically based on the island, our dedicated on-island staff ensure hands-on management and personalized guest care. With our global travel experience and local insights, we know exactly how to create unforgettable stays and maximize the potential of every property. Here’s how we accomplish that:
Lower fees:
– caymanvacation.com charges 10-15% less than traditional local management companies
– Technology
– Our dynamic pricing algorithm ensures you always get the best prices, no matter what time of year
– No time commitments or restrictive agreements
– Marketing power that blows the small fish out of the water
– Ability to control listings on all major booking sites
When we founded caymanvacation.com, we had a vision of combining a management company that had great local knowledge and advanced technology and resources of the big guys.
When you trust us with your home, we go above and beyond to be your partner.
caymanvacation.com – dedicated to managing your property with unwavering commitment and care.
It’s your home!
You can use it whenever you want. Your owner’s portal allows you to reserve stays for yourself and your guests.
Our team is here 24/7 to ensure we’re here to handle any guest experience emergencies.
As a homeowner, you’ll have a dedicated account manager that will communicate between you and the rest of our local staff. We’re always here to address your specific needs, and they are readily available to you.
We work hard to respond to our homeowners within 1 hour between the hours of 8 AM – 8 PM.
Don’t take it from us, listen to the voices of over 9600+ positive reviews and glowing customer testimonials.
Contracts & Fees FAQ’s
When you team up with caymanvacation.com, there are no terms or lock-in periods. Your part of our team and we treat you like family.
We’re confident that you’ll be satisfied with us. We take pride in our industry-leading client retention rate. Thanks to our dedication to providing a high-quality service, we’re becoming a vacation rental leader in Cayman.
caymanvacation.com has worked hard to get our management fee as low as possible for all partners. We pride ourselves in keeping everything wrapped up in one simple contingency-based fee based on your property.
If you want to know how much your property will make and what we’ll charge, you can get a super quick and easy quote from our team.
caymanvacation.com is a full-service vacation rental management company, which means everything you can think of (and more) is included in that fee.
Our management fee takes care of:
-Premier guest services
-Accounting and tax remittance
– Marketing and listing your property on all the best sites
– Dynamic pricing to get you the highest revenue possible
Homeowners are responsible for paying their HOA fees and utilities. Owners are also responsible for covering the cost of any repairs or maintenance that is outside the scope of a routine inspection.
Fees for outside services like hot tub maintenance, trash service, and snow plowing and shoveling are the owner’s responsibility.
Extra services are available from caymanvacation.com contractors at competitive rates.
Pricing, Marketing & Distribution FAQ’s
We make sure that guests can find your home, no matter where they are looking.
It’s more than that, though! You can be confident you’re getting the best coverage for your home because our listings make it to the top of Airbnb, Vrbo, HVMI Marriott, Booking.com, and more.
We’re obsessed with finding new ways to get you the best revenue for your home!
Our team uses dynamic pricing software systems, Beyond Pricing, as well as comparable rental on the island to help get you the best booking rates for any property, any time of the year. Our algorithm analyzes market data and trends and then uses that information to dynamically price your home.
To simplify things, think of how airlines are constantly changing their rates to fit the market. Our prices are adjusted on a daily basis to make sure you are getting the most out of your investment.
On top of that, we keep a close eye on your property’s performance by constantly tracking metrics to make sure we’re hitting benchmarks. This is where your personal manager comes in to make custom adjustments to help.
We set price floors and minimum night stay requirements using market data from across the region to make sure you’re getting the best price. But if you want to customize things, all of your holiday prices and floors can be adjusted.
With caymanvacation.com, custom tools are at your fingertips! We strike a balance between generating revenue and maintaining the long-term value of your home.
Detailed owner statements are given on a monthly basis. Each statement will show detailed breakdowns of every reservation and expense. Then the money is deposited directly into your bank account once you review it for accuracy.
Everything you need to stay up to date is easy to find in your Owner’s Portal. When you sign up you’ll receive login information that allows you to see your calendar, revenue, booking metrics, and more.
You will receive login information to our Owner’s Portal allowing you to see your calendar, revenue, booking metrics, and more.
Our Guest Experience FAQ’s
The caymanvacation.com team works hard to get you the best guests for your home. We’re confident that you’ll be happy with our guest vetting process.
We employ a full-time team to screen every reservation request that comes through for your property.
We accomplish that by:
– Sending guests your custom rental agreement
– Sending guests your custom questionnaire if required for larger bookings or events at a property
– Setting your custom house rules
– Executing your custom guest vetting process
– Setting a price floor and minimum night stay restrictions
– Detecting red flags
Our comprehensive 6-point messaging system ensures seamless communication throughout your entire booking journey. From initial contact to post-stay follow-up, we provide timely, relevant information at every crucial touchpoint. Our dedicated on-island property managers maintain direct communication before and during your stay, offering immediate assistance for any needs or concerns while you’re in paradise.
This systematic approach guarantees: • Proactive guest support • Clear, timely communication • Instant response to any requirements • Personal attention from local property managers • Seamless vacation experience • Peace of mind throughout your stay”+ How are guest emergencies handled?
Our guest services are available 24/7! When guests have a problem, they’ll contact us instead of you. Sleep easy knowing that your guests are taken care of.
One of the great things about caymanvacation.com is that we inspect your home after every guest stay – something you don’t get with other companies.
caymanvacation.com has partnered with Rental Guardian offering Property Protection Policies across all it vacation rental properties.
– Coverage starting from $10,000 with no deductible. There is a $25 minimum claim and a $5,000 limit per any one item.
– Bed Bug Coverage: Coverage starting from $3,000 with a $100 deductible.
– The policy fees are added as a line item and illustrated as HPP and are designed to protect both our guests and property, ensuring a pleasant and secure experience for everyone.
Airbnb and Booking.com have their own damage coverage for claims processes.
Local Regulations & Tax FAQ’s
YES, this must be completed on a monthly basis and filed with the Department of Tourism. This Is something property managers can assist with if needed.
Our property management team members are experts in the licensing process.
We’ve helped many clients avoid the headaches associated with doing things on their own.
It’s painless to get up to the standard with caymanvacation.com. We can guide you with assistance from on-island managers regarding how to go about the licensing and associated requirements.



