February 12, 2026
Escape the Cold
Quite often, around this time of the year, we hear: “Do you have any indoor courts available near New York?”
For years, winter tennis conversations were about coping. Finding bubbles. Booking scarce indoor court time. Planning trips around tournaments.
This year the conversation changed. Instead of asking how to keep playing at home, several clients asked a different question: What if we just played somewhere warm for a week?
And almost immediately, the same locations kept appearing in those conversations. Turks & Caicos. The Bahamas. Barbados. St. Barts.
Not for a vacation in the usual sense. For a tennis week.
A Small Shift That Became Noticeable
Six months ago, Tennis Homes had essentially no Caribbean rental presence. We had one property available for rent.
Today we have eleven. Every one of them has a private court. Some also include padel or pickleball.
The inventory expanded quickly because owners and brokers in warm-weather markets began reaching out to us after seeing the platform grow. What we did not expect was that renter inquiries would follow almost immediately.
Since the start of winter, we’ve received enough Caribbean-specific rental inquiries that we’ve made expanding warm-weather inventory a priority. For a niche network focused only on sports-amenity estates, even a handful of aligned inquiries is noticeable.
What Renters Actually Wanted
The conversations didn’t follow the usual pattern of luxury vacation rental inquiries.
Rather than leading with how many bedrooms or which beach access, renters wanted to talk about the court.
The underlying theme was consistent: they needed to know the facility was actually usable, not just photogenic.
Some renters also specifically asked about padel, which we had not anticipated but are now hearing more often—particularly from European and Latin American clients.
Most inquiries came from families or friend groups traveling together. The court wasn’t an amenity. It was the shared activity that made the trip make sense.
The tennis court was not treated as an extra feature. It was the organizing principle of the trip.
The Markets Getting the Most Interest
The locations renters asked about were remarkably consistent:
Turks & Caicos - Most requested (direct flights from major East Coast cities, established luxury villa market)
The Bahamas - Close second (proximity to Florida, tennis club culture)
Barbados - Growing interest (British influence, Sandy Lane proximity)
St. Barts - Ultra-luxury tier (limited inventory, high demand from UHNW clients)
St. Thomas/USVI - Practical choice (no passport required for US citizens)
We also received inquiries for Mexico (particularly Tulum), which suggests renters are simply searching for accessible warm-weather tennis rather than one specific destination.
The Markets Getting the Most Interest
The Caribbean tennis estates in our network range from approximately $7,500 to $28,500 per night during peak season. For a typical seven-night stay, this translates to $52,000 to $200,000 for the week.
Most of the time, this includes full-time staff (chef, housekeepers, property manager) and use of all amenities.
In other words, this is not hotel pricing. This is private estate rental, typically split among multiple families or groups.
When divided among two to three families (8-12 people), the per-person cost can range from $4,000 to $16,000+ for the week—a significant investment, but one that includes complete privacy, chef-prepared meals, and exclusive use of a championship tennis facility.
What This Tells Us
We are not seeing people abandon their home markets. We are seeing players unwilling to pause their routines.
Tennis players tend to be consistent. They play several times per week. When winter interrupts that rhythm, some are choosing temporary relocation instead of interruption.
This mirrors broader remote work trends: If you can work from anywhere, why not work from somewhere you can also play tennis daily?
The tennis court turns a trip into a purpose. It's no longer a week off—it's where you're playing tennis until spring.
For Property Owners
If you own a tennis estate in a warm climate, winter may quietly be your most relevant season.
What we're learning from successful rentals:
Court condition matters more than interior design. Renters will forgive dated furniture, but not an unplayable court.
Professional photography is non-negotiable. Show the court at sunrise, during play, under lights at night. Renters want to visualize themselves using the facility.
Market the tennis experience, not just the property. Lead with "Championship hard court with LED lighting" rather than "5-bedroom oceanfront villa (also has tennis court)."
Consider tennis-specific amenities. Partner with a local pro for on-call lessons. Stock quality equipment. These additions can justify premium pricing.
What We're Watching Next
We cannot claim a global market shift from a single season of conversations. But inside our niche corner of real estate, we began noticing something clear:
Some people are no longer planning winter vacations. They are planning where they will play tennis until spring.
If this pattern continues, we expect to see more Caribbean properties adding or upgrading tennis facilities, and year-round tennis “migration” patterns emerging.
We’ll report back after next season with more data.
Until the next match,
Tennis Homes
