Season Dates: When to Book a Wellington Seasonal Rental
Wellington's winter season is built around the show calendar at Wellington International. The 2027 Winter Equestrian Festival (WEF) runs 13 weeks, January 6 through April 4, 2027, with each show week running Wednesday to Sunday and the Rolex finale closing the season. Dressage, polo and the social calendar fill in the weeks around it, so most seasonal tenants want a home from late November or December through early April; three-month leases (January–March) are the most common, and some riders arrive as early as October to settle horses.
Demand builds long before the first class: the best furnished homes near the showgrounds are typically signed between August and November. If you are looking in December for a January start, expect fewer choices and firmer prices — and if you own a home you want to rent for the season, listing it by early fall gives you the widest pool of tenants.
What Seasonal Rentals Cost in Wellington (Live Snapshot)
The ranges below come from active rental listings in the Beaches MLS for Wellington on October 28, 2026 (407 active rentals). They are asking rents per month as listed, not a quote; seasonal homes are often listed per month for a three- to six-month term, and estates with barns are sometimes priced per season. We refresh this snapshot as the season approaches — ask us for today's numbers for your dates.
| Type of home | Typical asking rent (per month) | Notes |
|---|---|---|
| Annual lease, 2 bedrooms | $2,400 – $4,200 (median $2,900) | Townhomes and villas; unfurnished |
| Annual lease, 3 bedrooms | $3,000 – $4,500 (median $3,500) | Single-family in gated and golf communities |
| Annual lease, 4+ bedrooms | $3,900 – $5,250 (median $4,500) | Olympia, Binks Forest, Isles, Wellington's Edge |
| Seasonal, 2–3 bedrooms (furnished) | $9,000 – $12,500 (median $10,000) | Condos and villas near the showgrounds |
| Seasonal, 4 bedrooms (furnished) | $8,500 – $16,000 (median $11,000) | Gated communities, pool homes |
| Seasonal, 5+ bedrooms (furnished) | $10,000 – $25,000 (median $18,000) | Larger pool homes; some equestrian lots |
| Equestrian estate with barn | $40,000 – $200,000+ | Palm Beach Point, Grand Prix Village, Saddle Trail, Mallet Hill; often priced per season |
| Barn / stalls only | $750 – $10,500 (median $3,000) | Per stall or whole barn; Paddock Park, Saddle Trail, Sunnyland |
Two things move the price more than anything else: distance to the showgrounds (a hackable distance to Wellington International carries a premium) and whether the home comes turnkey — linens, kitchenware, Wi-Fi, pool service and lawn included. A well-presented 4-bedroom pool home in a gated community can earn in four months what an unfurnished annual lease earns in a year.
Where Seasonal Tenants Look
- Equestrian communities with barns: Palm Beach Point, Grand Prix Village, Saddle Trail Park, Paddock Park, Mallet Hill, Southfields, Palm Beach Polo & Country Club — hack or short trailer ride to the show.
- Gated pool homes 5–10 minutes away: Olympia, Isles at Wellington, Binks Forest, Wellington's Edge, Versailles — popular with families and trainers who keep horses at a boarding barn.
- Condos and villas: St. Andrews at Polo Club, Tennis Lodges, Golf Cottages, Bagattelle, Arissa Place — the most affordable furnished seasonal options.
Browse Wellington homes, Olympia and Isles at Wellington for community details.
What a Seasonal Lease Usually Includes
- Furnished and equipped: furniture, linens, kitchenware, TVs and Wi-Fi. Confirm what is included in writing before you sign.
- Utilities: often included up to a cap (electric can be high with a pool and A/C in a large home); water, trash, lawn and pool service are typically the owner's.
- Deposits: a security deposit (frequently equal to one month) plus, in many cases, a separate cleaning or pet deposit. Florida law requires the landlord to hold deposits in a Florida bank and to follow specific notice rules on returning them (Fla. Stat. 83.49).
- Term and payment: three to six months, commonly paid in full or in two or three installments before and during the stay.
- Taxes on short stays: rentals of six months or less in Palm Beach County are subject to the county Tourist Development Tax (6%) on top of state sales tax (6.5% in Palm Beach County) — the owner collects it from the tenant and remits it to the Palm Beach County Tax Collector. A written lease for more than six months of continuous residence is exempt. We flag this on every seasonal lease so neither side is surprised.
- HOA approval: many gated communities require an application for every tenant, with a fee and a review period of one to four weeks — build it into your timeline.
- Pets and horses: pets are negotiated case by case; horses stay at the barn on the property or at a boarding facility, never at a residential community.
Barns, Stalls and Equestrian Rentals
If you need stalls rather than a house, Wellington has a separate market of barn and stall rentals: individual stalls at a shared barn, private barns with paddocks and a groom's apartment, and full equestrian estates that combine house, barn and arena. Asking rents in the MLS run from about $750 per stall to $10,000+ per month for a private barn, with turnkey estates at $40,000 per month and up. Tell us how many stalls, whether you need turnout and an arena, and how close to the showgrounds you want to be — and use the Barns & Stalls tab above to see what is listed today.
For Tenants: How to Win the Home You Want
- Fix your dates and budget first. Owners prioritize tenants who can commit to clear dates and pay the first installment promptly.
- Have your package ready: ID, proof of funds or income, references, pet details. In season, the prepared tenant wins.
- Decide what matters: hack distance to the show, number of bedrooms for family and staff, pool, fenced yard, a quiet street.
- Let us search beyond the MLS. Many seasonal homes are rented through owner contacts before they are ever listed; we work both.
- Read the lease with us. We walk you through deposits, utility caps, cleaning, tax and HOA rules before you sign.
For Owners: Rent Your Wellington Home for the Season
A furnished seasonal lease can out-earn an annual tenant, but only when the home is presented, priced and papered correctly. Here is how we handle it:
- Pricing from live data — comparable seasonal rentals in your community, adjusted for furnishing, pool and distance to the showgrounds.
- Furnishing and photo guidance — what tenants expect in a turnkey home and what to put away.
- Marketing on the Beaches MLS and beyond — your home appears in every agent's search plus the equestrian networks that fill Wellington each winter.
- Screening — identity, income or funds, references and rental history on every applicant.
- A Florida seasonal lease that covers term, installments, deposits, utility caps, cleaning, pets, HOA approval and Tourist Development Tax collection.
- Handover and check-out — inventory, condition photos and deposit handling that follows Florida's rules.
Thinking about it for 2027–2028 instead? The best time to prepare is right after this season ends, so the home is ready to market by late summer. Ask for a free seasonal rent estimate.
Common Questions
When is the Wellington equestrian season?
The 2027 Winter Equestrian Festival runs January 6 through April 4, 2027 (13 weeks) at Wellington International. Seasonal tenants usually arrive between late November and early January and leave in April; demand for furnished homes builds from late summer.
How much does a seasonal rental in Wellington cost?
Based on active Beaches MLS listings in late October 2026, furnished seasonal homes are mostly asking $9,000–$12,500 per month for 2–3 bedrooms, $8,500–$16,000 for 4 bedrooms and $10,000–$25,000 for 5+ bedrooms; equestrian estates with barns start around $40,000 per month. Annual unfurnished leases run roughly $2,900–$4,500 per month.
Is a 3-month or 6-month lease better?
Three months (January–March) is the most common seasonal term and the easiest to fill. Leases of six months or less are subject to the Palm Beach County Tourist Development Tax; a lease of more than six months is not, which is one reason some owners prefer a longer winter-to-spring term. We model both for you.
Do seasonal rentals charge tax?
Yes, for stays of six months or less: Palm Beach County's Tourist Development Tax (6%) plus state sales tax (6.5% in Palm Beach County) apply to the rent, collected by the owner and remitted to the county Tax Collector. Stays over six months under a written lease are exempt.
Can I rent stalls without a house?
Yes. Wellington has an active market of stall and barn rentals, from a single stall at a shared barn to private barns with arenas. Use the Barns & Stalls tab in the search above, or tell us what you need.
Are pets allowed in seasonal rentals?
Often, with an added deposit or fee, but it is owner by owner and some HOAs have breed or size rules. Tell us about your pets up front so we only show homes that will accept them.
How far ahead should an owner list a seasonal home?
By August or September for the coming season. Homes listed in late fall still rent, but the best tenants and the strongest rents go to homes that were ready early.
Do you represent owners as well as tenants?
Yes. We market seasonal homes on the MLS and beyond, screen every applicant and prepare a Florida lease written for a seasonal term — handled personally by a licensed broker based in Wellington, in English or Spanish.
Also explore: houses for rent in Wellington · all rentals & leasing · Wellington homes for sale · Wellington market report
Sources: 2027 WEF dates per Wellington International / Visit Florida event listings; rent ranges from active Beaches MLS rental listings in Wellington, FL as of October 28, 2026 (asking rents, per month as listed); Tourist Development Tax per the Palm Beach County Tax Collector; deposits per Florida Statutes 83.49. This page is general information, not legal or tax advice.