The Villages, Florida
Seasonal Rentals in The Villages, FL
A seasonal rental is any multi-month stay — most often the winter, but plenty of guests take a spring or autumn stretch instead, when the weather is just as good and the rates are lower.
31 homes available
See all our homes →
Sumterville, FL — The Villages area
2BR · 2 Bath · Golf Cart · Mins to Eastport Sq
2.1 mi · 6 min drive to Eastport
Golf cart included
Village of Caroline · The Villages, FL
3BR in The Villages Near Lake Sumter | Golfcart
1.9 mi · 5 min drive to Lake Sumter Landing
Golf cart included
Village of Labelle · The Villages, FL
3BR Near Brownwood + Golf Cart + Office + Patio
4.4 mi · 10 min drive to Brownwood Paddock Square
Golf cart included
Village of Shady Brook · The Villages, FL
Brand New | Golf Cart Included | Walk to Saluki
2.8 mi · 10 min drive to Eastport
Golf cart included
Village of St. Catherine · The Villages, FL
Coastal Cottage | Golf Cart & Near Sawgrass
0.8 mi · 4 min drive to Sawgrass Grove
Golf cart included
Village of Oak Hollow · The Villages, FL
Cozy 2BR Near Eastport Sq. & Middleton | Patio
1.8 mi · 7 min drive to Eastport
Village of Moultrie Creek · The Villages, FL
Cozy 2BR With Golfcart | 5 Mins to Eastport Sq.
2.6 mi · 8 min drive to Eastport
Golf cart included
Village of Shady Brook · The Villages, FL
Dog-Friendly Coastal Cottage | Golf Cart
1.7 mi · 6 min drive to Eastport
Golf cart included
Village of Moultrie Creek · The Villages, FL
Eastport 3BR · Golf Cart · Patio · Near Pools
2.9 mi · 10 min drive to Eastport
Golf cart included
Village of Edenfield · The Villages, FL
Fire Pit Villa · 2BR · Golf Cart · Near Eastport
1.6 mi · 5 min drive to Sawgrass Grove
Golf cart included
Village of Liberty Park · The Villages, FL
Lake Sumter 2BR · Golf Cart · BBQ · Brownwood
2.8 mi · 7 min drive to Lake Sumter Landing
Golf cart included
Village of Pennecamp · The Villages, FL
Lake Sumter Retreat · Golf Cart · BBQ · Backyard
3.5 mi · 9 min drive to Lake Sumter Landing
Golf cart included
Village of Oak Hollow · The Villages, FL
Lakefront 3BR Retreat | Golfcart | Near Eastport
1.2 mi · 5 min drive to Eastport
Golf cart included
Village of Liberty Park · The Villages, FL
Lakeside Nest · 2BR · Golf Cart · Near Brownwood
3.1 mi · 8 min drive to Lake Sumter Landing
Golf cart included
Village of LaGrange · The Villages, FL
Luxe 3BR | Long & Short Stays l Walk to Eastport
0.8 mi · 4 min drive to Eastport
Golf cart included
Village of Edenfield · The Villages, FL
New 2BR The Villages | Golf Cart | Eastport Sq.
1.6 mi · 5 min drive to Sawgrass Grove
Golf cart included
Village of Newell · The Villages, FL
Palm Tree Pad | New 3BR | Sawgrass | Golf Cart
2.3 mi · 7 min drive to Sawgrass Grove
Golf cart included
Village of Lake Denham · The Villages, FL
Spacious 3BR · Sleeps 7 · King Bed · Lanai
3.5 mi · 10 min drive to Sawgrass Grove
Village of Pinellas · The Villages, FL
Sunnyside Escape in The Villages | Golfcart | BBQ
2.2 mi · 6 min drive to Brownwood Paddock Square
Golf cart included
Collier at Atwood Bungalows · The Villages, FL
The Admiral · 3BR · Golf Cart · BBQ · Brownwood
0.7 mi · 3 min drive to Brownwood Paddock Square
Golf cart included
Village of Moultrie Creek · The Villages, FL
The Eastport Escape | New 3BR | King + Golf Cart
2.7 mi · 9 min drive to Eastport
Golf cart included
Village of Well Point · The Villages, FL
The Golden Palm Mins to Middleton & Eastport Sq.
2.1 mi · 9 min drive to Eastport
Golf cart included
Village of Waters Edge · The Villages, FL
The Golfer's Edge
1.3 mi · 7 min drive to Eastport
Golf cart included
Village of Summerhill · The Villages, FL
The Hot Tub Haven | Golf Cart & BBQ | Lake Sumter
4.4 mi · 11 min drive to Lake Sumter Landing
Golf cart included
Village of Waters Edge · The Villages, FL
The Palmetto · Golf Cart · Near Eastport Sq
1.6 mi · 7 min drive to Eastport
Golf cart included
Village of Waters Edge · The Villages, FL
The Pin High Pad
1.7 mi · 5 min drive to Eastport
Golf cart included
Village of Shady Brook · The Villages, FL
The Strawbridge · 2 Ensuite Suites · Golf Cart
1.6 mi · 6 min drive to Eastport
Golf cart included
Collier at Atwood Bungalows · The Villages, FL
The Swift Fox | King Bed | Golf Cart | Brownwood
0.6 mi · 3 min drive to Brownwood Paddock Square
Golf cart included
Collier at Atwood Bungalows · The Villages, FL
The Villages with a View
0.7 mi · 3 min drive to Brownwood Paddock Square
Golf cart included
Village of Shady Brook · The Villages, FL
Villages Escape by Eastport Sq. | Golfcart | BBQ
2.3 mi · 8 min drive to Eastport
Golf cart included
Village of Cason Hammock · The Villages, FL
Walk to Sawgrass! Near Eastport | Golfcart | Patio
1 mi · 3 min drive to Sawgrass Grove
Golf cart included
Peak season is January through March and it books first. November, December and April are the value months: the same homes, the same golf carts, the same town squares, at a materially lower rate.
Every home is furnished and equipped for a long stay rather than a weekend. If you are deciding between months, tell us the range you are considering and we will show you what the difference actually costs.
Where a cart is included there is a $20 insurance charge for the stay and a short liability waiver to sign — the access code is emailed to you automatically once it is done.
What to know
- Peak: January–March. Value: November, December, April
- Multi-month pricing, well under the nightly equivalent
- Fully furnished and equipped for a long stay
- Most homes include a golf cart
- Lifestyle ID applications handled by us
Common questions
Which months are cheapest?
November, early December and April are consistently better value than January through March, and the community is no less active. If your dates are flexible, shifting by a few weeks can make a real difference.
How far ahead do seasonal rentals book?
Peak-season homes commonly go six to twelve months out. Shoulder months stay open much later.
Do I need a Villages Lifestyle ID?
Only if you want the pools, recreation centers, pickleball or golf. It is $50 per request form — not per person — and one form covers one or two IDs. Two is the maximum The Villages issues per home; everyone else in your group uses free guest passes from any Regional Recreation Center. We apply on your behalf, so you never contact The Villages yourself. Payment is cash or check made out to “The Villages” when you collect the cards — they do not take credit cards. It is not same-day, so send us your details as early as you can.
Is it cheaper to book direct?
Yes. Booking with us directly avoids the platform service fee Airbnb and Vrbo add at checkout, and you deal with the people who actually manage the home rather than a call centre.
Tell us your dates
Our calendar moves daily and we only publish part of it. Send us what you are looking for and we will come straight back with what is actually open — and what it costs.
Questions? Text us.
We answer fast — usually within an hour, seven days a week.
Text usOr reach us at (321) 635-0659.
What guests say about our homes
4.87
average rating
1,460
guest reviews
5
years hosting
We're Airbnb Superhosts with a 4.87 rating across 1,460 guest reviews, and we reply to 100% of messages — usually within an hour.
“Excellent home! Clean, spacious and well kept with all needed amenities. In a quiet and peaceful neighborhood with very little to no traffic on the street which is perfect for the kids playing outside. Even the neighbors were friendly and inviting. There were numerous restaurants and shopping areas within just few minutes. Host was great, very communicative and even gracious with extra time to check out. You will enjoy this home! A five star experience all around!”
“The home was perfect! Location was excellent close to so much. The host was awesome very quick responses to any questions we had. I would highly recommend this home great place and fantastic hosts.”
“This was my first time booking an Airbnb and when I tell you, I enjoyed myself so peaceful so clean environment. Everything I need was there I really appreciate them both and they always check on everything.”
“Everything was just as listed and we had a great stay!”
Reviews left by guests on Airbnb for homes managed by Hastings Home Ventures.