Winter Vacation Rentals & Cabin Rentals in The Villages, FL

Compare 2,452 available vacation home properties, starts from $52

Navigate forward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.

Navigate backward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.

Find the best vacation rental

ACCOMMODATION TYPES

Monthly & Short Term Winter Vacation Rentals in The Villages, FL: Top Deals

Comfort Inn & Suites Tavares North
Comfort Inn & Suites Tavares North
Comfort Inn & Suites Tavares North
Comfort Inn & Suites Tavares North
Comfort Inn & Suites Tavares North
Comfort Inn & Suites Tavares North
Comfort Inn & Suites Tavares North
4.4 (256 reviews)
Comfort Inn & Suites Tavares North
Hotel
$76 /night
View deal
La Bella Inn
La Bella Inn
La Bella Inn
La Bella Inn
La Bella Inn
La Bella Inn
La Bella Inn
4.0 (317 reviews)
La Bella Inn
Hotel
$59 /night
View deal
Holiday Inn Express & Suites Tavares
Holiday Inn Express & Suites Tavares
Holiday Inn Express & Suites Tavares
Holiday Inn Express & Suites Tavares
Holiday Inn Express & Suites Tavares
Holiday Inn Express & Suites Tavares
Holiday Inn Express & Suites Tavares
4.5 (209 reviews)
Holiday Inn Express & Suites Tavares
Hotel
$89 /night
View deal
Comfort Suites The Villages
Comfort Suites The Villages
Comfort Suites The Villages
Comfort Suites The Villages
Comfort Suites The Villages
Comfort Suites The Villages
Comfort Suites The Villages
4.4 (446 reviews)
Comfort Suites The Villages
Hotel
$82 /night
View deal
Key West Resort - Lake Dora
Key West Resort - Lake Dora
Key West Resort - Lake Dora
Key West Resort - Lake Dora
Key West Resort - Lake Dora
Key West Resort - Lake Dora
Key West Resort - Lake Dora
4.0 (311 reviews)
Key West Resort - Lake Dora
Resort
$109 /night
View deal
Farnsworth House Bed and Breakfast
Farnsworth House Bed and Breakfast
Farnsworth House Bed and Breakfast
Farnsworth House Bed and Breakfast
Farnsworth House Bed and Breakfast
Farnsworth House Bed and Breakfast
Farnsworth House Bed and Breakfast
4.7 (151 reviews)
Farnsworth House Bed and Breakfast
House
$140 /night
View deal
Heron Cay Lakeview Bed & Breakfast
Heron Cay Lakeview Bed & Breakfast
Heron Cay Lakeview Bed & Breakfast
Heron Cay Lakeview Bed & Breakfast
Heron Cay Lakeview Bed & Breakfast
Heron Cay Lakeview Bed & Breakfast
Heron Cay Lakeview Bed & Breakfast
4.6 (83 reviews)
Heron Cay Lakeview Bed & Breakfast
Hotel
$170 /night
View deal
Holiday Inn Express Hotel & Suites - The Villages
Holiday Inn Express Hotel & Suites - The Villages
Holiday Inn Express Hotel & Suites - The Villages
Holiday Inn Express Hotel & Suites - The Villages
Holiday Inn Express Hotel & Suites - The Villages
Holiday Inn Express Hotel & Suites - The Villages
Holiday Inn Express Hotel & Suites - The Villages
4.3 (141 reviews)
Holiday Inn Express Hotel & Suites - The Villages
Hotel
$82 /night
View deal
Hampton Inn & Suites Lady Lake/The Villages
Hampton Inn & Suites Lady Lake/The Villages
Hampton Inn & Suites Lady Lake/The Villages
Hampton Inn & Suites Lady Lake/The Villages
Hampton Inn & Suites Lady Lake/The Villages
Hampton Inn & Suites Lady Lake/The Villages
Hampton Inn & Suites Lady Lake/The Villages
4.5 (106 reviews)
Hampton Inn & Suites Lady Lake/The Villages
Hotel
$109 /night
View deal
Search all

Similar Inspirational Vacation Rental Destinations

Which Price Range Is Considered As A Good Deal in The Villages, FL Area?
Vacation House & Villa Rental Price Information in The Villages, FL
+
The graph shows the percentages of vacation homes in each price bucket. The Villages has the largest percentage (38.01%) of homes in $50 - $100 price range.
$0 to 50
$0 to 50
$50 to 100
$50 to 100
$100 to 150
$100 to 150
$150 to 200
$150 to 200
$200 to 250
$200 to 250
$250 to 300
$250 to 300
$300 to 350
$300 to 350
$350 to 400
$350 to 400
$400 to 450
$400 to 450
$450 to 500
$450 to 500
$500 +
$500 +
What are the best places of interest for snowbirds in The Villages, FL?
The Villages, FL - Top Places and Activities for Snowbirds
+
The Villages, FL is a great location for snowbirds to spend their winter or summer months. It's close proximity to healthcare facilities, peaceful environment, wide range of activities, and vibrant communities make it an ideal destination for seniors. Here are some of the top places and activities that snowbirds can enjoy:

  • Spanish Springs Town Square

    This lively outdoor plaza offers plenty of entertainment options for snowbirds. With live music playing throughout the day, shopping opportunities, and delicious dining options, Spanish Springs Town Square is a perfect spot for snowbirds to relax and unwind.

  • Lake Sumter Landing Market Square

    This unique shopping center features a variety of stores, restaurants, and nightlife venues. Snowbirds will find plenty of things to do here, from enjoying the local flavors to participating in the many events held at Lake Sumter Landing Market Square.

  • The Villages Golf & Country Club

    Snowbirds can enjoy a round of golf with friends and family at The Villages Golf & Country Club. The club also offers other amenities such as tennis courts, swimming pools, and more.

How Many Accommodations Are Pets Allowed in The Villages, FL?
Pets Allowed vs Not Allowed in The Villages, FL
+
34.67% of vacation homes in The Villages are pet friendly. Either you bring your loved pets on vacation or you have pet allergies, make sure to select the homes by applying the right filters.
Best Tourist Attractions in The Villages, FL?
Destinations To Visit During the Winter in The Villages, FL
+
Which Airports Should I Choose To Get To The Villages, FL?
Airports Options in The Villages, FL
+

Here are the airports that located near The Villages:

Other Vacation Rentals Ideas

* The displayed nightly rate may be estimated based on a future travel date. Narrow down your search with checkin and checkout dates to see the exact price.
See all offers