St. James stay.A stay at this St. James vacation home places you within 3 miles (5 km) of Cane Garden Country Club and 6 miles (10 km) of Lake Deaton. Brownwood Paddock Square and The Villages Market Square are also within 6 miles (10 km).
Cane Garden Country Club - 5 min drive - 2.1 miles
Brownwood Paddock Square - 5 min drive - 2.4 miles
Lake Deaton - 6 min drive - 3.0 miles
Lake Okahumpka Park - 6 min drive - 3.2 miles
The Villages Market Square - 6 min drive - 3.8 miles
Getting around
Leesburg, FL (LEE-Leesburg Intl.) - 33 min drive
Restaurants
Panda Express - 6 min drive
Starbucks - 5 min drive
Culver's - 6 min drive
Oakwood Smokehouse @ Grill Express - 8 min drive
Dunkin' - 9 min drive
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
Chesapeake Bright Retreat in The Villages
☀️ Chesapeake Bright Retreat in The Villages ☀️
Welcome to Chesapeake Bright Retreat, a beautifully maintained 2-bedroom, 2-bath villa perfectly situated in the Village of St. James — a central and vibrant location that gives you easy access to the best of The Villages lifestyle. This home offers a warm, bright atmosphere with an open-concept layout, extended enclosed lanai, and plenty of natural light that makes every morning feel like a Florida vacation.
🏡 Home Highlights
Two Bedrooms, Two Bathrooms: Each room features a comfortable queen bed, ample closet space, and inviting décor designed for rest and relaxation.
Spacious Kitchen: A large, fully equipped kitchen with everything you need — cookware, dishes, utensils, coffee maker, toaster, and more. Perfect for preparing meals or entertaining friends.
Enclosed Lanai & Outdoor Seating: The extended lanai is a guest favorite — ideal for enjoying your morning coffee or relaxing with an afternoon cocktail. The additional outdoor seating area makes it perfect for hosting friends or soaking in the Florida sunshine.
Living Area: Open and comfortable with plenty of seating and a bright, welcoming feel that makes it easy to unwind after a day out exploring.
Laundry: Washer and dryer included for convenience.
🚗 Getting Around
This home includes a two-seater golf cart, making it easy to explore The Villages in true local style! Take a short ride to golf courses, pools, shopping, restaurants, and entertainment.
🌴 Location – Village of Liberty Park
Liberty Park is one of the most central and desirable areas in The Villages — perfectly positioned between Lake Sumter Landing and Brownwood Paddock Square.
Lake Sumter Landing (about 10 minutes away): Enjoy nightly live music, waterfront dining, and boutique shopping. Top spots include RJ Gator’s, City Fire, Lighthouse Point Bar & Grill, and the Old Mill Playhouse movie theater.
Brownwood Paddock Square (about 12 minutes away): Home to Bluefin Grill, Gator’s Dockside, and World of Beer, plus outdoor concerts and weekly markets.
Colony Plaza (less than 10 minutes away): Convenient shopping at Publix, Walgreens, Chase Bank, Red Sauce, Bonifay Country Club, and other restaurants and services.
🎾 Recreation & Golf
You’ll have quick access to some of The Villages’ most popular recreation centers and golf courses:
Seabreeze Regional Recreation Center – offers pickleball, tennis, bocce, shuffleboard, fitness classes, and arts & crafts studios.
Colony Cottage Regional Recreation Center – features indoor and outdoor activities, pool tables, and a resort-style family pool.
Golf – Within minutes of Bonifay, Havana, and Mallory Hill Country Clubs, plus dozens of executive courses included with your guest ID.
🆔 Temporary Resident IDs
With your Temporary Resident ID ($50 paid directly to The Villages), you’ll have full access to:
40+ executive golf courses (free with the ID)
Championship golf courses (small fee applies)
All community pools, sports courts, and recreation centers
Fitness clubs, pickleball, tennis, bocce, and shuffleboard
Live music and entertainment at all three town squares nightly
🐾 Policies
Dog allowed upon approval (pet fee may apply)
No cats allowed
No smoking or vaping anywhere on the premises
🌟 Why Guests Love Chesapeake Bright Retreat
Bright, cheerful home filled with natural light
Extended enclosed lanai for relaxing or entertaining
Two cozy queen bedrooms for couples or friends traveling together
Large kitchen and open living space for comfort and ease
Perfect location between Lake Sumter Landing and Brownwood Square
Clean, well-cared-for home with a welcoming feel
Come experience The Villages lifestyle from your very own Chesapeake Bright Retreat — where comfort, convenience, and community come together for the perfect Florida stay. No Smoking or Vaping on Premises ($200 to $500 penalty charged if house rule is ignored) No Cats ($500 to $1,000 penalty charged if house rule is ignored) Dog Friendly - Shedding Breeds will require an additional $150 cleaning fee to make the checkout cleaning a deep cleaning. 2 pets limit Pets upon approval
Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
General
Garden
Policies
Check-in
Check-in time starts at 3:00 PM
Minimum check-in age: 30
Check-out
Check-out before 11:00 AM
Special check-in instructions
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Rules
No Smoking or Vaping on Premises ($200 to $500 penalty charged if house rule is ignored)
Pets
Pets are welcome
Service animals are exempt from fees
Children and extra beds
Children are welcome.
Events
No events allowed
Smoking
Smoking is not permitted
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector and a smoke detector in each accommodation.
Property is also known as
439432
Frequently asked questions
How close is Chesapeake Bright Retreat in The Villages to the airport?
This vacation home is 15.9 mi (33-min drive) away from the Leesburg, FL (LEE-Leesburg Intl.) airport, the closest popular airport to the property.
Does Chesapeake Bright Retreat in The Villages have an airport shuttle?
Airport shuttle services are not available at this vacation home.
Does Chesapeake Bright Retreat in The Villages offer free breakfast?
This vacation home does not offer free breakfast.
Is there a casino at Chesapeake Bright Retreat in The Villages?
No, there is no casino at this vacation home.
What time is check-in at Chesapeake Bright Retreat in The Villages?
Check-in begins at 3:00 PM.
Is there free parking at Chesapeake Bright Retreat in The Villages?
Free parking is not available at this vacation home.
Does Chesapeake Bright Retreat in The Villages have a pool?
Yes, there's a pool.
Does Chesapeake Bright Retreat in The Villages have a spa?
There are no spa services available at this vacation home.
How close is Chesapeake Bright Retreat in The Villages to downtown The Villages?
This vacation home is 4 mi away from The Villages.