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Chesapeake Bright Retreat in The Villages

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Exterior
Living area
Dining
Living area
Living area
2 bedrooms2 bathroomsSleeps 4

Popular amenities

  • Swimming pool
  • Garage parking available
  • Pet-friendly
  • Kitchen
  • Washing machine
  • Air-conditioning

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

2 bathrooms

Bathroom 1

Bathroom 2

Spaces

Kitchen
Garden
Dining area

About this property

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.
🏡 General House Rules
🚭 No Smoking or Vaping

Smoking or vaping of any kind is strictly prohibited inside the home, garage, lanai, or anywhere on the premises.

Failure to comply with this rule may result in:

Additional cleaning and deodorizing charges
A penalty fee between $200 and $500
Potential immediate termination of the reservation without refund
🐱 No Cats Allowed

Cats are not permitted in any of our properties under any circumstance unless explicitly authorized in writing prior to arrival.

Unauthorized cats in the property may result in:

Deep cleaning charges
Allergen remediation charges
Penalty fees between $500 and $1,000
Additional charges for damages, odors, or excessive cleaning requirements
🐶 Dog Policy (Pet-Friendly Homes Only)

Some homes may be designated as dog-friendly. Approval is required prior to booking or arrival.

Dog Requirements:
One dog maximum unless otherwise approved
Less than 30 lbs preferred
Non-shedding breeds preferred
Must be house-trained and well-behaved

Guests must contact the host prior to arrival with:

Breed
Weight/size
Age
Temperament/personality details
Whether the dog is potty trained and accustomed to indoor environments

Approval must be confirmed through the booking platform messaging system or in writing.

Additional Cleaning Fees

If excessive pet hair, odors, stains, waste, or damages are found after checkout:

Additional deep cleaning charges may apply
A minimum additional fee of $200 may be charged
Additional damages beyond cleaning may also be billed separately
👶 Children & Infant Safety

Families with children and infants are welcome; however, guests acknowledge that homes are not childproofed unless specifically stated otherwise.

Guests are fully responsible for:

Supervising children at all times
Safety around pools, lanais, golf carts, kitchens, and furniture
Bringing any baby-specific items needed for safety or comfort

The property owner and management company assume no responsibility for accidents or injuries related to inadequate supervision.

🚐 No RVs, Boats, Trailers, or Commercial Vehicles

Due to community deed restrictions within The Villages:

The following are not permitted to be parked overnight or stored at the property:

RVs
Boats
Trailers
Commercial vehicles
Large work vans or utility vehicles

Guests may need to arrange off-site storage accommodations for these vehicles during their stay.

Failure to comply may result in towing, fines, HOA violations, or additional charges passed through to the guest.

🎉 Respectful Use of the Property

Please treat the home and neighbors with care and respect.

No parties or events unless approved in writing
Quiet hours should be respected
Excessive noise or disruptive behavior may result in immediate termination of the stay without refund
🔑 Guest Responsibility

The registered guest making the reservation is responsible for:

All occupants and visitors
Compliance with house rules
Any damages, missing items, excessive cleaning, or violations occurring during the stay

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House Rules

Check in after 3:00 PM

Minimum age to rent: 30

Check out before 11:00 AM

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Children

Children allowed: ages 0–17

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Events

No events allowed

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Pets

Pets allowed

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Smoking

Smoking is not permitted

🏡 General House Rules 🚭 No Smoking or Vaping

Important information

You need to know

Property # 4884599vb
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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher

About the area

The Villages

St. James, a neighbourhood in The Villages, is home to this holiday home. Grand Oaks Resort and Carriage Museum and The Orange Blossom Opry are cultural highlights, and some of the area's attractions include Uncle Donald's Farm and Leesburg Center for the Arts. Kayaking and power boating offer great chances to get out on the surrounding water, or you can seek out an adventure with hunting and cycling nearby.
Map
The Villages, FL

What's nearby

  • Cane Garden Country Club - 8 min drive - 5.0 km
  • The Villages Market Square - 10 min drive - 6.4 km
  • Brownwood Paddock Square - 11 min drive - 5.7 km
  • Lake Deaton - 11 min drive - 6.4 km
  • Lake Okahumpka Park - 13 min drive - 7.5 km

Getting around

  • Leesburg, FL (LEE-Leesburg Intl.) - 33 min drive

Restaurants

  • ‪Panda Express - ‬6 min drive
  • ‪Culver's - ‬6 min drive
  • ‪Circle K - ‬5 min drive
  • ‪Oakwood Smokehouse @ Grill Express - ‬8 min drive
  • ‪Starbucks - ‬5 min drive

Frequently asked questions

Does Chesapeake Bright Retreat in The Villages have a pool?

Yes, this property has a pool.

How much does it cost to stay at Chesapeake Bright Retreat in The Villages?

As of 15 May 2026, prices found for a 1-night stay for 2 adults at Chesapeake Bright Retreat in The Villages on 1 November 2026 start from NZ$185, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Chesapeake Bright Retreat in The Villages pet-friendly?

Yes, pets are allowed at this property.

How much is parking at Chesapeake Bright Retreat in The Villages?

On-site parking is available at the property.

What time is check-in at Chesapeake Bright Retreat in The Villages?

Check-in begins at 3:00 PM.

What time is check-out at Chesapeake Bright Retreat in The Villages?

Checkout is at 11:00 AM.

Where is Chesapeake Bright Retreat in The Villages located?

Located in St. James, this holiday home is 2.6 mi (4.2 km) from Cane Garden Country Club and within 6 miles (10 km) of Lake Deaton and Brownwood Paddock Square. The Villages Market Square and Lake Okahumpka Park are also within 6 miles (10 km).

About the host

Hosted by Jessie | A&J Home Concierge

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Languages:

English, German, Spanish

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