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Vacation Rentals in Eastport

Thoughtfully managed homes in a charming Florida community.
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Corley Retreat at Shady Brook

Corley Retreat at Shady Brook

4.86 (7)

Sumterville, Florida

3 bedrooms•3 baths
$1,115for 5 nights•Nov 11 – Nov 16
Gallinule Court Retreat | Spacious Fenney Patio Villa

Gallinule Court Retreat | Spacious Fenney Patio Villa

The Villages, Florida

2 bedrooms•2 baths
$709for 5 nights•Oct 25 – Oct 30
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About Eastport

Eastport is the newest and most modern of The Villages' town squares, designed with a Mid-Century Coastal aesthetic that sets it apart from the more traditional squares to the north. Opened as part of The Villages' ongoing southern expansion, it brings a fresh, contemporary energy to the community: clean lines, light coastal tones, and airy gathering spaces that feel distinctly different from the Spanish Colonial, Old Florida, and Western themes of the older squares. The square is anchored by a waterfront setting that takes full advantage of its lakeside location. A broad promenade wraps the water, with restaurants and shops opening directly onto the boardwalk so you can dine or browse with lake views in every direction. An open-air entertainment pavilion hosts the same free nightly live music that has made The Villages famous, typically 5–9 PM, and 6–10 PM in summer, giving Eastport a lively, resort-style atmosphere as the sun goes down.

The Newest Corner of The Villages

Beyond dining and entertainment, Eastport was planned as a true neighborhood hub. A modern recreation center with a resort-style pool sits nearby, and the whole district is laced with golf cart paths connecting it to the surrounding southern neighborhoods. Because Eastport serves the fast-growing southern end of The Villages, many of our vacation rentals in this area are just a 5–10 minute golf cart ride away, making it the most convenient square for guests staying in the newest communities south of State Road 44.

Key Features

Discover the character and rhythm of this Florida community.

What Awaits in Eastport

Cream stucco home with a large golf cart in the driveway, dark roof, manicured lawn, and bright blue sky

Charming Community

Small-Town Character

Lit screened pool and spa at night with outdoor seating and open kitchen view

Guest-Focused Service

Hospitality You Can Trust

Large white stucco home with red front door, arched windows, manicured hedges, and a black lifted golf cart in the driveway

Outdoor Living

Florida's Natural Beauty

Gallery

What Guests Say

Trusted by Travelers

4.83

997 reviews

This is a beautifully decorated home and the outdoor living space is exceptional.

Lorraine

Stayed in October 2026

This was a perfect pet-friendly stay. The house was immaculate and the community activities kept us busy. We also enjoyed the outdoor space when we just wanted to relax at the house. We'll for sure be returning!

Geri

Stayed in October 2026

What an absolute treasure tucked away in the Eastport area of The Villages! We booked at the last minute and late at night, while evacuating a hurricane from the Florida Panhandle, and our host swiftly accommodated us within an hour. The home was beautifully appointed, thoughtfully decorated, impeccably clean and exceptionally comfortable. The location was fantastic and made exploring The Villages effortless. Our host was incredibly responsive, even answering a late-night question that I could have avoided by reading the instructions more carefully! After six stressful hours of bumper-to-bumper evacuation traffic, this peaceful little retreat was exactly what we needed. Every detail made us feel welcomed and at ease. We would happily stay here again. An exceptional experience from start to finish!

Rebecca

Stayed in October 2026

This rental was very convenient, and I really appreciated the hosts quick response. The four-seater golf cart was great for getting around, and having so many restaurants and activities nearby made the stay wonderful

Ruth

Stayed in October 2026

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