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Middleton Vacation Rentals

Thoughtfully managed homes in the heart of The Villages.
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Silvana Delight Villa (DeLuna)

Silvana Delight Villa (DeLuna)

The Villages, Florida

2 bedrooms•2 baths
$3,902for 27 nights•Jan 31 – Feb 28
Steele Path Waterlily Retreat (Marsh Bend)

Steele Path Waterlily Retreat (Marsh Bend)

5.00 (9)

The Villages, Florida

3 bedrooms•2 baths
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About Middleton

Middleton is a warm, close-knit family community within The Villages, beloved for its tree-lined streets, friendly neighbors, and peaceful neighborhood atmosphere. Unlike the bustling town squares, Middleton offers a quieter, more residential feel while still providing easy access to all the amenities that make The Villages so special. It's an ideal location for families, and those seeking a serene retreat.

Eat & Drink

Recommended Restaurants

A few good spots near Middleton for breakfast, lunch, or a relaxed dinner out.

Middleton Market Cafe $

Cafe

A cozy neighborhood cafe serving breakfast, lunch, and homemade pastries.

The Neighborhood Grill $$

American

A welcoming family restaurant with a broad menu and generous portions.

Sumter Landing Tavern $

Bar & Grill

A short golf cart ride from Middleton, great wings, cold beers, and a friendly crowd.

The Family Table $

Home Cooking

Home-style cooking with daily specials, beloved by local families for Sunday dinners.

Places to Go

Discover what makes this neighborhood special.

Life in Middleton

Single-story white house with solar panels, two-car garage, brick driveway, and manicured landscaping with flowering shrubs.

Community Character

Welcoming Middleton Streets

Black golf cart parked on driveway in front of white single-story house with garage and manicured landscaping

Outdoor Living

Golf and Recreation

Single-story beige stucco home with brick accents, three-car garage, manicured lawn, and landscaped front garden under blue sky.

Local Convenience

Shops and Dining Nearby

Guest Reviews

What Guests Say

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

Common Questions

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Events & Entertainment

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