Cottages in Sumter County

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Check prices for these dates

In two weeks
10 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 Jun - 21 Jun
In four months
17 Jul - 19 Jul

Top Cities in Sumter County

Beautiful sunset over the lake at The Villages in Leesburg, Florida creating a serene evening atmosphere
CottagesCottages

The Villages

The Villages

Our top choices for Sumter County cottages

House (3 Bedrooms) | Front of property

Single-story Home w/ Golf Cart in The Villages

Single-story Home w/ Golf Cart in The Villages
3.0 star property
Winifred
10.0 out of 10, Exceptional, (1 review)
Single-story Home w/ Golf Cart in The Villages
Exterior

Polo Garden Villa - 1/1 Villa On the Polo Field w/ Amazing Garden in The Village of Santiago

Polo Garden Villa - 1/1 Villa On the Polo Field w/ Amazing Garden in The Village of Santiago
Santiago
8.8 out of 10, Excellent, (6 reviews)
"Everything was amazing!"
United States
Chris
Polo Garden Villa - 1/1 Villa On the Polo Field w/ Amazing Garden in The Village of Santiago
Outdoor dining

NEW 3 bedroom cottage home in The Villages minutes to Eastport

NEW 3 bedroom cottage home in The Villages minutes to Eastport
Sumterville
10.0 out of 10, Exceptional, (3 reviews)
"This was an amazing home and community! House was spotless and so homey. Love that the golf cart was included in our stay! Close to the town centers and pools! We enjoyed our stay. Thank you so much!!"
United States
tonya w.
NEW 3 bedroom cottage home in The Villages minutes to Eastport
House (2 Bedrooms) | Interior

Dog-friendly Home in The Villages w/ Private Patio

Dog-friendly Home in The Villages w/ Private Patio
3.0 star property
Pennecamp
Dog-friendly Home in The Villages w/ Private Patio
House (2 Bedrooms) | Interior

Pet Friendly! Relaxing Retreat in The Villages

Pet Friendly! Relaxing Retreat in The Villages
3.0 star property
Lady Lake
Pet Friendly! Relaxing Retreat in The Villages
Property grounds

Peaceful Country Chic Cottage with King Bed Near The Villages Pet Friendly

Peaceful Country Chic Cottage with King Bed Near The Villages Pet Friendly
Coleman
9.8 out of 10, Exceptional, (27 reviews)
"Grateful peaceful kind environment "
United States
Dottie N.
Peaceful Country Chic Cottage with King Bed Near The Villages Pet Friendly
House (3 Bedrooms) | Interior

The Villages Golf Escape: Home w/ Pool Access!

The Villages Golf Escape: Home w/ Pool Access!
3.0 star property
Center Hill
The Villages Golf Escape: Home w/ Pool Access!
House (2 Bedrooms) | Interior

Lanai & Golf Cart: The Villages Vacation Rental!

Lanai & Golf Cart: The Villages Vacation Rental!
3.0 star property
Lynnhaven
10.0 out of 10, Exceptional, (1 review)
"Awesome place and conveniently located in the villages. Hosts were kind, helpful in making the trip perfect! We will be back!"
United States
Tory
The price is AED 287
AED 1,106 total
includes taxes & fees
31 Mar - 1 Apr
Lanai & Golf Cart: The Villages Vacation Rental!
Exterior

Great location between Sumter Landing/Spanish Springs. Golf cart included

Great location between Sumter Landing/Spanish Springs. Golf cart included
Alhambra
10.0 out of 10, Exceptional, (16 reviews)
"We enjoyed every second! Host Kevin was just amazing .. great place — reserved for next year "
United States
Audrey J.
Great location between Sumter Landing/Spanish Springs. Golf cart included
Interior

Swim, Golf & Unwind: Home 5 Mi to Lake Sumter!

Swim, Golf & Unwind: Home 5 Mi to Lake Sumter!
3.0 star property
Collier
The price is AED 426
AED 1,350 total
includes taxes & fees
17 Apr - 18 Apr
Swim, Golf & Unwind: Home 5 Mi to Lake Sumter!
House (3 Bedrooms) | Interior

Walk to Community Perks: Home in The Villages

Walk to Community Perks: Home in The Villages
3.0 star property
Belvedere
Walk to Community Perks: Home in The Villages
House (3 Bedrooms) | Interior

Walk to Golf & Pool: Pet-friendly Villages Home

Walk to Golf & Pool: Pet-friendly Villages Home
3.0 star property
Santiago
10.0 out of 10, Exceptional, (1 review)
Walk to Golf & Pool: Pet-friendly Villages Home
House (2 Bedrooms) | Interior

Renovated Villa Btwn Lake Sumter & Spanish Springs

Renovated Villa Btwn Lake Sumter & Spanish Springs
3.0 star property
Lady Lake
Renovated Villa Btwn Lake Sumter & Spanish Springs
House (3 Bedrooms) | Interior

Sunny Home w/ Golf Cart in The Villages!

Sunny Home w/ Golf Cart in The Villages!
3.0 star property
Winifred
10.0 out of 10, Exceptional, (2 reviews)
"It was the perfect place to stay while we visited relatives who live in The Villages. Would definitely stay there again on our next visit."
United States
Anonymous traveler
Sunny Home w/ Golf Cart in The Villages!
Exterior

3-bedroom cottage in the Villages Street of Dreams Golf Cart included

3-bedroom cottage in the Villages Street of Dreams Golf Cart included
Sumterville
10.0 out of 10, Exceptional, (1 review)
"Wonderful stay at a beautiful home in the villages. The house was beautiful and the owner was so welcoming. Ken was very assessable during our stay for any questions that we had. Definitely would stay there again. It’s in the newer part of the Villages so when it gets built up more it will be an amazing location!"
United States
Sandy S.
3-bedroom cottage in the Villages Street of Dreams Golf Cart included
House (2 Bedrooms) | Interior

Home in The Villages w/ Lanai & Private Hot Tub!

Home in The Villages w/ Lanai & Private Hot Tub!
3.0 star property
Sanibel
Home in The Villages w/ Lanai & Private Hot Tub!
House (3 Bedrooms) | Interior

1 Mi to Pickleball & Golf: Home in The Villages

1 Mi to Pickleball & Golf: Home in The Villages
3.0 star property
Pennecamp
10.0 out of 10, Exceptional, (1 review)
" Extremely clean, property looked new inside and out. Easy check in & out. Wish we could’ve stayed longer. "
United States
Steven Wayne
1 Mi to Pickleball & Golf: Home in The Villages
House (3 Bedrooms) | Interior

Lanai & Resort Amenities: The Villages Getaway

Lanai & Resort Amenities: The Villages Getaway
3.0 star property
Wildwood
Lanai & Resort Amenities: The Villages Getaway
House (3 Bedrooms) | Interior

Peaceful Escape w/ Golf Cart in The Villages!

Peaceful Escape w/ Golf Cart in The Villages!
3.0 star property
Liberty Park
9.0 out of 10, Wonderful, (2 reviews)
"Clean. Good price. Great location. "
United States
Mary
Peaceful Escape w/ Golf Cart in The Villages!
House (3 Bedrooms) | Interior

Riverfront Retreat w/ Patio in Withlacoochee

Riverfront Retreat w/ Patio in Withlacoochee
3.0 star property
Bushnell
10.0 out of 10, Exceptional, (1 review)
"Unit was clean, very complete with everything you need. I went when it was cold, but I would think summer fishing would be good. Screened in porch is beautiful. Property manager was polite and responsive. Might be difficult to locate after dark, but GPS take you straight to the cottage."
United States
Gregory
Riverfront Retreat w/ Patio in Withlacoochee
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Sumter County Hotel Reviews

Hotel Eastport

Hotel Eastport

10/10 Excellent
"Beautiful hotel, very clean, friendly staff."
Valarie 1-night trip
Posted 2 hours ago
Hotel Eastport