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Holiday rentals in Sumter County

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Top-rated holiday rentals in Sumter County

Guests agree: these stays are highly rated for location, cleanliness, and more.

Groovy on Sawgrass Grove w/ fire pit & golf cart ☆
SUPERHOST
Entire residential home · 6 guests · 4 beds · 2 bathrooms
Groovy on Sawgrass Grove w/ fire pit & golf cart ☆Get your groove on at our stylish vacation haven within walking distance to the new soon to come gathering place: Sawgrass Grove! Enjoy all The Villages has to offer while being able to retreat to your own vacation home. Let Groovy on the Grove bring you a lively gathering place with a fun spirit. This vacation home will make you smile, dance to the sound of the vinyl record player, and enjoy a cold beer in front of the fire pit. Come and get a feeling of how groovy your retirement could be…!
Private, remodeled 3/2, Golf Cart - 4, Pizza Oven!
Entire residential home · 6 guests · 4 beds · 2 bathrooms
Private, remodeled 3/2, Golf Cart - 4, Pizza Oven!Enjoy newly remodeled 3-bed(sleeps 6), 2-bath vacation home located in The Villages! Large screened lanai includes BBQ grill, pizza oven, hammock, and privacy - rare in the Villages! Rental includes access to community amenities - pools, tennis, pickleball, 54 golf courses, walking trails, gyms & more. Use our Yamaha 4 seat gas golf cart to get to it all! Newly furnished home includes 75 & 65" Smart TVs, fully equipped kitchen. Spanish Springs & Sumter Landing Town Squares 10 minutes away
The Love Shack at The Cove
SUPERHOST
Tiny house · 2 guests · 0 beds · 1 bathroom
The Love Shack at The CoveThe "Love Shack," (at The Cove) is our latest project. Approximately 400 sq. feet and originally built as a cabin for the fish camp. Completely remodeled the cabin is decorated with vintage furniture, granite countertops, live edge oak shelving, a smart TV and large shower. Nestled under hugh live oaks and surrounded by decking is perfect for that morning coffee or evening glass of wine. Pet friendly!

Holiday rentals for every style

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Popular amenities for Sumter County holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Sumter County

SUPERHOST
  1. Entire residential home
  2. Floral City
The 'Old Florida' Flamingo
$120 SGD per night
SUPERHOST
  1. Entire bungalow
  2. Inverness
The Cove Point House
$212 SGD per night
SUPERHOST
  1. Entire cottage
  2. Inverness
Sweetwater Cottage- Waterfront and Pet Friendly
$121 SGD per night
SUPERHOST
  1. Entire residential home
  2. The Villages
Paradise ⌂ w/ pool, golf cart & private backyard ♡
$185 SGD per night
SUPERHOST
  1. Entire cottage
  2. Floral City
Waterfront Cottage 2BR 1B
$108 SGD per night
SUPERHOST
  1. Entire cottage
  2. Brooksville
The Withlacoochee River Guesthouse
$144 SGD per night
  1. Entire cottage
  2. Brooksville
Charming Cozy Hideaway on Horse Farm
$106 SGD per night
SUPERHOST
  1. Entire guest house
  2. Dade City
Studio Zen
$88 SGD per night
  1. Entire rental unit
  2. Dade City
Duck Haven - Farm Stay - 7 miles from I-75
$55 SGD per night
  1. Entire cottage
  2. Dade City
Perfect Getaway
$148 SGD per night
SUPERHOST
  1. Entire residential home
  2. Inverness
NEW! Quiet Lake House, Basketball Court, Fishing
$179 SGD per night
SUPERHOST
  1. Entire residential home
  2. The Villages
The Villages Lifestyle of Optimism
$135 SGD per night