Vacation rentals in Sumter County, FL

Best vacation rentals and Airbnb offers in Sumter County, FL

10 ★ 107 reviews

Fully Furnished Brand New Villa in Village of St. Catherine's with Cart

Villa, Sumter County

Fully Furnished Brand New Villa in Village of St. Catherine's with Cart is a villa in Sumter County, with pool access and kitchen access. This stay gives travelers a comfortable base for…

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About Fully Furnished Brand New Villa in Village of St. Catherine's with Cart

Fully Furnished Brand New Villa in Village of St. Catherine's with Cart is a villa in Sumter County, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $669.

From$96/night

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10 ★ 40 reviews

Sunset Cove In the Village of St. John

Holiday Home, Sumter County

Sunset Cove In the Village of St. John is a holiday home in Sumter County, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Sunset Cove In the Village of St. John

Sunset Cove In the Village of St. John is a holiday home in Sumter County, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $999.

From$143/night

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10 ★ 26 reviews

Vintage Charm on Peaceful Mini Farm - Pet Friendly

Apartment, Sumter County

Vintage Charm on Peaceful Mini Farm - Pet Friendly is a apartment in Sumter County, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Vintage Charm on Peaceful Mini Farm - Pet Friendly

Vintage Charm on Peaceful Mini Farm - Pet Friendly is a apartment in Sumter County, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $878.

From$125/night

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10 ★ 11 reviews

Old Florida home with charm and beautiful settings.

Holiday Home, Sumter County

Old Florida home with charm and beautiful settings. is a holiday home in Sumter County, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Old Florida home with charm and beautiful settings.

Old Florida home with charm and beautiful settings. is a holiday home in Sumter County, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,047.

From$150/night

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Family-friendly vacation rentals in Sumter County, FL

Plan a trip with stays that give families more room to spread out.

10 ★ 29 reviews

Quiet Historic Family Retreat with Pool--Pet Friendly--No Events

Holiday Home, Sumter County

Quiet Historic Family Retreat with Pool--Pet Friendly--No Events is a holiday home in Sumter County, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a…

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About Quiet Historic Family Retreat with Pool--Pet Friendly--No Events

Quiet Historic Family Retreat with Pool--Pet Friendly--No Events is a holiday home in Sumter County, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, pet friendly, pets friendly, and kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,213.

From$316/night

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10 ★ 1 reviews

Anna’s Coastal Cottage Retreat at Oak Hollow

Holiday Home, Sumter County

Anna’s Coastal Cottage Retreat at Oak Hollow is a holiday home in Sumter County, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Anna’s Coastal Cottage Retreat at Oak Hollow

Anna’s Coastal Cottage Retreat at Oak Hollow is a holiday home in Sumter County, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, kitchen, with kitchen, parking, and free parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,119.

From$160/night

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9.8 ★ 28 reviews

Romantic Escape on Peaceful Mini Farm

Cottage, Sumter County

Romantic Escape on Peaceful Mini Farm is a cottage in Sumter County, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Romantic Escape on Peaceful Mini Farm

Romantic Escape on Peaceful Mini Farm is a cottage in Sumter County, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,179.

From$168/night

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9.6 ★ 28 reviews

Dreamy River Cottage

Cottage, Sumter County

Dreamy River Cottage is a cottage in Sumter County, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Dreamy River Cottage

Dreamy River Cottage is a cottage in Sumter County, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,119.

From$160/night

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Pet-friendly vacation rentals in Sumter County, FL

Bring your pet along with stays that welcome four-legged travelers.

9.8 ★ 22 reviews

Cozy Getaway w/ fenced yard

Holiday Home, Sumter County

Cozy Getaway w/ fenced yard is a holiday home in Sumter County, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Cozy Getaway w/ fenced yard

Cozy Getaway w/ fenced yard is a holiday home in Sumter County, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $961.

From$137/night

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9.6 ★ 44 reviews

Cozy water front getaway

Holiday Home, Sumter County

Cozy water front getaway is a holiday home in Sumter County, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Cozy water front getaway

Cozy water front getaway is a holiday home in Sumter County, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $963.

From$138/night

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9.4 ★ 6 reviews

Beautiful New 2/2 Dog Friendly Villa w/ GOLF CART, BBQ & FREE WiFi!

Holiday Home, Sumter County

Beautiful New 2/2 Dog Friendly Villa w/ GOLF CART, BBQ & FREE WiFi! is a holiday home in Sumter County, with pet-friendly space and pool access. This stay gives travelers a comfortable base…

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About Beautiful New 2/2 Dog Friendly Villa w/ GOLF CART, BBQ & FREE WiFi!

Beautiful New 2/2 Dog Friendly Villa w/ GOLF CART, BBQ & FREE WiFi! is a holiday home in Sumter County, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, pet friendly, and pets friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $962.

From$137/night

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8 ★ 2 reviews

Cabin on lake panasoffkee, near top spot big bass grill

Cabin, Sumter County

Cabin on lake panasoffkee, near top spot big bass grill is a cabin in Sumter County, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Cabin on lake panasoffkee, near top spot big bass grill

Cabin on lake panasoffkee, near top spot big bass grill is a cabin in Sumter County, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $979.

From$140/night

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Vacation rentals with a pool in Sumter County, FL

Add a pool to the search when you want an easy place to cool off between outings.

10 ★ 45 reviews

Lovely Villa in the Villages, FL GOLF CART INCLUDED AS A COURTESY

Holiday Home, Sumter County

Lovely Villa in the Villages, FL GOLF CART INCLUDED AS A COURTESY is a holiday home in Sumter County, with pool access, parking, and kitchen access. This stay gives travelers a comfortable…

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About Lovely Villa in the Villages, FL GOLF CART INCLUDED AS A COURTESY

Lovely Villa in the Villages, FL GOLF CART INCLUDED AS A COURTESY is a holiday home in Sumter County, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,108.

From$158/night

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10 ★ 20 reviews

Upgraded Home in The Villages! Golf Cart Included, Community Pools and Much More

Holiday Home, Sumter County

Upgraded Home in The Villages! Golf Cart Included, Community Pools and Much More is a holiday home in Sumter County, with pool access. This stay gives travelers a comfortable base for…

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About Upgraded Home in The Villages! Golf Cart Included, Community Pools and Much More

Upgraded Home in The Villages! Golf Cart Included, Community Pools and Much More is a holiday home in Sumter County, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, and free wifi.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,044.

From$149/night

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10 ★ 1 reviews

Weber Fun Escape at McClure

Holiday Home, Sumter County

Weber Fun Escape at McClure is a holiday home in Sumter County, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Weber Fun Escape at McClure

Weber Fun Escape at McClure is a holiday home in Sumter County, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,073.

From$153/night

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10 ★ 1 reviews

The Compton Comfort Retreat (Waters Edge)

Holiday Home, Sumter County

The Compton Comfort Retreat (Waters Edge) is a holiday home in Sumter County, with pet-friendly space, pool access, and a quieter setting. This stay gives travelers a comfortable base for…

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About The Compton Comfort Retreat (Waters Edge)

The Compton Comfort Retreat (Waters Edge) is a holiday home in Sumter County, with pet-friendly space, pool access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, pet friendly, and pets friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,105.

From$158/night

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Vacation rentals with parking in Sumter County, FL

Find vacation rentals that make arriving by car easier.

10 ★ 2 reviews

Bushnell Riverside Retreat w/ Hot Tub & Game Shed

Holiday Home, Sumter County

Bushnell Riverside Retreat w/ Hot Tub & Game Shed is a holiday home in Sumter County, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About Bushnell Riverside Retreat w/ Hot Tub & Game Shed

Bushnell Riverside Retreat w/ Hot Tub & Game Shed is a holiday home in Sumter County, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $780.

From$111/night

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10 ★ 1 reviews

Large 3 bedroom with Golf Cart!

Holiday Home, Sumter County

Large 3 bedroom with Golf Cart! is a holiday home in Sumter County, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Large 3 bedroom with Golf Cart!

Large 3 bedroom with Golf Cart! is a holiday home in Sumter County, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, parking, free parking, and washer.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $980.

From$140/night

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10 ★ 1 reviews

New 2/2 patio villa in The Village of Well Point, near Eastport, in The Villages

Villa, Sumter County

New 2/2 patio villa in The Village of Well Point, near Eastport, in The Villages is a villa in Sumter County, with outdoor space, parking, and kitchen access. This stay gives travelers a…

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About New 2/2 patio villa in The Village of Well Point, near Eastport, in The Villages

New 2/2 patio villa in The Village of Well Point, near Eastport, in The Villages is a villa in Sumter County, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, parking, free parking, and washer.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,005.

From$144/night

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8 ★ 1 reviews

Brand New! Modern Guesthouse!

Holiday Home, Sumter County

Brand New! Modern Guesthouse! is a holiday home in Sumter County, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Brand New! Modern Guesthouse!

Brand New! Modern Guesthouse! is a holiday home in Sumter County, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $593.

From$85/night

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Vacation rentals with a kitchen in Sumter County, FL

Compare stays with kitchen access for longer trips and easier meals.

10 ★ 9 reviews

Unique Waterfront Stilt House on the Withlacoochee River, Fish, Kayak, Relax

Holiday Home, Sumter County

Unique Waterfront Stilt House on the Withlacoochee River, Fish, Kayak, Relax is a holiday home in Sumter County, with easy beach access, parking, and kitchen access. This stay gives…

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About Unique Waterfront Stilt House on the Withlacoochee River, Fish, Kayak, Relax

Unique Waterfront Stilt House on the Withlacoochee River, Fish, Kayak, Relax is a holiday home in Sumter County, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $986.

From$141/night

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10 ★ 1 reviews

Brent’s Oak Hollow Hideaway – Heart of Eastport

Holiday Home, Sumter County

Brent’s Oak Hollow Hideaway – Heart of Eastport is a holiday home in Sumter County, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base…

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About Brent’s Oak Hollow Hideaway – Heart of Eastport

Brent’s Oak Hollow Hideaway – Heart of Eastport is a holiday home in Sumter County, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,120.

From$160/night

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9.6 ★ 25 reviews

Golfer's Paradise - The Villages in Wildwood!

Holiday Home, Sumter County

Golfer's Paradise - The Villages in Wildwood! is a holiday home in Sumter County, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Golfer's Paradise - The Villages in Wildwood!

Golfer's Paradise - The Villages in Wildwood! is a holiday home in Sumter County, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,138.

From$163/night

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9.2 ★ 29 reviews

Modern Conveniences with Old Florida Charm

Holiday Home, Sumter County

Modern Conveniences with Old Florida Charm is a holiday home in Sumter County, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Modern Conveniences with Old Florida Charm

Modern Conveniences with Old Florida Charm is a holiday home in Sumter County, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,165.

From$166/night

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