Vacation rentals in Sumter County, FL

Best Vacation rentals and Airbnb offers in Sumter County, FL

CHARMING 2 BDRM 2 BATH Sm Dog Friendly Patio Villa w/FREE WIFI

Holiday Home, Sumter County

CHARMING 2 BDRM 2 BATH Sm Dog Friendly Patio Villa w/FREE WIFI is a holiday home in Sumter County, with pet-friendly space, pool access, and outdoor space. This stay gives travelers a…

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About CHARMING 2 BDRM 2 BATH Sm Dog Friendly Patio Villa w/FREE WIFI

CHARMING 2 BDRM 2 BATH Sm Dog Friendly Patio Villa w/FREE WIFI is a holiday home in Sumter County, with pet-friendly space, pool access, and outdoor space. 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $965.

From$70/night

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Stylish retreat with comfort, charm, and entertainment all around!

Holiday Home, Sumter County

Stylish retreat with comfort, charm, and entertainment all around! 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 Stylish retreat with comfort, charm, and entertainment all around!

Stylish retreat with comfort, charm, and entertainment all around! 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 onsite parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $978.

From$70/night

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The Villages-DeSoto, 3/2 Home Cul-de-Sac, Pet-Friendly with Golf Cart Option

Holiday Home, Sumter County

The Villages-DeSoto, 3/2 Home Cul-de-Sac, Pet-Friendly with Golf Cart Option is a holiday home in Sumter County, with pet-friendly space and pool access. This stay gives travelers a…

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About The Villages-DeSoto, 3/2 Home Cul-de-Sac, Pet-Friendly with Golf Cart Option

The Villages-DeSoto, 3/2 Home Cul-de-Sac, Pet-Friendly with Golf Cart Option 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $852.

From$71/night

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Fun Virgil Villa (Hawkins) 🐶

Villa, Sumter County

Fun Virgil Villa (Hawkins) 🐶 is a villa in Sumter County, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Fun Virgil Villa (Hawkins) 🐶

Fun Virgil Villa (Hawkins) 🐶 is a villa 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $942.

From$74/night

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Browse 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.

The Center of The South in The Villages

Villa, Sumter County

The Center of The South in The Villages is a villa 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 The Center of The South in The Villages

The Center of The South in The Villages 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: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,156.

From$88/night

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Discover Your Florida Getaway in the Village of Hawkins!

Villa, Sumter County

Discover Your Florida Getaway in the Village of Hawkins! is a villa in Sumter County, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Discover Your Florida Getaway in the Village of Hawkins!

Discover Your Florida Getaway in the Village of Hawkins! is a villa 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,292.

From$96/night

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Rhett Breeze Villa (Linden)

Villa, Sumter County

Rhett Breeze Villa (Linden) is a villa in Sumter County, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Rhett Breeze Villa (Linden)

Rhett Breeze Villa (Linden) is a villa 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,156.

From$99/night

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Chic, comfy, and ready for Villages adventures—golf cart included!

Holiday Home, Sumter County

Chic, comfy, and ready for Villages adventures—golf cart included! 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 Chic, comfy, and ready for Villages adventures—golf cart included!

Chic, comfy, and ready for Villages adventures—golf cart included! 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 onsite parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,247.

From$100/night

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Best Sumter County, FL vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Relaxing 2BR Villa in Waters Edge located by the newest town square Eastport

Holiday Home, Sumter County

Relaxing 2BR Villa in Waters Edge located by the newest town square Eastport is a holiday home in Sumter County, with pet-friendly space, parking, and kitchen access. This stay gives…

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About Relaxing 2BR Villa in Waters Edge located by the newest town square Eastport

Relaxing 2BR Villa in Waters Edge located by the newest town square Eastport 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,062.

From$100/night

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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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,045.

From$103/night

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Living The Dream - 2/2 w/ Golf Cart in The Village of McClure

Holiday Home, Sumter County

Living The Dream - 2/2 w/ Golf Cart in The Village of McClure is a holiday home in Sumter County, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base…

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About Living The Dream - 2/2 w/ Golf Cart in The Village of McClure

Living The Dream - 2/2 w/ Golf Cart in The Village of McClure 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,359.

From$104/night

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Brand New Designer Home!- 5 minutes from East Port

Holiday Home, Sumter County

Brand New Designer Home!- 5 minutes from East Port 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 Brand New Designer Home!- 5 minutes from East Port

Brand New Designer Home!- 5 minutes from East Port 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,068.

From$104/night

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Best Pet-Friendly Vacation Rentals in Sumter County, FL

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

3/2 IN THE VILLAGE OF ST. CATHERINE GAS GOLF CART, CLOSE TO SAWGRASS GROVE

Holiday Home, Sumter County

3/2 IN THE VILLAGE OF ST. CATHERINE GAS GOLF CART, CLOSE TO SAWGRASS GROVE is a holiday home in Sumter County, with pool access, parking, and kitchen access. This stay gives travelers a…

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About 3/2 IN THE VILLAGE OF ST. CATHERINE GAS GOLF CART, CLOSE TO SAWGRASS GROVE

3/2 IN THE VILLAGE OF ST. CATHERINE GAS GOLF CART, CLOSE TO SAWGRASS GROVE 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,256.

From$88/night

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Stunning Modern Oasis in The Villages, FL.

Holiday Home, Sumter County

Stunning Modern Oasis in The Villages, FL. is a holiday home in Sumter County, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for…

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About Stunning Modern Oasis in The Villages, FL.

Stunning Modern Oasis in The Villages, FL. 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $915.

From$89/night

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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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,110.

From$94/night

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Beautiful Upgraded Patio Villa in The Villages of Marsh Bend

Villa, Sumter County

Beautiful Upgraded Patio Villa in The Villages of Marsh Bend is a villa in Sumter County, with pet-friendly space and outdoor space. This stay gives travelers a comfortable base for…

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About Beautiful Upgraded Patio Villa in The Villages of Marsh Bend

Beautiful Upgraded Patio Villa in The Villages of Marsh Bend is a villa in Sumter County, with pet-friendly space and outdoor space. 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, for couples, and wine or champagne.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,126.

From$94/night

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Best Sumter County, FL vacation rentals with a kitchen

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

Rhett Isles Retreat at Linden

Holiday Home, Sumter County

Rhett Isles Retreat at Linden 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 Rhett Isles Retreat at Linden

Rhett Isles Retreat at Linden 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,156.

From$99/night

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Newly renovated vacation house!

Holiday Home, Sumter County

Newly renovated vacation house! 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 Newly renovated vacation house!

Newly renovated vacation house! 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $879.

From$105/night

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Newly built 3 bedroom with Golf Cart!

Holiday Home, Sumter County

Newly built 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…

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About Newly built 3 bedroom with Golf Cart!

Newly built 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,056.

From$105/night

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Welcome to our Shady Brook Retreat!

Holiday Home, Sumter County

Welcome to our Shady Brook Retreat! is a holiday home in Sumter County, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About Welcome to our Shady Brook Retreat!

Welcome to our Shady Brook Retreat! is a holiday home in Sumter County, with pet-friendly space, 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 wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,131.

From$107/night

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Our Favorite Family-Friendly Vacation Rentals in Sumter County, FL

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

Bushnell Riverside Retreat w/ Hot Tub & Game Shed

Cottage, Sumter County

Bushnell Riverside Retreat w/ Hot Tub & Game Shed is a cottage 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 cottage 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $882.

From$98/night

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Riverfront Floral City Stay w/ Dock & Hot Tub!

Cottage, Sumter County

Riverfront Floral City Stay w/ Dock & Hot Tub! is a cottage in Sumter County, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Riverfront Floral City Stay w/ Dock & Hot Tub!

Riverfront Floral City Stay w/ Dock & Hot Tub! is a cottage in Sumter County, with 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, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,049.

From$114/night

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561d Large 3 Bedroom With Golf Cart!

Cottage, Sumter County

561d Large 3 Bedroom With Golf Cart! is a cottage 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 561d Large 3 Bedroom With Golf Cart!

561d Large 3 Bedroom With Golf Cart! is a cottage 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 dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,428.

From$138/night

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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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,232.

From$138/night

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