Vacation rentals in Leesburg, FL

Best vacation rentals and Airbnb offers in Leesburg, FL

10 ★ 1 reviews

Courtyard Villa w/ Lanai & Community Amenities!

Villa, Leesburg

Courtyard Villa w/ Lanai & Community Amenities! is a villa in Leesburg, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Courtyard Villa w/ Lanai & Community Amenities!

Courtyard Villa w/ Lanai & Community Amenities! is a villa in Leesburg, 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 $1,116.

From$114/night

Show›

10 ★ 1 reviews

Outdoor Oasis w/ Bar & Lanai: Tavares Escape

Cottage, Leesburg

Outdoor Oasis w/ Bar & Lanai: Tavares Escape is a cottage in Leesburg, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Outdoor Oasis w/ Bar & Lanai: Tavares Escape

Outdoor Oasis w/ Bar & Lanai: Tavares Escape is a cottage in Leesburg, 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: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,787.

From$174/night

Show›

10 ★ 1 reviews

Pool Access & Screened Patio: Home in The Villages

Cottage, Leesburg

Pool Access & Screened Patio: Home in The Villages is a cottage in Leesburg, with pool access, outdoor space, and kitchen access. This stay gives travelers a comfortable base for exploring…

Read more

About Pool Access & Screened Patio: Home in The Villages

Pool Access & Screened Patio: Home in The Villages is a cottage in Leesburg, with pool access, outdoor 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, pool, free wifi, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,766.

From$181/night

Show›

8 ★ 1 reviews

Updated Tavares Retreat < 1 Mile to Boat Ramp

Cottage, Leesburg

Updated Tavares Retreat < 1 Mile to Boat Ramp is a cottage in Leesburg, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the…

Read more

About Updated Tavares Retreat < 1 Mile to Boat Ramp

Updated Tavares Retreat < 1 Mile to Boat Ramp is a cottage in Leesburg, 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, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,303.

From$133/night

Show›

Family-friendly vacation rentals in Leesburg, FL

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

1 Mi to Lake Sumter! Family Retreat w/ Large Patio

Holiday Home, Leesburg

1 Mi to Lake Sumter! Family Retreat w/ Large Patio is a holiday home in Leesburg, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for…

Read more

About 1 Mi to Lake Sumter! Family Retreat w/ Large Patio

1 Mi to Lake Sumter! Family Retreat w/ Large Patio is a holiday home in Leesburg, with pet-friendly space, outdoor space, and parking. 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 parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,646.

From$160/night

Show›

Bring Your Boat! Canal-front Tavares Home w/ Dock

Cottage, Leesburg

Bring Your Boat! Canal-front Tavares Home w/ Dock is a cottage in Leesburg, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Bring Your Boat! Canal-front Tavares Home w/ Dock

Bring Your Boat! Canal-front Tavares Home w/ Dock is a cottage in Leesburg, 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 $1,463.

From$149/night

Show›

New Designer Home in The Villages: Shady Brook

Cottage, Leesburg

New Designer Home in The Villages: Shady Brook is a cottage in Leesburg, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About New Designer Home in The Villages: Shady Brook

New Designer Home in The Villages: Shady Brook is a cottage in Leesburg, 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 $1,521.

From$169/night

Show›

Community Pool & Tennis Court: Gem in The Villages

Cottage, Leesburg

Community Pool & Tennis Court: Gem in The Villages is a cottage in Leesburg, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Community Pool & Tennis Court: Gem in The Villages

Community Pool & Tennis Court: Gem in The Villages is a cottage in Leesburg, 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 $1,712.

From$181/night

Show›

Pet-friendly vacation rentals in Leesburg, FL

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

3 Bed, 2 Bath, Waterfront, Dock, Large Driveway

Holiday Home, Leesburg

3 Bed, 2 Bath, Waterfront, Dock, Large Driveway is a holiday home in Leesburg, with pet-friendly space, easy beach access, and parking. This stay gives travelers a comfortable base for…

Read more

About 3 Bed, 2 Bath, Waterfront, Dock, Large Driveway

3 Bed, 2 Bath, Waterfront, Dock, Large Driveway is a holiday home in Leesburg, with pet-friendly space, easy beach access, and parking. 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 parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,550.

From$164/night

Show›

Serene Mountain Retreat With Pool

Holiday Home, Leesburg

Serene Mountain Retreat With Pool is a holiday home in Leesburg, with pet-friendly space, pool access, and parking. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Serene Mountain Retreat With Pool

Serene Mountain Retreat With Pool is a holiday home in Leesburg, with pet-friendly space, pool access, and parking. 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 parking.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $2,802.

From$315/night

Show›

All-season 3BR w/ Large Outdoor Area

Cottage, Leesburg

All-season 3BR w/ Large Outdoor Area is a cottage in Leesburg, with pet-friendly space, pool access, and room for a group. This stay gives travelers a comfortable base for exploring the…

Read more

About All-season 3BR w/ Large Outdoor Area

All-season 3BR w/ Large Outdoor Area is a cottage in Leesburg, with pet-friendly space, pool 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: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,709.

From$194/night

Show›

Vacation rentals with a pool in Leesburg, FL

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

Canal-front Retreat w/ Hot Tub & Dock in Tavares

Apartment, Leesburg

Canal-front Retreat w/ Hot Tub & Dock in Tavares is a apartment in Leesburg, with pool access, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

Read more

About Canal-front Retreat w/ Hot Tub & Dock in Tavares

Canal-front Retreat w/ Hot Tub & Dock in Tavares is a apartment in Leesburg, with pool access, 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, pool, free wifi, kitchen, and with kitchen.

Sat, Sep 26 - Sat, Oct 3 · 7 nights · total from $1,242.

From$138/night

Show›

Golf & Swim in The Villages! Modern Home w/ Lanai

Cottage, Leesburg

Golf & Swim in The Villages! Modern Home w/ Lanai is a cottage in Leesburg, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Golf & Swim in The Villages! Modern Home w/ Lanai

Golf & Swim in The Villages! Modern Home w/ Lanai is a cottage in Leesburg, 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 $1,650.

From$181/night

Show›

Spacious Tavares Home w/ Private Outdoor Oasis!

Cottage, Leesburg

Spacious Tavares Home w/ Private Outdoor Oasis! is a cottage in Leesburg, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Spacious Tavares Home w/ Private Outdoor Oasis!

Spacious Tavares Home w/ Private Outdoor Oasis! is a cottage in Leesburg, 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 $2,313.

From$254/night

Show›