Vacation rentals in Winter Garden, FL

Best vacation rentals and Airbnb offers in Winter Garden, FL

10 ★ 1 reviews

Lakefront Retreat w/ Kayaks & Fire Pit in Clermont

Cottage, Winter Garden

Lakefront Retreat w/ Kayaks & Fire Pit in Clermont is a cottage in Winter Garden, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

Read more

About Lakefront Retreat w/ Kayaks & Fire Pit in Clermont

Lakefront Retreat w/ Kayaks & Fire Pit in Clermont is a cottage in Winter Garden, 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, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,851.

From$212/night

Show›

8 ★ 2 reviews

Landing Furnished Apartments - Maitland

Apartment, Winter Garden

Landing Furnished Apartments - Maitland is a apartment in Winter Garden, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Landing Furnished Apartments - Maitland

Landing Furnished Apartments - Maitland is a apartment in Winter Garden, 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, Oct 3 - Sat, Oct 10 · 7 nights · total from $906.

From$92/night

Show›

Studio near Universal Studios with great view

Apartment, Winter Garden

Studio near Universal Studios with great view is a apartment in Winter Garden, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

Read more

About Studio near Universal Studios with great view

Studio near Universal Studios with great view is a apartment in Winter Garden, 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: pool, hot tub, and free wifi.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $858.

From$97/night

Show›

Near Disney cozy quiet place, 2 rooms with queen bed up to 4 people

Homestay, Winter Garden

Near Disney cozy quiet place, 2 rooms with queen bed up to 4 people is a homestay in Winter Garden, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers…

Read more

About Near Disney cozy quiet place, 2 rooms with queen bed up to 4 people

Near Disney cozy quiet place, 2 rooms with queen bed up to 4 people is a homestay in Winter Garden, 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, Oct 3 - Sat, Oct 10 · 7 nights · total from $503.

From$59/night

Show›

Family-friendly vacation rentals in Winter Garden, FL

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

10 ★ 1 reviews

Apopka Single-story Home w/ Private Lanai + Pool!

Cottage, Winter Garden

Apopka Single-story Home w/ Private Lanai + Pool! is a cottage in Winter Garden, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Apopka Single-story Home w/ Private Lanai + Pool!

Apopka Single-story Home w/ Private Lanai + Pool! is a cottage in Winter Garden, 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, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,198.

From$218/night

Show›

Orlando Escape - Carrier Dr

Condo, Winter Garden

Orlando Escape - Carrier Dr is a condo in Winter Garden, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

Read more

About Orlando Escape - Carrier Dr

Orlando Escape - Carrier Dr is a condo in Winter Garden, 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, free wifi, kids friendly, and kids pool.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,173.

From$110/night

Show›

~ 9 Mi to Universal: Orlando Retreat w/ Sun Porch!

Cottage, Winter Garden

~ 9 Mi to Universal: Orlando Retreat w/ Sun Porch! is a cottage in Winter Garden, with kitchen access and a quieter setting. This stay gives travelers a comfortable base for exploring the…

Read more

About ~ 9 Mi to Universal: Orlando Retreat w/ Sun Porch!

~ 9 Mi to Universal: Orlando Retreat w/ Sun Porch! is a cottage in Winter Garden, with 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, free wifi, kitchen, and with kitchen.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,233.

From$126/night

Show›

~ 12 Mi to Disney: Downtown Winter Garden Cottage!

Cottage, Winter Garden

~ 12 Mi to Disney: Downtown Winter Garden Cottage! is a cottage in Winter Garden, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

Read more

About ~ 12 Mi to Disney: Downtown Winter Garden Cottage!

~ 12 Mi to Disney: Downtown Winter Garden Cottage! is a cottage in Winter Garden, 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, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,917.

From$212/night

Show›

Pet-friendly vacation rentals in Winter Garden, FL

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

Pet-Friendly Apopka Home: 30 Mi to WDW!

Holiday Home, Winter Garden

Pet-Friendly Apopka Home: 30 Mi to WDW! is a holiday home in Winter Garden, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Pet-Friendly Apopka Home: 30 Mi to WDW!

Pet-Friendly Apopka Home: 30 Mi to WDW! is a holiday home in Winter Garden, with pet-friendly 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, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,295.

From$112/night

Show›

Pet-friendly Apopka Home: 30 Mi to Wdw!

Cottage, Winter Garden

Pet-friendly Apopka Home: 30 Mi to Wdw! is a cottage in Winter Garden, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Pet-friendly Apopka Home: 30 Mi to Wdw!

Pet-friendly Apopka Home: 30 Mi to Wdw! is a cottage in Winter Garden, 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, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,341.

From$144/night

Show›

Modern Family Retreat Near Orlando Attractions

Cottage, Winter Garden

Modern Family Retreat Near Orlando Attractions is a cottage in Winter Garden, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

Read more

About Modern Family Retreat Near Orlando Attractions

Modern Family Retreat Near Orlando Attractions is a cottage in Winter Garden, with pet-friendly space, 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: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,700.

From$188/night

Show›

Landing Furnished Apartments near Lake Apopka

Apartment, Winter Garden

Landing Furnished Apartments near Lake Apopka is a apartment in Winter Garden, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Landing Furnished Apartments near Lake Apopka

Landing Furnished Apartments near Lake Apopka is a apartment in Winter Garden, 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, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,713.

From$197/night

Show›

Vacation rentals with a pool in Winter Garden, FL

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

Stunning 3 Bed Former Model Home

Villa, Winter Garden

Stunning 3 Bed Former Model Home is a villa in Winter Garden, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

Read more

About Stunning 3 Bed Former Model Home

Stunning 3 Bed Former Model Home is a villa in Winter Garden, 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, heated pool, ac, and air conditioning.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,215.

From$131/night

Show›

Apopka Single-Story Home w/ Private Lanai + Pool!

Holiday Home, Winter Garden

Apopka Single-Story Home w/ Private Lanai + Pool! is a holiday home in Winter Garden, with pool access and parking. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Apopka Single-Story Home w/ Private Lanai + Pool!

Apopka Single-Story Home w/ Private Lanai + Pool! is a holiday home in Winter Garden, with 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, pool, free wifi, parking, and paid parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,117.

From$183/night

Show›

3BR Disney Escape for Families - 8990

Holiday Home, Winter Garden

3BR Disney Escape for Families - 8990 is a holiday home in Winter Garden, with pool access, parking, and room for a group. This stay gives travelers a comfortable base for exploring the…

Read more

About 3BR Disney Escape for Families - 8990

3BR Disney Escape for Families - 8990 is a holiday home in Winter Garden, with pool access, parking, 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, parking, and free parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,128.

From$131/night

Show›

5 Mi to Dtwn Clermont: Family Home w/ Water Views!

Cottage, Winter Garden

5 Mi to Dtwn Clermont: Family Home w/ Water Views! is a cottage in Winter Garden, with pool access and room for a group. This stay gives travelers a comfortable base for exploring the area,…

Read more

About 5 Mi to Dtwn Clermont: Family Home w/ Water Views!

5 Mi to Dtwn Clermont: Family Home w/ Water Views! is a cottage in Winter Garden, with 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, hot tub, and free wifi.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,491.

From$157/night

Show›

Vacation rentals with parking in Winter Garden, FL

Find vacation rentals that make arriving by car easier.

Lakefront Retreat w/ Kayaks & Fire Pit in Clermont

Holiday Home, Winter Garden

Lakefront Retreat w/ Kayaks & Fire Pit in Clermont is a holiday home in Winter Garden, with parking and a quieter setting. This stay gives travelers a comfortable base for exploring the…

Read more

About Lakefront Retreat w/ Kayaks & Fire Pit in Clermont

Lakefront Retreat w/ Kayaks & Fire Pit in Clermont is a holiday home in Winter Garden, with parking 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, parking, paid parking, and heating.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,782.

From$177/night

Show›

~ 9 Mi to Universal: Orlando Retreat w/ Sun Porch!

Holiday Home, Winter Garden

~ 9 Mi to Universal: Orlando Retreat w/ Sun Porch! is a holiday home in Winter Garden, with parking and a quieter setting. This stay gives travelers a comfortable base for exploring the…

Read more

About ~ 9 Mi to Universal: Orlando Retreat w/ Sun Porch!

~ 9 Mi to Universal: Orlando Retreat w/ Sun Porch! is a holiday home in Winter Garden, with parking 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, parking, paid parking, and heating.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,193.

From$101/night

Show›

Pool Therapy - New Pool Home

Holiday Home, Winter Garden

Pool Therapy - New Pool Home is a holiday home in Winter Garden, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

Read more

About Pool Therapy - New Pool Home

Pool Therapy - New Pool Home is a holiday home in Winter Garden, with 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, pool, parking, paid parking, and ourdoor pool.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,503.

From$157/night

Show›

Flint and Kingscrest, LLC - Private Rooms in Shared Home

Holiday Home, Winter Garden

Flint and Kingscrest, LLC - Private Rooms in Shared Home is a holiday home in Winter Garden, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Flint and Kingscrest, LLC - Private Rooms in Shared Home

Flint and Kingscrest, LLC - Private Rooms in Shared Home is a holiday home in Winter Garden, with 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, parking, onsite parking, washer, and internet.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $845.

From$96/night

Show›

Vacation rentals with a kitchen in Winter Garden, FL

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

Sunny Clermont Retreat w/ Lanai: 12 Mi to Disney!

Cottage, Winter Garden

Sunny Clermont Retreat w/ Lanai: 12 Mi to Disney! is a cottage in Winter Garden, with pool access, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

Read more

About Sunny Clermont Retreat w/ Lanai: 12 Mi to Disney!

Sunny Clermont Retreat w/ Lanai: 12 Mi to Disney! is a cottage in Winter Garden, 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, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,706.

From$196/night

Show›

Theme Park Base! Suburban Home 14 Mi to Universal

Cottage, Winter Garden

Theme Park Base! Suburban Home 14 Mi to Universal is a cottage in Winter Garden, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Theme Park Base! Suburban Home 14 Mi to Universal

Theme Park Base! Suburban Home 14 Mi to Universal is a cottage in Winter Garden, 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, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,014.

From$212/night

Show›

Hh123

Cottage, Winter Garden

Hh123 is a cottage in Winter Garden, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

Read more

About Hh123

Hh123 is a cottage in Winter Garden, 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, free wifi, kitchen, with kitchen, and dryer.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,986.

From$214/night

Show›

12 Mi to Disney: Home w/ Pool & Spa in Clermont

Cottage, Winter Garden

12 Mi to Disney: Home w/ Pool & Spa in Clermont is a cottage in Winter Garden, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About 12 Mi to Disney: Home w/ Pool & Spa in Clermont

12 Mi to Disney: Home w/ Pool & Spa in Clermont is a cottage in Winter Garden, 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, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,091.

From$242/night

Show›