Vacation rentals in Windermere, FL

Best vacation rentals and Airbnb offers in Windermere, FL

10 ★ 22 reviews

🌿 European-Style 2BR Guest House in Orlando. Modern Comfort & Italian Coffee.

Guest House, Windermere

🌿 European-Style 2BR Guest House in Orlando. Modern Comfort & Italian Coffee. is a guest house in Windermere, with parking, kitchen access, and room for a group. This stay gives travelers…

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About 🌿 European-Style 2BR Guest House in Orlando. Modern Comfort & Italian Coffee.

🌿 European-Style 2BR Guest House in Orlando. Modern Comfort & Italian Coffee. is a guest house in Windermere, 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: free cancellation, free parking, kitchen, with kitchen, and gym.

Sat, Nov 28 - Sat, Dec 5 · 7 nights · total from $1,487.

From$212/night

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10 ★ 10 reviews

Lakeview apt 2 suítes 6 min Universal Studios free parking resort no extra fee

Apartment, Windermere

Lakeview apt 2 suítes 6 min Universal Studios free parking resort no extra fee is a apartment in Windermere, with pool access and parking. This stay gives travelers a comfortable base for…

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About Lakeview apt 2 suítes 6 min Universal Studios free parking resort no extra fee

Lakeview apt 2 suítes 6 min Universal Studios free parking resort no extra fee is a apartment in Windermere, 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, hot tub, and free parking.

Sat, Nov 28 - Sat, Dec 5 · 7 nights · total from $1,360.

From$194/night

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10 ★ 1 reviews

NEW - Spacious Studio close to Theme Parks

Condo, Windermere

NEW - Spacious Studio close to Theme Parks is a condo in Windermere, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About NEW - Spacious Studio close to Theme Parks

NEW - Spacious Studio close to Theme Parks is a condo in Windermere, 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, free parking, kitchen, and with kitchen.

Sat, Nov 28 - Sat, Dec 5 · 7 nights · total from $857.

From$122/night

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10 ★ 1 reviews

Shore Steps Cottage - Walking Distance To The Town Of Windermere

Cottage, Windermere

Shore Steps Cottage - Walking Distance To The Town Of Windermere is a cottage in Windermere, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Shore Steps Cottage - Walking Distance To The Town Of Windermere

Shore Steps Cottage - Walking Distance To The Town Of Windermere is a cottage in Windermere, 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 parking, kitchen, with kitchen, and washer.

Sat, Nov 28 - Sat, Dec 5 · 7 nights · total from $1,042.

From$149/night

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Family-friendly vacation rentals in Windermere, FL

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

6 ★ 1 reviews

Orlando Escape - Carrier Dr

Condo, Windermere

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

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About Orlando Escape - Carrier Dr

Orlando Escape - Carrier Dr is a condo in Windermere, 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, Nov 28 - Sat, Dec 5 · 7 nights · total from $1,392.

From$136/night

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4 ★ 1 reviews

3 Bedroom Lakefront Tropical Paradise Villa, few miles from Disney/ Universal

Condo, Windermere

3 Bedroom Lakefront Tropical Paradise Villa, few miles from Disney/ Universal is a condo in Windermere, with room for a group. This stay gives travelers a comfortable base for exploring the…

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About 3 Bedroom Lakefront Tropical Paradise Villa, few miles from Disney/ Universal

3 Bedroom Lakefront Tropical Paradise Villa, few miles from Disney/ Universal is a condo in Windermere, with 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, family friendly, game room, arcade, and non smoking.

Sat, Nov 28 - Sat, Dec 5 · 7 nights · total from $2,468.

From$353/night

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The Enclave 2BR Near Universal, Pool & Gym

Villa, Windermere

The Enclave 2BR Near Universal, Pool & Gym is a villa in Windermere, with pool access, parking, and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About The Enclave 2BR Near Universal, Pool & Gym

The Enclave 2BR Near Universal, Pool & Gym is a villa in Windermere, 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, free parking, free wifi, family friendly, and kids playground.

Sat, Nov 28 - Sat, Dec 5 · 7 nights · total from $1,010.

From$111/night

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Estate 20 Minutes from Walt Disney

Holiday Home, Windermere

Estate 20 Minutes from Walt Disney is a holiday home in Windermere, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Estate 20 Minutes from Walt Disney

Estate 20 Minutes from Walt Disney is a holiday home in Windermere, 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 parking, kitchen, with kitchen, and kids friendly.

Sat, Nov 28 - Sat, Dec 5 · 7 nights · total from $2,879.

From$411/night

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Pet-friendly vacation rentals in Windermere, FL

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

9 ★ 2 reviews

Quaint 4 Bedroom Farm House with Modern Vibe

Holiday Home, Windermere

Quaint 4 Bedroom Farm House with Modern Vibe is a holiday home in Windermere, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Quaint 4 Bedroom Farm House with Modern Vibe

Quaint 4 Bedroom Farm House with Modern Vibe is a holiday home in Windermere, 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, kitchen, with kitchen, pet friendly, and pets friendly.

Sat, Nov 28 - Sat, Dec 5 · 7 nights · total from $2,506.

From$358/night

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1 Full Bed | Premium, Micfridge

Apartment, Windermere

1 Full Bed · Premium, Micfridge is a apartment in Windermere, 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 1 Full Bed | Premium, Micfridge

1 Full Bed · Premium, Micfridge is a apartment in Windermere, 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, pet friendly, pets friendly, and ac.

Sat, Nov 28 - Sat, Dec 5 · 7 nights · total from $443.

From$63/night

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2 Full Beds | Micfridge

Apartment, Windermere

2 Full Beds · Micfridge is a apartment in Windermere, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About 2 Full Beds | Micfridge

2 Full Beds · Micfridge is a apartment in Windermere, 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, pet friendly, pets friendly, and ac.

Sat, Nov 28 - Sat, Dec 5 · 7 nights · total from $457.

From$65/night

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Rustic Hideaway - Great Location + Pet Friendly!

Villa, Windermere

Rustic Hideaway - Great Location + Pet Friendly! is a villa in Windermere, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Rustic Hideaway - Great Location + Pet Friendly!

Rustic Hideaway - Great Location + Pet Friendly! is a villa in Windermere, 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, free parking, kitchen, with kitchen, and pet friendly.

Sat, Nov 28 - Sat, Dec 5 · 7 nights · total from $1,640.

From$154/night

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Vacation rentals with a pool in Windermere, FL

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

9 ★ 7 reviews

Tropical Paradise in Orlando

Holiday Home, Windermere

Tropical Paradise in Orlando is a holiday home in Windermere, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Tropical Paradise in Orlando

Tropical Paradise in Orlando is a holiday home in Windermere, 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, free parking, kitchen, and with kitchen.

Sat, Nov 28 - Sat, Dec 5 · 7 nights · total from $1,639.

From$234/night

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Lovely Studio near Universal

Apartment, Windermere

Lovely Studio near Universal is a apartment in Windermere, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Lovely Studio near Universal

Lovely Studio near Universal is a apartment in Windermere, 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: pool, hot tub, and free parking.

Sat, Nov 28 - Sat, Dec 5 · 7 nights · total from $883.

From$100/night

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Spacious Studio close to Theme Parks

Apartment, Windermere

Spacious Studio close to Theme Parks is a apartment in Windermere, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Spacious Studio close to Theme Parks

Spacious Studio close to Theme Parks is a apartment in Windermere, 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: pool, hot tub, and free parking.

Sat, Nov 28 - Sat, Dec 5 · 7 nights · total from $883.

From$100/night

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2 Full Beds | Premium, Mini Fridge

Apartment, Windermere

2 Full Beds · Premium, Mini Fridge is a apartment in Windermere, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About 2 Full Beds | Premium, Mini Fridge

2 Full Beds · Premium, Mini Fridge is a apartment in Windermere, 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, pet friendly, pets friendly, and ac.

Sat, Nov 28 - Sat, Dec 5 · 7 nights · total from $478.

From$68/night

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Vacation rentals with parking in Windermere, FL

Find vacation rentals that make arriving by car easier.

8.4 ★ 7 reviews

Theme Park Retreat, 4BR near Universal Studios

Holiday Home, Windermere

Theme Park Retreat, 4BR near Universal Studios is a holiday home in Windermere, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Theme Park Retreat, 4BR near Universal Studios

Theme Park Retreat, 4BR near Universal Studios is a holiday home in Windermere, 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: free parking, kitchen, with kitchen, and washer.

Sat, Nov 28 - Sat, Dec 5 · 7 nights · total from $1,915.

From$274/night

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“Modern Studio Orlando | Full Kitchen, Near Epic & Universal Parks”

Apartment, Windermere

“Modern Studio Orlando · Full Kitchen, Near Epic & Universal Parks” is a apartment in Windermere, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base…

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About “Modern Studio Orlando | Full Kitchen, Near Epic & Universal Parks”

“Modern Studio Orlando · Full Kitchen, Near Epic & Universal Parks” is a apartment in Windermere, 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, free parking, kitchen, and with kitchen.

Sat, Nov 28 - Sat, Dec 5 · 7 nights · total from $726.

From$104/night

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Studio Near Universal Lake View Pool & Gym

Villa, Windermere

Studio Near Universal Lake View Pool & Gym is a villa in Windermere, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Studio Near Universal Lake View Pool & Gym

Studio Near Universal Lake View Pool & Gym is a villa in Windermere, 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, free parking, free wifi, and tv.

Sat, Nov 28 - Sat, Dec 5 · 7 nights · total from $1,021.

From$112/night

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Wizard-Themed Condo Near Universal

Condo, Windermere

Wizard-Themed Condo Near Universal is a condo in Windermere, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Wizard-Themed Condo Near Universal

Wizard-Themed Condo Near Universal is a condo in Windermere, 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, hot tub, free parking, and condominium.

Sat, Nov 28 - Sat, Dec 5 · 7 nights · total from $806.

From$115/night

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Vacation rentals with a kitchen in Windermere, FL

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

9.4 ★ 6 reviews

Orlando Bliss Near Disney, Universal parks Two bedroom Apart with full kitchen

Apartment, Windermere

Orlando Bliss Near Disney, Universal parks Two bedroom Apart with full kitchen is a apartment in Windermere, with pool access, parking, and kitchen access. This stay gives travelers a…

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About Orlando Bliss Near Disney, Universal parks Two bedroom Apart with full kitchen

Orlando Bliss Near Disney, Universal parks Two bedroom Apart with full kitchen is a apartment in Windermere, 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, hot tub, and free parking.

Sat, Nov 28 - Sat, Dec 5 · 7 nights · total from $1,991.

From$284/night

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The Enclave 2BR near Universal, Pool & Gym

Villa, Windermere

The Enclave 2BR near Universal, Pool & Gym is a villa in Windermere, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About The Enclave 2BR near Universal, Pool & Gym

The Enclave 2BR near Universal, Pool & Gym is a villa in Windermere, 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, free parking, kitchen, and with kitchen.

Sat, Nov 28 - Sat, Dec 5 · 7 nights · total from $948.

From$135/night

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Studio Near Universal | Lake View | Pool & Gym

Villa, Windermere

Studio Near Universal · Lake View · Pool & Gym is a villa in Windermere, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Studio Near Universal | Lake View | Pool & Gym

Studio Near Universal · Lake View · Pool & Gym is a villa in Windermere, 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, free parking, kitchen, and with kitchen.

Sat, Nov 28 - Sat, Dec 5 · 7 nights · total from $964.

From$138/night

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The Farm House - Great Location + Pet Friendly!

Villa, Windermere

The Farm House - Great Location + Pet Friendly! is a villa in Windermere, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About The Farm House - Great Location + Pet Friendly!

The Farm House - Great Location + Pet Friendly! is a villa in Windermere, 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, free parking, kitchen, with kitchen, and pet friendly.

Sat, Nov 28 - Sat, Dec 5 · 7 nights · total from $1,644.

From$160/night

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