Vacation rentals in Windermere, FL

Best vacation rentals and Airbnb offers in Windermere, FL

8.4 ★ 5 reviews

Cozy Escape

Apartment, Windermere

Cozy Escape is a apartment in Windermere, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Cozy Escape

Cozy Escape is a apartment in Windermere, 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 $1,368.

From$144/night

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3BR Condo with Pool Close to Disney

Holiday Home, Windermere

3BR Condo with Pool Close to Disney is a holiday home in Windermere, with pool access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About 3BR Condo with Pool Close to Disney

3BR Condo with Pool Close to Disney is a holiday home in Windermere, 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 $950.

From$98/night

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3BR Condo with Pool - Near Disney

Holiday Home, Windermere

3BR Condo with Pool - Near Disney is a holiday home in Windermere, with pool access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About 3BR Condo with Pool - Near Disney

3BR Condo with Pool - Near Disney is a holiday home in Windermere, 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 $981.

From$102/night

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

Homestay, Windermere

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

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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 Windermere, 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

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Family-friendly vacation rentals in Windermere, FL

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

~ 12 Mi to Disney: Downtown Winter Garden Cottage!

Holiday Home, Windermere

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

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

~ 12 Mi to Disney: Downtown Winter Garden Cottage! is a holiday home in Windermere, 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 wifi, pet friendly, pets friendly, parking, and paid parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,845.

From$177/night

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

Cottage, Windermere

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

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

~ 9 Mi to Universal: Orlando Retreat w/ Sun Porch! is a cottage in Windermere, 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

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Walkable Winter Garden Bungalow: 3 Blocks to Dtwn

Cottage, Windermere

Walkable Winter Garden Bungalow: 3 Blocks to Dtwn is a cottage in Windermere, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Walkable Winter Garden Bungalow: 3 Blocks to Dtwn

Walkable Winter Garden Bungalow: 3 Blocks to Dtwn 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 wifi, kitchen, with kitchen, and parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,177.

From$132/night

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Walk to Dtwn: Winter Garden Home w/ Patio

Cottage, Windermere

Walk to Dtwn: Winter Garden Home w/ Patio is a cottage in Windermere, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Walk to Dtwn: Winter Garden Home w/ Patio

Walk to Dtwn: Winter Garden Home w/ Patio is a cottage in Windermere, 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: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,456.

From$163/night

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Pet-friendly vacation rentals in Windermere, FL

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

2BR Condo with pool, near Disney!

Holiday Home, Windermere

2BR Condo with pool, near Disney! is a holiday home in Windermere, with pet-friendly space, pool access, and room for a group. This stay gives travelers a comfortable base for exploring the…

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About 2BR Condo with pool, near Disney!

2BR Condo with pool, near Disney! is a holiday home in Windermere, 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, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,007.

From$108/night

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Spacious 2BR Condo with Pool , near Disney!

Holiday Home, Windermere

Spacious 2BR Condo with Pool , near Disney! is a holiday home in Windermere, with pet-friendly space, pool access, and room for a group. This stay gives travelers a comfortable base for…

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About Spacious 2BR Condo with Pool , near Disney!

Spacious 2BR Condo with Pool , near Disney! is a holiday home in Windermere, 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, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,007.

From$108/night

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Upstay 3BR Condo w Pool Patio Near Disney

Apartment, Windermere

Upstay 3BR Condo w Pool Patio Near Disney is a apartment in Windermere, with pet-friendly space, pool access, and outdoor space. This stay gives travelers a comfortable base for exploring…

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About Upstay 3BR Condo w Pool Patio Near Disney

Upstay 3BR Condo w Pool Patio Near Disney is a apartment in Windermere, 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: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,122.

From$120/night

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Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly

Apartment, Windermere

Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly is a apartment in Windermere, with pet-friendly space, pool access, and parking. This stay gives travelers a comfortable base…

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About Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly

Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly is a apartment in Windermere, 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, pool, pet friendly, pets friendly, and parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,409.

From$157/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.

Stunning 2BR Condo with Pool, near Disney!

Holiday Home, Windermere

Stunning 2BR Condo with Pool, near Disney! is a holiday home in Windermere, with pool access and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Stunning 2BR Condo with Pool, near Disney!

Stunning 2BR Condo with Pool, near Disney! is a holiday home in Windermere, 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 $1,026.

From$111/night

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403 Top Lake View-Disney, Universal/Convention Center

Holiday Home, Windermere

403 Top Lake View-Disney, Universal/Convention Center is a holiday home in Windermere, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About 403 Top Lake View-Disney, Universal/Convention Center

403 Top Lake View-Disney, Universal/Convention Center is a holiday home 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: pool, hot tub, and free wifi.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,428.

From$158/night

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Orlando Resort: 3BD and electric fireplace

Apartment, Windermere

Orlando Resort: 3BD and electric fireplace is a apartment in Windermere, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Orlando Resort: 3BD and electric fireplace

Orlando Resort: 3BD and electric fireplace is a apartment 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, hot tub, and free wifi.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,336.

From$149/night

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Spacious 2Bd Condo - Pool Hot Tub - Near I-drive

Apartment, Windermere

Spacious 2Bd Condo - Pool Hot Tub - Near I-drive is a apartment in Windermere, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Spacious 2Bd Condo - Pool Hot Tub - Near I-drive

Spacious 2Bd Condo - Pool Hot Tub - Near I-drive 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, free wifi, parking, and free parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,480.

From$159/night

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Vacation rentals with parking in Windermere, FL

Find vacation rentals that make arriving by car easier.

10 ★ 1 reviews

Lakefront Retreat w/ Kayaks & Fire Pit in Clermont

Cottage, Windermere

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

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About Lakefront Retreat w/ Kayaks & Fire Pit in Clermont

Lakefront Retreat w/ Kayaks & Fire Pit in Clermont is a cottage in Windermere, 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

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Luxury Tiny Home 2 Miles from Downtown Orlando

Guest House, Windermere

Luxury Tiny Home 2 Miles from Downtown Orlando is a guest house in Windermere, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Luxury Tiny Home 2 Miles from Downtown Orlando

Luxury Tiny Home 2 Miles from Downtown Orlando is a guest house in Windermere, 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, free wifi, parking, paid parking, and ac.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,117.

From$129/night

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Lakefront Retreat w/ Kayaks & Fire Pit in Clermont

Holiday Home, Windermere

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

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About Lakefront Retreat w/ Kayaks & Fire Pit in Clermont

Lakefront Retreat w/ Kayaks & Fire Pit in Clermont is a holiday home in Windermere, 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

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Cozy Condo w FREE Vista Cay Resort Access

Apartment, Windermere

Cozy Condo w FREE Vista Cay Resort Access is a apartment in Windermere, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Cozy Condo w FREE Vista Cay Resort Access

Cozy Condo w FREE Vista Cay Resort Access is a apartment in Windermere, 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 wifi, parking, paid parking, ac, and air conditioning.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,448.

From$156/night

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Vacation rentals with a kitchen in Windermere, FL

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

Modern Family Retreat Near Orlando Attractions

Cottage, Windermere

Modern Family Retreat Near Orlando Attractions is a cottage 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 Modern Family Retreat Near Orlando Attractions

Modern Family Retreat Near Orlando Attractions is a cottage 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, free wifi, pet friendly, pets friendly, and kitchen.

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

From$188/night

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~ 12 Mi to Disney: Downtown Winter Garden Cottage!

Cottage, Windermere

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

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

~ 12 Mi to Disney: Downtown Winter Garden Cottage! is a cottage in Windermere, 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

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Theme Park Base! Suburban Home 14 Mi to Universal

Cottage, Windermere

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

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About Theme Park Base! Suburban Home 14 Mi to Universal

Theme Park Base! Suburban Home 14 Mi to Universal 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 wifi, kitchen, with kitchen, and parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,014.

From$212/night

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

Cottage, Windermere

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

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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 Windermere, 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

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