Vacation rentals in Windermere, FL

Best Vacation rentals and Airbnb offers in Windermere, FL

Modern Guest Suite Near Downtown

Apartment, Windermere

Modern Guest Suite Near Downtown is a apartment in Windermere. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family…

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About Modern Guest Suite Near Downtown

Modern Guest Suite Near Downtown is a apartment in Windermere. 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, ac, air conditioning, heating, and internet.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $511.

From$53/night

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Modern Private Room With Private Entrance

Holiday Home, Windermere

Modern Private Room With Private Entrance is a holiday home in Windermere, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Modern Private Room With Private Entrance

Modern Private Room With Private Entrance is a holiday home 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, parking, free parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $628.

From$68/night

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Private Cozy Studio

B & B, Windermere

Private Cozy Studio is a b & b in Windermere, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About Private Cozy Studio

Private Cozy Studio is a b & b 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, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $617.

From$73/night

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2nd Floor Studio Downtown Winter Garden

Apartment, Windermere

2nd Floor Studio Downtown Winter Garden is a apartment 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 2nd Floor Studio Downtown Winter Garden

2nd Floor Studio Downtown Winter Garden is a apartment 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: kitchen, with kitchen, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $776.

From$81/night

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Browse 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.

Orlando getaway with all the comforts of home!

Condo, Windermere

Orlando getaway with all the comforts of home! is a condo 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 getaway with all the comforts of home!

Orlando getaway with all the comforts of home! 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, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,326.

From$116/night

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Vista Cay 2 Bed 2 BT Totally Remodeled Beauty

Condo, Windermere

Vista Cay 2 Bed 2 BT Totally Remodeled Beauty is a condo 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 Vista Cay 2 Bed 2 BT Totally Remodeled Beauty

Vista Cay 2 Bed 2 BT Totally Remodeled Beauty 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, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,377.

From$116/night

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Rich décor and modern luxuries at this Vista Cay condo!

Condo, Windermere

Rich décor and modern luxuries at this Vista Cay condo! is a condo in Windermere, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Rich décor and modern luxuries at this Vista Cay condo!

Rich décor and modern luxuries at this Vista Cay condo! 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, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,323.

From$117/night

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Vista Cay Condo w/ FREE Resort Access, Near Disney and Conv. Ctr!

Condo, Windermere

Vista Cay Condo w/ FREE Resort Access, Near Disney and Conv. Ctr! is a condo in Windermere, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Vista Cay Condo w/ FREE Resort Access, Near Disney and Conv. Ctr!

Vista Cay Condo w/ FREE Resort Access, Near Disney and Conv. Ctr! 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, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,317.

From$117/night

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Best Windermere, FL vacation rentals with parking

Find vacation rentals that make arriving by car easier.

First floor apartment Downtown Winter Garden

Apartment, Windermere

First floor apartment Downtown Winter Garden is a apartment in Windermere, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About First floor apartment Downtown Winter Garden

First floor apartment Downtown Winter Garden is a apartment 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: kitchen, with kitchen, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $975.

From$99/night

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Walkable Winter Garden Bungalow: 3 Blocks to Dtwn

Holiday Home, Windermere

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

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About Walkable Winter Garden Bungalow: 3 Blocks to Dtwn

Walkable Winter Garden Bungalow: 3 Blocks to Dtwn is a holiday home 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, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,133.

From$106/night

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Walk to Dtwn: Winter Garden Home w/ Patio

Holiday Home, Windermere

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

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About Walk to Dtwn: Winter Garden Home w/ Patio

Walk to Dtwn: Winter Garden Home w/ Patio is a holiday home in Windermere, with 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 wifi, parking, paid parking, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,301.

From$117/night

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Rustic Hideaway - Modern Estate - Great Location + Pet Friendly!

Villa, Windermere

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

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About Rustic Hideaway - Modern Estate - Great Location + Pet Friendly!

Rustic Hideaway - Modern Estate - 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,814.

From$159/night

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Best Pet-Friendly Vacation Rentals in Windermere, FL

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

The Single Vacation Rental Dwelling

Apartment, Windermere

The Single Vacation Rental Dwelling is a apartment 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 The Single Vacation Rental Dwelling

The Single Vacation Rental Dwelling is a apartment 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $705.

From$70/night

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Tiny tropical Orlando Univesal-Disney

Holiday Home, Windermere

Tiny tropical Orlando Univesal-Disney is a holiday home in Windermere, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Tiny tropical Orlando Univesal-Disney

Tiny tropical Orlando Univesal-Disney is a holiday home in Windermere, 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 $710.

From$79/night

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Charming 1-bedroom apartment with pool, WiFi, AC centrally located!

Apartment, Windermere

Charming 1-bedroom apartment with pool, WiFi, AC centrally located! is a apartment in Windermere, with pool access, kitchen access, and room for a group. This stay gives travelers a…

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About Charming 1-bedroom apartment with pool, WiFi, AC centrally located!

Charming 1-bedroom apartment with pool, WiFi, AC centrally located! is a apartment in Windermere, with pool access, 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, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,104.

From$115/night

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Modern 2BR/2BA Orlando Condo/10 minutes to Universal/30 minutes Disney

Apartment, Windermere

Modern 2BR/2BA Orlando Condo/10 minutes to Universal/30 minutes Disney is a apartment in Windermere, with pet-friendly space and room for a group. This stay gives travelers a comfortable…

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About Modern 2BR/2BA Orlando Condo/10 minutes to Universal/30 minutes Disney

Modern 2BR/2BA Orlando Condo/10 minutes to Universal/30 minutes Disney is a apartment in Windermere, with pet-friendly space 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, pet friendly, pets friendly, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,151.

From$127/night

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Best Windermere, FL vacation rentals with a kitchen

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

Cozy 1-bedroom studio tiny home experience

Apartment, Windermere

Cozy 1-bedroom studio tiny home experience is a apartment in Windermere, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the…

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About Cozy 1-bedroom studio tiny home experience

Cozy 1-bedroom studio tiny home experience is a apartment 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, kitchen, with kitchen, gym, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $645.

From$72/night

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Adorable 1-bedroom right on the bike trail

Apartment, Windermere

Adorable 1-bedroom right on the bike trail is a apartment in Windermere, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the…

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About Adorable 1-bedroom right on the bike trail

Adorable 1-bedroom right on the bike trail is a apartment 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,080.

From$121/night

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Walk to Dtwn: Winter Garden Home w/ Patio

Holiday Home, Windermere

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

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About Walk to Dtwn: Winter Garden Home w/ Patio

Walk to Dtwn: Winter Garden Home w/ Patio is a holiday home 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,439.

From$121/night

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Cozy 2-bedroom house in fabulous Ocoee with AC

Holiday Home, Windermere

Cozy 2-bedroom house in fabulous Ocoee with AC 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 Cozy 2-bedroom house in fabulous Ocoee with AC

Cozy 2-bedroom house in fabulous Ocoee with AC 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 cancellation, hot tub, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,211.

From$127/night

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Our Favorite Family-Friendly Vacation Rentals in Windermere, FL

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

16 Mi to Disney: Cottage w/ Deck in Winter Garden

Cottage, Windermere

16 Mi to Disney: Cottage w/ Deck in Winter Garden is a cottage in Windermere, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About 16 Mi to Disney: Cottage w/ Deck in Winter Garden

16 Mi to Disney: Cottage w/ Deck in Winter Garden 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,091.

From$94/night

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16 Mi to Disney: Cottage w/ Deck in Winter Garden

Holiday Home, Windermere

16 Mi to Disney: Cottage w/ Deck in Winter Garden is a holiday home in Windermere, with outdoor space and parking. This stay gives travelers a comfortable base for exploring the area,…

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About 16 Mi to Disney: Cottage w/ Deck in Winter Garden

16 Mi to Disney: Cottage w/ Deck in Winter Garden is a holiday home in Windermere, with 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, parking, paid parking, and heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,148.

From$112/night

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Dtwn Winter Garden Home: 12 Mi to Disney!

Cottage, Windermere

Dtwn Winter Garden Home: 12 Mi to Disney! is a cottage 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 Dtwn Winter Garden Home: 12 Mi to Disney!

Dtwn Winter Garden Home: 12 Mi to Disney! 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,689.

From$132/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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,177.

From$132/night

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