Cabin rentals and cottages in Windermere

56 available cabin and cottage offers

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Best cabin rentals and cottages in Windermere

Lovely Spacious Guesthouse in Mills 50 District, Orlando - Windermere

Lovely Spacious Guesthouse in Mills 50 District, Orlando

Cottage, Windermere

Lovely Spacious Guesthouse in Mills 50 District, Orlando is a cottage in Windermere, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Lovely Spacious Guesthouse in Mills 50 District, Orlando

Lovely Spacious Guesthouse in Mills 50 District, Orlando is a cottage in Windermere, 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, kitchen, with kitchen, washer, and dryer.

Sat, Sep 19 - Sat, Sep 26 · 7 nights · total from $599.

From$86/night
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Charming Lakefront Cottage Near Disney - Windermere

Charming Lakefront Cottage Near Disney

Cottage, Windermere

Charming Lakefront Cottage Near 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 Charming Lakefront Cottage Near Disney

Charming Lakefront Cottage Near 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Sep 19 - Sat, Sep 26 · 7 nights · total from $725.

From$104/night
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20 Minutes to Disney - Cozy Cottage - Windermere

20 Minutes to Disney - Cozy Cottage

Cottage, Windermere

20 Minutes to Disney - Cozy Cottage is a cottage in Windermere, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About 20 Minutes to Disney - Cozy Cottage

20 Minutes to Disney - Cozy Cottage 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, Sep 19 - Sat, Sep 26 · 7 nights · total from $750.

From$107/night
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Downtown Cottage - Windermere

Downtown Cottage

Cottage, Windermere

Downtown Cottage 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…

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About Downtown Cottage

Downtown Cottage 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, Sep 19 - Sat, Sep 26 · 7 nights · total from $815.

From$116/night
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Cabins and cottages with hot tubs in Windermere

Clermont Vacation Rental w/ Pool: 11 Mi to Disney - Windermere

Clermont Vacation Rental w/ Pool: 11 Mi to Disney

Cottage, Windermere

Clermont Vacation Rental w/ Pool: 11 Mi to Disney is a cottage in Windermere, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Clermont Vacation Rental w/ Pool: 11 Mi to Disney

Clermont Vacation Rental w/ Pool: 11 Mi to Disney is a cottage 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, Sep 19 - Sat, Sep 26 · 7 nights · total from $1,754.

From$175/night
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Spacious 6 Bed Home With Pool in Storey Lake - Windermere

Spacious 6 Bed Home With Pool in Storey Lake

Cottage, Windermere

Spacious 6 Bed Home With Pool in Storey Lake is a cottage 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 Spacious 6 Bed Home With Pool in Storey Lake

Spacious 6 Bed Home With Pool in Storey Lake is a cottage 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, Sep 19 - Sat, Sep 26 · 7 nights · total from $1,954.

From$206/night
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Home 6bed , Themed Rooms, Game Room, Storey Lake - Windermere

Home 6bed , Themed Rooms, Game Room, Storey Lake

Cottage, Windermere

Home 6bed , Themed Rooms, Game Room, Storey Lake is a cottage in Windermere, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Home 6bed , Themed Rooms, Game Room, Storey Lake

Home 6bed , Themed Rooms, Game Room, Storey Lake is a cottage 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, Sep 19 - Sat, Sep 26 · 7 nights · total from $2,223.

From$240/night
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1-acre Backyard & Gym: Spacious Apopka Escape! - Windermere

1-acre Backyard & Gym: Spacious Apopka Escape!

Cottage, Windermere

1-acre Backyard & Gym: Spacious Apopka Escape! is a cottage in Windermere, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About 1-acre Backyard & Gym: Spacious Apopka Escape!

1-acre Backyard & Gym: Spacious Apopka Escape! is a cottage in Windermere, with pet-friendly 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, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Sep 19 - Sat, Sep 26 · 7 nights · total from $2,757.

From$273/night
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Secluded cabins and cottages in Windermere

Beautiful Home W/private Pool & Spa, Near Wdw! - Windermere

Beautiful Home W/private Pool & Spa, Near Wdw!

Cottage, Windermere

Beautiful Home W/private Pool & Spa, Near Wdw! is a cottage in Windermere, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area,…

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About Beautiful Home W/private Pool & Spa, Near Wdw!

Beautiful Home W/private Pool & Spa, Near Wdw! is a cottage 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, free wifi, pet friendly, and pets friendly.

Sat, Sep 19 - Sat, Sep 26 · 7 nights · total from $1,933.

From$197/night
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Apopka Single-story Home w/ Private Lanai + Pool! - Windermere

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

Cottage, Windermere

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

Apopka Single-story Home w/ Private Lanai + Pool! 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, Sep 19 - Sat, Sep 26 · 7 nights · total from $2,198.

From$218/night
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Happy Ours Cottage near Disney with Private Hot Tub and Margaritaville Resort &. - Windermere

Happy Ours Cottage near Disney with Private Hot Tub and Margaritaville Resort &.

Cottage, Windermere

Happy Ours Cottage near Disney with Private Hot Tub and Margaritaville Resort &. is a cottage in Windermere, with pool access. This stay gives travelers a comfortable base for exploring the…

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About Happy Ours Cottage near Disney with Private Hot Tub and Margaritaville Resort &.

Happy Ours Cottage near Disney with Private Hot Tub and Margaritaville Resort &. is a cottage 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, Sep 19 - Sat, Sep 26 · 7 nights · total from $1,994.

From$285/night
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Pineapple Dream Cottage with Private Hot Tub near Disney with Margaritaville. - Windermere

Pineapple Dream Cottage with Private Hot Tub near Disney with Margaritaville.

Cottage, Windermere

Pineapple Dream Cottage with Private Hot Tub near Disney with Margaritaville. is a cottage in Windermere, with pool access. This stay gives travelers a comfortable base for exploring the…

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About Pineapple Dream Cottage with Private Hot Tub near Disney with Margaritaville.

Pineapple Dream Cottage with Private Hot Tub near Disney with Margaritaville. is a cottage 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, Sep 19 - Sat, Sep 26 · 7 nights · total from $2,360.

From$337/night
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Nearby cabin rentals around Windermere

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Family cabins and cottages in Windermere

1617 Retreat Circle, Clermont, 3 BED - Windermere

1617 Retreat Circle, Clermont, 3 BED

Cottage, Windermere

1617 Retreat Circle, Clermont, 3 BED is a cottage in Windermere, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area,…

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About 1617 Retreat Circle, Clermont, 3 BED

1617 Retreat Circle, Clermont, 3 BED 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, Sep 19 - Sat, Sep 26 · 7 nights · total from $1,467.

From$141/night
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5 Mi to Disney World: Spacious Kissimmee Home! - Windermere

5 Mi to Disney World: Spacious Kissimmee Home!

Cottage, Windermere

5 Mi to Disney World: Spacious Kissimmee Home! is a cottage in Windermere, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About 5 Mi to Disney World: Spacious Kissimmee Home!

5 Mi to Disney World: Spacious Kissimmee Home! 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, Sep 19 - Sat, Sep 26 · 7 nights · total from $1,560.

From$150/night
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Peaceful Clermont Gem w/ Pool, 9 Mi to Disney! - Windermere

Peaceful Clermont Gem w/ Pool, 9 Mi to Disney!

Cottage, Windermere

Peaceful Clermont Gem w/ Pool, 9 Mi to Disney! is a cottage in Windermere, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Peaceful Clermont Gem w/ Pool, 9 Mi to Disney!

Peaceful Clermont Gem w/ Pool, 9 Mi to Disney! 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, Sep 19 - Sat, Sep 26 · 7 nights · total from $1,396.

From$150/night
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Theme Park Base! Suburban Home 14 Mi to Universal - Windermere

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, Sep 19 - Sat, Sep 26 · 7 nights · total from $2,014.

From$212/night
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Pet-friendly cabins and cottages in Windermere

~ 12 Mi to Disney: Downtown Winter Garden Cottage! - Windermere

~ 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, Sep 19 - Sat, Sep 26 · 7 nights · total from $1,917.

From$212/night
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6 Mi to Lake Louisa State Park: Home w/ Pool - Windermere

6 Mi to Lake Louisa State Park: Home w/ Pool

Cottage, Windermere

6 Mi to Lake Louisa State Park: Home w/ Pool is a cottage in Windermere, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About 6 Mi to Lake Louisa State Park: Home w/ Pool

6 Mi to Lake Louisa State Park: Home w/ Pool is a cottage 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, free wifi, pet friendly, and pets friendly.

Sat, Sep 19 - Sat, Sep 26 · 7 nights · total from $1,912.

From$212/night
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~ 12 Mi to Disney: Downtown Winter Garden Cottage! - Windermere

~ 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, parking, and kitchen access. This stay gives travelers a comfortable base for…

Read more

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, 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, Sep 19 - Sat, Sep 26 · 7 nights · total from $1,592.

From$227/night
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Charming 2BD Cottage near Hotel & Disney - Windermere

Charming 2BD Cottage near Hotel & Disney

Cottage, Windermere

Charming 2BD Cottage near Hotel & Disney is a cottage in Windermere, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Charming 2BD Cottage near Hotel & Disney

Charming 2BD Cottage near Hotel & Disney 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, Sep 19 - Sat, Sep 26 · 7 nights · total from $1,952.

From$279/night
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Other places to stay in Windermere

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