Vacation rentals in Windsor Hills, FL

Best Vacation rentals and Airbnb offers in Windsor Hills, FL

Lovely 1-bedroom apartment with AC in charming Osteen

Apartment, Windsor Hills

Lovely 1-bedroom apartment with AC in charming Osteen is a apartment in Windsor Hills, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Lovely 1-bedroom apartment with AC in charming Osteen

Lovely 1-bedroom apartment with AC in charming Osteen is a apartment in Windsor Hills, 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, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $623.

From$73/night

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1 Mi to Historic Dtwn Sanford! Pet-Friendly Unit

Apartment, Windsor Hills

1 Mi to Historic Dtwn Sanford! Pet-Friendly Unit is a apartment in Windsor Hills, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About 1 Mi to Historic Dtwn Sanford! Pet-Friendly Unit

1 Mi to Historic Dtwn Sanford! Pet-Friendly Unit is a apartment in Windsor Hills, 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 $898.

From$75/night

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Charming and Tranquil 1-bedroom apartment close to Historic Downtown Sanford

Apartment, Windsor Hills

Charming and Tranquil 1-bedroom apartment close to Historic Downtown Sanford is a apartment in Windsor Hills, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Charming and Tranquil 1-bedroom apartment close to Historic Downtown Sanford

Charming and Tranquil 1-bedroom apartment close to Historic Downtown Sanford is a apartment in Windsor Hills, 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 wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $722.

From$77/night

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Cozy 2-bedroom apartment in centrally located Deltona. SLEEPS 7 PEOPLE!

Apartment, Windsor Hills

Cozy 2-bedroom apartment in centrally located Deltona. SLEEPS 7 PEOPLE! is a apartment in Windsor Hills, with kitchen access and room for a group. This stay gives travelers a comfortable…

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About Cozy 2-bedroom apartment in centrally located Deltona. SLEEPS 7 PEOPLE!

Cozy 2-bedroom apartment in centrally located Deltona. SLEEPS 7 PEOPLE! is a apartment in Windsor Hills, with 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: hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $899.

From$82/night

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Browse Vacation Rentals with a Pool in Windsor Hills, FL

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

Lakefront Sanford Home w/ Community Pool

Holiday Home, Windsor Hills

Lakefront Sanford Home w/ Community Pool is a holiday home in Windsor Hills, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Lakefront Sanford Home w/ Community Pool

Lakefront Sanford Home w/ Community Pool is a holiday home in Windsor Hills, 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, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,117.

From$79/night

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Hot Tub, Hammock, & Pool Oh My! The #Sanfording Pool House

Guest House, Windsor Hills

Hot Tub, Hammock, & Pool Oh My! The #Sanfording Pool House is a guest house in Windsor Hills, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Hot Tub, Hammock, & Pool Oh My! The #Sanfording Pool House

Hot Tub, Hammock, & Pool Oh My! The #Sanfording Pool House is a guest house in Windsor Hills, 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 $958.

From$95/night

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COZY 2BR Condo with Pool bike-trail near lake beach fireplace SAFE community

Apartment, Windsor Hills

COZY 2BR Condo with Pool bike-trail near lake beach fireplace SAFE community is a apartment in Windsor Hills, with pool access, easy beach access, and parking. This stay gives travelers a…

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About COZY 2BR Condo with Pool bike-trail near lake beach fireplace SAFE community

COZY 2BR Condo with Pool bike-trail near lake beach fireplace SAFE community is a apartment in Windsor Hills, with pool access, easy beach 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,199.

From$116/night

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Condo w/ Pool & Beach Access Near Theme Park

Apartment, Windsor Hills

Condo w/ Pool & Beach Access Near Theme Park is a apartment in Windsor Hills, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for…

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About Condo w/ Pool & Beach Access Near Theme Park

Condo w/ Pool & Beach Access Near Theme Park is a apartment in Windsor Hills, with pool access, easy beach 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, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,250.

From$131/night

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Best Windsor Hills, FL vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Orlando Oasis

Holiday Home, Windsor Hills

Orlando Oasis is a holiday home in Windsor Hills, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family…

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About Orlando Oasis

Orlando Oasis is a holiday home in Windsor Hills, 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, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $755.

From$76/night

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Chic Studio -10 Min to SFB Airport & Boombah Sports Complex

Apartment, Windsor Hills

Chic Studio -10 Min to SFB Airport & Boombah Sports Complex is a apartment in Windsor Hills, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Chic Studio -10 Min to SFB Airport & Boombah Sports Complex

Chic Studio -10 Min to SFB Airport & Boombah Sports Complex is a apartment in Windsor Hills, 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 $773.

From$88/night

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Home Sweet Home

Holiday Home, Windsor Hills

Home Sweet Home is a holiday home in Windsor Hills, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Home Sweet Home

Home Sweet Home is a holiday home in Windsor Hills, 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 $1,137.

From$92/night

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City Guesthouse in beautiful Historic Downtown Sanford

Guest House, Windsor Hills

City Guesthouse in beautiful Historic Downtown Sanford is a guest house in Windsor Hills, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About City Guesthouse in beautiful Historic Downtown Sanford

City Guesthouse in beautiful Historic Downtown Sanford is a guest house in Windsor Hills, 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 $1,055.

From$107/night

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Best Pet-Friendly Vacation Rentals in Windsor Hills, FL

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

Bella Breeze

Apartment, Windsor Hills

Bella Breeze is a apartment in Windsor Hills, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Bella Breeze

Bella Breeze is a apartment in Windsor Hills, 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: pet friendly, pets friendly, parking, paid parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $860.

From$97/night

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Serenity @ Court

Apartment, Windsor Hills

Serenity @ Court is a apartment in Windsor Hills, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Serenity @ Court

Serenity @ Court is a apartment in Windsor Hills, 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, pet friendly, pets friendly, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,008.

From$108/night

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FL LAKEFRONT full house 2/1

Holiday Home, Windsor Hills

FL LAKEFRONT full house 2/1 is a holiday home in Windsor Hills, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About FL LAKEFRONT full house 2/1

FL LAKEFRONT full house 2/1 is a holiday home in Windsor Hills, 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, pet friendly, pets friendly, gym, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,025.

From$108/night

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King Suite + Sleeps 10 | Cozy Deltona Home

Holiday Home, Windsor Hills

King Suite + Sleeps 10 · Cozy Deltona Home is a holiday home in Windsor Hills, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About King Suite + Sleeps 10 | Cozy Deltona Home

King Suite + Sleeps 10 · Cozy Deltona Home is a holiday home in Windsor Hills, 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: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,305.

From$130/night

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Best Windsor Hills, FL vacation rentals with a kitchen

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

Walk to Historic Dtwn: Sanford Home w/ Gas Grill!

Holiday Home, Windsor Hills

Walk to Historic Dtwn: Sanford Home w/ Gas Grill! is a holiday home in Windsor Hills, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Walk to Historic Dtwn: Sanford Home w/ Gas Grill!

Walk to Historic Dtwn: Sanford Home w/ Gas Grill! is a holiday home in Windsor Hills, 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 $1,376.

From$109/night

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Downtown Duplex A Amazing Location

Apartment, Windsor Hills

Downtown Duplex A Amazing Location is a apartment in Windsor Hills, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Downtown Duplex A Amazing Location

Downtown Duplex A Amazing Location is a apartment in Windsor Hills, 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 $1,073.

From$123/night

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WHAT A HIDDEN GEM!! Lakehouse Paradise Retreat, ESCAPE... RELAX... REJUVENATE...

Holiday Home, Windsor Hills

WHAT A HIDDEN GEM!! Lakehouse Paradise Retreat, ESCAPE... RELAX... REJUVENATE... is a holiday home in Windsor Hills, with kitchen access and a quieter setting. This stay gives travelers a…

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About WHAT A HIDDEN GEM!! Lakehouse Paradise Retreat, ESCAPE... RELAX... REJUVENATE...

WHAT A HIDDEN GEM!! Lakehouse Paradise Retreat, ESCAPE... RELAX... REJUVENATE... is a holiday home in Windsor Hills, 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, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,441.

From$146/night

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The Cozy Euphoric cottage nestled in nature with relaxing River front views.

Cottage, Windsor Hills

The Cozy Euphoric cottage nestled in nature with relaxing River front views. is a cottage in Windsor Hills, with parking, kitchen access, and a quieter setting. This stay gives travelers a…

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About The Cozy Euphoric cottage nestled in nature with relaxing River front views.

The Cozy Euphoric cottage nestled in nature with relaxing River front views. is a cottage in Windsor Hills, 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,416.

From$147/night

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Our Favorite Family-Friendly Vacation Rentals in Windsor Hills, FL

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

Relaxing 2-bedroom cottage in beautiful Sanford

Cottage, Windsor Hills

Relaxing 2-bedroom cottage in beautiful Sanford is a cottage in Windsor Hills, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Relaxing 2-bedroom cottage in beautiful Sanford

Relaxing 2-bedroom cottage in beautiful Sanford is a cottage in Windsor Hills, 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 $1,170.

From$99/night

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Tiny Cottage w/ private courtyard steps from Historic Downtown Sanford

Holiday Home, Windsor Hills

Tiny Cottage w/ private courtyard steps from Historic Downtown Sanford is a holiday home in Windsor Hills, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Tiny Cottage w/ private courtyard steps from Historic Downtown Sanford

Tiny Cottage w/ private courtyard steps from Historic Downtown Sanford is a holiday home in Windsor Hills, 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 $1,033.

From$105/night

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2BR COTTAGE IN SANFORD HISTORIC DISTRICT

Cottage, Windsor Hills

2BR COTTAGE IN SANFORD HISTORIC DISTRICT is a cottage in Windsor Hills, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About 2BR COTTAGE IN SANFORD HISTORIC DISTRICT

2BR COTTAGE IN SANFORD HISTORIC DISTRICT is a cottage in Windsor Hills, with 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, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,097.

From$112/night

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Sandford Vacation Rental Near Airport & Lake!

Cottage, Windsor Hills

Sandford Vacation Rental Near Airport & Lake! is a cottage in Windsor Hills, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Sandford Vacation Rental Near Airport & Lake!

Sandford Vacation Rental Near Airport & Lake! is a cottage in Windsor Hills, 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 $1,274.

From$123/night

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