Vacation rentals in Winter Springs, FL

Best vacation rentals and Airbnb offers in Winter Springs, FL

MainStay Suites Orlando Altamonte Springs

Homestay, Winter Springs

MainStay Suites Orlando Altamonte Springs is a homestay in Winter Springs, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area,…

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About MainStay Suites Orlando Altamonte Springs

MainStay Suites Orlando Altamonte Springs is a homestay in Winter Springs, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $482.

From$59/night

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Charming 1-bedroom house in Casselberry

Holiday Home, Winter Springs

Charming 1-bedroom house in Casselberry is a holiday home in Winter Springs, with room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Charming 1-bedroom house in Casselberry

Charming 1-bedroom house in Casselberry is a holiday home in Winter Springs, 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, ac, air conditioning, internet, and hair dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $487.

From$70/night

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Lake Marion Apt w/ Canoe in Altamonte Springs!

Apartment, Winter Springs

Lake Marion Apt w/ Canoe in Altamonte Springs! is a apartment in Winter Springs, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Lake Marion Apt w/ Canoe in Altamonte Springs!

Lake Marion Apt w/ Canoe in Altamonte Springs! is a apartment in Winter Springs, 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 $908.

From$86/night

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Cozy Modern Studio

Apartment, Winter Springs

Cozy Modern Studio is a apartment in Winter Springs, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About Cozy Modern Studio

Cozy Modern Studio is a apartment in Winter Springs, 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, internet, and lang::en.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $752.

From$86/night

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Vacation rentals with a pool in Winter Springs, 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, Winter Springs

Lakefront Sanford Home w/ Community Pool is a holiday home in Winter Springs, 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 Winter Springs, 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 $1,009.

From$144/night

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Gorgeous Lake Howell Townhouse

Holiday Home, Winter Springs

Gorgeous Lake Howell Townhouse is a holiday home in Winter Springs, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Gorgeous Lake Howell Townhouse

Gorgeous Lake Howell Townhouse is a holiday home in Winter Springs, 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, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,244.

From$178/night

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Florida Vacation with pool fun for families

Holiday Home, Winter Springs

Florida Vacation with pool fun for families is a holiday home in Winter Springs, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the…

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About Florida Vacation with pool fun for families

Florida Vacation with pool fun for families is a holiday home in Winter Springs, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,283.

From$183/night

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Family Pool Home Near Orlando Attractions

Holiday Home, Winter Springs

Family Pool Home Near Orlando Attractions is a holiday home in Winter Springs, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Family Pool Home Near Orlando Attractions

Family Pool Home Near Orlando Attractions is a holiday home in Winter Springs, 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 $1,466.

From$209/night

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Vacation rentals with parking in Winter Springs, FL

Find vacation rentals that make arriving by car easier.

Sandford Vacation Rental Near Airport & Lake!

Holiday Home, Winter Springs

Sandford Vacation Rental Near Airport & Lake! is a holiday home in Winter Springs, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Sandford Vacation Rental Near Airport & Lake!

Sandford Vacation Rental Near Airport & Lake! is a holiday home in Winter Springs, 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 heating.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,230.

From$92/night

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

Apartment, Winter Springs

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

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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 Winter Springs, 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 $652.

From$93/night

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Dog-Friendly Apt w/ Fenced Yard in Winter Park

Holiday Home, Winter Springs

Dog-Friendly Apt w/ Fenced Yard in Winter Park is a holiday home in Winter Springs, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Dog-Friendly Apt w/ Fenced Yard in Winter Park

Dog-Friendly Apt w/ Fenced Yard in Winter Park is a holiday home in Winter Springs, 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, free wifi, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,056.

From$95/night

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Quiet 2 bedroom Suite, close to Advent Health Hospitals and downtown Orlando

Holiday Home, Winter Springs

Quiet 2 bedroom Suite, close to Advent Health Hospitals and downtown Orlando is a holiday home in Winter Springs, with parking, kitchen access, and room for a group. This stay gives…

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About Quiet 2 bedroom Suite, close to Advent Health Hospitals and downtown Orlando

Quiet 2 bedroom Suite, close to Advent Health Hospitals and downtown Orlando is a holiday home in Winter Springs, 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: kitchen, with kitchen, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $896.

From$128/night

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Pet-friendly vacation rentals in Winter Springs, FL

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

Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix

Villa, Winter Springs

Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix is a villa in Winter Springs, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix

Renovated ✓Nature ✓Cozy ✓Walk to Mall Park Publix is a villa in Winter Springs, 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, free wifi, pet friendly, pets friendly, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $704.

From$101/night

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Peaceful Private Gated Patio Walk to Mall Publix

Holiday Home, Winter Springs

Peaceful Private Gated Patio Walk to Mall Publix is a holiday home in Winter Springs, with pet-friendly space and outdoor space. This stay gives travelers a comfortable base for exploring…

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About Peaceful Private Gated Patio Walk to Mall Publix

Peaceful Private Gated Patio Walk to Mall Publix is a holiday home in Winter Springs, with pet-friendly space 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, free wifi, pet friendly, pets friendly, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $775.

From$111/night

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Home away from home in Orlando!

Holiday Home, Winter Springs

Home away from home in Orlando! is a holiday home in Winter Springs, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Home away from home in Orlando!

Home away from home in Orlando! is a holiday home in Winter Springs, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,376.

From$140/night

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Refreshing Oasis with Massage Chair, Game Garage, Large Fenced Yard +Retro games

Holiday Home, Winter Springs

Refreshing Oasis with Massage Chair, Game Garage, Large Fenced Yard +Retro games is a holiday home in Winter Springs, with pet-friendly space and parking. This stay gives travelers a…

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About Refreshing Oasis with Massage Chair, Game Garage, Large Fenced Yard +Retro games

Refreshing Oasis with Massage Chair, Game Garage, Large Fenced Yard +Retro games is a holiday home in Winter Springs, 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, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,240.

From$177/night

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Vacation rentals with a kitchen in Winter Springs, FL

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

Altamonte Luxury Studio: Shops, Parks

Apartment, Winter Springs

Altamonte Luxury Studio: Shops, Parks is a apartment in Winter Springs, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Altamonte Luxury Studio: Shops, Parks

Altamonte Luxury Studio: Shops, Parks is a apartment in Winter Springs, 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 $619.

From$88/night

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Sunshine Escape Guesthouse ☀

Holiday Home, Winter Springs

Sunshine Escape Guesthouse ☀ is a holiday home in Winter Springs, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Sunshine Escape Guesthouse ☀

Sunshine Escape Guesthouse ☀ is a holiday home in Winter Springs, 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 $671.

From$96/night

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Comfortable Guest Suite in Altamonte Springs - Large Pool

Guest House, Winter Springs

Comfortable Guest Suite in Altamonte Springs - Large Pool is a guest house in Winter Springs, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring…

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About Comfortable Guest Suite in Altamonte Springs - Large Pool

Comfortable Guest Suite in Altamonte Springs - Large Pool is a guest house in Winter Springs, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $853.

From$122/night

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Cozy 5 Room Villa Central to Attractions restaurants shopping and the beaches

Villa, Winter Springs

Cozy 5 Room Villa Central to Attractions restaurants shopping and the beaches is a villa in Winter Springs, with pool access, easy beach access, and kitchen access. This stay gives…

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About Cozy 5 Room Villa Central to Attractions restaurants shopping and the beaches

Cozy 5 Room Villa Central to Attractions restaurants shopping and the beaches is a villa in Winter Springs, 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, pool, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,010.

From$144/night

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Family-friendly vacation rentals in Winter Springs, FL

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

Sandford Vacation Rental Near Airport & Lake!

Cottage, Winter Springs

Sandford Vacation Rental Near Airport & Lake! is a cottage in Winter Springs, 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 Winter Springs, 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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Lakefront Sanford Home w/ Community Pool

Cottage, Winter Springs

Lakefront Sanford Home w/ Community Pool is a cottage in Winter Springs, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Lakefront Sanford Home w/ Community Pool

Lakefront Sanford Home w/ Community Pool is a cottage in Winter Springs, 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, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,193.

From$126/night

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Poolside Weekday Retreat – Just 119 Night!

Cottage, Winter Springs

Poolside Weekday Retreat – Just 119 Night! is a cottage in Winter Springs, with pool access, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About Poolside Weekday Retreat – Just 119 Night!

Poolside Weekday Retreat – Just 119 Night! is a cottage in Winter Springs, with pool access, 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, pool, free wifi, kitchen, and with kitchen.

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

From$162/night

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Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!

Holiday Home, Winter Springs

Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home! is a holiday home in Winter Springs, with kitchen access and room for a group. This stay gives travelers a…

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About Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home!

Sleeps 8-3 Bedrooms 2 Full Bathroms+Gameroom your perfect vacation home! is a holiday home in Winter Springs, 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 $1,166.

From$167/night

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