Vacation rentals in Winter Park, FL

Best Vacation rentals and Airbnb offers in Winter Park, FL

Love Nest Studio nearby highways and Airport

Guest House, Winter Park

Love Nest Studio nearby highways and Airport is a guest house in Winter Park, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Love Nest Studio nearby highways and Airport

Love Nest Studio nearby highways and Airport is a guest house in Winter Park, 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 $453.

From$50/night

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Virbo Host Website is not working for me. Do not book this property. Thank you

Apartment, Winter Park

Virbo Host Website is not working for me. Do not book this property. Thank you is a apartment in Winter Park. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Virbo Host Website is not working for me. Do not book this property. Thank you

Virbo Host Website is not working for me. Do not book this property. Thank you is a apartment in Winter Park. 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 $551.

From$60/night

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Beautiful East Orlando Home Near Everything

Holiday Home, Winter Park

Beautiful East Orlando Home Near Everything is a holiday home in Winter Park, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Beautiful East Orlando Home Near Everything

Beautiful East Orlando Home Near Everything is a holiday home in Winter Park, 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, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $574.

From$61/night

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\"The Sweet Suite\" - Private & Quiet, Near 408/417

Apartment, Winter Park

\"The Sweet Suite\" - Private & Quiet, Near 408/417 is a apartment in Winter Park, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for…

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About \"The Sweet Suite\" - Private & Quiet, Near 408/417

\"The Sweet Suite\" - Private & Quiet, Near 408/417 is a apartment in Winter Park, 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 $575.

From$62/night

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Browse Vacation Rentals with a Pool in Winter Park, FL

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

MainStay Suites Orlando Altamonte Springs

Homestay, Winter Park

MainStay Suites Orlando Altamonte Springs is a homestay in Winter Park, 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 Park, 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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Traveler's Dream: Refresh & Recharge Poolside

Apartment, Winter Park

Traveler's Dream: Refresh & Recharge Poolside is a apartment in Winter Park, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Traveler's Dream: Refresh & Recharge Poolside

Traveler's Dream: Refresh & Recharge Poolside is a apartment in Winter Park, 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 $700.

From$75/night

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Comfortable Guest Suite in Altamonte Springs - Large Pool

Guest House, Winter Park

Comfortable Guest Suite in Altamonte Springs - Large Pool is a guest house in Winter Park, 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 Park, 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 $944.

From$97/night

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Anysel Pool house

Holiday Home, Winter Park

Anysel Pool house is a holiday home in Winter Park, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Anysel Pool house

Anysel Pool house is a holiday home in Winter Park, 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, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,134.

From$126/night

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Best Winter Park, FL vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Comfortable 1 bedroom home

Holiday Home, Winter Park

Comfortable 1 bedroom home is a holiday home in Winter Park, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Comfortable 1 bedroom home

Comfortable 1 bedroom home is a holiday home in Winter Park, 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 $578.

From$61/night

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King Bed Escape: Private Patio, Grill, Fire Pit Near Everything in Orlando

Apartment, Winter Park

King Bed Escape: Private Patio, Grill, Fire Pit Near Everything in Orlando is a apartment in Winter Park, with outdoor space, parking, and kitchen access. This stay gives travelers a…

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About King Bed Escape: Private Patio, Grill, Fire Pit Near Everything in Orlando

King Bed Escape: Private Patio, Grill, Fire Pit Near Everything in Orlando is a apartment in Winter Park, 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 $793.

From$73/night

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Galaxy by Airport, Downtown, 408/417 , Theme Park

Apartment, Winter Park

Galaxy by Airport, Downtown, 408/417 , Theme Park is a apartment in Winter Park, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About Galaxy by Airport, Downtown, 408/417 , Theme Park

Galaxy by Airport, Downtown, 408/417 , Theme Park is a apartment in Winter Park, 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 $672.

From$76/night

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Yania's Cozy Getaway

Apartment, Winter Park

Yania's Cozy Getaway is a apartment in Winter Park, 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 Yania's Cozy Getaway

Yania's Cozy Getaway is a apartment in Winter Park, 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 $742.

From$76/night

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Best Pet-Friendly Vacation Rentals in Winter Park, FL

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

Spacious half 1/1 duplex in amazing location!

Holiday Home, Winter Park

Spacious half 1/1 duplex in amazing location! is a holiday home in Winter Park, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Spacious half 1/1 duplex in amazing location!

Spacious half 1/1 duplex in amazing location! is a holiday home in Winter Park, 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 $839.

From$90/night

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Sunny Baldwin Park Studio • Walk to Cafés • Near Downtown

Apartment, Winter Park

Sunny Baldwin Park Studio · Walk to Cafés · Near Downtown is a apartment in Winter Park, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base…

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About Sunny Baldwin Park Studio • Walk to Cafés • Near Downtown

Sunny Baldwin Park Studio · Walk to Cafés · Near Downtown is a apartment in Winter Park, 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 $796.

From$92/night

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Charming Private Studio/Full Amenities / Great Location

Apartment, Winter Park

Charming Private Studio/Full Amenities / Great Location is a apartment in Winter Park, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Charming Private Studio/Full Amenities / Great Location

Charming Private Studio/Full Amenities / Great Location is a apartment in Winter Park, 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 $850.

From$93/night

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Dog-Friendly Apt w/ Fenced Yard in Winter Park

Holiday Home, Winter Park

Dog-Friendly Apt w/ Fenced Yard in Winter Park is a holiday home in Winter Park, 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 Park, 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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Best Winter Park, FL vacation rentals with a kitchen

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

“The Clementine” Boho Home in Orlando’s Food Scene

Holiday Home, Winter Park

“The Clementine” Boho Home in Orlando’s Food Scene is a holiday home in Winter Park, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About “The Clementine” Boho Home in Orlando’s Food Scene

“The Clementine” Boho Home in Orlando’s Food Scene is a holiday home in Winter Park, 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, hot tub, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $898.

From$95/night

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Sleek, Spacious & Central – Your Ideal Getaway

Holiday Home, Winter Park

Sleek, Spacious & Central – Your Ideal Getaway is a holiday home in Winter Park, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Sleek, Spacious & Central – Your Ideal Getaway

Sleek, Spacious & Central – Your Ideal Getaway is a holiday home in Winter Park, 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 wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $923.

From$98/night

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Charming home @wp. Patio +Gazebo. close to highwys

Holiday Home, Winter Park

Charming home @wp. Patio +Gazebo. close to highwys is a holiday home in Winter Park, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Charming home @wp. Patio +Gazebo. close to highwys

Charming home @wp. Patio +Gazebo. close to highwys is a holiday home in Winter Park, 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 $1,065.

From$112/night

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10 Minutes from Universal - Relaxing Guest Suite

B & B, Winter Park

10 Minutes from Universal - Relaxing Guest Suite is a b & b in Winter Park, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring…

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About 10 Minutes from Universal - Relaxing Guest Suite

10 Minutes from Universal - Relaxing Guest Suite is a b & b in Winter Park, 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $734.

From$92/night

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Our Favorite Family-Friendly Vacation Rentals in Winter Park, FL

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

TINY unit in cottage in the middle of Downtown

Apartment, Winter Park

TINY unit in cottage in the middle of Downtown is a apartment in Winter Park, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

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About TINY unit in cottage in the middle of Downtown

TINY unit in cottage in the middle of Downtown is a apartment in Winter Park, 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, free parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $600.

From$60/night

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Tranquil Hideaway: 2-Bedroom Retreat near Mills/50

Apartment, Winter Park

Tranquil Hideaway: 2-Bedroom Retreat near Mills/50 is a apartment in Winter Park, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base…

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About Tranquil Hideaway: 2-Bedroom Retreat near Mills/50

Tranquil Hideaway: 2-Bedroom Retreat near Mills/50 is a apartment in Winter Park, 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $843.

From$90/night

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Downtown Cottage

Cottage, Winter Park

Downtown Cottage is a cottage in Winter Park, 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 Winter Park, 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 $935.

From$98/night

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8th Green Cottage \"A relaxing Oasis in the city\" Guesthouse

Holiday Home, Winter Park

8th Green Cottage \"A relaxing Oasis in the city\" Guesthouse is a holiday home in Winter Park, with pool access and a quieter setting. This stay gives travelers a comfortable base for…

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About 8th Green Cottage \"A relaxing Oasis in the city\" Guesthouse

8th Green Cottage \"A relaxing Oasis in the city\" Guesthouse is a holiday home in Winter Park, with pool 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, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,174.

From$121/night

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