Vacation rentals in Winter Park, FL

Best vacation rentals and Airbnb offers in Winter Park, FL

10 ★ 26 reviews

3bdrm Fruit Tree Home near downtown Orlando

Holiday Home, Winter Park

3bdrm Fruit Tree Home near downtown Orlando is a holiday home in Winter Park, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area,…

Read more

About 3bdrm Fruit Tree Home near downtown Orlando

3bdrm Fruit Tree Home near downtown Orlando 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 wifi, pet friendly, pets friendly, parking, and paid parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,331.

From$138/night

Show›

10 ★ 1 reviews

Lake Marion Apt w/ Canoe in Altamonte Springs!

Cottage, Winter Park

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

Read more

About Lake Marion Apt w/ Canoe in Altamonte Springs!

Lake Marion Apt w/ Canoe in Altamonte Springs! is a cottage in Winter Park, 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, free wifi, kitchen, with kitchen, and washer.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,016.

From$120/night

Show›

8 ★ 2 reviews

Landing Furnished Apartments - Maitland

Apartment, Winter Park

Landing Furnished Apartments - Maitland is a apartment in Winter Park, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Landing Furnished Apartments - Maitland

Landing Furnished Apartments - Maitland is a apartment 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, Oct 3 - Sat, Oct 10 · 7 nights · total from $906.

From$92/night

Show›

7.8 ★ 7 reviews

3697 Orlando Vacational Apartment 1st floor near Universal Studios

Apartment, Winter Park

3697 Orlando Vacational Apartment 1st floor near Universal Studios is a apartment in Winter Park, with pool access and parking. This stay gives travelers a comfortable base for exploring…

Read more

About 3697 Orlando Vacational Apartment 1st floor near Universal Studios

3697 Orlando Vacational Apartment 1st floor near Universal Studios is a apartment in Winter Park, 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, gym, parking, and free parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,160.

From$111/night

Show›

Family-friendly vacation rentals in Winter Park, FL

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

10 ★ 2 reviews

Sandford Vacation Rental Near Airport & Lake!

Cottage, Winter Park

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

Read more

About Sandford Vacation Rental Near Airport & Lake!

Sandford Vacation Rental Near Airport & Lake! 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, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,265.

From$122/night

Show›

10 ★ 1 reviews

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

Cottage, Winter Park

Apopka Single-story Home w/ Private Lanai + Pool! is a cottage in Winter Park, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

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

Apopka Single-story Home w/ Private Lanai + Pool! is a cottage 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, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,198.

From$218/night

Show›

Lakefront Sanford Home w/ Community Pool

Cottage, Winter Park

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

Read more

About Lakefront Sanford Home w/ Community Pool

Lakefront Sanford Home w/ Community Pool is a cottage 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, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,115.

From$116/night

Show›

Luxury House - Sleeps 8 Golf Disney Family Fun

Holiday Home, Winter Park

Luxury House - Sleeps 8 Golf Disney Family Fun is a holiday home in Winter Park, with pool access, parking, and room for a group. This stay gives travelers a comfortable base for exploring…

Read more

About Luxury House - Sleeps 8 Golf Disney Family Fun

Luxury House - Sleeps 8 Golf Disney Family Fun is a holiday home in Winter Park, with pool access, parking, 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: pool, free wifi, parking, and free parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,823.

From$187/night

Show›

Pet-friendly vacation rentals in Winter Park, FL

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

3brdrm home near Downtown Orlando and Winterpark

Holiday Home, Winter Park

3brdrm home near Downtown Orlando and Winterpark is a holiday home in Winter Park, with pet-friendly space, parking, and room for a group. This stay gives travelers a comfortable base for…

Read more

About 3brdrm home near Downtown Orlando and Winterpark

3brdrm home near Downtown Orlando and Winterpark is a holiday home in Winter Park, with pet-friendly space, parking, 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 wifi, pet friendly, pets friendly, parking, and paid parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,435.

From$151/night

Show›

Home away from home in Orlando!

Holiday Home, Winter Park

Home away from home in Orlando! 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…

Read more

About Home away from home in Orlando!

Home away from home in Orlando! 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 wifi, pet friendly, pets friendly, parking, and paid parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,330.

From$134/night

Show›

Orlando Vacational Apartment 3919

Apartment, Winter Park

Orlando Vacational Apartment 3919 is a apartment in Winter Park, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

Read more

About Orlando Vacational Apartment 3919

Orlando Vacational Apartment 3919 is a apartment in Winter Park, 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, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,068.

From$118/night

Show›

3919 Orlando Vacational Apartment

Apartment, Winter Park

3919 Orlando Vacational Apartment 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…

Read more

About 3919 Orlando Vacational Apartment

3919 Orlando Vacational Apartment 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, kitchen, with kitchen, and gym.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,016.

From$110/night

Show›

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.

3648 Orlando Vacational Apartment

Apartment, Winter Park

3648 Orlando Vacational Apartment is a apartment in Winter Park, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

Read more

About 3648 Orlando Vacational Apartment

3648 Orlando Vacational Apartment is a apartment in Winter Park, 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, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,158.

From$128/night

Show›

3697 Orlando Vacational Apartment

Apartment, Winter Park

3697 Orlando Vacational Apartment is a apartment in Winter Park, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

Read more

About 3697 Orlando Vacational Apartment

3697 Orlando Vacational Apartment is a apartment in Winter Park, 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, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,100.

From$121/night

Show›

Vacational Apartment at Orlando 3608

Apartment, Winter Park

Vacational Apartment at Orlando 3608 is a apartment in Winter Park, with pet-friendly space, pool access, and parking. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Vacational Apartment at Orlando 3608

Vacational Apartment at Orlando 3608 is a apartment in Winter Park, with pet-friendly space, 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: pool, pet friendly, pets friendly, parking, and free parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $940.

From$111/night

Show›

Luxury Villas Collection - Near Parks & Shopping

Apartment, Winter Park

Luxury Villas Collection - Near Parks & Shopping is a apartment in Winter Park, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Luxury Villas Collection - Near Parks & Shopping

Luxury Villas Collection - Near Parks & Shopping is a apartment in Winter Park, 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 ac.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,471.

From$113/night

Show›

Vacation rentals with parking in Winter Park, FL

Find vacation rentals that make arriving by car easier.

Pet-Friendly Apopka Home: 30 Mi to WDW!

Holiday Home, Winter Park

Pet-Friendly Apopka Home: 30 Mi to WDW! 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…

Read more

About Pet-Friendly Apopka Home: 30 Mi to WDW!

Pet-Friendly Apopka Home: 30 Mi to WDW! 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, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,295.

From$112/night

Show›

Sandford Vacation Rental Near Airport & Lake!

Holiday Home, Winter Park

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

Read more

About Sandford Vacation Rental Near Airport & Lake!

Sandford Vacation Rental Near Airport & Lake! is a holiday home 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, free wifi, parking, paid parking, and heating.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,222.

From$91/night

Show›

Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly

Apartment, Winter Park

Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly is a apartment in Winter Park, with pet-friendly space, pool access, and parking. This stay gives travelers a comfortable base…

Read more

About Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly

Solara Apartments Spacious 2BR Apartment Sleeps 6 Pet-Friendly is a apartment in Winter Park, with pet-friendly space, 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, pet friendly, pets friendly, and parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,409.

From$157/night

Show›

Virelli Apartments Upscale King Suite in the Heart of Orlando w Pool

Apartment, Winter Park

Virelli Apartments Upscale King Suite in the Heart of Orlando w Pool is a apartment in Winter Park, with pet-friendly space, pool access, and parking. This stay gives travelers a…

Read more

About Virelli Apartments Upscale King Suite in the Heart of Orlando w Pool

Virelli Apartments Upscale King Suite in the Heart of Orlando w Pool is a apartment in Winter Park, with pet-friendly space, 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, pet friendly, pets friendly, and parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,813.

From$195/night

Show›

Vacation rentals with a kitchen in Winter Park, FL

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

Pet-friendly Apopka Home: 30 Mi to Wdw!

Cottage, Winter Park

Pet-friendly Apopka Home: 30 Mi to Wdw! is a cottage in Winter Park, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Pet-friendly Apopka Home: 30 Mi to Wdw!

Pet-friendly Apopka Home: 30 Mi to Wdw! is a cottage 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 cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $1,341.

From$144/night

Show›

Spacious Central Florida Home: Family Friendly!

Cottage, Winter Park

Spacious Central Florida Home: Family Friendly! is a cottage in Winter Park, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Spacious Central Florida Home: Family Friendly!

Spacious Central Florida Home: Family Friendly! is a cottage in Winter Park, 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 washer.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,109.

From$234/night

Show›

Screened Lanai & Yard! Family Getaway in Apopka

Cottage, Winter Park

Screened Lanai & Yard! Family Getaway in Apopka is a cottage in Winter Park, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring…

Read more

About Screened Lanai & Yard! Family Getaway in Apopka

Screened Lanai & Yard! Family Getaway in Apopka is a cottage 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, free wifi, kitchen, with kitchen, and parking.

Sat, Oct 3 - Sat, Oct 10 · 7 nights · total from $2,528.

From$273/night

Show›

Private Outdoor Oasis w/ Pool: Home in Longwood!

Cottage, Winter Park

Private Outdoor Oasis w/ Pool: Home in Longwood! is a cottage in Winter Park, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Private Outdoor Oasis w/ Pool: Home in Longwood!

Private Outdoor Oasis w/ Pool: Home in Longwood! is a cottage 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, Oct 3 - Sat, Oct 10 · 7 nights · total from $3,439.

From$395/night

Show›