Winter Park, FL vacation rentals

Vacation rentals in Winter Park, FL

2565 available vacation rental offers

2 1
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2565 Rentals and Airbnb in Winter Park, FL

Bungalow Central To Downtown Orl And Winter Park🦩 - Winter Park, FL
9.8Excellent 217 reviews
Winter Park, FL
2 1
$213/nighttotal: $639 (3 )

Bungalow Central To Downtown Orl And Winter Park🦩

studio - Orlando
Accommodation for 2 people with an excellent rating of 98% based on 217 reviews. You will be in Orlando.
Facilities and services: a garden, a freeze and a coffee place. Take advantage of the Free Parking with this accommodation in Orlando!
Oasis Garden Cottage -Cozy, Chic, Near Everything! - Winter Park, FL
9.9Excellent 270 reviews
Winter Park, FL
2 1
$221/nighttotal: $663 (3 )

Oasis Garden Cottage -Cozy, Chic, Near Everything!

house - Fairview Shores
House rental listing for up to 5 guests with an excellent rating of 99% based on 270 reviews. Your accommodation will be based in Fairview Shores.
Services and facilities include an iron, a garden and a fridge. Take advantage of the Free Parking with this accommodation in Fairview Shores!
"The Sweet Suite" - Private & Quiet, Near 408/417 - Winter Park, FL
9.9Excellent 115 reviews
Winter Park, FL
2 1
$152/nighttotal: $456 (3 )

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

apartment - Azalea Park
Apartment rental listing for up to 2 guests with an excellent rating of 99% based on 115 reviews. You will stay in Azalea Park.
Services and facilities: a freeze, a washing machine and a garden.
Unique Place! East End Market! Baldwin/winter Park - Winter Park, FL
9.9Excellent 222 reviews
Winter Park, FL
2 1
$235/nighttotal: $705 (3 )

Unique Place! East End Market! Baldwin/winter Park

- Winter Park
Downtown Lake Eola Historic House 1 Or 2 Bed - Winter Park, FL
9.5Excellent 663 reviews
Winter Park, FL
2 2
$178/nighttotal: $534 (3 )

Downtown Lake Eola Historic House 1 Or 2 Bed

- Orlando
Downtown (Ivanhoe Village) Loft Apartment - Winter Park, FL
9.7Excellent 1052 reviews
Winter Park, FL
2 1
$153/nighttotal: $459 (3 )

Downtown (Ivanhoe Village) Loft Apartment

studio - Orlando
Apartment rental for 2 people with an excellent rating of 97% based on 1052 reviews. This accommodation is located in Orlando.
Facilities and services include air conditioning, a kitchen and free parking.
On Campus Without Being On Campus Rollins College! - Winter Park, FL
9.7Excellent 54 reviews
Winter Park, FL
2 2
$482/nighttotal: $1446 (3 )

On Campus Without Being On Campus Rollins College!

apartment - Winter Park
Apartment rental listing for 5 guests with an excellent rating of 97% based on 54 reviews. Your accommodation will be located in Winter Park.
Facilities and services include a fridge, air conditioning and a washing machine. Pets are allowed in this apartment.
A Rare Jewel In The Heart Of Winter Park. Can Walk - Winter Park, FL
9.8Excellent 97 reviews
Winter Park, FL
2 3
$678/nighttotal: $2034 (3 )

A Rare Jewel In The Heart Of Winter Park. Can Walk

apartment - Winter Park
Apartment listing for 6 people with an excellent rating of 98% based on 97 reviews. You will be based in Winter Park.
Facilities and services include a washing machine, an iron and a barbecue. This apartment in Winter Park also has a garden!
Guest Suite! Key West In Altamonte Springs! - Winter Park, FL
9.9Excellent 374 reviews
Winter Park, FL
2 1
$161/nighttotal: $483 (3 )

Guest Suite! Key West In Altamonte Springs!

- Altamonte Springs
St. Augustine Suite - Winter Park, FL
9.9Excellent 302 reviews
Winter Park, FL
2 1
$154/nighttotal: $462 (3 )

St. Augustine Suite

- Altamonte Springs
Greatest Location In Winter Park! (2) - Winter Park, FL
10Excellent 29 reviews
Winter Park, FL
2 2
$482/nighttotal: $1446 (3 )

Greatest Location In Winter Park! (2)

apartment - Winter Park
Apartment to rent for 5 people with an excellent rating of 100% based on 29 reviews. You will be in Winter Park.
Services and facilities include a garden, a washing machine and free parking. Pets are welcome in this apartment.
17'coachman Clipper Tiny Trailer - Winter Park, FL
9.8Excellent 43 reviews
Winter Park, FL
2 1
$152/nighttotal: $456 (3 )

17'coachman Clipper Tiny Trailer

house - Orlando
Vacation house rental with an excellent rating of 98% based on 43 reviews. You will be based in Orlando.
Services and facilities: air conditioning, a fridge and a terrace. This house in Orlando has a swimming pool!

Other accommodation types in Winter Park, FL

Best Winter Park, FL vacation rentals with a pool

Among the 2565 accommodations in Winter Park, FL, here are the 8 best rentals with a pool

Lakefront Studio Apartment (Private Entrance) - Winter Park, FL
10Excellent 417 reviews
Winter Park, FL
2 1
$318/nighttotal: $954 (3 )

Lakefront Studio Apartment (Private Entrance)

studio - Orlando
Book this vacation rental for 2 guests with an excellent rating of 100% based on 417 reviews. Your accommodation will be based in Orlando.
Facilities and services include a fridge, air conditioning and an iron. This apartment also has a garden!
Lakefront Artist's Studio- Isolate In Luxury! - Winter Park, FL
9.7Excellent 229 reviews
Winter Park, FL
2 1
$307/nighttotal: $921 (3 )

Lakefront Artist's Studio- Isolate In Luxury!

apartment - Orlando
Book this vacation rental for 2 people with an excellent rating of 97% based on 229 reviews. You will be based in Orlando.
Services and facilities: an iron, free parking and a swimming pool. Take advantage of the jacuzzi in this apartment.
Casa Bella - Winter Park, FL
10Excellent 257 reviews
Winter Park, FL
2 5
$676/nighttotal: $2028 (3 )

Casa Bella

house - Maitland
House with an excellent rating of 100% based on 257 reviews. You will be based in Maitland.
Facilities and services include a cleaning service, an iron and a barbecue. This house in Maitland has a swimming pool!
Lakefront Artist's Loft - Isolate In Luxury! - Winter Park, FL
9.8Excellent 145 reviews
Winter Park, FL
2 1
$289/nighttotal: $867 (3 )

Lakefront Artist's Loft - Isolate In Luxury!

house - Orlando
Vacation house for 2 people with an excellent rating of 98% based on 145 reviews. This accommodation is located in Orlando.
Services and facilities include a garden, air conditioning and a washing machine. This house in Orlando also has a terrace!
Luxe Guesthouse W/pool/hot Tub-near Rollins/ucf - Winter Park, FL
10Excellent 97 reviews
Winter Park, FL
2 2
$370/nighttotal: $1110 (3 )

Luxe Guesthouse W/pool/hot Tub-near Rollins/ucf

house - Goldenrod
Vacation house rental for up to 6 people with an excellent rating of 100% based on 97 reviews. You will stay in Goldenrod.
Services and facilities: a coffee place, air conditioning and an iron. You can also relax in the jacuzzi!
\"The Mouse\" + The \"Comforts Of Home\" - Winter Park, FL
9.6Excellent 71 reviews
Winter Park, FL
2 2
$266/nighttotal: $798 (3 )

\"The Mouse\" + The \"Comforts Of Home\"

apartment - Orlando
Accommodation from $141 for up to 6 guests with an excellent rating of 96% based on 71 reviews. Your accommodation will be based in Orlando.
Facilities and services: air conditioning, a washing machine and a dish washer. Take advantage of the Free Parking with this accommodation in Orlando!
Luxury High Rise - Winter Park, FL
8.8Very good 20 reviews
Winter Park, FL
2 1
$637/nighttotal: $1911 (3 )

Luxury High Rise

apartment - Orlando
Apartment rental listing for up to 2 people with an excellent rating of 88% based on 20 reviews. This accommodation is based in Orlando.
Facilities and services: a garden, a kitchen and a fridge. Take advantage of the air conditioning in this apartment in Orlando.
Salt Pool, Cozy House Near Downtown And International Airport - Winter Park, FL
9.6Excellent 63 reviews
Winter Park, FL
2 3
$401/nighttotal: $1203 (3 )

Salt Pool, Cozy House Near Downtown And International Airport

apartment - Orlando
Apartment at 252 dollars for up to 6 guests with an excellent rating of 96% based on 63 reviews. You will be in Orlando.
Services and facilities: a kitchen, a swimming pool and free parking. This apartment also has air conditioning!

Best family friendly Winter Park, FL vacation rentals

Among the 2565 accommodations in Winter Park, FL, here are the 8 best family friendly rentals

Apartment In Central Area With Lake View. - Winter Park, FL
8.0Very good 37 reviews
Winter Park, FL
2 1
$231/nighttotal: $693 (3 )

Apartment In Central Area With Lake View.

apartment - Orlando
Apartment rental listing with a good rating of 80% based on 37 reviews. Your accommodation will be based in Orlando.
Facilities and services include free parking, a cleaning service and a fridge. This apartment in Orlando is ideal for families.
Amazing Location- Walk To Everything - Winter Park, FL
9.8Excellent 56 reviews
Winter Park, FL
2 2
$743/nighttotal: $2229 (3 )

Amazing Location- Walk To Everything

apartment - Winter Park
Vacation rental with an excellent rating of 98% based on 56 reviews. You will be located in Winter Park.
Services and facilities include a spa, an iron and a dish washer. This is a family-friendly apartment!
Private Studio In The Heart Of Downtown Orlando. Modern Zen Vibe - Winter Park, FL
10Excellent 50 reviews
Winter Park, FL
2 2
$584/nighttotal: $1752 (3 )

Private Studio In The Heart Of Downtown Orlando. Modern Zen Vibe

apartment - Orlando
Book this vacation rental with an excellent rating of 100% based on 50 reviews. This accommodation is located in Orlando.
Services and facilities: a child space, free parking and a coffee place. Take advantage of the air conditioning in this apartment!
Winter Park Oasis - Winter Park, FL
9.8Excellent 50 reviews
Winter Park, FL
2 2
$298/nighttotal: $894 (3 )

Winter Park Oasis

house - Winter Park
House rental with an excellent rating of 98% based on 50 reviews. Your accommodation will be based in Winter Park.
Facilities and services include a child space, an iron and a kitchen. Pets are allowed in this house.
2 Bedr Condo Close To Winter Park, Ucf, Full Sail - Winter Park, FL
9.4Excellent 103 reviews
Winter Park, FL
2 2
$199/nighttotal: $597 (3 )

2 Bedr Condo Close To Winter Park, Ucf, Full Sail

studio - Goldenrod
Vacation rental listing for 4 guests with an excellent rating of 94% based on 103 reviews. Your accommodation will be located in Goldenrod.
Facilities and services: a dish washer, a fridge and a garden.
Drayton Place Staycation - Private Lk/pk Front Ste - Winter Park, FL
9.3Excellent 40 reviews
Winter Park, FL
2 2
$359/nighttotal: $1077 (3 )

Drayton Place Staycation - Private Lk/pk Front Ste

house - Orlando
Accommodation for up to 4 people with an excellent rating of 93% based on 40 reviews. This accommodation is located in Orlando.
Facilities and services: a barbecue, a child space and a freeze. This house is ideal for families.
The Grand Palm Tropical Paradise 🍀🦩 🌴Self Check In⭐️ - Winter Park, FL
10Excellent 60 reviews
Winter Park, FL
2 3
$406/nighttotal: $1218 (3 )

The Grand Palm Tropical Paradise 🍀🦩 🌴Self Check In⭐️

house - Goldenrod
Book this vacation rental for 8 people with an excellent rating of 100% based on 60 reviews. You will be based in Goldenrod.
Services and facilities: a terrace, a swimming pool and a barbecue. This house is very convenient for families.
Sunflower Victorian Beauty - Winter Park, FL
9.9Excellent 51 reviews
Winter Park, FL
2 3
$570/nighttotal: $1710 (3 )

Sunflower Victorian Beauty

house - Altamonte Springs
House rental for 8 people with an excellent rating of 99% based on 51 reviews. This accommodation is located in Altamonte Springs.
Facilities and services include a washing machine, a kitchen and air conditioning. This is a pet-friendly house!

Frequently asked questions for the vacation rentals in Winter Park, FL

Destinations nearby

Best pet friendly Winter Park, FL vacation rentals

Among the 2565 accommodations in Winter Park, FL, here are the 8 best pet friendly rentals

Great Location | Downtown | Lake - Winter Park, FL
8.8Very good 189 reviews
Winter Park, FL
2 1
$263/nighttotal: $789 (3 )

Great Location | Downtown | Lake

apartment - Orlando
Vacation rental with an excellent rating of 88% based on 189 reviews. You will be located in Orlando.
Services and facilities include a washing machine, a fridge and a freeze. Take advantage of the air conditioning in this apartment!
Downtown Orlando 2 Bedroom Home W/ Full Kitchen & Parking Spots - Winter Park, FL
9.2Excellent 109 reviews
Winter Park, FL
2 2
$269/nighttotal: $807 (3 )

Downtown Orlando 2 Bedroom Home W/ Full Kitchen & Parking Spots

apartment - Orlando
Vacation rental for up to 5 people with an excellent rating of 92% based on 109 reviews. Your accommodation will be located in Orlando.
Facilities and services: a garden, a room service and a coffee place. This apartment in Orlando is ideal for families.
"Orlando Magic At 3697 Vacation Apartment: Your Getaway!" - Winter Park, FL
8.3Very good 135 reviews
Winter Park, FL
2 2
$227/nighttotal: $681 (3 )

"Orlando Magic At 3697 Vacation Apartment: Your Getaway!"

apartment - Orlando
Apartment rental listing for 5 people with a good rating of 83% based on 135 reviews. This accommodation is located in Orlando.
Services and facilities: a barbecue, a spa and a dish washer. This apartment in Orlando also has a terrace!
Lovely Winter Park Home Close To Hospitals ! - Winter Park, FL
9.7Excellent 53 reviews
Winter Park, FL
2 1
$243/nighttotal: $729 (3 )

Lovely Winter Park Home Close To Hospitals !

apartment - Winter Park
Vacation rental listing for up to 3 guests with an excellent rating of 97% based on 53 reviews. This accommodation is based in Winter Park.
Facilities and services: an iron, free parking and a kitchen. Take advantage of the garden in this apartment!
Charming Getaway W/ Pool, Near Downtown & Disney - Winter Park, FL
9.9Excellent 92 reviews
Winter Park, FL
2 1
$201/nighttotal: $603 (3 )

Charming Getaway W/ Pool, Near Downtown & Disney

- Orlando
Brand New Beautiful Tiny Cottage /1 Bed/1 Bath - Winter Park, FL
9.6Excellent 37 reviews
Winter Park, FL
2 1
$190/nighttotal: $570 (3 )

Brand New Beautiful Tiny Cottage /1 Bed/1 Bath

house - Longwood
Vacation rental for up to 2 people with an excellent rating of 96% based on 37 reviews. You will be located in Longwood.
Facilities and services: a fitness center, a washing machine and free parking. This house also has air conditioning!
Greatest Location! Condo With Private Yard! - Winter Park, FL
Winter Park, FL
2 2
$714/nighttotal: $2142 (3 )

Greatest Location! Condo With Private Yard!

apartment - Winter Park
Apartment rental from $507 per night. Your accommodation will be based in Winter Park.
Services and facilities: a garden, a kitchen and free parking.
Total Serenity #2, 2 Bdrm, 2 Bath - Winter Park, FL
9.0Excellent 6 reviews
Winter Park, FL
2 2
$468/nighttotal: $1404 (3 )

Total Serenity #2, 2 Bdrm, 2 Bath

apartment - Winter Park
Apartment rental from 239 dollars for up to 8 people with an excellent rating of 90% based on 6 reviews. You will be located in Winter Park.
Facilities and services: air conditioning and a washing machine. Pets are welcome in this apartment.