Vacation Rentals in Winter Park, FL

PRICE PER NIGHT

ACCOMMODATION TYPES

Perfect Winter Getaway ~ Turnkey ~ Naples, FL
10

Excellent

·
Winter Park
·
2 br
·
Sleeps 4
·
Balcony · Outdoor Space · Assigned Parking ·
From
$135/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Assigned Parking
Fitness Center
Oven
Dishwasher
Pool
In Unit Laundry
Wifi
Air Conditioning
Other spaces
Balcony, Kitchen
Naples at Winterpark!

No reviews

·
Winter Park
·
2 br
·
Sleeps 4
·
Carpet · Fitness Center · Beach ·
From
$130/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Carpet
Fitness Center
Beach
Oven
Dishwasher
Pool
In Unit Laundry
Wifi
Other spaces
Kitchen
Beautiful, updated 2/2 condo close to shops, restaurants and beaches
2

Poor

·
Winter Park
·
2 br
·
Sleeps 5
·
Beach · Oven · Dishwasher ·
From
$275/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Beach
Oven
Dishwasher
Pool
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Kitchen
Golf club Villa located in beautiful Naples , 5 min from Beaches and Downtown
10

Excellent

·
Winter Park
·
2 br
·
Sleeps 6
·
Walk In Closets · Pool · In Unit Laundry ·
From
$109/night
Check availability
Property
House · 2 Beds · 2 baths
Amenities
Walk In Closets
Pool
In Unit Laundry
Wifi
Air Conditioning
Furnished
Swimming Pool
Other spaces
Kitchen
Beautiful lake view huge pool 4 miles to Gulf beaches
10

Excellent

·
Winter Park
·
2 br
·
Sleeps 4
·
Lake · Waterfront · High Ceilings ·
From
$70/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Lake
Waterfront
High Ceilings
On Site Laundry
Assigned Parking
Fitness Center
Oven
Dishwasher
Other spaces
Workspace, Kitchen
Huge Heated Pool, 10 min to the Beach & Downtown 5th Ave
10

Excellent

·
Winter Park
·
2 br
·
Sleeps 4
·
Workspace · On Site Laundry · Assigned Parking ·
From
$135/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
On Site Laundry
Assigned Parking
Walk In Closets
Fitness Center
Beach
Oven
Dishwasher
Pool
Other spaces
Workspace, Kitchen
Luxurious Fully Equipped Condo, Minutes From Beach!
9.3

Excellent

·
Winter Park
·
2 br
·
Ceiling Fan · High Ceilings · Walk In Closets ·
From
$179/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Ceiling Fan
High Ceilings
Walk In Closets
Fitness Center
Oven
Dishwasher
Pool
In Unit Laundry
Other spaces
Kitchen
Luxurious holiday condo with oversize pool
9.8

Excellent

·
Winter Park
·
2 br
·
Sleeps 4
·
Outdoor Space · Oven · Dishwasher ·
From
$133/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Oven
Dishwasher
Pool
In Unit Laundry
Wifi
Air Conditioning
Furnished
Swimming Pool
Other spaces
Kitchen

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Walk In With Tooth Brush In Your Pocket In This Beautiful Naples Apartment

No reviews

·
Winter Park
·
2 br
·
Sleeps 6
·
Balcony · On Site Laundry · Oven ·
From
$115/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
On Site Laundry
Oven
Dishwasher
Pool
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Balcony, Kitchen
Beautiful 2 Br. Single_family (366626) by Houzlet

No reviews

·
Winter Park
·
2 br
·
Sleeps 5
·
Smoking Allowed · Hardwood Floor · Beach ·
From
$128/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
Smoking Allowed
Hardwood Floor
Beach
Dishwasher
In Unit Laundry
Air Conditioning
Furnished
Garage Parking
Other spaces
Kitchen
2021 Availability Winter Park Close to Pool1st Floor
10

Excellent

·
Winter Park
·
2 br
·
Sleeps 4
·
Outdoor Space · Walk In Closets · Oven ·
From
$85/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Walk In Closets
Oven
Dishwasher
Pool
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Kitchen
Winterpark community in Naples

No reviews

·
Winter Park
·
2 br
·
Sleeps 4
·
Wifi · Air Conditioning · Furnished ·
From
$185/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Wifi
Air Conditioning
Furnished
Welcome to the beach hut. Your home away from home !

No reviews

·
Winter Park
·
2 br
·
Sleeps 4
·
Beach · Oven · Dishwasher ·
From
$105/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Beach
Oven
Dishwasher
Pool
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Kitchen
Home away from home

No reviews

·
Winter Park
·
2 br
·
Sleeps 4
·
Pool · Wifi · Air Conditioning ·
From
$105/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Pool
Wifi
Air Conditioning
Furnished
Swimming Pool
Showing 1 - 14 of 14 results
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SUNSET LAKE VILLA
9.8

Excellent

·
Naples
·
3 br
·
Sleeps 8
·
Hot Tub · Lake · Waterfront ·
From
$399/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Hot Tub
Lake
Waterfront
Oven
Dishwasher
In Unit Laundry
Wifi
Air Conditioning
Other spaces
Kitchen
Beautiful remodeled house , short drive to Olde Naples and beaches
10

Excellent

·
Naples
·
3 br
·
Sleeps 6
·
Private Pool · Hot Tub · Ev Charging ·
From
$304/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Private Pool
Hot Tub
Ev Charging
Oven
Dishwasher
Pool
In Unit Laundry
Wifi
Other spaces
Kitchen
Magnificent views, fabulous location and lovely accommodations on King's Lake
7.3

Very good

·
Kings Lake
·
3 br
·
Sleeps 4
·
Fireplace · Private Pool · Hot Tub ·
From
$150/night
Check availability
Property
Condo · 3 Beds · 3 baths
Amenities
Fireplace
Private Pool
Hot Tub
Lake
Waterfront
Fitness Center
Oven
Dishwasher
Other spaces
Workspace, Kitchen
BEAUTIFUL East Naples, 2 Bedroom with Office in sought after KINGS LAKE!

No reviews

·
Kings Lake
·
2 br
·
Lake · Waterfront · Walk In Closets ·
From
$120/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Lake
Waterfront
Walk In Closets
Beach
Oven
Dishwasher
Pool
In Unit Laundry
Other spaces
Kitchen
2 bed/2bath condo 3 miles from downtown Naples

No reviews

·
Kings Lake
·
2 br
·
Sleeps 5
·
Balcony · Outdoor Space · Oven ·
From
$250/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Oven
Dishwasher
Pool
In Unit Laundry
Wifi
Air Conditioning
Furnished
Swimming Pool
Other spaces
Balcony, Kitchen
Grnd Floor Modern Reno Villa In Glades Golf Gem 5 Mins Drive To 5th Ave, Beach
10

Excellent

·
Naples
·
2 br
·
Sleeps 6
·
Workspace · Walk In Closets · Fitness Center ·
From
$90/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
Walk In Closets
Fitness Center
Beach
Oven
Dishwasher
Pool
In Unit Laundry
Wifi
Other spaces
Workspace, Kitchen
AVAILABLE FEB/MARCH 2023 NEW LISTING!

No reviews

·
Kings Lake
·
3 br
·
Outdoor Space · Fitness Center · Oven ·
From
$177/night
Check availability
Property
Condo · 3 Beds · 2 baths
Amenities
Fitness Center
Oven
Dishwasher
Pool
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Kitchen
Lovely Cozy 2-Bed/2bath Condo near Downtown Naples

No reviews

·
Kings Lake
·
2 br
·
Sleeps 5
·
Pool · In Unit Laundry · Kitchen ·
From
$179/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Pool
In Unit Laundry
Wifi
Air Conditioning
Furnished
Swimming Pool
Other spaces
Kitchen

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Be the first to hear about new listings matching your search.

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By clicking submit, I accept Zumper's Terms and Conditions, Privacy Policy, and Community Values.
Beautiful 2 Bedroom Condo with Pool & Tennis Court

No reviews

·
Kings Lake
·
2 br
·
Balcony · Walk In Closets · Oven ·
From
$170/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Walk In Closets
Oven
Dishwasher
Pool
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Balcony, Kitchen
Kings Lake Blvd 1804-204, Naples Florida Vacation Rental

No reviews

·
Kings Lake
·
2 br
·
Sleeps 4
·
Ceiling Fan · Hardwood Floor · High Ceilings ·
From
$183/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Ceiling Fan
Hardwood Floor
High Ceilings
Assigned Parking
Oven
Dishwasher
Pool
In Unit Laundry
Other spaces
Balcony, Workspace, Kitchen
Home > Florida Vacation Rentals > Bonita Springs-Naples Vacation Rentals > Winter Park Vacation Rentals
Updated: March 27, 2023

Learn about vacation rentals in

Winter Park

Browse 17 vacation rentals near Winter Park in Bonita Springs-Naples, Florida. If you’re interested in touring around Bonita Springs-Naples, and you want to stay in the Winter Park neighborhood, use our interactive map to find your next rental. You can see pictures of Winter Park vacation rentals, view amenities and features, browse by property types, and more. Whether you’re looking for a Winter Park staycation, weekend getaway, or a long vacation, we’ve got you covered. The lowest vacation rental price in Winter Park is $70 per night and goes up to as much as $275 per night. Use the date filters at the top to select your travel dates and view availability.
16 of the vacation rentals near Winter Park are apartments or condos. The average bathroom count for this property type is 2. The median price for these vacation units is $130 per night. There are currently 9 vacation units under this price. 1 of the vacation rentals near Winter Park are houses. The average bathroom count for a vacation house near Winter Park is 2. The average price for vacation houses near Winter Park is $109 per night. There are 0 vacation homes under this price. The most common amenities for vacation rentals near Winter Park are: furnished, air conditioning, and swimming pool. To find vacation properties that might be a good option for large groups or families, use our filters for bedroom count, bathroom count and more.

2 bed rentals

17 available

Vacation Rentals in Winter Park, FL FAQ

How many vacation rentals in Winter Park are available?

There are currently 17 vacation rentals in Winter Park available. Choose from nightly rentals, monthly rentals, weekend rentals, and weekly rentals to find your perfect stay in Winter Park.

What types of vacation rental properties are available in Winter Park, FL?

As of March 27, 2023, there are 1 vacation houses for rent in Winter Park and 16 vacation condos and apartments for rent in Winter Park, FL. Check each listing to view photos and get more details about pricing and available amenities.

Are there any vacation rentals in Winter Park, FL with more than 1 bedroom?

Yes, there are 17 Winter Park vacation rentals with more than 1 bedroom. To view a more detailed amenity list, click on the available properties on Vacations by Zumper.

How many pet friendly Winter Park vacation rentals are available?

As of March 27, 2023, there are no pet friendly vacation rentals in Winter Park, Florida available. For more information about pet policies regarding dogs and cats, view the property listing or contact the leasing agent.

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