Vacation Rentals in Winter Springs, FL

PRICE PER NIGHT

ACCOMMODATION TYPES

Cozy 3/2 with Pool, Hot Tub, Patio + 5* Location!
10

Excellent

·
Winter Springs
·
3 br
·
Sleeps 11
·
Dishwasher · Hot Tub · Fitness Center ·
From
$209/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Dishwasher
Hot Tub
Fitness Center
Oven
Pool
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Workspace, Kitchen
1x1 Guest Suite 15 mins from UCF
10

Excellent

·
Winter Springs
·
1 br
·
Sleeps 2
·
Smoking Allowed · Pool · Air Conditioning ·
From
$41/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Smoking Allowed
Pool
Air Conditioning
Furnished
Wifi
Swimming Pool
Gorgeous Master Bedroom with Private Bath

No reviews

·
Winter Springs
·
1 br
·
Sleeps 2
·
Fitness Center · Workspace · Oven ·
From
$86/night
Check availability
Property
House · 1 Bed · 1 bath
Amenities
Fitness Center
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Swimming Pool
Other spaces
Workspace, Kitchen
3B/2Ba Home with Commmunity Pool. 30min from Universal Studios
9.4

Excellent

·
Highlands
·
3 br
·
Sleeps 8
·
Pool · In Unit Laundry · Kitchen ·
From
$230/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Pool
In Unit Laundry
Air Conditioning
Furnished
Wifi
Swimming Pool
Other spaces
Kitchen
Showing 1 - 4 of 4 results
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Cheerful & Peaceful 3 Bedroom 1 Bathroom Home

No reviews

·
Casselberry-Altamonte Springs
·
3 br
·
Sleeps 5
·
On Site Laundry · Kitchen · Furnished ·
From
$250/night
Check availability
Property
House · 3 Beds · 1 bath
Amenities
On Site Laundry
Furnished
Wifi
Wheelchair Accessible
Other spaces
Kitchen
Beautiful 2 bed townhome 35 minutes from Disney
10

Excellent

·
Casselberry
·
2 br
·
Sleeps 6
·
Furnished ·
From
$200/night
Check availability
Property
House · 2 Beds · 2 baths
Amenities
Furnished
The Orlando perfect villa
9.7

Excellent

·
Oviedo
·
2 br
·
Balcony · Dishwasher · Fitness Center ·
From
$266/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
Dishwasher
Fitness Center
Oven
Pool
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Balcony, Kitchen
House with Pool and fantastic patio
9

Excellent

·
Casselberry
·
5 br
·
Sleeps 10
·
Dishwasher · Oven · Pool ·
From
$332/night
Check availability
Property
House · 5 Beds · 2 baths
Amenities
Dishwasher
Oven
Pool
In Unit Laundry
Air Conditioning
Furnished
Wifi
Garage Parking
Other spaces
Kitchen
The Tiny Cottage in the Springs!

No reviews

·
Hickory Square
·
2 br
·
Sleeps 4
·
Outdoor Space · Ceiling Fan · Fireplace ·
From
$129/night
Check availability
Property
House · 2 Beds · 1 bath
Amenities
Ceiling Fan
Fireplace
Smoking Allowed
In Unit Laundry
Air Conditioning
Furnished
Wifi
Wheelchair Accessible
Other spaces
Kitchen
Winter Park charm. Close to Park Ave
9.7

Excellent

·
Winter Park
·
2 br
·
Sleeps 4
·
Workspace · In Unit Laundry · Air Conditioning ·
From
$150/night
Check availability
Property
House · 2 Beds · 1 bath
Amenities
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Workspace
Pondside Retreat with Koi in Charming Winter Park, FL

No reviews

·
Winter Park
·
4 br
·
Sleeps 6
·
Air Conditioning · Furnished · Wifi ·
From
$195/night
Check availability
Property
House · 4 Beds · 2 baths
Amenities
Air Conditioning
Furnished
Wifi
Mid Century Luxury, 1 block from Park Ave (#2)
10

Excellent

·
Winter Park
·
2 br
·
Sleeps 5
·
Outdoor Space · Dishwasher · Oven ·
From
$140/night
Check availability
Property
Apartment · 2 Beds · 1 bath
Amenities
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Kitchen

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NEW! Spacious Oviedo Townhouse Near UCF!

No reviews

·
Oviedo
·
3 br
·
Sleeps 6
·
Ceiling Fan · Dishwasher · Oven ·
From
$227/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
Ceiling Fan
Dishwasher
Oven
Pool
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
Affordable, convenient and pet-friendly family space
10

Excellent

·
Maitland
·
1 br
·
Sleeps 4
·
Balcony · Dishwasher · Fitness Center ·
From
$100/night
Check availability
Property
Condo · 1 Bed · 1 bath
Amenities
Dishwasher
Fitness Center
Oven
Pool
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Balcony, Kitchen
Paradise in a country setting . ( Note this an upstairs apartment 1100 sq ft )
10

Excellent

·
Lake Mary
·
2 br
·
Sleeps 4
·
Outdoor Space · Balcony · Private Pool ·
From
$159/night
Check availability
Property
Apartment · 2 Beds · 1 bath
Amenities
Private Pool
Oven
Pool
In Unit Laundry
Air Conditioning
Furnished
Wifi
Swimming Pool
Other spaces
Balcony, Kitchen
Beautiful Resort like Chalet - North Of Orlando In Longwood, Florida
10

Excellent

·
Longwood
·
4 br
·
Sleeps 8
·
Outdoor Space · Assigned Parking · Lake ·
From
$307/night
Check availability
Property
Apartment · 4 Beds · 3 baths
Amenities
Assigned Parking
Lake
Waterfront
Dishwasher
Fitness Center
Oven
In Unit Laundry
Air Conditioning
Other spaces
Workspace, Kitchen
Modern Elegance In The Heart Of Winter Park - 2 beds/2 baths

No reviews

·
Winter Park
·
2 br
·
Sleeps 4
·
Outdoor Space · Assigned Parking · Balcony ·
From
$156/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
Assigned Parking
Hardwood Floor
Dishwasher
Hot Tub
Fitness Center
Oven
Pool
In Unit Laundry
Other spaces
Balcony, Workspace, Kitchen
Winter Park Oasis

No reviews

·
Winter Park
·
2 br
·
Sleeps 8
·
Fireplace · Oven · Kitchen ·
From
$175/night
Check availability
Property
House · 2 Beds · 1 bath
Amenities
Fireplace
Oven
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
Cozy Private In-Law Room with Own Bath & Entrance

No reviews

·
Winter Park
·
1 br
·
Sleeps 2
·
Assigned Parking · Walk In Closets · Fitness Center ·
From
$63/night
Check availability
Property
House · 1 Bed · 1 bath
Amenities
Assigned Parking
Walk In Closets
Fitness Center
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Workspace
Lakefront Luxury Furnished Split Floor Plan First Floor Condo

No reviews

·
Casselberry
·
3 br
·
Sleeps 4
·
Lake · Waterfront · Dishwasher ·
From
$63/night
Check availability
Property
Condo · 3 Beds · 2 baths
Amenities
Lake
Waterfront
Dishwasher
Hot Tub
Fitness Center
Oven
Pool
In Unit Laundry
Other spaces
Kitchen
The Suite at Lake Mary
10

Excellent

·
Lake Mary
·
1 br
·
Sleeps 2
·
On Site Laundry · Waterfront · Walk In Closets ·
From
$55/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
On Site Laundry
Waterfront
Walk In Closets
Oven
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Workspace, Kitchen
Cozy 3/2, on ⭐ Beautiful Lake, 🧡 Hot Tub & 😎 Chill Patio

No reviews

·
Oviedo
·
3 br
·
Sleeps 10
·
Outdoor Space · Lake · Waterfront ·
From
$350/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Lake
Waterfront
Dishwasher
Hot Tub
Fitness Center
Oven
In Unit Laundry
Air Conditioning
Other spaces
Workspace, Kitchen
Three Blocks to Park Ave, 2 Blocks to WP Village!!!
9

Excellent

·
Winter Park
·
2 br
·
Sleeps 4
·
Outdoor Space · Ev Charging · Dishwasher ·
From
$125/night
Check availability
Property
Apartment · 2 Beds · 1 bath
Amenities
Ev Charging
Dishwasher
Oven
Pool
In Unit Laundry
Air Conditioning
Furnished
Wifi
Other spaces
Workspace, Kitchen
Ideal Orlando Getaway -Entire Home

No reviews

·
Orlando
·
4 br
·
Sleeps 5
·
Fireplace · Private Pool · Dishwasher ·
From
$323/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Fireplace
Private Pool
Dishwasher
Hot Tub
Oven
Pool
In Unit Laundry
Air Conditioning
Other spaces
Kitchen
Home > Florida Vacation Rentals > Winter Springs Vacation Rentals
Updated: March 27, 2023

Learn about vacation rentals in

Winter Springs

Explore 5 vacation rentals near Winter Springs, Florida. Whether you’re a tourist or on a staycation, there’s plenty of things to do and restaurants to try around the city. If you’re looking to take a trip to Winter Springs, you can see photos of Winter Springs vacation rentals, view amenities and features, browse by specific property types, and more. Use our interactive map to find Winter Springs vacation rentals in specific areas. Whether you’re looking for a Winter Springs staycation, weekend getaway, or a long vacation, we’ve got you covered. Use the date filters at the top to select your travel dates and view availability. The lowest vacation rental price in Winter Springs is $41 per night and the highest price is $230 per night.
4 of the vacation rentals near Winter Springs are houses. The average bathroom count for a vacation house near Winter Springs is 2. The average price for vacation houses near Winter Springs is $175 per night. There are 2 vacation homes under this price. The most common amenities for vacation rentals near Winter Springs are: furnished, swimming pool, and air conditioning. 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.

1 bed rentals

2 available

2 bed rentals

1 available

3 bed rentals

2 available

Getting around Winter Springs

Walking

3/10
Fewer daily needs are within walking distance (unless you’re up for a challenge).

Car

9/10
Commuting is easy with multiple accessible routes and plenty of parking.

Transit

1/10
FYI, there are little to no public transit options within walking distance.

Points of interest in Winter Springs

Groceries

3/10
No grocery stores within walking distance

Shopping

2/10
Few or no shops within walking distance

Cafes

3/10
Few or no cafés within walking distance

Restaurants

3/10
Few or no restaurants within walking distance

Parks

6/10
Moderate amount of park space nearby

Nightlife

2/10
Few or no bars within walking distance

Vacation Rentals in Winter Springs, FL FAQ

How many vacation rentals in Winter Springs are available?

There are currently 5 vacation rentals in Winter Springs available. Our vacation rentals in Winter Springs include nightly rentals, weekend rentals, weekly rentals, and monthly rentals.

Are there any pet friendly vacation rentals in Winter Springs?

Yes, right now there are 1 pet friendly vacation rentals in Winter Springs. A pet friendly vacation rental in Winter Springs means a rental home that is dog friendly or cat friendly. Some pet friendly homes may accommodate other types of pets, as well. Contact the listing agent for any pet related inquiries.

Are there any vacation rentals in Winter Springs with a pool?

Yes there are vacation rentals with a pool available in Winter Springs, FL. View more detailed vacation spots on Vacations by Zumper.

Are there any vacation rentals in Winter Springs with internet access?

As of March 27, 2023, there are vacation rentals with internet access available in Winter Springs, Florida. Check out more enjoyable destinations on Vacations by Zumper.

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