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Short Term Rentals in Winter Park, FL

25 rentals available

410 N. Orange Ave - Photo 1 of 1

11h ago

9.2

Excellent

Our team has verified this company

Verified

410 N. Orange Ave

410 N Orange Ave, Orlando, FL 32801

Short term | Furnished

Studio–2 beds

1–2 baths

$2,210–$3,360

Apartment for rent

Liv at Winter Park Apartment Homes - Photo 1 of 1
Rent special

1d ago

9.2

Excellent

Liv at Winter Park Apartment Homes

4755 N Goldenrod Rd, Goldenrod, FL 32817

Short term | In-unit laundry | Swimming pool

Studio–3 beds

1–2 baths

$1,204–$4,840

Apartment for rent

Available Sep 1

Top amenities
Ceiling Fan
Fitness Center
Hardwood Floor
In-Unit Laundry
On-Site Management

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480 N. Orange Ave. - Photo 1 of 1

1d ago

9.2

Excellent

Our team has verified this company

Verified

480 N. Orange Ave.

480 N Orange Ave, Orlando, FL 32801

Short term | Furnished

1–2 beds

1 bath

$2,165–$2,825

Apartment for rent

2801 Biltmore Park Dr - Photo 1 of 1

1d ago

9.2

Excellent

Our team has verified this company

Verified

2801 Biltmore Park Dr

2801 Biltmore Park Dr, Orlando, FL 32835

Short term | Furnished

1–2 beds

1–2 baths

$1,919–$2,782

Apartment for rent

110 Zora Place - Photo 1 of 1

1d ago

9.2

Excellent

Our team has verified this company

Verified

110 Zora Place

110 Zora Pl, Eatonville, FL 32810

Short term | Furnished

1–2 beds

1–2 baths

$2,150–$2,596

Apartment for rent

102 W King St - Photo 1 of 1

2d ago

Our team has verified this company

Verified

102 W King St, Orlando, FL 32804

Short term | Furnished | Air conditioning

2 beds

1 bath

$3,944

Apartment for rent

Top amenities
Air Conditioning
Assigned Parking
Central Heat
Garage Parking
TV
Wi-Fi

Nearby rental good for eco-living

Nearby rental good for pet owners

2710 Amherst Ave - Photo 1 of 1

3d ago

Our team has verified this company

Verified

2710 Amherst Ave, Orlando, FL 32804

Short term | Furnished | Air conditioning

1 bed

1 bath

$3,879

Apartment for rent

Top amenities
Assigned Parking
Central Heat
Furnished
Microwave
TV
Wi-Fi
4886 Matteo Trl - Photo 1 of 1

4d ago

Short Term Millenia townhouse for rent in Orlando

Live by Millenia

4886 Matteo Trl, Orlando, FL 32839

Short term | In-unit laundry | Furnished

1 bed

1 bath

$900

House for rent

Available Aug 24

Top amenities
Dishwasher
Furnished
In-Unit Laundry
Microwave
Storage
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10200 Falcon Pine Blvd - Photo 1 of 1
Highly rated

5d+ ago

9.2

Excellent

Our team has verified this company

Verified

10200 Falcon Pine Blvd

10200 Falcon Pine Blvd, Orlando, FL 32829

Short term | Furnished

1–2 beds

1–2 baths

$1,947–$2,094

Apartment for rent

6844 Westborough Ln #4 - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

Nice and Area - Rent $900- 1 Bedroom 1 Shared Bathroom Unit In Orlando With Great Amenities

6844 Westborough Ln #4, Orlando, FL 32818

Short term | Air conditioning | On-site laundry

1 bed

1 bath

$900

Apartment for rent

Available Jun 20

Top amenities
Air Conditioning
Dishwasher
On-Site Laundry
On-Site Management
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Find sweet deals near Winter Park

These rentals are 10%-30% cheaper than the local average price for similar rentals.

$850

Fern Park

$1,850

Metro West

$1,100

Engelwood Park

$1,250

Florida Center North

6844 Westborough Ln #12 - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

Safe Orlando One-Room Near Hiawassee, Clarcona & Ocoee—Utilities Included, Affordable Move-In!

6844 Westborough Ln #12, Orlando, FL 32818

Short term | Air conditioning | On-site laundry

1 bed

1 bath

$930

Apartment for rent

Available Aug 1

Top amenities
Air Conditioning
Hardwood Floor
On-Site Laundry
On-Site Management
7524 Marietta St - Photo 1 of 1

5d+ ago

Short Term house for rent in Orlando

The Sunflower Bungalow | Cozy, Bright & Perfect for Relaxation

7524 Marietta St, Orlando, FL 32807

Short term | In-unit laundry | Furnished

4 beds

2 baths

$3,600

House for rent

Available Apr 3

Top amenities
Furnished
In-Unit Laundry
On-Site Laundry
7508 Carolyn Ave - Photo 1 of 1

5d+ ago

Short Term house for rent in Orlando

Chic 3-Bedroom Getaway | Prime Location in the Heart of Orlando

7508 Carolyn Ave, Orlando, FL 32807

Short term | In-unit laundry | Furnished

3 beds

1 bath

$3,600

House for rent

Available Oct 23

Top amenities
In-Unit Laundry
On-Site Laundry
3225 Pickfair St - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

3225 Pickfair St, Orlando, FL 32803

Short term | Furnished | Air conditioning

3 beds

2 baths

$5,979

$5,365

Price drop

Apartment for rent

Top amenities
Microwave
Oven
Storage
Swimming Pool
TV
Wi-Fi
1500 Silverstone Ave #A - Photo 1 of 1

5d+ ago

Short Term Dover Shores West apartment for rent in Orlando

$875 - 1 Bed/1 Bath Room for Rent In Charming, Centrally Located, Orlando Home

1500 Silverstone Ave #A, Orlando, FL 32806

Short term | Air conditioning | On-site laundry

1 bed

1 bath

$875

Apartment for rent

Available Dec 27

Top amenities
Air Conditioning
Assigned Parking
On-Site Laundry
8328 Cristobal Cir - Photo 1 of 1

5d+ ago

Short Term house for rent in Orlando

Large Room for Rent in Orlando - with private entrance

8328 Cristobal Cir, Orlando, FL 32825

Short term | In-unit laundry | Furnished

1 bed

1 bath

$850

House for rent

Available Aug 16

Top amenities
In-Unit Laundry
Microwave
6221 Yorktown Dr - Photo 1 of 1

5d+ ago

Short Term Engelwood Park townhouse for rent in Orlando

Peaceful Private Bedroom in a Gated Lakefront Community Ideal for Traveling Healthcare Professionals

6221 Yorktown Dr, Orlando, FL 32807

Short term | In-unit laundry | Furnished

1 bed

1 bath

$1,100

House for rent

Available Aug 31

Top amenities
Air Conditioning
Dishwasher
Furnished
In-Unit Laundry
Swimming Pool
3616 Wd Judge Dr - Photo 1 of 1

5d+ ago

Short Term house for rent in Orlando

Cozy Room for Rent in Orlando | Available 08/05 | $800/mo

3616 Wd Judge Dr, Orlando, FL 32808

Short term | In-unit laundry | Furnished

1 bed

1 bath

$800

House for rent

Available Aug 5

Top amenities
Cable
In-Unit Laundry
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6913 Cocos Dr - Photo 1 of 1

5d+ ago

Short Term Azalea Park house for rent in Azalea Park

Fully Furnished Room For Rent in Prime Orlando Location

6913 Cocos Dr, Azalea Park, FL 32807

Short term | In-unit laundry | Furnished

1 bed

1 bath

$750

House for rent

Available Aug 31

Top amenities
In-Unit Laundry
On-Site Laundry
2007 Cornell Ave - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

2007 Cornell Ave, Fairview Shores, FL 32789

Short term | Furnished | Air conditioning

3 beds

2 baths

$4,578

Apartment for rent

Top amenities
Air Conditioning
Assigned Parking
Furnished
Microwave
TV
Wi-Fi
415 Lochmond Dr - Photo 1 of 1

5d+ ago

Short Term house for rent in Fern Park

Traveling Medical Professional/ Students

415 Lochmond Dr, Fern Park, FL 32730

Short term | In-unit laundry | Furnished

1 bed

1 bath

$850

House for rent

Top amenities
Dishwasher
Hardwood Floor
In-Unit Laundry
Microwave
On-Site Laundry
6466 Cava Alta Dr - Photo 1 of 1

5d+ ago

Short Term Metro West apartment for rent in Orlando

6466 Cava Alta Dr, Orlando, FL 32835

Short term | In-unit laundry | Assigned parking

3 beds

2 baths

$1,850

Apartment for rent

Top amenities
Assigned Parking
Dishwasher
In-Unit Laundry
Swimming Pool
5325 Curry Ford Rd - Photo 1 of 1

5d+ ago

Short Term Monterey condo for rent in Orlando

5325 Curry Ford Rd, Orlando, FL 32812

Short term | On-site laundry | Swimming pool

1 bed

1 bath

$1,199

Condo for rent

Top amenities
Microwave
On-Site Laundry
5838 Sage Dr - Photo 1 of 1

5d+ ago

Short Term Azalea Park apartment for rent in Azalea Park

Duplex - ORLANDO, FL

5838 Sage Dr, Azalea Park, FL 32807

Short term | In-unit laundry | Furnished

1 bed

1 bath

$1,450

Apartment for rent

Top amenities
Furnished
In-Unit Laundry
Tile Floor
S Kirkman Rd #1203 - Photo 1 of 1

5d+ ago

Short Term Kirkman South condo for rent in Orlando

S Kirkman Rd #1203, Orlando, FL 32811

Short term | In-unit laundry | Furnished

2 beds

2 baths

$3,000

Condo for rent

Available Apr 14

Top amenities
Furnished
In-Unit Laundry
Swimming Pool
Showing 1 - 25 of 25 results
Home > Apartments in Winter Park > Winter Park Short term rentals
Updated: August 28, 2026

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Looking for apartments in Winter Park, FL near you?

🔑Available apartment rentals25
💰Best rent deal6913 Cocos Dr
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