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Short Term Rentals in Winter Park, FL

25 rentals

2801 Biltmore Park Dr - Photo 1 of 1

8h 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 | Package service

1–2 beds

1–2 baths

$1,712–$2,845

Apartment for rent

5256 International Dr. - Photo 1 of 1

1d ago

9.2

Excellent

Our team has verified this company

Verified

5256 International Dr.

5256 International Dr, Orlando, FL 32819

Short term | Furnished | Package service

1–2 beds

1–2 baths

$2,079–$2,528

Apartment for rent

Liv at Winter Park Apartment Homes - Photo 1 of 1

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

$1,257–$3,558

Price drop

Apartment for rent

Available Sep 7

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

Call

10200 Falcon Pine Blvd - Photo 1 of 1
Highly rated

1d 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 | Package service

1–2 beds

1–2 baths

$2,021–$2,311

Apartment for rent

Polos - Photo 1 of 1
Rent special

1d ago

8.7

Very good

Polos

5583 Gatlin Ave, Orlando, FL 32812

Short term | In-unit laundry | Air conditioning

1–3 beds

1–2 baths

$1,295–$1,995

Price drop

Apartment for rent

Top amenities
Air Conditioning
Ceiling Fan
Dishwasher
Garage Parking
High Ceilings
In-Unit Laundry
Atrium Dr - Photo 1 of 1

2d ago

Our team has verified this company

Verified

Atrium Dr, Orlando, FL 32822

Short term | Furnished | Air conditioning

2 beds

2 baths

$3,540

$2,470

Price drop

Apartment for rent

Top amenities
Dishwasher
Fitness Center
On-Site Laundry
Oven
Swimming Pool
Wi-Fi

Nearby rental good for eco-living

Nearby rental good for pet owners

Nearby rental good for social life

$3,130

College Park

Homeland St - Photo 1 of 1

2d ago

Our team has verified this company

Verified

Homeland St, Orlando, FL 32806

Short term | Furnished | Air conditioning

1 bed

1 bath

$3,340

Apartment for rent

Top amenities
Furnished
Microwave
Oven
Storage
Wi-Fi
Loring Pl - Photo 1 of 1

2d ago

Our team has verified this company

Verified

Loring Pl, Orlando, FL 32812

Short term | Furnished | Air conditioning

2 beds

1 bath

$4,670

Apartment for rent

Top amenities
Air Conditioning
Furnished
Storage
Wi-Fi
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Berwyn Rd - Photo 1 of 1

2d ago

Our team has verified this company

Verified

Berwyn Rd, Orlando, FL 32806

Short term | Furnished | Air conditioning

Studio

1 bath

$3,080

Apartment for rent

Top amenities
Air Conditioning
Microwave
On-Site Laundry
Oven
Storage
Wi-Fi
Lake Gem Cir - Photo 1 of 1

2d ago

Our team has verified this company

Verified

Lake Gem Cir, Orlando, FL 32806

Short term | Furnished | Air conditioning

4 beds

2 baths

$15,000

Apartment for rent

Top amenities
Air Conditioning
EV Charging
Garage Parking
Microwave
On-Site Laundry
Wi-Fi
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Find sweet deals near Winter Park

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

$1,700

Orlando

$1,773–$3,558

Goldenrod

$1,995

South Semoran

Amherst Ave - Photo 1 of 1

2d ago

Our team has verified this company

Verified

Amherst Ave, Orlando, FL 32804

Short term | Furnished | Air conditioning

1 bed

1 bath

$3,130

Apartment for rent

Top amenities
Air Conditioning
Furnished
Microwave
On-Site Laundry
Oven
Wi-Fi
553 Notre Dame Dr #NA - Photo 1 of 1

5d+ ago

Short Term Weathersfield house for rent in Altamonte Springs

House for rent

Available Aug 22

Top amenities
Ceiling Fan
Fireplace
Furnished
Hardwood Floor
In-Unit Laundry
On-Site Management
4143D Lake Lawne Ave #43D - Photo 1 of 1

5d+ ago

Short Term Mercy Drive condo for rent in Orlando

Park Place of Orlando

4143D Lake Lawne Ave #43D, Orlando, FL 32808

Short term | In-unit laundry | Furnished

1 bed

1 bath

$978

Condo for rent

Top amenities
Furnished
In-Unit Laundry
Microwave
On-Site Laundry
4143B Lake Lawne Ave #43B - Photo 1 of 1

5d+ ago

Short Term Mercy Drive condo for rent in Orlando

Park Place of Orlando

4143B Lake Lawne Ave #43B, Orlando, FL 32808

Short term | In-unit laundry | Furnished

1 bed

1 bath

$1,086

Condo for rent

Top amenities
In-Unit Laundry
On-Site Laundry
3328 Coleman Pl #B - Photo 1 of 1

5d+ ago

Short Term Lake Mann Estates condo for rent in Orlando

Beautiful lake Mann states

3328 Coleman Pl #B, Orlando, FL 32805

Short term | In-unit laundry | Furnished

4 beds

2 baths

$2,500

Condo for rent

Available Sep 1

Top amenities
Air Conditioning
Dishwasher
Fitness Center
Garage Parking
In-Unit Laundry
Microwave
281 Shell Pt E #NA - Photo 1 of 1

5d+ ago

Short Term house for rent in Maitland

Stunning Luxury Lakefront Estate 4 Bed | 4.5 Bath | 4,100 Sq Ft | 100' Waterfront

281 Shell Pt E #NA, Maitland, FL 32751

Short term | In-unit laundry | Furnished

4 beds

4 baths

$25,000

House for rent

Available Sep 1

Top amenities
Assigned Parking
Furnished
Hardwood Floor
In-Unit Laundry
Residents Lounge
Swimming Pool
518 Oranole Rd - Photo 1 of 1

5d+ ago

Short Term house for rent in Maitland

518 Oranole Rd, Maitland, FL 32751

Short term | Outdoor space

3 beds

1 bath

$2,450

House for rent

1000 S Semoran Blvd - Photo 1 of 1

5d+ ago

Short Term Golfside condo for rent in Winter Park

Short term

1 bed

1 bath

$1,450

Condo for rent

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1250 S Pennsylvania Ave #8 - Photo 1 of 1

5d+ ago

Short Term Virginia Heights apartment for rent in Winter Park

$5750 - 3 brm townhome -walkable downtown WP / chain of lake access, private community park.

1250 S Pennsylvania Ave #8, Winter Park, FL 32789

Short term | In-unit laundry | Air conditioning

3 beds

2 baths

$5,550

Apartment for rent

Available Jul 14

Top amenities
Assigned Parking
Dishwasher
Garage Parking
Hardwood Floor
In-Unit Laundry
Storage
1325 Lake Shadow Cir - Photo 1 of 1

5d+ ago

Short Term condo for rent in Maitland

1325 Lake Shadow Cir, Maitland, FL 32751

Short term | Air conditioning | Carpet

2 beds

2 baths

$1,850

Condo for rent

1240 Holly Springs Cir - Photo 1 of 1

5d+ ago

Short Term house for rent in Orlando

Short term | Outdoor space

3 beds

2 baths

$2,250

House for rent

101 S Eola Dr - Photo 1 of 1

5d+ ago

Short Term South Eola condo for rent in Orlando

Short term | In-unit laundry | On-site laundry

1 bed

1 bath

$1,650

Condo for rent

Top amenities
In-Unit Laundry
On-Site Laundry
3319 S Kirkman Rd - Photo 1 of 1

5d+ ago

Short Term Kirkman North condo for rent in Orlando

3319 S Kirkman Rd, Orlando, FL 32811

Short term | Swimming pool | Fitness center

1 bed

1 bath

$1,450

Condo for rent

952 Courtyard Ln - Photo 1 of 1

5d+ ago

Short Term condo for rent in Orlando

952 Courtyard Ln, Orlando, FL 32825

Short term | In-unit laundry | On-site laundry

2 beds

2 baths

$1,700

Condo for rent

Top amenities
Carpet
Fitness Center
In-Unit Laundry
On-Site Laundry
8431 Chamberlain Pl - Photo 1 of 1

5d+ ago

Short Term townhouse for rent in Oviedo

Townhouse - OVIEDO, FL

8431 Chamberlain Pl, Oviedo, FL 32765

Short term | In-unit laundry | Air conditioning

3 beds

2 baths

$2,400

House for rent

Top amenities
Garage Parking
Hardwood Floor
In-Unit Laundry
Oven
Storage
Swimming Pool
Showing 1 - 25 of 25 results
Home > Apartments in Winter Park > Winter Park Short term rentals
Updated: September 7, 2025

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Looking for short term apartments in Winter Park, FL near you?

🔑Available apartment rentals25
💰Best rent deal553 Notre Dame Dr #NA
✨Popular amenities, ,

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