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Short Term Rentals in Winter Park, FL

25 rentals

412 Harwood Street - Photo 1 of 1

2h ago

9.4

Excellent

Our team has verified this company

Verified

412 Harwood Street

412 E Harwood St, Orlando, FL 32803

Short term | Furnished | Air conditioning

1 bed

1 bath

$2,522

Apartment for rent

Top amenities
Furnished
Microwave
Oven
TV
Wi-Fi
480 N. Orange Ave. - Photo 1 of 1

18h 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

$2,070–$2,689

Apartment for rent

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

2d 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

$1,319–$3,632

Apartment for rent

Available Mar 9

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

Call

173 S Orange Ave - Photo 1 of 1

2d ago

Our team has verified this company

Verified

173 S Orange Ave, Orlando, FL 32801

Short term | In-unit laundry | Furnished

2 beds

1 bath

$3,366

Apartment for rent

Top amenities
Air Conditioning
Central Heat
Dishwasher
In-Unit Laundry
TV
Wi-Fi
1204 Country Ln - Photo 1 of 1

2d ago

Our team has verified this company

Verified

1204 Country Ln, Orlando, FL 32804

Short term | Furnished | Air conditioning

Studio

1 bath

$2,651

Apartment for rent

Top amenities
Assigned Parking
Central Heat
Furnished
TV
Wi-Fi
14 Bel Air St - Photo 1 of 1

5d+ ago

Short Term Eatonville house for rent in Eatonville

Charming Room in Orlando

14 Bel Air St, Eatonville, FL 32751

Short term | In-unit laundry | Furnished

1 bed

1 bath

$800

House for rent

Available Sep 27

Top amenities
In-Unit Laundry
Microwave
On-Site Laundry

Nearby rental good for eco-living

Nearby rental good for pet owners

$2,651

Spring Lake

417 N Tampa Ave - Photo 1 of 1

5d+ ago

Short Term Rock Lake house for rent in Orlando

Private room for rent in Orlando - Utilities & wifi included!

417 N Tampa Ave, Orlando, FL 32805

Short term | In-unit laundry | Furnished

1 bed

1 bath

$750

House for rent

Available Aug 18

Top amenities
Dishwasher
In-Unit Laundry
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

$20,000

House for rent

Available Feb 1

Top amenities
Assigned Parking
Furnished
Hardwood Floor
In-Unit Laundry
Residents Lounge
Swimming Pool
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1011 Terry Dr #5 - Photo 1 of 1

5d+ ago

Short Term house for rent in Altamonte Springs

1011 Terry Dr #5, Altamonte Springs, FL 32714

Short term | In-unit laundry | Furnished

1 bed

2 baths

$1,100

House for rent

Available Apr 2

Top amenities
Air Conditioning
Dishwasher
In-Unit Laundry
1011 Terry Dr #1 - Photo 1 of 1

5d+ ago

Short Term house for rent in Altamonte Springs

1011 Terry Dr #1, Altamonte Springs, FL 32714

Short term | In-unit laundry | Furnished

1 bed

2 baths

$1,100

House for rent

Available Jan 2

Top amenities
Air Conditioning
Furnished
In-Unit Laundry
Storage
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Find sweet deals near Winter Park

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

$1,100

Altamonte Springs

$1,100

Altamonte Springs

$800

Eatonville

$1,850

Maitland

1614 Ferris Ave #1 - Photo 1 of 1

5d+ ago

Short Term Lake Formosa house for rent in Orlando

Cozy 3BR Home in the Heart of Orlando | Move-In Ready 2/21 | $3,345/Month

1614 Ferris Ave #1, Orlando, FL 32803

Short term | In-unit laundry | Furnished

3 beds

1 bath

$3,445

House for rent

Available Feb 21

Top amenities
Furnished
In-Unit Laundry
Microwave
On-Site Laundry
511 San Juan Blvd #1 - Photo 1 of 1

5d+ ago

Short Term Monterey condo for rent in Orlando

Sunshine Modern 3BR Retreat - Sleeps 8, With Office & Laundry!

511 San Juan Blvd #1, Orlando, FL 32807

Short term | In-unit laundry | Furnished

3 beds

1 bath

$3,445

Condo for rent

Available Oct 18

Top amenities
Dishwasher
Furnished
In-Unit Laundry
On-Site Laundry
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

$3,000

House for rent

Available Apr 3

Top amenities
Business Center
Furnished
In-Unit Laundry
On-Site Laundry
412 E Harwood St #4 - Photo 1 of 1

5d+ ago

Short Term Lake Eola Heights condo for rent in Orlando

Modern and comfortable apartment

412 E Harwood St #4, Orlando, FL 32803

Short term | Furnished | Outdoor space

Studio

1 bath

$1,800

Condo for rent

Available Oct 24

412 E Harwood St #2 - Photo 1 of 1

5d+ ago

Short Term Lake Eola Heights condo for rent in Orlando

Downtown Apt Near Lake Eola

412 E Harwood St #2, Orlando, FL 32803

Short term | Furnished | Outdoor space

Studio

1 bath

$1,800

Condo for rent

Available Oct 24

1731 Grayson Dr #3 - Photo 1 of 1

5d+ ago

Short Term Union Park condo for rent in Union Park

Yin and Yang Tiny Guest House East Orlando UCF

1731 Grayson Dr #3, Union Park, FL 32825

Short term | In-unit laundry | Furnished

Studio

1 bath

$1,600

Condo for rent

Available Dec 2

Top amenities
In-Unit Laundry
On-Site Laundry
1731 Grayson Dr #2 - Photo 1 of 1

5d+ ago

Short Term Union Park condo for rent in Union Park

Stylish In-Law Suite Near UCF & Downtown

1731 Grayson Dr #2, Union Park, FL 32825

Short term | In-unit laundry | Furnished

1 bed

1 bath

$1,700

Condo for rent

Available Oct 24

Top amenities
In-Unit Laundry
Microwave
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

$2,800

House for rent

Available Oct 23

Top amenities
In-Unit Laundry
On-Site Laundry
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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
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

$2,300

House for rent

1000 Semoran Boulevard - Photo 1 of 1

5d+ ago

Short Term Golfside condo for rent in Winter Park

Short term

1 bed

1 bath

$1,299

Condo for rent

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

1240 Holly Springs Cir, Orlando, FL 32825

Short term | Outdoor space

3 beds

2 baths

$2,250

House 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
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
Fitness Center
Garage Parking
Hardwood Floor
In-Unit Laundry
Oven
Swimming Pool
Showing 1 - 25 of 25 results
Home > Apartments in Winter Park > Winter Park Short term rentals
Updated: March 9, 2026

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

🔑Available apartment rentals25
💰Best rent deal417 N Tampa Ave
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