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Short Term Rentals in Winter Park, FL

25 rentals

2801 Biltmore Park Dr - Photo 1 of 1
Rent special

4h 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
Rent special

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

10200 Falcon Pine Blvd - Photo 1 of 1
Highly rated
Rent special

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

1307 Formosa Avenue - Photo 1 of 1

2d ago

Our team has verified this company

Verified

1307 Formosa Avenue, Orlando, FL 32789

Short term | In-unit laundry | Furnished

2 beds

1 bath

$4,980

$3,364

Price drop

Apartment for rent

Top amenities
Air Conditioning
Central Heat
In-Unit Laundry
Oven
TV
Wi-Fi
1882 Lake Street - Photo 1 of 1

2d ago

Our team has verified this company

Verified

1882 Lake Street, Oviedo, FL 32765

Short term | Furnished | Air conditioning

3 beds

1 bath

$2,217

$1,985

Price drop

Apartment for rent

Top amenities
Air Conditioning
Business Center
Furnished
On-Site Laundry
TV
Wi-Fi
1932 Lake Street - Photo 1 of 1

2d ago

Our team has verified this company

Verified

1932 Lake Street, Winter Springs, FL 32765

Short term | Furnished | Air conditioning

3 beds

2 baths

$4,310

$3,558

Price drop

Apartment for rent

Top amenities
Air Conditioning
Furnished
On-Site Laundry
TV
Wi-Fi

Nearby rental good for eco-living

$1,700

Orlando

Nearby rental good for pet owners

1229 Berwyn Road - Photo 1 of 1

2d ago

Our team has verified this company

Verified

1229 Berwyn Road, Orlando, FL 32806

Short term | In-unit laundry | Furnished

Studio

1 bath

$2,754

$2,376

Price drop

Apartment for rent

Top amenities
Air Conditioning
In-Unit Laundry
Oven
Storage
TV
Wi-Fi
1330 Catalpa Lane - Photo 1 of 1

2d ago

Our team has verified this company

Verified

1330 Catalpa Lane, Orlando, FL 32806

Short term | In-unit laundry | Furnished

6 beds

4 baths

$6,922

$4,247

Price drop

Apartment for rent

Top amenities
Air Conditioning
Dishwasher
Furnished
In-Unit Laundry
Microwave
TV
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4501 Loring Place - Photo 1 of 1

2d ago

Our team has verified this company

Verified

4501 Loring Place, Orlando, FL 32812

Short term | Furnished | Air conditioning

2 beds

1 bath

$2,959

Apartment for rent

Top amenities
Air Conditioning
Central Heat
Storage
Swimming Pool
TV
Wi-Fi
1711 Asher Lane - Photo 1 of 1

2d ago

Our team has verified this company

Verified

1711 Asher Lane, Orlando, FL 32803

Short term | In-unit laundry | Furnished

3 beds

1 bath

$4,539

$4,403

Price drop

Apartment for rent

Top amenities
Business Center
Dishwasher
In-Unit Laundry
Microwave
Oven
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.

$650

Holden-Parramore

$1,200

Maitland

$1,780–$3,162

Goldenrod

$2,079–$2,213

Florida Center

4544 Gilpin Way - Photo 1 of 1

2d ago

Our team has verified this company

Verified

4544 Gilpin Way, Conway, FL 32812

Short term | Furnished | Air conditioning

3 beds

2 baths

$5,151

Apartment for rent

Top amenities
Air Conditioning
Central Heat
Furnished
Microwave
TV
Wi-Fi
1610 Goldenrod Road - Photo 1 of 1

2d ago

Our team has verified this company

Verified

1610 Goldenrod Road, Azalea Park, FL 32807

Short term | In-unit laundry | Furnished

3 beds

1 bath

$4,915

$4,766

Price drop

Apartment for rent

Top amenities
Air Conditioning
In-Unit Laundry
Microwave
Oven
TV
Wi-Fi
2301 Carlton Drive - Photo 1 of 1

2d ago

Our team has verified this company

Verified

2301 Carlton Drive, Orlando, FL 32806

Short term | Furnished | Air conditioning

1 bed

1 bath

$2,446

Apartment for rent

Top amenities
Business Center
Furnished
Microwave
Swimming Pool
TV
Wi-Fi
Liv at Winter Park Apartment Homes - Photo 1 of 1
Rent special

2d ago

8.9

Very good

Liv at Winter Park Apartment Homes

4755 Goldenrod Road, Goldenrod, FL 32792

Short term | In-unit laundry | Swimming pool

Studio–3 beds

1–2 baths

$1,233–$3,162

Price drop

Apartment for rent

Available Dec 7

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

Call

3328 Coleman Place #A - Photo 1 of 1

3d ago

Short Term Lake Mann Estates apartment for rent in Orlando

Coleman

3328 Coleman Place #A, Orlando, FL 32805

Short term | Furnished | On-site laundry

1 bed

2 baths

$1,500

Apartment for rent

Available Nov 3

Top amenities
Dishwasher
Furnished
On-Site Laundry
Marvera Casselberry - Photo 1 of 1
Rent special

4d ago

9.6

Excellent

Our team has verified this company

Verified

Marvera Casselberry

3851 Grandpine Way, Casselberry, FL 32707

Short term | In-unit laundry | Garage parking

1–3 beds

1–2 baths

$1,461–$2,551

Price drop

Apartment for rent

Top amenities
Business Center
In-Unit Laundry
Roof Deck
Swimming Pool

Call

981 Hamlet Court #NA - Photo 1 of 1

5d+ ago

Short Term house for rent in Maitland

$1,200 - Cozy Room for Rent In Maitland With Great Amenities

981 Hamlet Court #NA, Maitland, FL 32751

Short term | In-unit laundry | Air conditioning

1 bed

1 bath

$1,200

House for rent

Available Dec 1

Top amenities
In-Unit Laundry
6844 Westborough Lane #12 - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

$900 - 1 Bedroom with Two Roommates, Shared Bathroom House In Orlando With Great Amenities

6844 Westborough Lane #12, Orlando, FL 32818

Short term | Air conditioning | On-site laundry

1 bed

1 bath

$900

Apartment for rent

Available Oct 19

Top amenities
Air Conditioning
Dishwasher
On-Site Laundry
Advertisement
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 Dec 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

$2,300

House for rent

745 Easy Ave #4 - Photo 1 of 1

5d+ ago

Short Term Holden-Parramore apartment for rent in Orlando

$650 - 1 Bedroom In Orlando With Great Amenities

745 Easy Ave #4, Orlando, FL 32805

Short term | Air conditioning | On-site laundry

1 bed

1 bath

$650

Apartment for rent

Available Sep 30

Top amenities
On-Site Laundry
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

$1,299

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
Swimming Pool
8431 Chamberlain Place - Photo 1 of 1

5d+ ago

Short Term townhouse for rent in Oviedo

Townhouse - OVIEDO, FL

8431 Chamberlain Place, 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
Storage
Showing 1 - 25 of 25 results
Home > Apartments in Winter Park > Winter Park Short term rentals
Updated: December 7, 2025

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

🔑Available apartment rentals25
💰Best rent deal745 Easy Ave #4
✨Popular amenities, ,

For more in depth rent prices, check out our Winter Park, FL rent data, which covers average and median rents in Winter Park, FL.

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