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Short Term Rentals in Winter Park, FL

25 rentals available

410 N. Orange Ave - Photo 1 of 1

5h 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

$2,505–$3,685

Total Monthly Price. The price shown includes base rent and all known required monthly fees, based on information provided by the property.
480 N. Orange Ave. - Photo 1 of 1

5h 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

$2,210–$2,924

Total Monthly Price. The price shown includes base rent and all known required monthly fees, based on information provided by the property.
110 Zora Place - Photo 1 of 1

5h 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

$2,195–$2,671

Total Monthly Price. The price shown includes base rent and all known required monthly fees, based on information provided by the property.
2801 Biltmore Park Dr - Photo 1 of 1

5h 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

$1,964–$2,857

Total Monthly Price. The price shown includes base rent and all known required monthly fees, based on information provided by the property.
10200 Falcon Pine Blvd - Photo 1 of 1
Highly rated

5h 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

$2,277–$2,389

Total Monthly Price. The price shown includes base rent and all known required monthly fees, based on information provided by the property.
2710 Amherst Ave - Photo 1 of 1

11h ago

Our team has verified this company

Verified

2710 Amherst Ave, Orlando, FL 32804

Short term | Furnished | Air conditioning

1 bed

1 bath

$3,324

Price dropped $486Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.

Nearby rental good for eco-living

Nearby rental good for pet owners

3348 Basie Pl - Photo 1 of 1

1d ago

Short Term Lake Mann Estates house for rent in Orlando

3348 Basie Pl, Orlando, FL 32805

Short term | In-unit laundry | Air conditioning

4 beds

2 baths

$1,400

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
2007 Cornell Ave - Photo 1 of 1

3d ago

Our team has verified this company

Verified

2007 Cornell Ave, Fairview Shores, FL 32789

Short term | Furnished | Air conditioning

3 beds

2 baths

$4,916

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
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105 Durham Pl #105 - Photo 1 of 1

5d+ ago

Short Term Wekiva Club Estates condo for rent in Wekiwa Springs

$1,995 - 2 Bedroom 2 Bathroom Furnished Condo In Longwood With Great Amenities

105 Durham Pl #105, Wekiwa Springs, FL 32779

Short term | In-unit laundry | Air conditioning

2 beds

2 baths

$1,995

Price dropped $105Additional fees apply. The price shown reflects base rent. Based on information provided by the property, additional fees may apply, but no required monthly charges have been confirmed. See all fees for details.
432 1/2 Highland Ave - Photo 1 of 1

5d+ ago

Short Term Lake Eola Heights apartment for rent in Orlando

432 1/2 Highland Ave, Orlando, FL 32801

Short term | In-unit laundry | Garage parking

1 bed

1 bath

$1,400

Price dropped $100Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
2511 Metro Sevilla Dr - Photo 1 of 1

5d+ ago

Short Term Metro West condo for rent in Orlando

2511 Metro Sevilla Dr, Orlando, FL 32835

Short term | In-unit laundry | Swimming pool

3 beds

2 baths

$2,300

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.

Find sweet deals near Winter Park

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

$3,200

Lake Formosa

$1,975

Millenia

$1,800

Florida Center North

$1,475

Florida Center North

102 W King St - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

102 W King St, Orlando, FL 32804

Short term | Furnished | Air conditioning

2 beds

1 bath

$3,048

Price dropped $911Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
6844 Westborough Ln #12 - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

Rent Reduction: 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

$830

Additional fees apply. The price shown reflects base rent. Based on information provided by the property, additional fees may apply, but no required monthly charges have been confirmed. See all fees for details.
5152 Conroy Rd - Photo 1 of 1

5d+ ago

Short Term Florida Center North condo for rent in Orlando

5152 Conroy Rd, Orlando, FL 32811

Short term | In-unit laundry | Swimming pool

1 bed

1 bath

$1,200

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
1214 N Pine Hills Rd #2 - Photo 1 of 1

5d+ ago

Short Term condo for rent in Orlando

Casa Azul Studio - Charming Pine Hills Stay for Up to 5!

1214 N Pine Hills Rd #2, Orlando, FL 32808

Short term | In-unit laundry | Furnished

1 bed

1 bath

$2,100

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
1614 Ferris Ave #1 - Photo 1 of 1

5d+ ago

Short Term Lake Formosa townhouse for rent in Orlando

1614 Ferris ave

1614 Ferris Ave #1, Orlando, FL 32803

Short term | In-unit laundry | Furnished

3 beds

1 bath

$3,200

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
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

$700

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
3328 Coleman Pl #A - Photo 1 of 1

5d+ ago

Short Term Lake Mann Estates apartment for rent in Orlando

Coleman

3328 Coleman Pl #A, Orlando, FL 32805

Short term | Furnished | On-site laundry

1 bed

2 baths

$1,300

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
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

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
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

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
3611 Conroy Rd - Photo 1 of 1

5d+ ago

Short Term Millenia condo for rent in Orlando

3611 Conroy Rd, Orlando, FL 32839

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

3 beds

2 baths

$1,975

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
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

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
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

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
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

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
4680 Sussex Ter - Photo 1 of 1

5d+ ago

Short Term Florida Center North condo for rent in Orlando

Condominium - ORLANDO, FL

4680 Sussex Ter, Orlando, FL 32811

Short term | Air conditioning | Swimming pool

3 beds

2 baths

$1,800

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
Showing 1 - 25 of 25 results
Home > Apartments in Winter Park > Winter Park Short term rentals
Updated: October 15, 2026

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🔑Available apartment rentals25
💰Best rent deal417 N Tampa Ave
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