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Short Term Rentals in Highlands, FL

25 rentals

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

4h 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

$1,333–$3,849

Price drop

Apartment for rent

Available May 6

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

Call

662 Callahan St - Photo 1 of 1

18h ago

Our team has verified this company

Verified

662 Callahan St, Winter Park, FL 32789

Short term | In-unit laundry | Furnished

2 beds

1 bath

$2,824

Apartment for rent

Top amenities
Air Conditioning
Furnished
In-Unit Laundry
Microwave
TV
Wi-Fi
9096 Dubois Blvd - Photo 1 of 1

18h ago

Our team has verified this company

Verified

9096 Dubois Blvd, Orlando, FL 32825

Short term | In-unit laundry | Furnished

3 beds

1 bath

$4,307

Apartment for rent

Top amenities
Air Conditioning
Assigned Parking
Fireplace
In-Unit Laundry
Oven
TV
1211 Country Ln - Photo 1 of 1

18h ago

Our team has verified this company

Verified

1211 Country Ln, Orlando, FL 32804

Short term | In-unit laundry | Furnished

4 beds

2 baths

$4,243

Apartment for rent

Top amenities
Air Conditioning
Assigned Parking
Furnished
In-Unit Laundry
TV
Wi-Fi
1731 Grayson Drive - Photo 1 of 1

18h ago

8.8

Very good

Our team has verified this company

Verified

1731 Grayson Drive

1731 Grayson Dr, Union Park, FL 32825

Short term | Furnished | Balcony

1 bed

1 bath

$2,888

Apartment for rent

Top amenities
Assigned Parking
Furnished
TV
Wi-Fi
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

$995

House for rent

Available Apr 2

Top amenities
Air Conditioning
Dishwasher
In-Unit Laundry

Nearby rental good for eco-living

$4,439

Lake Mary

Nearby rental good for pet owners

480 N. Orange Ave. - Photo 1 of 1
Rent special

5d+ 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

$2,200–$2,825

Apartment for rent

2014 Newman St #RV - Photo 1 of 1

5d+ ago

Short Term Lake Como condo for rent in Orlando

Newman RV: Your Ultimate Mobile Oasis

2014 Newman St #RV, Orlando, FL 32803

Short term | Furnished | Outdoor space

Studio

1 bath

$1,200

Condo for rent

Available Oct 22

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2014 Newman St #3 - Photo 1 of 1

5d+ ago

Short Term Lake Como condo for rent in Orlando

Elegant and Charming Luxury Farmhouse

2014 Newman St #3, Orlando, FL 32803

Short term | In-unit laundry | Furnished

Studio

1 bath

$2,100

Condo for rent

Available Apr 15

Top amenities
In-Unit Laundry
On-Site Laundry
2014 Newman St #2 - Photo 1 of 1

5d+ ago

Short Term Lake Como condo for rent in Orlando

Chic 1-Bedroom Private Apartment in Downtown!

2014 Newman St #2, Orlando, FL 32803

Short term | In-unit laundry | Furnished

Studio

1 bath

$2,100

Condo for rent

Available Nov 10

Top amenities
Furnished
In-Unit Laundry
On-Site Laundry
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Find sweet deals near Highlands

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

$995

Altamonte Springs

$1,448–$3,849

Goldenrod

$1,850

Maitland

$2,129–$2,199

Florida Center

2014 Newman St #1 - Photo 1 of 1

5d+ ago

Short Term Lake Como condo for rent in Orlando

Stunning Pet-Friendly Home Near Downtown Orlando!

2014 Newman St #1, Orlando, FL 32803

Short term | In-unit laundry | Furnished

2 beds

1 bath

$2,700

Condo for rent

Available Oct 22

Top amenities
In-Unit Laundry
Microwave
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

5319 Orange Ave - Photo 1 of 1

5d+ ago

Short Term Goldenrod apartment for rent in Goldenrod

Newly Remodeled Studio with Pool

5319 Orange Ave, Goldenrod, FL 32792

Short term | In-unit laundry | Furnished

1 bed

1 bath

$1,350

Apartment for rent

Available Aug 1

Top amenities
Assigned Parking
In-Unit Laundry
Microwave
On-Site Laundry
Storage
1224 Alexandra Ct #NA - Photo 1 of 1

5d+ ago

Short Term College Park house for rent in Orlando

Beautiful Fully Furnished Lakefront Pool Home - Short Terms Available

1224 Alexandra Ct #NA, Orlando, FL 32804

Short term | In-unit laundry | Furnished

3 beds

3.5 baths

$12,000

$11,499

Price drop

House for rent

Available Jul 1

Top amenities
Assigned Parking
Dishwasher
Fitness Center
Garage Parking
In-Unit Laundry
Swimming Pool
917 Paddington Ter - Photo 1 of 1

5d+ ago

Short Term house for rent in Lake Mary

917 Paddington Ter, Lake Mary, FL 32746

Short term | Garage parking | Swimming pool

4 beds

2.5 baths

$3,000

House for rent

489 Harvest Oak Ct #NA - Photo 1 of 1

5d+ ago

Short Term house for rent in Lake Mary

*Furnished 2 Beds 2 Baths Midcentury Modern Farmhouse in Lake Mary With Water view, Pool & Great Amenities

489 Harvest Oak Ct #NA, Lake Mary, FL 32746

Short term | In-unit laundry | Furnished

2 beds

2 baths

$4,439

House for rent

Available May 1

Top amenities
Air Conditioning
Assigned Parking
Business Center
Garage Parking
Swimming Pool
Wi-Fi
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
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
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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

1.5 baths

$2,300

House for rent

225 Arnold Ln - Photo 1 of 1

5d+ ago

Short Term apartment for rent in Winter Springs

225 Arnold Ln, Winter Springs, FL 32708

Short term | Garage parking | On-site laundry

2 beds

1 bath

$1,800

Apartment for rent

Top amenities
On-Site Laundry
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

486 Sycamore Springs St - Photo 1 of 1

5d+ ago

Short Term house for rent in Debary

Single Family Residence - DEBARY, FL

486 Sycamore Springs St, Debary, FL 32713

Short term | Air conditioning | On-site laundry

4 beds

2.5 baths

$2,800

House for rent

Top amenities
Air Conditioning
Ceiling Fan
Dishwasher
On-Site Laundry
Swimming Pool
Tile Floor
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

2.5 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
Showing 1 - 25 of 25 results
Home > Apartments in Winter Springs > Highlands > Highlands Short term rentals
Updated: May 6, 2026

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

🔑Available apartment rentals25
💰Best rent deal417 N Tampa Ave
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