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Short Term Rentals in Highlands, FL

25 rentals

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

1h 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

$1,321–$3,121

Price drop

Apartment for rent

Available Dec 15

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

Call

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

7h 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

316 East Amelia Street - Photo 1 of 1

12h ago

Our team has verified this company

Verified

316 East Amelia Street, Orlando, FL 32801

Short term | Furnished | Air conditioning

2 beds

1 bath

$3,104

Apartment for rent

Top amenities
Air Conditioning
Fireplace
Furnished
Microwave
TV
Wi-Fi
7371 Universal Boulevard - Photo 1 of 1

12h ago

Our team has verified this company

Verified

7371 Universal Boulevard, Orlando, FL 32819

Short term | Furnished | Air conditioning

1 bed

1 bath

$3,041

$2,070

Price drop

Apartment for rent

Top amenities
Air Conditioning
Central Heat
Elevator
Residents Lounge
TV
Wi-Fi
102 King Street - Photo 1 of 1

12h ago

Our team has verified this company

Verified

102 King Street, Orlando, FL 32804

Short term | In-unit laundry | Furnished

2 beds

1 bath

$2,900

$2,079

Price drop

Apartment for rent

Top amenities
Central Heat
In-Unit Laundry
Microwave
Oven
TV
Wi-Fi
2008 Grant Street - Photo 1 of 1

12h ago

Our team has verified this company

Verified

2008 Grant Street, Orlando, FL 32806

Short term | In-unit laundry | Furnished

1 bed

1 bath

$2,724

Apartment for rent

Top amenities
Air Conditioning
Furnished
In-Unit Laundry
Microwave
TV
Wi-Fi

Nearby rental good for eco-living

Nearby rental good for pet owners

1629 Goldenrod Road - Photo 1 of 1

12h ago

Our team has verified this company

Verified

1629 Goldenrod Road, Orlando, FL 32807

Short term | In-unit laundry | Furnished

4 beds

2 baths

$4,701

Apartment for rent

Top amenities
Air Conditioning
Central Heat
Furnished
In-Unit Laundry
TV
Wi-Fi
1330 Catalpa Lane - Photo 1 of 1

12h ago

Our team has verified this company

Verified

1330 Catalpa Lane, Orlando, FL 32806

Short term | In-unit laundry | Furnished

4 beds

2 baths

$6,922

$6,066

Price drop

Apartment for rent

Top amenities
Air Conditioning
Dishwasher
Furnished
In-Unit Laundry
Microwave
TV
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Marvera Casselberry - Photo 1 of 1
Rent special

13h 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

$1,435–$2,551

Price drop

Apartment for rent

Top amenities
Business Center
Fitness Center
In-Unit Laundry
Residents Lounge

Call

981 Hamlet Court #NA - Photo 1 of 1

1d ago

Short Term house for rent in Maitland

$1,150 - Cozy Room for Rent In Maitland. Prime location to Winter Park Village and Mill District!

981 Hamlet Court #NA, Maitland, FL 32751

Short term | In-unit laundry | Air conditioning

1 bed

1 bath

$1,150

House for rent

Available Jan 1

Top amenities
Assigned Parking
In-Unit Laundry
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Find sweet deals near Highlands

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

$1,249

Sanford

$1,387–$3,121

Goldenrod

$1,738

Orlando

$800

Holden Heights

2801 Biltmore Park Dr - Photo 1 of 1
Rent special

1d 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

2d 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

700 Magnolia Avenue - Photo 1 of 1

2d ago

8.2

Very good

700 Magnolia Avenue

700 Magnolia Ave, Sanford, FL 32771

Short term

1 bed

1 bath

$1,249

Apartment for rent

1118 Overdale Street - Photo 1 of 1

5d+ ago

Short Term house for rent in Orlando

Spacious 3-Bedroom Retreat | Private Pool & Game Room

1118 Overdale Street, Orlando, FL 32825

Short term | In-unit laundry | Furnished

3 beds

1 bath

$3,200

House for rent

Available Apr 3

Top amenities
In-Unit Laundry
Microwave
On-Site Laundry
3328 Coleman Place #A - Photo 1 of 1

5d+ 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
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
281 Shell Point East #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 Point East #NA, Maitland, FL 32751

Short term | In-unit laundry | Furnished

4 beds

4 baths

$25,000

House for rent

Available Feb 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

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656 Boniview Ln - Photo 1 of 1

5d+ ago

Short Term house for rent in Altamonte Springs

656 Boniview Ln, Altamonte Springs, FL 32714

Short term | In-unit laundry | Garage parking

2 beds

2 baths

$2,000

House for rent

Available Nov 1

Top amenities
Ceiling Fan
In-Unit Laundry
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 baths

$2,800

House for rent

Top amenities
Air Conditioning
Ceiling Fan
Dishwasher
On-Site Laundry
Swimming Pool
Tile Floor
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 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
Hardwood Floor
In-Unit Laundry
Oven
Storage
Swimming Pool
Showing 1 - 25 of 25 results
Home > Apartments in Winter Springs > Highlands > Highlands Short term rentals
Updated: December 15, 2025

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

🔑Available apartment rentals25
💰Best rent deal6844 Westborough Lane #12
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