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Short Term Rentals in Highlands, FL

25 rentals

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

14h 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

$1,263–$3,702

Apartment for rent

Available Mar 18

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

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5343 Hermosa St - Photo 1 of 1

1d ago

Our team has verified this company

Verified

5343 Hermosa St, Orlando, FL 32807

Short term | In-unit laundry | Furnished

5 beds

3 baths

$7,549

$7,328

Price drop

Apartment for rent

Top amenities
Dishwasher
In-Unit Laundry
Microwave
Oven
TV
Wi-Fi
5885 Lakehurst Drive - Photo 1 of 1

1d ago

9.5

Excellent

Our team has verified this company

Verified

5885 Lakehurst Drive

5885 Lakehurst Dr, Orlando, FL 32819

Short term | Furnished

1–2 beds

1–2 baths

$1,917–$2,504

Apartment for rent

480 N. Orange Ave. - Photo 1 of 1

1d 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

$1,999–$2,620

Apartment for rent

6844 Westborough Ln #8 - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

Large Bed Room, Private Bathroom, Large Walk-In Closet, and Large TV,

6844 Westborough Ln #8, Orlando, FL 32818

Short term | Air conditioning | On-site laundry

1 bed

1 bath

$930

Apartment for rent

Available Mar 7

Top amenities
Air Conditioning
Central Heat
On-Site Laundry
On-Site Management
6844 Westborough Ln #12 - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

$830 - 1 Bedroom with Two Roommates, Shared Bathroom House In Orlando With Great Amenities

6844 Westborough Ln #12, Orlando, FL 32818

Short term | Air conditioning | On-site laundry

1 bed

1 bath

$830

Apartment for rent

Available Mar 7

Top amenities
Air Conditioning
Central Heat
Dishwasher
On-Site Laundry
On-Site Management

Nearby rental good for eco-living

Nearby rental good for pet owners

$7,328

Monterey

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
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
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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
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Find sweet deals near Highlands

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

$1,100

Altamonte Springs

$1,850

Maitland

$3,445

Lake Formosa

$1,917–$1,997

Florida Center

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
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

1.5 baths

$2,300

House for rent

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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
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

2.5 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 Springs > Highlands > Highlands Short term rentals
Updated: March 18, 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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