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Short Term Rentals in Highlands, FL

25 rentals

Liv at Winter Park Apartment Homes - Photo 1 of 1

1h 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

$1,257–$3,462

Price drop

Apartment for rent

Available Sep 12

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

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5256 International Dr. - Photo 1 of 1

4h 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

3841 Atrium Dr - Photo 1 of 1

7h ago

Our team has verified this company

Verified

3841 Atrium Dr, Orlando, FL 32822

Short term | In-unit laundry | Furnished

2 beds

2 baths

$4,101

Apartment for rent

Top amenities
Central Heat
Furnished
In-Unit Laundry
Swimming Pool
TV
Wi-Fi
1307 Formosa Ave - Photo 1 of 1

7h ago

Our team has verified this company

Verified

1307 Formosa Ave, Orlando, FL 32789

Short term | In-unit laundry | Furnished

2 beds

1 bath

$4,964

Apartment for rent

Top amenities
Air Conditioning
In-Unit Laundry
Microwave
Oven
TV
Wi-Fi
4501 Loring Pl - Photo 1 of 1

7h ago

Our team has verified this company

Verified

4501 Loring Pl, Orlando, FL 32812

Short term | Furnished | Air conditioning

2 beds

1 bath

$4,052

Apartment for rent

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

7h ago

Our team has verified this company

Verified

1711 Asher Ln, Orlando, FL 32803

Short term | In-unit laundry | Furnished

3 beds

1 bath

$5,432

Apartment for rent

Top amenities
Business Center
Dishwasher
In-Unit Laundry
Microwave
Oven
Wi-Fi

Nearby rental good for eco-living

$4,439

Lake Mary

Nearby rental good for pet owners

$2,547–$3,170

Sanford

Nearby rental good for social life

2704 Raeford Rd - Photo 1 of 1

7h ago

Our team has verified this company

Verified

2704 Raeford Rd, Conway, FL 32806

Short term | Furnished | Air conditioning

2 beds

1 bath

$3,440

Apartment for rent

Top amenities
Dishwasher
Furnished
Microwave
Oven
TV
Wi-Fi
10200 Falcon Pine Blvd - Photo 1 of 1
Highly rated

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

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2801 Biltmore Park Dr - Photo 1 of 1

3d 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

2995 Railside Lp - Photo 1 of 1

5d+ ago

8

Very good

Our team has verified this company

Verified

2995 Railside Lp

2995 Railside Loop, Sanford, FL 32771

Short term | Furnished | Package service

1–2 beds

1–2 baths

$2,547–$3,170

Apartment for rent

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Find sweet deals near Highlands

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

$1,721–$3,462

Goldenrod

$1,700

Orlando

$1,995

South Semoran

112 Crown Oaks Way - Photo 1 of 1

5d+ ago

Short Term Medith Manor Nob Hill condo for rent in Wekiwa Springs

Springs

112 Crown Oaks Way, Wekiwa Springs, FL 32779

Short term | In-unit laundry | Furnished

1 bed

1 bath

$899

Condo for rent

Available Sep 1

Top amenities
Fitness Center
Furnished
In-Unit Laundry
Microwave
On-Site Laundry
Swimming Pool
4143D Lake Lawne Ave #43D - Photo 1 of 1

5d+ ago

Short Term Mercy Drive condo for rent in Orlando

Park Place of Orlando

4143D Lake Lawne Ave #43D, Orlando, FL 32808

Short term | In-unit laundry | Furnished

1 bed

1 bath

$978

Condo for rent

Top amenities
Furnished
In-Unit Laundry
Microwave
On-Site Laundry
4143B Lake Lawne Ave #43B - Photo 1 of 1

5d+ ago

Short Term Mercy Drive condo for rent in Orlando

Park Place of Orlando

4143B Lake Lawne Ave #43B, Orlando, FL 32808

Short term | In-unit laundry | Furnished

1 bed

1 bath

$1,086

Condo for rent

Top amenities
In-Unit Laundry
On-Site Laundry
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 Oct 1

Top amenities
Air Conditioning
Assigned Parking
Business Center
Garage Parking
Swimming Pool
Wi-Fi
3328 Coleman Pl #B - Photo 1 of 1

5d+ ago

Short Term Lake Mann Estates condo for rent in Orlando

Beautiful lake Mann states

3328 Coleman Pl #B, Orlando, FL 32805

Short term | In-unit laundry | Furnished

4 beds

2 baths

$2,500

Condo for rent

Available Sep 1

Top amenities
Air Conditioning
Dishwasher
Fitness Center
Garage Parking
In-Unit Laundry
Microwave
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
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
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

$2,450

House for rent

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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

$1,450

Condo for rent

1250 S Pennsylvania Ave #8 - Photo 1 of 1

5d+ ago

Short Term Virginia Heights apartment for rent in Winter Park

$5750 - 3 brm townhome -walkable downtown WP / chain of lake access, private community park.

1250 S Pennsylvania Ave #8, Winter Park, FL 32789

Short term | In-unit laundry | Air conditioning

3 beds

2 baths

$5,550

Apartment for rent

Available Jul 14

Top amenities
Assigned Parking
Dishwasher
Garage Parking
Hardwood Floor
In-Unit Laundry
Storage
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

Short term | Outdoor space

3 beds

2 baths

$2,250

House for rent

101 S Eola Dr - Photo 1 of 1

5d+ ago

Short Term South Eola condo for rent in Orlando

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

1 bed

1 bath

$1,650

Condo for rent

Top amenities
In-Unit Laundry
On-Site Laundry
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
Fitness Center
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 baths

$2,400

House for rent

Top amenities
Garage Parking
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: September 12, 2025

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

🔑Available apartment rentals25
💰Best rent deal112 Crown Oaks Way
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