Rentals Under $2000 in Windermere, FL

9 rentals

Sort:

Recommended

NEW 20 HRS AGODEAL

ABOUT THIS HOME
Rentals Under $2000 in Windermere, FL
Experience the finest apartments in Windermere, Florida at The Citra at Windermere. Our apartment community offers a variety of distinctive one, two, and three bedroom apartment homes. Conveniently lo

1 bd: $1,554

2 bd: $1,760

Citra at Windermere

| 11353 Citra Cir, Windermere, FL 34786

31 units available • Pets welcome • A/C

NEW 30 HRS AGO6 WEEKS FREE

ABOUT THIS HOME
Rentals Under $2000 in Windermere, FL
Casa Mirella Apartments in Windermere, FL Welcome to Casa Mirella Apartments, where lakeside living meets luxury in the heart of Windermere, FL. Enjoy sunny Florida days by the resort-style swimming

1 bd: $1,691

2 bd: $1,941

101 Casa Mirella Way, Windermere, FL 34786

14 units available • Pets welcome • Parking

NEW 26 HRS AGO3D WALKTHROUGH

ABOUT THIS HOME
Rentals Under $2000 in Windermere, FL
Talcott at Windermere With thoughtful design and exclusive amenities, Talcott at Windermere, is your premier destination for luxury living in Windermere, Florida! Our luxury one, two, and three-bedro

$1,618+/mo

1 bed1 bath656-866 sq ft

Talcott at Windermere

| 5820 Nature View Dr, Windermere, FL 34786

18 units available • Pets welcome • Car-dependent

DEAL

ABOUT THIS HOME
Rentals Under $2000 in Windermere, FL
Price shown is Base Rent. Residents are required to pay: At Application: Admin Fee ($250.00/unit); Application Fee ($85.00/applicant, nonrefundable); At Move-in: Security Deposit (Refundable) ($200.00

$1,724+/mo

1 bed1 bath863 sq ft

Venetian Isle

| 6506 San Francesco Way, Windermere, FL 34786

15 units available • Pets welcome • Parking

ABOUT THIS HOME
Rentals Under $2000 in Windermere, FL
Discover this stunning, remodeled above-garage studio with a private, independent entrance in the peaceful and highly sought-after Summerport neighborhood of Windermere. Perfect for a single tenant, t

$1,350/mo

0 beds1 bath400 sq ft

14451 Bluebird Park Rd, Windermere, FL 34786

Laundry in unit • Parking • A/C

ABOUT THIS HOME
Rentals Under $2000 in Windermere, FL
Casita with private entrance. Located in the Summer Port Neighborhood of Windemere Florida, one block from the community pool and elementary school. The Casita is located over the garage and it is jus

$1,350/mo

0 beds1 bath400 sq ft

14225 Confetti Dr Unit B, Windermere, FL 34786

Laundry in unit • Parking • A/C

Property at 8635 Via Trieste Dr, Windermere, FL, 34786, 1 bed, 1 bath, [object Object]

$1,599/mo

1 bed1 bath2,419 sq ft

8635 Via Trieste Dr, Windermere, FL 34786

Property at 12663 Salomon Cove Dr, Windermere, FL, 34786, 1 bed, 1 bath, [object Object]

$1,349/mo

1 bed1 bath500 sq ft

12663 Salomon Cove Dr, Windermere, FL 34786

Property at 8256 Maritime Flag St #1722, Windermere, FL, 34786, 2 beds, 2 baths, [object Object]

$1,995/mo

2 beds2 baths1,161 sq ft

8256 Maritime Flag St #1722, Windermere, FL 34786

End of results (Download All)

Here are some rentals close to your search

3D WALKTHROUGH

ABOUT THIS HOME
Rentals Under $2000 in Windermere, FL
Bella Casa Apartments are splendid apartments with a prime location. Each of our two bedroom apartments features carpet throughout, spacious walk-in closets and central air conditioning and heat. Each

$1,729/mo

2 beds1.5 baths930 sq ft

Bella Casa

| 5501 Conroy Rd, Orlando, FL 32811

1 unit match • Somewhat walkable •

NEW 6 HRS AGO3D WALKTHROUGH

ABOUT THIS HOME
Rentals Under $2000 in Windermere, FL
Amalfi is a lavishly landscaped apartment home community surrounded by a peaceful, wooded setting. Each of our one and two bedroom apartment floor plans include washer and dryer, open concept kitchens

1 bd: $1,179

2 bd: $1,399

Amalfi

| 4860 Cypress Woods Dr, Orlando, FL 32811

8 units match • Car-dependent •

ABOUT THIS HOME
Rentals Under $2000 in Windermere, FL
Welcome Home to The Fitzgerald The Fitzgerald is in an ideal location. You are close to the most exciting features our city has to offer. Only one mile from Universal Studios and close to Walt Disney

1 bd: $1,376

2 bd: $1,664

The Fitzgerald

| 4581 S Kirkman Rd, Orlando, FL 32811

9 units match • Pets welcome •

NEW 26 HRS AGO3D WALKTHROUGH

ABOUT THIS HOME
Rentals Under $2000 in Windermere, FL
WELCOME TO OUR COMMUNITY In the heart of Florida's city of Orlando, Rosemont Windermere redefines luxury apartment living. Not only do we offer a convenient and popular location, our recently renovat

1 bd: $1,387

2 bd: $1,578

Rosemont Windermere

| 6421 Conroy Rd, Orlando, FL 32835

23 units match • Pets welcome • Somewhat walkable

1 MONTH FREE

ABOUT THIS HOME
Rentals Under $2000 in Windermere, FL
Introducing The New Vista Verde - A New Look with A Fresh Attitude! Offering newly remodeled one and two-bedroom apartment homes, Vista Verde Apartments in located in MetroWest, Orlando. Enjoy the co

1 bd: $1,465

2 bd: $1,670

Vista Verde

| 1658 S Hiawassee Rd, Orlando, FL 32835

8 units match • Pets welcome •

3D WALKTHROUGH

ABOUT THIS HOME
Rentals Under $2000 in Windermere, FL
Welcome to Century Millenia Apartments, where comfort meets convenience in the heart of Orlando, FL. Nestled amidst the vibrant urban landscape, our apartment community offers a range of floor plans d

1 bd: $1,446

2 bd: $1,845

Century Millenia

| 5100 Millenia Waters Dr, Orlando, FL 32839

9 units match • Pets welcome • Parking

Property at Village Townhomes - 4401 Scenic Lake Dr, Orlando, FL, 32808, 2 beds, 2.5 baths, [object Object]

$1,560+/mo

2 beds2.5 baths1,278 sq ft

Village Townhomes

| 4401 Scenic Lake Dr, Orlando, FL 32808

Property at Ellery at Lake Sherwood - 8008 Balasands Blvd, Orlando, FL, 32818, 1-2 bed, 1-2 bath, [object Object]

$1,425+/mo

1-2 bed1-2 bath783-1,348 sq ft

Ellery at Lake Sherwood

| 8008 Balasands Blvd, Orlando, FL 32818

Property at Fountains at Millenia Apartments - 5316 Millenia Blvd, Orlando, FL, 32839, 1-3 bed, 1-2 bath, [object Object]

$1,349+/mo

1-3 bed1-2 bath774-1,214 sq ft

Fountains at Millenia Apartments

| 5316 Millenia Blvd, Orlando, FL 32839

Property at The Summit at MetroWest - 6500 Metrowest Blvd, Orlando, FL, 32835, 1-3 bed, 1-2 bath, [object Object]

$1,213+/mo

1-3 bed1-2 bath635-1,187 sq ft

The Summit at MetroWest

| 6500 Metrowest Blvd, Orlando, FL 32835

Property at The Hudson - 464 S Kirkman Rd, Orlando, FL, 32811, 1-2 bed, 1-2 bath, [object Object]

$1,473+/mo

1-2 bed1-2 bath756-1,176 sq ft

The Hudson

| 464 S Kirkman Rd, Orlando, FL 32811

Property at Bella Capri - 4822 Cason Cove Dr, Orlando, FL, 32811, 1-2 bed, 1-2 bath, [object Object]

$1,399+/mo

1-2 bed1-2 bath698-951 sq ft

Bella Capri

| 4822 Cason Cove Dr, Orlando, FL 32811

Property at Fourteen01 Apartments - 1401 S Kirkman Rd, Orlando, FL, 32811, 1-2 bed, 1-2 bath, [object Object]

$1,420+/mo

1-2 bed1-2 bath658-1,045 sq ft

Fourteen01 Apartments

| 1401 S Kirkman Rd, Orlando, FL 32811

Property at Regatta at Universal - 6350 Vineland Rd, Orlando, FL, 32819, 1-2 bed, 1-2 bath, [object Object]

$1,506+/mo

1-2 bed1-2 bath579-1,091 sq ft

Regatta at Universal

| 6350 Vineland Rd, Orlando, FL 32819

Property at Portofino - 5974 Windhover Dr, Orlando, FL, 32819, 1 bed, 1 bath, [object Object]

$1,249/mo

1 bed1 bath800 sq ft

Portofino

| 5974 Windhover Dr, Orlando, FL 32819

Property at Rolling Hills Apartment Homes - 5402 Pine Chase Dr, Orlando, FL, 32808, 2-3 beds, 2 baths, [object Object]

$1,595+/mo

2-3 beds2 baths1,100-1,167 sq ft

Rolling Hills Apartment Homes

| 5402 Pine Chase Dr, Orlando, FL 32808

Property at Rosala West Apartments - 4500 Silver Star Rd, Orlando, FL, 32808, 2 beds, 2 baths, [object Object]

$1,269/mo

2 beds2 baths1,000 sq ft

Rosala West Apartments

| 4500 Silver Star Rd, Orlando, FL 32808

Property at Studio Parc - 4601 S Kirkman Rd, Orlando, FL, 32811, 1 bed, 1 bath, [object Object]

$1,299+/mo

1 bed1 bath550 sq ft

Studio Parc

| 4601 S Kirkman Rd, Orlando, FL 32811

Property at Riva - 4771 Walden Cir, Orlando, FL, 32811, 1 bed, 1 bath, [object Object]

$1,229+/mo

1 bed1 bath719-762 sq ft

Riva

| 4771 Walden Cir, Orlando, FL 32811

Property at Cypress Run - 7100 Head Ave, Orlando, FL, 32808, 1-3 bed, 1-2 bath, [object Object]

$1,300+/mo

1-3 bed1-2 bath600-1,200 sq ft

Cypress Run

| 7100 Head Ave, Orlando, FL 32808

Based on information submitted to the MLS GRID as of Thu Sep 18 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

More to explore in Windermere, FL

Property Types
Bedrooms
Amenities
Price

Popular rental markets in Florida

Rentals
Apartments

Rentals Under $2000 in Windermere, FL

More to explore in Windermere, FL

Rentals near Windermere, FL

Cities

Apartments for rent near Windermere, FL

Zip Codes

Popular rental markets in Florida

Related searches in Windermere, FL