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Condos for Rent in Winter Park, FL with 2-Bedrooms

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  • /20

    $1,730 Per Month

    • 2 Beds
    • 2 Baths
    • 1,037 Sq Ft
    • Condo for Rent

    659 Montego Bay Ct, Winter Park, FL 32792

    Welcome to your dream condo in Winter Park! This charming **2-bedroom, 2-full bathrooms** home offers the perfect blend of comfort, convenience, and an unbeatable location, making it an ideal place to call home. With 1,037 square feet of well-designed living space, you'll enjoy modern conveniences, desirable community amenities, and easy access to everything you need for everyday

    659 Montego Bay Ct, Winter Park, FL 32792
  • /13

    $2,499

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 882 Sq Ft
    • Condo for Rent

    662 Callahan St Unit SI ID1545989P, Winter Park, FL 32789

    The advertised rate of $2,500/month is the lowest available price, based on a 30 day(s) stay with a move-in date of January 6, 2027.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    662 Callahan St Unit SI ID1545989P, Winter Park, FL 32789
  • /6

    $1,850

    Total Monthly Price

    • 2 Beds
    • 2.5 Baths
    • 1,100 Sq Ft
    • Condo for Rent

    2924 Antique Oaks Cir Unit 48, Winter Park, FL 32792

    Close to Park Avenue Winter Park Restaurants and shopping near UCF and Full sail University also Rollins Colllege, Great Public schools. Close to the Orlando Airport and 30 minutes from Disney World and Universal Studios.

    2924 Antique Oaks Cir Unit 48, Winter Park, FL 32792
  • /37

    $2,000

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 911 Sq Ft
    • Condo for Rent

    1250 S Denning Dr Unit 127, Winter Park, FL 32789

    Updated 2BR/2BA First-Floor Condo in Winter Park – Pool View, Water Included!1250 S. Denning Drive – Winter Park, FLEnjoy comfortable, low-maintenance living in this beautifully updated 2-bedroom, 2-bathroom condo located in one of Winter Park's most convenient neighborhoods.This 910-square-foot, first-floor unit features luxury vinyl plank flooring throughout, a modern

    1250 S Denning Dr Unit 127, Winter Park, FL 32789
  • /21

    $2,100

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,295 Sq Ft
    • Condo for Rent

    2383 Sun Valley Cir Unit Winter Park, Winter Park, FL 32792

    Welcome to this charming and beautifully updated home in the serene Cedarwood Village community! Tucked away in a peaceful location, this unit offers a quiet retreat from traffic noise and features a private backyard with no rear neighbors perfect for enjoying the spacious, enclosed lanai. The modern kitchen features sleek granite countertops and matching cabinets, with the bathrooms and dining

    2383 Sun Valley Cir Unit Winter Park, Winter Park, FL 32792
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    $1,950

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,236 Sq Ft
    • Condo for Rent

    1920 Woodcrest Dr Unit 13, Winter Park, FL 32792

    Unit 13 is a direct pool front unit. Large (1,236 sq. ft.), quiet first floor 2 bedroom 2 bathroom condo in smaller community with only 18 units in the City of Winter Park, Florida. The Floor plan has a double primary bedroom layout. Ceramic tile flooring in the foyer, living/dining area, kitchen, and both bathrooms. Both bedrooms have new easy-care luxury vinyl wood-look flooring. Primary bath

    1920 Woodcrest Dr Unit 13, Winter Park, FL 32792
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    $2,100 Per Month

    • 2 Beds
    • 1 Bath
    • 800 Sq Ft
    • Condo for Rent

    151 N Orlando Ave Unit 203, Winter Park, FL 32789

    FURNISHED 6-12 month executive rental available immediately in Lake Killarney Condominiums. Perfect for one or two residents, this condooffers a bedroom with King-sized bed and walk-in closet, a separate office, and a sunroom with floor to ceiling windows. Newly installedbathroom and central air system. Combo washer/dryer unit in kitchen or optional coin laundry in building. Sorry, no

    Robert Arnold SAND DOLLAR REALTY GROUP INC

    151 N Orlando Ave Unit 203, Winter Park, FL 32789
  • /23

    $2,100 Per Month

    • 2 Beds
    • 2 Baths
    • 1,050 Sq Ft
    • Condo for Rent

    955 Aragon Ave Unit A, Winter Park, FL 32789

    Property Id: 1217869 Spacious 1,055 Sq Ft Duplex - Winter Park Move-In Date: August 1st! Rent: $2,100/month Message me to schedule an appointment or to request a full video walkthrough sent directly to your phone! Key Features Fully renovated 2-Bed / 2-Bath front duplex layout (Unit A) on a tree-lined brick street. Nearly 10-foot ceilings create a bright, airy

    955 Aragon Ave Unit A, Winter Park, FL 32789
  • /21

    $1,500 Per Month

    • 2 Beds
    • 1 Bath
    • 881 Sq Ft
    • Condo for Rent

    1695 Lee Rd Unit B204, Winter Park, FL 32789

    2 bedroom, 1 bathroom condo located in the desirable and well maintained Waterfall Cove community in Winter Park. New tile floor was installed and freshly painted. Washer & Dryer in the unit. No min credit score is required. Enjoy a highly walkable location close to Whole Foods, LA Fitness, Winter Park Village, shopping, dining, and more. Community amenities include a pool, dog park, and mature

    Mauricio Toro MTRE GROUPE LLC

    1695 Lee Rd Unit B204, Winter Park, FL 32789
  • /24

    $2,300 Per Month

    • 2 Beds
    • 1 Bath
    • 710 Sq Ft
    • Condo for Rent

    151 N Orlando Ave Unit 207, Winter Park, FL 32789

    Welcome to your future home in the heart of Winter Park, located in the desirable Maitland district! This charming property offers a comfortable and convenient lifestyle, with easy access to an array of amenities and attractions.Experience the ease of living with central heating and cooling, complemented by air conditioning and ceiling fans for your comfort throughout the year. This

    151 N Orlando Ave Unit 207, Winter Park, FL 32789
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    $1,650 Per Month

    • 2 Beds
    • 2 Baths
    • 1,062 Sq Ft
    • Condo for Rent

    3045 Aaron Burr Ave Unit 12, Winter Park, FL 32792

    Condominium located in The Colonies in Winter Park. Conveniently situated near UCF (University of Central Florida) and Full Sail University, with easy access to shopping centers, major highways, restaurants, and Orlando's world-famous theme parks. Just 11 minutes from Orlando International Airport (Orlando International Airport).This cozy 2-bedroom apartment is perfectly located for quick access

    Angel Ramirez LPT REALTY, LLC

    3045 Aaron Burr Ave Unit 12, Winter Park, FL 32792
  • /16

    $1,600 Per Month

    • 2 Beds
    • 2 Baths
    • 964 Sq Ft
    • Condo for Rent

    3254 Howell Branch Rd Unit Howell Branch Rd - 3254, Winter Park, FL 32792

    3254 Howell Branch Rd Unit Howell Branch Rd - 3254, Winter Park, FL 32792
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    $2,600 Per Month

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft
    • Condo for Rent

    151 N Orlando Ave Unit 238, Winter Park, FL 32789

    Experience lakefront living at its finest in this exceptional Winter Park condo overlooking beautiful Lake Killarney. Enjoy breathtaking sunset views from your private waterfront retreat, complete with access to a community dock, private boat ramp, and a fenced lakeside pool perfect for relaxing and entertaining. Ideally located just minutes from the heart of Winter Park, this home offers

    Alex Scures COLONIALTOWN REALTY

    151 N Orlando Ave Unit 238, Winter Park, FL 32789
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    $1,799 Per Month

    • 2 Beds
    • 2 Baths
    • 1,120 Sq Ft
    • Fabulous 2/2 Condo @ Winter Park x Rent Next to Full Sail.

    610 Saint Johns Ct Unit 610, Winter Park, FL 32792

    Amazing Winter Park Condo for Rent – Prime Location!Welcome home to this beautifully maintained 2-bedroom, 2-bathroom condo in the heart of Winter Park, conveniently located just minutes from Park Avenue, Full Sail University, shopping, restaurants, and entertainment.This spacious home features a modern kitchen with granite countertops and stainless steel appliances, beautifully

    610 Saint Johns Ct Unit 610, Winter Park, FL 32792
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    $1,445 Per Month

    • 2 Beds
    • 2 Baths
    • 756 Sq Ft
    • Condo for Rent

    7302 Swallow Run, Winter Park, FL 32792

    This 2 bedroom, 2 bathroom condo is located in Winter Park's Whisperwood community near local shops, restaurants, and schools. Features include a spacious living area with dining room, lovely kitchen with granite countertops, a wonderful primary suite, and outdoor patio. Community amenities include a swimming pool. Pets under 35 lbs. Schedule a showing or submit an application online. All Real

    Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

    7302 Swallow Run, Winter Park, FL 32792
  • /15

    $1,850 Per Month

    • 2 Beds
    • 2 Baths
    • 1,043 Sq Ft
    • Condo for Rent

    419 Warrenton Rd Unit 419, Winter Park, FL 32792

    AVAILABLE NOW! Please call or text to schedule a showing. This 2 bedroom, 2 bathroom townhome is located in Winter Park's desirable Winter Park Pines community. Enjoy all Winter Park has to offer, Park Avenue's shops and restaurants, Winter Park Village, highly rated schools, and an abundance of entertainment options to include Mead Gardens, WP Tennis Center, WP Golf Course, and much more.

    419 Warrenton Rd Unit 419, Winter Park, FL 32792
  • /20

    $2,000 Per Month

    • 2 Beds
    • 1 Bath
    • 1,500 Sq Ft
    • Condo for Rent

    151 N Orlando Ave Unit 118, Winter Park, FL 32789

    Investment opportunity! Discover this hidden gem—a 2-bed, 1-bath condo nestled in the heart of Winter Park. Situated in the serene Lake Killarney Condos, this property offers some of the town's most breathtaking sunsets from a sprawling lakefront lot. Enjoy extensive grassy areas and a community pool right on your doorstep. Ideally located near essentials and leisure spots including Publix,

    Adriana Montes MBA FLORIDA DREAMS REALTY GRP INC

    151 N Orlando Ave Unit 118, Winter Park, FL 32789
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    $2,000 Per Month

    • 2 Beds
    • 2 Baths
    • 902 Sq Ft
    • Condo for Rent

    2404 Gallery View Dr, Winter Park, FL 32792

    Fantastic condo! Ready move-in Aug 1st!! Super Location: 2nd floor 2/2 condo in sought-after Winter Park, walking distance from restaurants, grocery stores, etc... Convenient to Rollins College. You will love living in this small luxury complex that has been kept in superb condition. The condo is in a quiet setting with wood floors, vaulted ceilings, wood blinds, and a split floor plan. Enjoy the

    2404 Gallery View Dr, Winter Park, FL 32792
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    $2,695 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,428 Sq Ft
    • Condo for Rent

    630 Killarney Bay Ct Unit 3, Winter Park, FL 32789

    Lakefront townhome in desirable Killarney Bay directly on Lake Killarney, offering 2 bedrooms, 2.5 baths, and a one-car carport. This spacious residence features an open living and dining area that flows to a screened porch, perfect for relaxing and enjoying tranquil lake views in a well-maintained complex. Both bedrooms are upstairs for privacy, each with its own bath. A convenient half bath is

    Anthony Consalvo FLORIDA ONE REAL ESTATE LLC

    630 Killarney Bay Ct Unit 3, Winter Park, FL 32789
  • /21

    $1,595 Per Month

    • 2 Beds
    • 1 Bath
    • 881 Sq Ft
    • SPACIOUS 2BR CONDO | MOVE-IN READY | LIMITED AVAILABILITY

    1695 Lee Rd, Winter Park, FL 32789

    MOVE-IN SPECIAL – $1,000 RENT CREDIT*Beautiful and move-in ready 2 Bedroom / 1 Bathroom condo located on the second floor in a quiet, well-maintained community.Take advantage of a limited-time move-in special and receive a $1,000 rent credit applied toward your first month's rent. Certain terms and conditions apply.This unit offers the perfect combination of comfort,

    1695 Lee Rd, Winter Park, FL 32789
  • /19

    $1,450 Per Month

    • 2 Beds
    • 2 Baths
    • 840 Sq Ft
    • Condo for Rent

    3651 N Goldenrod Rd Unit 110, Winter Park, FL 32792

    Beautiful 2-bedroom, 2-bath condo available for rent in the highly desirable Winter Park area. This inviting home is thoughtfully designed for comfortable family living and features no carpet, with durable laminate flooring throughout perfect for easy cleaning and everyday use. The condo offers a spacious and functional layout, including a bright living area ideal for family time and

    Praveen Setty RIGHTHOUSE REALTY LLC

    3651 N Goldenrod Rd Unit 110, Winter Park, FL 32792
  • /15

    $1,375 Per Month

    • 2 Beds
    • 2 Baths
    • 840 Sq Ft
    • Spacious 2/2 Condo In Lancelot at Winter Park

    3651 N Goldenrod Rd Unit B203, Winter Park, FL 32792

    AVAILABLE NOW!!! This beautiful 2 bedroom, 2 bathroom condo in the Lancelot at Winter Park community near local shops, restaurants, and schools. Features include tile throughout, vaulted ceilings, a fully equipped and remodeled kitchen with granite counters and a breakfast bar, updated bathrooms, and spacious bedrooms. Community amenities include a pool and clubhouse. MUST SEE! Won't last long!

    3651 N Goldenrod Rd Unit B203, Winter Park, FL 32792
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    $2,350 Per Month

    • 2 Beds
    • 2 Baths
    • 1,074 Sq Ft
    • Condo for Rent

    700 Melrose Ave Unit A5, Winter Park, FL 32789

    Beautifully upgraded 2-bedroom, 2-bath condo in the heart of Winter Park! Located in a sought-after 55+ community surrounded by mature, lush landscaping, this charming condo offers the perfect blend of comfort and convenience. Enjoy a short walk to Mead Botanical Garden or the shops, dining, and entertainment along Park Avenue. With easy access to I-4, downtown Orlando, hospitals, shopping, and

    Nicole Howell FANNIE HILLMAN & ASSOCIATES

    700 Melrose Ave Unit A5, Winter Park, FL 32789
  • /11

    $1,375 Per Month

    • 2 Beds
    • 2 Baths
    • 1,045 Sq Ft
    • Condo for Rent

    1000 S Semoran Blvd Unit 806, Winter Park, FL 32792

    LB/O - Nice 2 bedroom 2 bathrooms, 2nd Floor Unit, Open Floor Concept, Living Area, Breakfast Area, Community Pool, Water Included! Apply Today!TO SCHEDULE A SHOWING YOU MUST EMAIL US WITH YOUR CONTACT INFORMATION AND THE PROPERTY YOU WISH TO SEE AT AND AN AGENT WILL RESPOND BACK WITH THE AVAILABLE SHOW TIMES.HOW TO APPLY/ABOUT OUR APPLICATION PROCESS: Our application process

    1000 S Semoran Blvd Unit 806, Winter Park, FL 32792
  • /15

    $1,500 Per Month

    • 2 Beds
    • 1 Bath
    • 881 Sq Ft
    • Condo for Rent

    Unlisted Address

    2 Bedrooms, 1 Bathroom located on the first floor. IGalley kitchen (with a dishwasher, microwave, range, refrigerator, and a washer/dryer combo), walk-in closet in the primary bedroom, and an open living/dining room combo filled with natural light. A private patio, playground, and park. It includes 1 assigned parking space.

    Kirsten Cantello TRUSTHOME PROPERTIES INC

    Unlisted Address
  • /23

    $1,545 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,079 Sq Ft
    • Condo for Rent

    3004 George Mason Ave Unit K5d, Winter Park, FL 32792

    This beautiful 2-bedroom, 2.5-bathroom, 2-Story condo located in the highly desirable Colonies community of Winter Park, Florida, offers 1,079 square feet of thoughtfully designed living space while featuring modern updates throughout, including durable tile flooring in the main living areas, crisp white cabinetry, and sleek stainless-steel appliances. The layout transitions seamlessly into a

    3004 George Mason Ave Unit K5d, Winter Park, FL 32792
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    $2,400 Per Month

    • 2 Beds
    • 2 Baths
    • 1,140 Sq Ft
    • Condo for Rent

    150 Killarney Bay Ct Unit 5-5, Winter Park, FL 32789

    Welcome to this beautifully updated first-floor 2-bedroom, 2-bath condo in the highly desirable Killarney Bay community in Winter Park, offering a perfect blend of comfort, style, and lakefront living. Step inside to an inviting open-concept layout filled with natural light and designed for both everyday living and entertaining. The modern kitchen features upgraded cabinetry, sleek countertops,

    Giovanna D'Alessandro RP INVESTMENT REALTY LLC

    150 Killarney Bay Ct Unit 5-5, Winter Park, FL 32789
  • /12

    $1,600 Per Month

    • 2 Beds
    • 2 Baths
    • 840 Sq Ft
    • 2 Bedroom/2 Bathroom at Lancelot AVAILABLE AUGUST 10th!

    3651 N Goldenrod Rd Unit A103, Winter Park, FL 32792

    Super nice, 2 bed/2 bath, ground floor unit. Wonderful open floor plan, laminate and tile flooring, updated bathrooms, all kitchen appliances, washer and dryer, and ceiling fans. Water is included. No Pets Allowed. Conveniently located. Call today for an appointment!EQUAL HOUSING OPPORTUNITYFEATURES:Ground Floor UnitAll AppliancesBreakfast BarLiving Room/Dining

    3651 N Goldenrod Rd Unit A103, Winter Park, FL 32792
  • /14

    $1,600 Per Month

    • 2 Beds
    • 1 Bath
    • 881 Sq Ft
    • Condo for Rent

    1695 Lee Rd Unit C103, Winter Park, FL 32789

    Charming condo for Lease! location , Location , location ! This 2-bedroom, 1-bathroom apartment offers an open layout with plenty of natural light, a spacious living area, and a well-equipped kitchen with brand new interior paint job.Enjoy the convenience of in-unit laundry and modern amenities throughout. The apartment is situated in a serene community, offering easy access to shopping, dining,

    Yigit Orer EMPIRE NETWORK REALTY

    1695 Lee Rd Unit C103, Winter Park, FL 32789
  • /13

    $1,445 Per Month

    • 2 Beds
    • 2 Baths
    • 756 Sq Ft
    • Condo for Rent

    7302 Swallow Run Unit 7302, Winter Park, FL 32792

    AVAILABLE NOW! Please call or text to schedule a showing. This 2 bedroom, 2 bathroom condo is located in Winter Park's Whisperwood community near local shops, restaurants, and schools. Features include a spacious living area with dining room, lovely kitchen with granite countertops, a wonderful primary suite, and outdoor patio. Community amenities include a swimming pool. Pets under 35

    7302 Swallow Run Unit 7302, Winter Park, FL 32792
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    $1,700 Per Month

    • 2 Beds
    • 2 Baths
    • 927 Sq Ft
    • Condo for Rent

    205 Lewfield Cir Unit 205, Winter Park, FL 32792

    Wonderful! Owners pays Water & Internet. Exceptional Winter Park location! Amenities include 2 pools, lighted tennis courts, fitness center, car care facilities & clubhouse, enjoy the simple life in this 2 bedroom, 2 bath, ground floor unit. Sip your morning coffee while admiring the garden landscaping from your screen enclosed patio. Host a barbeque with family and friends at the community

    Eimi Moreno Carrera LPT REALTY, LLC

    205 Lewfield Cir Unit 205, Winter Park, FL 32792
  • /21

    $1,250 Per Month

    • 2 Beds
    • 2 Baths
    • 840 Sq Ft
    • Spacious and Affordable 2/2 Condo In Lancelot at Winter Park

    3651 N Goldenrod Rd Unit B202, Winter Park, FL 32792

    AVAILABLE NOW!!! This beautiful 2 bedroom, 2 bathroom condo in the Lancelot at Winter Park community near local shops, restaurants, and schools. Features include tile throughout, vaulted ceilings, kitchen with stainless appliances and breakfast bar, two full bathrooms, and spacious bedrooms. Community amenities include a pool and clubhouse. MUST SEE! Won't last long! Schedule your showing

    3651 N Goldenrod Rd Unit B202, Winter Park, FL 32792
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    $1,500 Per Month

    • 2 Beds
    • 2 Baths
    • 802 Sq Ft
    • Condo for Rent

    7340 Swallow Run Unit 7340, Winter Park, FL 32792

    Check out this 2nd floor 2-bedroom, 2 bathroom condo with brand new beautiful wood floors throughout. The condo is centrally located between UCF and Full Sail University and is just a short distance to major roadways, shopping, and several dining options.

    Jennifer Linton METRO CITY REALTY

    7340 Swallow Run Unit 7340, Winter Park, FL 32792
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    $1,800 Per Month

    • 2 Beds
    • 1 Bath
    • 750 Sq Ft
    • Condo for Rent

    2510 Boyd Ave, Orlando, FL 32803

    Step into the allure of this meticulously renovated one-bedroom and bathroom apartment unit. The open-concept space boasts a granite countertop and stainless steel appliances, creating a modern and inviting ambiance. The unit also features an extra room, perfect for an office, with direct access to the private backyard. Conveniently situated near Baldwin Park, downtown Orlando, and a plethora of

    2510 Boyd Ave, Orlando, FL 32803
  • /14

    $1,500 Per Month

    • 2 Beds
    • 1 Bath
    • 881 Sq Ft
    • Condo for Rent

    1695 Lee Rd Unit Apartment A103, Winter Park, FL 32789

    2 Bedrooms, 1 Bathroom located on the first floor. IGalley kitchen (with a dishwasher, microwave, range, refrigerator, and a washer/dryer combo), walk-in closet in the primary bedroom, and an open living/dining room combo filled with natural light. A private patio, playground, and park. It includes 1 assigned parking space.This property offers an option of a security deposit-free lease

    1695 Lee Rd Unit Apartment A103, Winter Park, FL 32789
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    $1,700 Per Month

    • 2 Beds
    • 2 Baths
    • 1,059 Sq Ft
    • Excellent location

    4968 Tangerine Ave Unit 4968, Winter Park, FL 32792

    This roomy condo is available for immediate occupancy. New Luxury Vinyl Plank floors just installed. The unit is ideally located in Winter Park, not far from Full Sail or UCF. You're just a short drive from downtown and other Orlando hotspots. Wrenwood is a very quiet community with plenty of privacy. Amenities include a pool and workout room. Call today for your private tour of this amazing

    4968 Tangerine Ave Unit 4968, Winter Park, FL 32792

Rental Home Trends

Number of 2 Bedroom Condos for Rent
36
Median 2 Bedroom Condo Rent
$1,665
Median 2 Bedroom Townhouse Rent
$1,798
How to Rent a Home